We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals in South Orleans

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    ₹ 23,633 Average
    |||
    |||
    ₹ 0₹ 72,000+
    Suitability
    More filters
    Travellers to South Orleans are booking July dates now. Secure your holiday home today, and have the perfect trip.
    All 303 Rentals in South Orleans
    Sort by:
    Default
    South Orleans
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    South Orleans
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    South Orleans
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    South Orleans
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Balcony
    • Ocean Views
    • Patio
    • Waterfront
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Six feet of plush lawn separate the MainHouse from the waters of Pleasant Bay. The large garden has plenty of quiet places for reading, relaxing and/or snoozing in the shade or in the sun. Swim or fish from the dock or the nearby beach. Arrangements for a boat mooring are possible. Off-street...
    View all property information
    Location Information
    South Orleans, Cape Cod 02662
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    Large House On Private Acre - Newly Remodeled & New Furnishings1 / 16
    (1)Excellent
    South Orleans
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Grill
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 June 2018
    Outstanding House!! Nicely furnished and all the convenience of clean sheet and towels, out door space and shower and alot of space for privacy! Great location and very...
    See all reviews
    About this property
    STUNNING 4 BEDROOM IN HARWICH FOR 10 GUESTS! NEW LISTING!! 4 BEDROOM FOR 10 IN HARWICH COMPLETELY RENOVATED, ALL NEW FURNISHINGS, CLOSE TO JACKNIFE POINT! Located on a private acre in East Harwich, this 4 bedroom house has been completely remodeled with brand new mattresses, appliances, and...
    View all property information
    Location Information
    South Orleans, Cape Cod 02645
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    Topside BoatHouse on Pleasant Bay1 / 10
    (2)Excellent
    South Orleans
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Grill
    • Cable/satellite TV
    • Ocean Views
    • Balcony
    • Wi-Fi
    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    If you’re looking for a relaxing, peaceful, and entertaining vacation, this is the place! We’ve only ever visited in the fall and it’s my favorite time of year to be on the Cape...
    Reviewed 27 January 2016
    I stayed here on my honeymoon many years ago, and have returned every year since then. I could roll out of bed, onto the deck, and into the water without walking 5 steps...
    See all reviews
    About this property
    The BoatHouse is unique. Built and furnished in Cape Cod Cottage style, it sits literally right on Pleasant Bay with deck and stairs leading into the water. In the master bedroom look out across Pleasant Bay before you get out of bed. Full bathroom inside and delightful outside shower. Lounge,...
    View all property information
    Location Information
    South Orleans, Cape Cod 02662
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    South Orleans
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Exquisite Custom Built 5BR Home in Orleans, Tons of Stuff for the Kids! (linens included) Peak Summer Weekly Rates: $6,800 Rents Saturday to Saturday If you're looking for upscale accommodations yet plenty for the kids to do, this stunning new home is the one for you. Situated on a quiet...
    View all property information
    Location Information
    South Orleans, Cape Cod 02662
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Enquiry
    South Orleans
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Grill
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    22 Little Bay Rd (ID #18416) ~ Oceanside with gorgeous views of Little Pleasant Bay~ 5 Bedroom Home 2018 Season A striking contemporary home only 300 yards to an association beach on Little Pleasant Bay and located in the prestigious East Egg neighborhood of S. Orleans. Open, bright, and very...
    View all property information
    Location Information
    South Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
    Make Enquiry
    South Orleans
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Parking
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    9 Woodridge Road (ID# 99912) ~ Bayside 4 Bedroom Home ~ Pleasant Bay Area 2019 Season! Enjoy a Cape Cod vacation. This 4 Bedroom, 2.5 bath home includes a finished basement great for entertaining and access out to the outdoor shower. There are two Bedrooms and a full bathroom on each floor. All 4...
    View all property information
    Location Information
    South Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    52 Forest Way 184231 / 18
    (2)Very good
    South Orleans
    5 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Grill
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    52 Forest Way, Orleans MA (ID# 18423) 2018 Season! Contemporary home with lots of space, nestled in a quiet wooded area of Orleans. This home is ideal for a casual vacation. 5 Bedrooms (2 Queens, 1 Double, 4 Twins) and 3 Baths. No Pets Accepted. Weekly Rental (7 Night Minimum in Season) _Rent:...
    View all property information
    Location Information
    South Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Save time - get the best South Orleans rentals sent straight to your email!
    Get the List
    South Orleans
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Waterfront
    • DVD Player
    • Cable/satellite TV
    • Hot Tub
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront Home with Large Private Deck and Hot Tub  Peak Summer Weekly Rates: $2,950 - $3,800 Linens Included Rents Sunday - Sunday during peak season If you love nature, privacy and water views this comfortable home is for you. You will wake up each morning to find the water sparkle over Uncle...
    View all property information
    Location Information
    South Orleans, Cape Cod 02662
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    South Orleans
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    As a vacation rental, this exquisite 5 bedroom/3 full bath home in South Orleans hits all the right notes exactly on pitch. It is both elegant and relaxed, with plenty of indoor and outdoor space to comfortably accommodate 10 guests. The front door opens directly into a living room which is...
    View all property information
    Location Information
    South Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    South Orleans
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Private Garden
    • Washer
    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Walk to Pleasant Bay, close to downtown Orleans and Chatham Bring the family together for a memorable summer vacation at this spacious, well appointed home in South Orleans. Filled with natural light and wonderfully furnished with hardwood and tile floors throughout, this 5 bedroom is also...
    View all property information
    Location Information
    South Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    The following rentals are within 10 kilometres of South Orleans.
    Cape Charmer Near Private Beach!1 / 20
    (2)Very good
    Brewster
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Patio
    • Parking
    • Private Garden
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 July 2017
    Wonderful location with the beach a short 3 minute walk away. This home is inviting and comfortable with plenty of room for our family of six. Our contact owner while renting...
    Reviewed 9 August 2016
    This is what it says - a charmer. Lovely wood panelled home surrounded by very large grounds and very, very close to the beach. Yes it maybe a tad old fashioned in parts for...
    See all reviews
    About this property
    Nestled on three lots in private association, only minutes walk from private beach. Perfect for guests to enjoy high and low tides on Cape Cod Bay, finishing the days with brilliant sunsets. Centrally located on the Lower Cape, Brewster has quick access to all that a vacation on Cape Cod has to...
    View all property information
    Location Information
    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Brewster
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    For rent is a 4 bedroom oceanfront house in Brewster, MA. The high tide mark is about 40 feet from face of house, no obstructions or trees to the view. Brewster is the site on the Cape where the tide goes out almost a mile at dead low tide. This exposes sandbars and tide pools which are great fun...
    View all property information
    Location Information
    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
    Make Enquiry
    Walk to Ridgevale Beach From Family Friendly Home1 / 23
    (3)Excellent
    West Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Grill
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Patio
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 July 2018
    Great house—-convenient to beach and all Chatham attractions— very responsive owner— comfortably furnished and super clean— great vacation!
    Reviewed 30 September 2016
    We had a lovely weekend here while attending a family wedding. The house was comfortable and equipped with everything a family might need. The neighborhood is quiet and an...
    See all reviews
    About this property
    This bright and airy family-friendly home is just a 1/2 mile walk to this fabulous sandy beach where you can enjoy swimming both on Nantucket Sound or in the milder waters in the adjoining tidal creek. Ridgevale Beach is one of Chatham's most popular destinations for vacationing families. A clean,...
    View all property information
    Location Information
    West Chatham, Chatham 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Charming Restored Cottage near Nauset Beach: The Summer House: walk to ice cream1 / 21
    (6)Excellent
    East Orleans
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Patio
    • Parking
    • DVD Player
    • Grill
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 September 2018
    This charming and beautifully renovated cottage was beyond expectations. Great quiet location close to restaurants, beaches and shopping. Jim and Barbara made us feel at home...
    Reviewed 10 September 2018
    Close to Skaket Beach and Orleans, latter for great food. Beautiful house, and so comfortable. The porch is fantastic as is the outside shower. The location cannot be beat - we...
    See all reviews
    About this property
    Our East Orleans cottage has been thoughtfully and lovingly restored, with many unique details. The cottage is bright and airy, and has classic features, including beadboard ceilings, ship lap walls, restored pine floors and classic built-ins. The open living area has cable TV and wi-fi and is...
    View all property information
    Location Information
    East Orleans, Orleans 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    North Chatham
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Wi-Fi
    • DVD Player
    • Patio
    • Washer
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to ChathamBeachCruiser! Relax in our 5 bedroom 4.5 bathroom home with central air. The entire house is equipped with all new furniture in June of 2016 and a few antiques (including a coffee table made from a real ship’s wheel). The house sits at the end of a private drive with plenty of...
    View all property information
    Location Information
    North Chatham, Chatham 02650
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
    Make Enquiry
    Cape Charmer Near Private Beach!1 / 22
    (1)Very good
    Brewster
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Grill
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 July 2018
    My family and I had a very satisfying and enjoyable vacation at this house during July 2018. All the facilities were excellently maintained and clean. The beach is very close...
    See all reviews
    About this property
    Nestled on three lots in private association, only minutes walk from private beach. Perfect for guests to enjoy high and low tides on Cape Cod Bay, finishing the days with brilliant sunsets. Centrally located on the Lower Cape, Brewster has quick access to all that a vacation on Cape Cod has to...
    View all property information
    Location Information
    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    #602: Make memories in this Chatham beach home within steps to Nantucket Sound!1 / 32
    (1)Excellent
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 September 2017
    Would totally stay here again. Super clean & comfy, plenty of room for 3 adults & a dog, nice quiet neighborhood with friendly neighbors, close to beach. Had one small...
    See all reviews
    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
    View all property information
    Location Information
    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    List your property for free!
    List your holiday home where TripAdvisor travellers can find it.
    Add a Listing
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Grill
    • Patio
    • Cable/satellite TV
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated kitchen with quartz “Sea Glass” countertops, backsplash and Nantucket farm sink. Truly a well equipped cooks kitchen. This year round low allergen, open concept home has 3 bedrooms, 2 newly updated baths, a large two level outdoor deck with electric retractable awning, creating a...
    View all property information
    Location Information
    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Spectacular Beach Front Home on Cape Cod Bay1 / 12
    (7)Very good
    Brewster
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Waterfront
    • Ocean Views
    • DVD Player
    • Wi-Fi
    • Washer
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2016
    This cottage had it all for us. Amazing sunsets, beautiful beach, great location!And a dishwasher. What more could I ask for!
    Reviewed 2 June 2016
    We love this house! Perfect - house is comfortable, well maintained, spectacular setting. Loved the incredible view over Cape Cod Bay, walks along the beach, watching the oyster...
    See all reviews
    About this property
    Located atop the dunes overlooking Cape Cod Bay in Brewster MA this amazing home is the answer to your vacation wish list. Recent renovations include new washer/dryer, fresh paint, new décor and linens, wireless internet and cable. Weeks still available in July, August and September. You will enjoy...
    View all property information
    Location Information
    Brewster, Cape Cod 02631
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Townhouse in Brewster, Ocean Edge Resort1 / 14
    (11)Excellent
    Brewster
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Patio
    • Washer
    • Wi-Fi
    • DVD Player
    • Sauna
    • Hot Tub
    • Shared Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 January 2016
    Charming unit, very clean, and exactly as described, we loved it.Great communication with the owner; Quick follow-up on our questions / transaction process.We enjoyed our stay...
    Reviewed 9 November 2015
    We usually don't go twice at the same place two years in a row, but for the first we might. My 7 years-old girl, 5 years-old boy, my wife and I loved it. The pools are success...
    See all reviews
    About this property
    - 2 bedroom C-style townhouse in Ocean Edge Resort. 1 1/2 baths, AC, HDTV, Wi-Fi, free phone, washer & dryer and dishwasher. - Private patio with BBQ grill. - Resort swimming pools, whirlpools, fitness center and amenities access. (passes need to be acquired directly at the resort (2015...
    View all property information
    Location Information
    Brewster, Cape Cod 02631
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Hydrangea House with Cape Charm Near Seymour Pond1 / 13
    (5)Excellent
    Brewster
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Patio
    • Wi-Fi
    • Hot Tub
    • Grill
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 July 2018
    Great sized holiday home with everything you would need for a holiday. Super sized rooms, plenty of garden & beach chairs and umbrellas. Very well appointed kitchen. Lots of...
    Reviewed 19 July 2015
    My family and extended family total 10 people including my 2 year old nephew stayed here July 11-18th and we had a blast! This house is truly charming with its different decor...
    See all reviews
    About this property
    We rent our property by the week, Saturday to Saturday. This bright attractive home in a lovely, residential setting features something for everyone in your vacationing group... For the gourmet: a fun, light, stainless and Corian kitchen, fully equipped with appliances, butcher block island, gas...
    View all property information
    Location Information
    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    South Chatham
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Parking
    • Internet Access
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    62 PATUXET TRAIL Sweet cottage close to Cockle Cove Beach in South Chatham. Sleeps 5. First bedroom 1 Double, 2nd bedroom 2 twins, 3rd bedroom 1 twin. $950 off season and $1200 in season * $100 Handling Fee * choice of $55 Damage Insurance or $350 Security Deposit Please contact Courtney...
    View all property information
    Location Information
    South Chatham, Chatham 02633
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    North Chatham
    5 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Washer
    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2019 Rental Rates (Cleaning Fee Included): In-Season: $5350 per week (linens also included) Off-Season: $4400 per week (linens also included) for 8/24 to 9/7 - No Other Off-Season Availability Click for More Photos, Map, and Availability Calendar *Weekly Rentals Only* Gorgeous home in high-end...
    View all property information
    Location Information
    North Chatham, Chatham 02650
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 11
    Make Enquiry
    South Chatham
    3 Bedrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Waterfront
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2019 Rental Rates (Cleaning Fee Included): In-Season: $3000 per week Call About Off-Season Click for More Photos, Map, and Availability Calendar Fabulous Cape Cod beach rental located steps from Nantucket Sound with breathtaking views from the huge deck overlooking the marsh and the ocean. Airy,...
    View all property information
    Location Information
    South Chatham, Chatham 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 8
    Make Enquiry
    Walk to Beach, Beautiful Brewster Home! Crosby1 / 26
    (4)Very good
    Brewster
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Wi-Fi
    • Washer
    • Patio
    • Porch
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 December 2017
    Great proximity to the beach, only a 5 min walk for the family. New outdoor shower is great after a lazy beach day. John was very responsive for checkin and questions. Even...
    Reviewed 21 July 2016
    The house was spacious, clean, and perfect for a family get together. Everything we needed was provided, the host was responsive and welcoming. The location was perfect! An easy...
    See all reviews
    About this property
    Very close to the beach for family & pet friendly fun! This magical 4 bedroom 2 bathroom home on a quiet cul-de-sac on Cape Cod in the Sea Captains' town of Brewster. Close to everything including directly across the street from Nickerson State Park and the bike trail. Enjoy lazy summer days in the...
    View all property information
    Location Information
    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    East Orleans
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • Waterfront
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    26 Tides End Lane, East Orleans MA (ID# 52984) 2019 Season! Waterfront home with private dock on Meetinghouse Pond and access to Pleasant Bay. Casual living with water views from almost every room. Picturesque grounds and a nice sunny porch is just about everything you need to enjoy your Cape Cod...
    View all property information
    Location Information
    East Orleans, Orleans 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    North Chatham
    2 Bedrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Washer
    • Grill
    • DVD Player
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2019 Rental Rates (Cleaning Fee Included): In-Season: $1375 per week Off-Season: $1075 per week Click for More Photos, Map, and Availability Calendar Quaint two bedroom cottage surrounded by beautiful gardens! Located in lovely North Chatham, this little cottage is just what the doctor ordered....
    View all property information
    Location Information
    North Chatham, Chatham 02650
    Holiday Rental House - 2 Bedrooms, Sleeps 4
    Make Enquiry
    10 Captain Curtis Way 184361 / 17
    (2)Average
    East Orleans
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    10 Captain Curtis Way, Orleans (ID#18436) 2018 Season! Cute as a button with Seaside touches and well equipped for your Cape Cod Vacation! Located on a lovely, quiet street with easy access to Nauset Beach and the Village of East Orleans. Living/Dining/Kitchen Area is centrally located with 2...
    View all property information
    Location Information
    East Orleans, Orleans 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    North Chatham
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Internet Access
    • DVD Player
    • Washer
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming renovated home with central a/c in North Chatham! Charming renovated home in North Chatham, approx. .5 mile to Chatham Fish Pier, less than 2 miles to Chatham Lighthouse Beach and convenient to Scatteree Beach and the Cow Yard Landing! Approx. 1 mile to Main St., Chatham for shopping,...
    View all property information
    Location Information
    North Chatham, Chatham 02650
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    North Chatham
    5 Bedrooms, Sleeps 11 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Grill
    • Air Conditioning
    • Washer
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2019 Rental Rates (Cleaning Fee Included): In-Season: $5350 per week (linens included) ~ June 22-29 and August 24-31: $4400 per week (linens included) Click for More Photos, Map, and Availability Calendar Gorgeous home in secluded North Chatham neighborhood. The home features hardwood floors, WiFi...
    View all property information
    Location Information
    North Chatham, Chatham 02650
    Holiday Rental House - 5 Bedrooms, Sleeps 11
    Make Enquiry
    South Chatham
    4 Bedrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Internet Access
    • Washer
    • Grill
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2019 Rental Rates (Cleaning Fee Included): In-Season: $2,150 per week Off-Season: $1750 per week Click for More Photos, Map, and Availability Calendar Spacious 4 BR home on quiet street near Cockle Cove Beach. Lots of living space in this private and centrally located home. Minutes from bike trail...
    View all property information
    Location Information
    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, Sleeps 8
    Make Enquiry
    Sleeps 10 Near Crosby Landing Beach -- 050-B1 / 30
    (1)Excellent
    Brewster
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sleeps 8, Walk to Crosby Landing Beach, Brewster.  Totally renovated kitchen for 2017. Peak Summer Weekly Rates:  $3,800 - $4,500 Rents Saturday to Saturday   An 8-10 minute walk from this big and neat-as-a-pin two-story home brings you to sweeping Crosby Landing Beach, considered Brewster's...
    View all property information
    Location Information
    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    North Chatham
    3 Bedrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2019 Rental Rates (Cleaning Fee Included): In-Season: $6,425 per week Off-Season: $3,325 per week Click for More Photos, Map, and Availability Calendar Gorgeous home near picturesque Scatteree Beach in N. Chatham! The 'upside-down' floor plan features the kitchen and master bedroom on the second...
    View all property information
    Location Information
    North Chatham, Chatham 02650
    Holiday Rental House - 3 Bedrooms, Sleeps 8
    Make Enquiry
    East Orleans
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Patio
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    6 Cedar Land Road, East Orleans (ID#18315) 2019 Season! Adorable home in East Orleans 6/10 mile to Nauset Beach with central air conditioning. This 2 bedroom/1 bath home features an open kitchen/living room and den/TV room leading to the deck and back yard. The bedrooms are furnished with 2 twins...
    View all property information
    Location Information
    East Orleans, Orleans 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    251 Seaway Brewster 1211231 / 14
    (1)Excellent
    Brewster
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • DVD Player
    • Washer
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 October 2015
    This location is superb. Views are spectacular. The beach is great even in the fall. Great for walking. Living space (kitchen, dining room and living room) are upstairs and very...
    See all reviews
    About this property
    251 Seaway Brewster (ID# 121123) ~ Pineland Private Beach Association 2018 Season! Air conditioned beach house, four large bedrooms, and two full baths. Sleeps 8 with two queens, and 4 twins. 100 yards to private Pineland Park Association beach. Custom upside-down design provides great views of...
    View all property information
    Location Information
    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Unit 11 372461 / 9
    (1)Very good
    East Orleans
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    170 Beach Rd Unit #11 (ID# 37246)~Oceanside one bedrom Cottontail Cottage~A/C Nauset Beach Area 2019 Season! This adorable one bedroom cottage is located less than 1/2 mile from beautiful Nauset Beach on the Atlantic Ocean! After a day of fun in the sun, gather in the outdoor eating area and enjoy...
    View all property information
    Location Information
    East Orleans, Orleans 02653
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    DETACHED HOME IN THE PERFECT LOCATION AT OCEAN EDGE RESORT!1 / 23
    (1)Excellent
    Brewster
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • DVD Player
    • Washer
    • Air Conditioning
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 February 2018
    We have stayed at 10 Gray Lane in Brewster several times. We love coming back to stay. The home is well furnished and comfortable. It offers close and easy access to the pools...
    See all reviews
    About this property
    5 Star Review from TripAdvisor, 'We have stayed at 10 Gray Lane in Brewster several times. We love coming back to stay. The home is well furnished and comfortable. It offers close and easy access to the pools, local beaches, Cape Cod Rail Trail, and Route 6A. The full kitchen, free wifi, and cable...
    View all property information
    Location Information
    Brewster, Cape Cod 2631
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    6 Bayberry Way 185911 / 20
    (2)Very good
    East Orleans
    2 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Grill
    • Waterfront
    • Balcony
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    6 Bayberry Way, East Orleans MA (ID# 18591) Waterfront and Waterview on Meetinghouse Pond 2019 Season! Kayak or Canoe- this is the perfect location! Water front on Meetinghouse Pond with access to The River and to Pleasant Bay and less than 2 miles to Nauset Beach. This home offers Air Conditioning...
    View all property information
    Location Information
    East Orleans, Orleans 02653
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 7
    Make Enquiry
    Brewster
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Custom Beach House Directly on the Water Prime Summer Weekly Rates:  $5,800-$6,200 Rents Saturday to Saturday Owners have replaced the original cottage on this property with a totally new, two-story vacation home.  From its perfect perch above the Bay you have panoramic 180-degree water views. The...
    View all property information
    Location Information
    Brewster, Cape Cod 02631
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    South Chatham
    3 Bedrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Grill
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2019 Rental Rates (Cleaning Fee Included): In-Season: $1675 per week Off-Season: $1325 per week Click for More Photos, Map, and Availability Calendar Adorable, updated rental located on a quiet street in South Chatham. New furnishings and fresh paint make this a very comfortable spot for your...
    View all property information
    Location Information
    South Chatham, Chatham 02669
    Holiday Rental House - 3 Bedrooms, Sleeps 8
    Make Enquiry
    Classic home w/ deck, patio & yard - walk to Cockle Cove & Forest Beaches!1 / 26
    (1)Excellent
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Cable/satellite TV
    • DVD Player
    • Parking
    • Patio
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beach-going families will find a welcoming retreat at this three-bedroom South Chatham home, a darling Cape Cod escape with a private deck and patio, a fenced yard, and a wonderful location within a short walk of the beach! This classic home sits a block off Main Street in South Chatham, just...
    View all property information
    Location Information
    South Chatham, Chatham 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    East Orleans
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Private Garden
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private, beautiful family home located on a child-safe street in East Orleans. Three levels of living for a maximum of 10 people. Plenty of room for all. The deck with dining table overlooking private back yard is located off the kitchen. Outside shower and spacious back yard. Garage is where...
    View all property information
    Location Information
    East Orleans, Orleans 02653
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Enquiry
    South Chatham
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 4 bedroom, 2.5 bathroom home in South Chatham has plenty of space inside and out. There are two dining areas, one in the kitchen and another off the main living room that opens to a small patio with gas grill. A second living space on the lower level has a TV, foosball table, half-bath,...
    View all property information
    Location Information
    South Chatham, Chatham 02695
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Brewster
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Walk 4 Min.to Beach, New Custom Home, New Everything, Linens Included Peak Summer Weekly Rates:  $4,500 - $4,800 Rents Saturday to Saturday This newly constructed home will welcome its first guests in the summer of 2018. The custom home has the highest level of amenities including a gourmet...
    View all property information
    Location Information
    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Brewster
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4-Minute Walk to Sandy Beach, Loads of Living Space, In & Out Peak Summer Weekly Rates: $4,000 - $4,200 Rents Sunday - Sunday during peak season You'll love vacationing in this quiet bay front neighborhood, so close to a beautiful, uncrowded, private Brewster beach. There's always plenty of...
    View all property information
    Location Information
    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
    Make Enquiry
    East Orleans
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • DVD Player
    • Washer
    • Wi-Fi
    • Grill
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    59 Gibson Road Rear Cottage (ID# 18015) ~Central Air~ Town Cove Area ~ 2018 Season! Every reservation includes 2 Lobsters and a Bottle of Wine Complementary! This recently renovated 2 bedroom, 1 bath cottage is nicely appointed in a prime East Orleans location, convenient to Nauset Beach on the...
    View all property information
    Location Information
    East Orleans, Orleans 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    North Chatham
    7 Bedrooms, 5 Bathrooms, Sleeps 24 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Historic North Chatham Estate. Sleeps 20, private beach! Linens included and new beds/furniture for 2018 Peak Summer Weekly Rates: $12,500 - $14,000 Rents Saturday to Saturday during peak season Two-night rentals available in the offseason   Please click on the 'Virtual Tour' to see a 3D tour of...
    View all property information
    Location Information
    North Chatham, Chatham 02650
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 24
    Make Enquiry
    1
    List your property
    Owner log in