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Holiday Rentals in Chatham

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    ₹ 28,418 Average
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    All 389 Rentals in Chatham
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    Cape Escape Chatham Walk to Beach! Private-Newly Renovated-Hear Waves at Night1 / 53
    (20)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Beach Chic Cape Escape! Chatham 5 Star Private-Newly Renovated 5m walk to beach1 / 54
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife! Welcome to The Chatham Bars Carriage House, located within walking distance to Historic Main St. with it's endless variety of boutiques, restaurants, galleries, and nightlife! Enjoy this traditional, yet well-appointed...
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    Chatham, Cape Cod 02633
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    All New Cottage in Chatham Near Hardings Beach1 / 19
    (5)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Porch
    • Grill
    • Washer
    • Wi-Fi
    • Outdoor Dining Area
    • Air Conditioning
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 September 2018
    Recently rented this cottage for a week and it was wonderful. Everything was set up so nice and the renting process was made seamless by the owners. It felt like we were the...
    Reviewed 7 November 2015
    Wonderful house, very nice quiet location within easy reach of beaches. House very clean with everything that we needed. Would highly recommend.
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    About this property
    Welcome to our entirely renovated 'old Cape' cottage, with a sunny, open floor plan, brand new appliances and furnishings, washer/dryer and central air. After the beach, rinse off in the private outdoor shower before relaxing on the sunny patio. The Space: Create cherished family memories in our...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • 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...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Walk to Ridgevale Beach From Family Friendly Home1 / 46
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • 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...
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    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,...
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    West Chatham, Chatham 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    #602: Make memories in this Chatham beach home within steps to Nantucket Sound!1 / 32
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
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    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...
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    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...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Chatham 1 Bedroom Beachfront Old Village1 / 9
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Outdoor Dining Area
    • Waterfront
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Private Garden
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 October 2014
    We enjoyed our stay at the condo in Chatham. It was comfortable for 3 people. It was clean and the kitchen was well stocked. Kris gave us excellent directions and suggestions.
    Reviewed 15 August 2014
    Having coffee each morning on the deck of this adorable cottage was one the highlights of my stay in Chatham. The view is terrific - of a lovely harbor that is called Mill Pond...
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    About this property
    Beachfront property, close to town and lighthouse. Cottage is in Chatham's Old Village.
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    Chatham, Cape Cod 02633
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Beautiful sunsets in Chatham!1 / 20
    (6)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Outdoor Dining Area
    • Wi-Fi
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 August 2018
    We had a wonderful time in Chatham. Joy's house was beautiful. Spacious and really well designed with lovely views over a lake; and located on a quiet private road. The outside...
    Reviewed 29 July 2018
    My son proposed to his girlfriend on Jackknife Beach (a short walk away) while we were on vacation here. It’s a beautiful home. Would highly recommend it if your looking for a...
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    About this property
    Enjoy this spacious home on the Monomoy River with glimpses of Pleasant Bay. Recently renovated, our home boasts a gourmet kitchen with granite counters, 6 burner Wolf cooktop and Sub Zero refrigerator and wine frig . Extra bonus: a second dishwasher and frig in the laundry room offof the kitchen!...
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    Chatham, Cape Cod 02148
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brand new custom built beauty in Chatham, walk to Ridgevale Beach! (linens included) Peak Summer Weekly Rates: $6,300 - $7,200 Rents Saturday to Saturday during peak season NEW Listing for 2018!  This brand new custom home provides a luxurious vacation experience just a short walk from...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    • Wi-Fi
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This perfectly situated Chatham rental is welcoming to you and your four legged friends. Located close to Shore Road, you and your guests will enjoy the best of being near the ocean and close to Main Street. Stroll to town on sidewalks and enjoy the amazing shops and restaurants. Head to the...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Comfortable 3 bedroom, 2 bath quiet summer retreat only a half mile to downtown Chatham!  Offering Central AC & free WiFi with over 1600 sq. ft. of finished living space, 3 bedrooms, 2 full bathrooms, and a large den there is plenty of space for you to relax in with the entire family.    Welcome...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location, location, location. Enjoy this classic 2 bedroom, 1 full bath Cape beach cottage less than 2/10ths of a mile to popular Ridgevale Beach. Amenities include window AC units in the queen bedroom as well as the kitchen/living room area, washer, dryer, dishwasher, cable TV (including sports...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • DVD Player
    • Air Conditioning
    • Washer
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    195 Cedar Street Chatham - ID# 106000 Location, location, location! Only a half mile to the beach at Oyster Pond and 3/4 mile to the Village of Chatham. Located on the Chatham Loop, this is a wonderful newly renovated home including a fabulous new kitchen with sunny breakfast nook. Living room,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This traditional, 3 bedroom, 1.5 bathroom Chatham vacation cottage has beautiful views of the Cockle Cove salt marsh and is just steps to Cockle Cove Beach and the warm waters of Nantucket Sound. Amenities include AC splits (one in each queen bedroom), Wi-Fi, cable TV, DVD player, washer, dryer,...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Quiet Lakeside Cottage - Ideal for Couple1 / 14
    (18)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Parking
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 weeks ago
    We had a wonderful stay at Helene's cottage. Great location for bike riding, swimming and canoeing. Our host provided many local areas of interest in the form of a binder...
    Reviewed 8 August 2018
    This cottage is a one bedroom on White Lake, nestled amount trees and other cottages. It is charming and a very comfortable way to spend a week in the Chatham, MA area. The...
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    About this property
    At this quiet lakeside cottage you can experience classic Cape Cod with all the modern amenities -- wireless internet, cable TV, air conditioning. Enjoy beautiful sunsets as well as swimming, kayaking and canoeing at the lake---and only be a short trip to the beach or Chatham center. The cottage...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Parking
    • Washer
    • Grill
    • Balcony
    • Terrace
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4 minutes to Harding Beach, 10 minutes to downtown Chatham This bright and cozy 4 bedroom, 1.5 bathroom home is located in a quiet neighborhood just minutes from downtown Chatham. Walk to a scenic town landing on Oyster Pond River, or drive to popular Harding Beach in less than 5 minutes. Oyster...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Sea Glass! This Cape Cod Vacation Rental home is just .2 miles from Pleasant Street Beach in Chatham. Warm water, sunsets, and miles of beach on Nantucket Sound awaits you just around the corner. The proximity to the beach is so close, you will frequent beach visits and be pleased with...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Come stay at: Misty Meadow! Enjoy this lovely condo with all amenities including Central AC mini splits and free WiFi Conveniently located too. Situated in a very quiet area of North Chatham offering private conservation views from this charming one bedroom, first floor, end unit condo. An open...
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    North Chatham, Chatham 02650
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Pleasant Forest Shores cottages #3 : So. Chatham1 / 14
    (2)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Central Heating
    • Grill
    • Parking
    • Wi-Fi
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 September 2017
    Our stay at Pleasant Forest Shores was awesome! The cottage was very clean, had a sizable living room & kitchen and was located within a quiet neighborhood. It was also about...
    Reviewed 1 July 2017
    We actually stayed in cottage #2 but they appear to fairly similar. I used to vacation in Chatham as a kid in the late 60's and early 70's. These cottages are VERY reminiscent...
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    About this property
    Yes, the price is low but that's why so many customers have come for decades! Looking for a nice clean quiet cottage close to Nantucket Sound beaches? And one that you can afford on a tight budget with some money left for gas & dining? Well, then...Pleasant Forest Shores just may be the place for...
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    South Chatham, Chatham 02659 1525
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Classic Chatham Charm -- Walk to Beach & Town! (Linens included) Peak Summer Weekly Rates: $5,310 - $6,750 (Pets Considered)  Rents Saturday to Saturday during peak season Located in a premier Chatham Village location, this classic antique home has everything to experience an idyllic Chatham...
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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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    CONDO NEXT TO COCKLE COVE BEACH IS JUST 0.9 MILES AWAY!1 / 17
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2014
    rental was everything we expected. Place was clean and in a great location. There were bikes, boogie boards and beach chairs for your use.
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    About this property
    Cockle Cove Beach is just 0.9 miles away from this light & bright Chatham Condominium located at Cockle Cove Ridge. The Chatham Village center is just 3 miles away for shopping, dining, Chatham A's baseball games, & the bandstand. The entry level of this 2 bedroom, 2 bath home features a living...
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    Chatham, Cape Cod 2659
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Light & Bright Chatham Home, Walking Distance to Beach Linens Included, Pets Considered Peak Weeks - $2,000 Rents Saturday - Saturday during peak season Please note:  This property is part of a larger estate, and is only available to rent individually in the months outside of July and August...
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    North Chatham, Chatham 02650
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    North Chatham, Chatham 02650
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    South Chatham Cape Cod Vacation Rental (3388)1 / 20
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Air Conditioning
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 August 2018
    The location of the house was perfect, with family in Orleans and Chatham. We were just steps from the beach, and there were a ton of great restaurants and shops within a short...
    Reviewed 19 August 2016
    We loved this houseIt had everything we needed Great house screen porch and deckMaybe 1 more tv would be good
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    About this property
    This 4 bedroom, 2 bathroom South Chatham rental home is only .2 mile to Pleasant Street Beach and .3 mile to Forest Beach. The recently renovated kitchen has granite countertops and new stainless appliances. The screened-in porch with vaulted ceiling overlooks a wooded area making it a peaceful...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, Sleeps 11 Quick View
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    • Internet Access
    • Patio
    • Washer
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 Rental Rates (Cleaning Fee Included): In-Season: $8600 per week Off-Season: $6650 per week Click for More Photos, Map, and Availability Calendar This gorgeous home offers over 5000 square feet of living space spanning three levels, and manages to be both elegant and comfortable. It features...
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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, Sleeps 11
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come stay at: The Cozy Beach Cottage! Chatham Vacation Rental Cottage at the beach! Get away to this 1 bedroom cozy cottage located right at the beach in Chatham, the best of Cape Cod-Sleeps 4. Perfect for a relaxing, romantic getaway, this cottage is steps from the sand, and is ready for your...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, Sleeps 8 Quick View
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    • Grill
    • Air Conditioning
    • Internet Access
    • Washer
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    key # 158 Additional amenities: 1/2 Bath 2, A/C Units 4 ~ 1 in each BR, Area Town, Bedding rm1 King Ensuite ~ 2nd Fl., Bedding rm2 Queen ~ 1st Fl., Bedding rm3 Two Twins ~ 2nd Fl., Bedding rm4 Two Twins ~ 2nd Fl., Bedrooms 4.00, CD, Dist. To Downtown 3/4 mile, Distance to Beach 7/10 mile, Fans 4,...
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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 8
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    55 Sears Point Road Chatham Cape Cod- The Sears Point House1 / 39
    (1)Excellent
    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    • Air Conditioning
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    • Patio
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 August 2018
    We enjoyed a lovely week at this great home. Our nine member family had plenty of room and two other family members were also able to join for a night or two. Chatham is...
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    About this property
    Enjoy this classic Cape Cod Style waterfront home with sparkling water views, a private beach, and large yard in Chatham. Over 180 degree views of Stage Harbor, Nantucket Sound, Monomoy Island, and the Atlantic Ocean beyond. Pet Friendly! Sleeping 12 there is plenty of space for everyone. Each...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Exquisitely Renovated Chatham Sea Captain's Home Linens included, brand new furnishings, hot tub Peak Summer Weekly Rates: $4,500-$5,500/week This immaculate newly renovated home is set close to everything in Chatham.  The property is located about a mile from the center of Chatham, and about a...
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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Captain's Haven1 / 16
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Garden
    • Grill
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 July 2016
    It was a nice little spot for my boyfriend and I to get away for the weekend. Had no issues with the facilities. Please keep in mind the cabin isn't air conditioned. There are...
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    About this property
    An old-fashion Cape vacation set in a secluded village of quaint, privately owned cottages on 4 acres of pine forest located on White Pond. This true Cape cottage is ideal for a couple or a small family. It has a complete kitchen/ living area with a pull out sofa bed, one bedroom with 2 twin beds...
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    West Chatham, Chatham 02633
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Quintessential Cape Cod Vacation Home in N.Chatham1 / 41
    (1)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
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    Reviewed 24 September 2014
    Amazing home with a great owner who was 100 percent accessible our whole trip. Huge house, our party of 10 didn't even know one another was there. Highly recommend the...
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    Welcome to the Whydah Figawai - a privately-owned five bed room vacation home in exclusive North Chatham, just a few steps away from the private beach on Pleasant Bay. This traditional Cape Cod home is located in a serene setting and offers the perfect combination of quiet and accessibility for...
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    Chatham, Cape Cod 02650
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Gorgeous views of Nantucket Sound, Ridgevale Beach and Bucks Creek from this charming 2 bedroom, 1 bath authentic Cape cottage. Located just steps to popular Ridgevale Beach, the only public beach with watersports rentals and a snack bar, this cottage has one bedroom with a full size bed and...
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    Chatham, Cape Cod 02669
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Chatham Cape Cod Waterfront Vacation Rental (8927)1 / 18
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Pet friendly
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    Reviewed 3 September 2016
    Chatham Vacation rentals followed our guidelines and helped us find the perfect vacation house. Home had exquisite views of Pleasant Bay - private pier was a bonus House was...
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    Magnificent waterfront home with views of Pleasant Bay, North Beach and the Atlantic beyond. This updated and well-appointed 4 bedroom, 3 1/2 bath home is located in an association neighborhood, water-front home with breathtaking views of Pleasant Bay, North Beach and the Atlantic beyond. The...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    About this property
    Enjoy staying in the heart of Chatham Village in this new,er tastefully appointed 2 bedroom, 2.5 bath 1,300 sq. ft. home. Downtown Chatham is just steps away where you can enjoy shopping, fine restaurants, band concerts, ball games and much, much more. This home is only 2/10ths of a mile to...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Welcome to: Sandy Paws! Pet Friendly. Newly renovated with Central air (Slim line units). Come have some fun in the sun at this Cape Cod Vacation home in Chatham! You will enjoy deeded access to the 'Little Beach flats'. Just moments away from the top attractions near our Chatham vacation rentals,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 7 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $2450 No Off-Season Click for More Photos, Map, and Availability Calendar Comfortable and airy post & beam home located in a quiet neighborhood near Harding's Beach. Tons of windows and skylights throughout bring in the sunlight! The eat-in...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 7
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    3 Bedrooms, Sleeps 8 Quick View
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    Pet friendly
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    2019 Rental Rates (Cleaning Fee Included): In-Season: $2,100 per week Click for More Photos, Map, and Availability Calendar This is a well maintained property located in a quiet area in W. Chatham. Spacious bedrooms, one with two double beds. Updated kitchen, with a skylight, opens to dining area &...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Located in the heart of Chatham Village with its many delightful shops, galleries, and restaurants this 2 bedroom home is close to everything Chatham has to offer. Enjoy a short stroll to Lighthouse Beach, the Chatham Fish Pier, tranquil Mill Pond or the Orpheum Theatre. The first floor offers a...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    This 4 bedroom, 2.5 bathroom house is within walking distance to downtown Chatham with some of the best restaurants and shopping that Cape Cod has to offer. The living room offers plenty of new, comfortable seating and the kitchen, with granite countertops and stainless appliances, is fully...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    241 Training Field Road PET FRIENDLY Charming and updated 3 bedroom air conditioned ranch style home, just 1 mile from beautiful Pleasant Bay at Jacknife Point Beach. $1900 per week in season * $160 Cleaning Fee * $100 Handling Fee * $55 Damage Insurance OR $500 Security Deposit Please contact...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Welcome to: Cape Cranberry! Quintessential Cape Cod Vacation Rental Cottage in Chatham on the way to Cockle Cove Beach. Enjoy this Cape Cod beach cottage with casual coastal decor. AC units in living area and bedrooms and free WiFi too. This home offers 2 bedrooms and a full bath with...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    2018 Rental Rates (Cleaning Fee Included): In-Season: $1850 per week Off-Season: $1250 per week Click for More Photos, Map, and Availability Calendar Light and bright home located close to downtown and the Chatham Bike Trail, as well as the middle school tennis and basketball courts. It is an easy...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Paradise Found at this special retreat in this Cape Cod Vacation home Rental in Chatham called the Heron's Nest! This spacious four bedroom, 3 bath Chatham Rental will surely delight you in every way. Just a short walk to the warm waters and gentle waves of Ridgevale beach – this home is perfectly...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    255 Tanglewood Drive CHATHAM Just a short drive to many salt water beaches and fresh water ponds, as well as both downtown Chatham and Harwich Port, this house is convenient indeed! The backyard is fully enclosed and offers a great place to relax and grill after enjoying all the many things this...
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    Location Information
    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    30 Seabeach Road Chatham Cape Cod - The Bluff House1 / 36
    (4)Very good
    6 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Reviewed 23 November 2016
    Our family rented the Bluff House the last week of July and had a lovely time.As boat owners we took advantage of the mooring and dingy that comes with the house. Days were...
    Reviewed 19 September 2016
    My family has rented The Bluff House for the past ten years and we can’t imagine summer anywhere else! The rooms are airy and light, with amazing views across Oyster Pond River...
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    Come Stay at: The Bluff House! Dog Friendly!! High atop Sears Point in Chatham sits a Classic, Quintessential, New England Bluff house from yesteryear overlooking the sparkling, blue sea. This spot is a boater's paradise! From kayaking to boating enthusiasts, there is a mooring available for your...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 12
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    Ides of Marsh1 / 12
    (5)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Internet Access
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    Pet friendly
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    Smoking allowed
    About this property
    $1150/week-High Season-lower other times Foote-steps Chatham Charmer - Weekly Rentals The charm of a Cape Cod cottage with all the amenities of home. Relaxation and conveniences on a private circle with idyllic nature views... Enjoy our enclosed porch overlooking the salt marsh and a short (4/10...
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    Location Information
    Chatham, Cape Cod 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    About this property
    Located in the highly desirable town of Chatham, this five bedroom, three bath rental home will meet all your vacation needs. Sleeping twelve people comfortably, you will have plenty of room to enjoy your stay in the large living room while the kids hang out in the adjoining family room. Featuring...
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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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