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Holiday Rentals in Orleans, MA

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    ₹ 18,643 Average
    ₹ 67,000+
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    Travellers to Orleans are booking May dates now. Secure your holiday home today, and have the perfect trip.
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Three bedroom Cape Cod Cottage for rent. Waterview sunsets. Private location on quiet cul-de-sac. 2.9 miles to Nauset Beach, voted Best Beach on Lower Cape. Walk to Asa's Landing for boating and water activities. Three bedroom, One and half baths, sleeps six. Upper level master bedroom and half... View all property information
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    Orleans, Cape Cod 02653
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Nice 2 bedroom, 1.5 bath home so close you can WALK to your own private association beach on PLEASANT BAY. When you walk in the front door you go up a few stairs to get to the main level. The first level has a nice living room/dining room, a galley kitchen, and a relaxing 3 SEASON ROOM where you... View all property information
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    Orleans, Cape Cod
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    DEEP DISCOUNT! We still have the week of 6/17 to 6/24 available at $2,400 as well as the following High Season week of 6/24 to 7/1 which we have DEEPLY DISCOUNTED from $3,100 to $2,800. The High Season Week of 8/27 to 9/3/2016 is also still available at the same low price of $2,800. Yes, we... View all property information
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    Orleans, Cape Cod 02653
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    Charming Cape, just off historic Town Cove. With two bedrooms down, one up, plus a child's nook, this comfortable home can accommodate 7 guests. Features bathrooms up and down; a sunny family room/dining area; fully-equipped kitchen; and a cozy living room with fireplace. Only a short walk to Asa's... View all property information
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    Orleans, Cape Cod 02653
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    6 Bedrooms, 7 Bathrooms, Sleeps 16 | Quick View
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    About this property
    This one of a kind, magnificent, 6 bedroom estate is perfectly situated on Little Pleasant Bay and on nearly 4 acres of pristine, wooded land with 170 feet of private, sand beach front. Stunning views from almost every place in the home, multi-level decks. The property consists of the main house,... View all property information
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    Orleans, Cape Cod 02653
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Layout of Bedrooms: 1st Floor: * Living room with gas fireplace * Dining room / Kitchen / lounge area and dining nook * Master Suite with 1 Queen bed and with private bathroom Full bath/ shower * 1/2 bath 2nd Floor: * Library/office * 2 Twins room and sitting area * Master Bedroom with King... View all property information
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    Orleans, Cape Cod 02653
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    This beautiful 2 bedroom home is located in the Tonset area of East Orleans with a great swimming area a mile down the street, a boat or kayak launch 3/10’s of mile away, and only 2 miles to Nauset Beach or everything Main Street in Orleans has to offer. The home is situated on a corner lot with a... View all property information
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    Orleans, Cape Cod
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    1 / 18
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    Brand new to the rental market for the 2016 Season! This 3 bedroom Cape Cod charm is bright and airy. This beautiful summer home is appointed with your comfort in mind and decorated with your love of Cape Cod at heart. Simple luxuries include hardwood floors, flat screen TV, DVD, Ping Pong Table... View all property information
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    Orleans, Cape Cod 02653
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    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Enjoy a nice private location with a large yard and extra garage for storage of bikes and beach items. This studio cottage offers a living room with a Full Sleeper Sofa and Cable TV, WIFI Internet & A/C. For your convenience there is a small kitchenette with a stove (no oven) and small apartment... View all property information
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    Orleans, Cape Cod
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    Home sleeps 14 close to Nauset Beach RATES DRASTICALLY REDUCED Nauset Heights Gem-- Nestled at the end of a gravel cul de sac, this well-loved home is ready to become the canvas for new Cape Cod memories. 6 Rabbit Run was designed for entertaining & accommodating family & friends. The Great Room,... View all property information
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    Orleans, Cape Cod 02643
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    19 Uncle Harveys Way (ID #130652) ~ 3 Bedroom Home with WiFi and a/c units Not far from town landing for launching your kayak. Three bedroom 2.5 bath home that sleeps 7. One king and 5 singles. About a 1.4 to Nauset Beach in Orleans. Spacious, airy and bright best describes this home. First floor... View all property information
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    Orleans, Cape Cod 02643
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    A very unique haven situated on what was a private family compound with private beach on Cape Cod Bay. The beach is less than 700 feet away via a beautiful sandy path which passes a cranberry bog along the way. The rambling, airy & bright 3000 sq. ft. home has been renovated over the past several... View all property information
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    Orleans, Cape Cod 02653
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Open updated home only 1/10th of a mile to The River that leads out to Pleasant BAY NEW LISTING FOR 2016 Great Cape Escape Vacation Home sitting on 1.53 acre lot offers privacy in East Orleans! This bright, open contemporary home located in the exclusive Jack Knife Point Association offers peeks of... View all property information
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    Orleans, Cape Cod 06543
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    4 Seaview Rd East Orleans (ID #130778) ~ Oceanside Two Bedroom cottage ~ Mill Pond Area Darling little Cape cottage. Enjoy simple summer living in this peaceful setting of cottages near Mill Pond. This property offers wireless internet, two comfortable bedrooms with A/C units, a bright living... View all property information
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    Orleans, Cape Cod 02653
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Overlooking the salt waters of Mill Pond and located in grand Ocean Harbor Estates! The Atlantic Ocean is just beyond this amazing waterway. Only 2 miles from Nauset Beach and 1.5 miles to East Orleans Village. This property has it all. Views, association dock and tennis court privileges. Open... View all property information
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    Orleans, Cape Cod 02653
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    This clean, spacious 3 bedroom 2.5 bath sits on a beautifully landscaped stretch of land. This home is on a quiet private lane off Nauset Heights Rd. Access to Nauset Beach and inland water is just minutes from this house. 6 minute walk to the Ocean side at Nauset Beach. 10 minute walk to Priscilla... View all property information
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    Orleans, Cape Cod 02653
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    NEW LISTING! Beautiful vacation home perfect for the extended family- set on an acre-plus lot on a quiet cul-de-sac offering association access to Pilgrim Lake (just a short 1/2 mile walk through the neighborhood), along with saltwater access to Arey's Pond less than 1/4 mile away! This rambling... View all property information
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    Orleans, Cape Cod 02653
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    New Listing! Bright and spacious ranch located on a wonderful, 1.2 acre level lot off a quiet lane the desirable Barley Neck area of East Orleans. With A/C units in the living area, loft and bedrooms, and brand new finishes and furnishings throughout! Two bedrooms are on the main floor, each with a... View all property information
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    Orleans, Cape Cod 02653
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    5 of 5 stars (2) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Classic Nauset Heights! Walk to Nauset Beach & Views of Atlantic Ocean! Unique extras like rain shower, summer reading library, mid-cen artwork, mature gardens and 900 sq ft deck. New Outdoor Shower, A/C in Beds, Beach chairs /wagon provided! 5-minute walk to Nauset Beach, views of the Atlantic... View all property information
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    Orleans, Cape Cod 02653
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    This beautiful Cape Cod home sits on Barley Neck, which is small peninsula just a few minutes drive to Nauset Beach. Beach sticker for parking is included in your rental! It is surrounded by Meeting House Pond and Little Pleasant Bay. This area is harbored from the Atlantic Ocean by Pochet Island.... View all property information
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    Orleans, Cape Cod 02653
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    40 Fox Ridge Drive, East Orleans MA (ID# 130420) Light and Bright custom built Post & Beam is perfectly situated on the .62 lot surrounded by perennials for every season of the year including Hollies, white viburnums, PJM Rhodys, Laurel, weeping cherry, Norway Maples to name a few. This custom home... View all property information
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    Orleans, Cape Cod 02643
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    This 4 bedroom, 3 and a half bath rental sits in a quiet area of Orleans. It is a quarter mile to Pah Wah Landing Conservation area on Little Pleasant Bay and a short walk through the conservation area to the beach. Little Pleasant Bay has great kayaking and boating from nearby Portanimicut Launch... View all property information
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    Orleans, Cape Cod
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    On the grounds of the Pleasant Bay Community Boating property, Square Top Cottage is a true Cape Cod Gem. Included with your stay is a residential membership in the organization. This entitles your family to one free sailing lesson during your vacation. The cottage is simply stunning, with endless... View all property information
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    Orleans, Cape Cod
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Beautifully furnished historic home in the Nauset Heights area of East Orleans. Walk to private Association beach or to Nauset Beach (public/lifeguards) on the Atlantic in minutes. Sliders from open dining room and living room to large screened porch overlooking expansive backyard. There is also a... View all property information
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    Orleans, Cape Cod 02653
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    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    12 Heritage Drive, Orleans MA (ID#118899) Lovely, spacious colonial home near Pah Wah Pond and equidistant to Nauset Beach or Skaket Beach and centrally located to Pleasant Bay, Chatham and National Seashore Beaches. A gorgeous kitchen with stainless appliances and granite counters opens to a... View all property information
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    Orleans, Cape Cod 02653
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    The elegantly refined 5 bedroom home overlooking the water is a true vacationer's dream. Outfitted with every amenity one could want, this home will impress the most discerning renter. Spend the day at the beach, and come home and rinse off in the outdoor shower. Or soak in the Jacuzzi Tub in the... View all property information
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    Orleans, Cape Cod
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    This elegant retreat overlooking the water is perfect for discerning renters looking for a true Cape Cod experience. Enjoy the breathtaking views from your open concept main floor. Sit outside and watch the water as you soak in all that nature has to offer. Spend the day at the beach, and come home... View all property information
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    Orleans, Cape Cod
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    A classic but not ordinary cape!!! Newly all renovated sunny cape home in East Orleans very close to the fabulous Nauset beach. Walk to the village for dinner or ice cream. Situated on a lovely cul-de-sac with great yard and gardens. All furnishings are brand new with all the amenities-- bright... View all property information
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    Orleans, Cape Cod 02653
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    Just 0.3 miles to Private Pleasant Bay Beach!! This 4 bedroom / 2 bath home features nice furnishings and amenities with access to a deeded path to a private beach on Pleasant Bay. It is about 3/10ths of a mile to the beach. The path is up a slight hill and wooded. The first floor features a... View all property information
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    Orleans, Cape Cod 02653
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    AT SKAKET BEACH! This charming renovated 1927 Cape has ample room for 6, a master bedroom with a vaulted ceiling and a private half-bath, plus a lovely wraparound porch with hammock. The sunny interior features newly-painted floors, comfy furnishings throughout and excellent amenities, including... View all property information
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    Orleans, Cape Cod 02653
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    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    25 B Doane Road, East Orleans (ID# 106441) Nauset Heights Adorable 2 bedroom cottage in Nauset Heights. Peeks of Mill Pond and around the corner from the landing. Cute, clean and charming 2 bedroom, 1 bath cottage with central air conditioning, part of the Pilgrim Lane cottages. Comfortable... View all property information
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    Orleans, Cape Cod 02653
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Nauset Beach!! At this lovely East Orleans vacation rental home you can enjoy the best of Cape Cod. This 4 bedroom, 2 bath home has everything you need for a comfortable stay here in East Orleans. There are A/C units, WIFI internet access,, outdoor grill and plenty of outdoor living space. The... View all property information
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    Orleans, Cape Cod 02653
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    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Location, Location! Popular duplex cottage very close to Skaket Beach on Cape Cod Bay. Simple and beachy, each side rents separately and has their own deck. Unit 1 has three bedrooms (#428); Unit 2 has two bedrooms (#429). Both share the enclosed outdoor shower. Brand new Central AC! Additional... View all property information
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    Orleans, Cape Cod 02653
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    27 Pond Road, Orleans (ID# 22347) Nestled on a private 1.5-acre wooded lot, this charming and newly constructed home combine’s comfort with gracious living! The large kitchen features high-end appliances, marble counters, breakfast booth with bay windows and opens to the dining area and living... View all property information
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    Orleans, Cape Cod 02653
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    Bright and newly remodeled beach house located at the end of a sandy lane only 2/10ths of a mile from Skaket Beach on Cape Cod Bay. Enjoy the panoramic salt marsh views and peeks out the The Bay. The brand new kitchen, two living areas, flat-screen TV and multiple decks make this home a great spot... View all property information
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    Orleans, Cape Cod 02653
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Charming home located on a nice wooded lot in South Orleans with lovely furnishings, central Air Conditioning, and all amenities. Just a short distance (1/4 mile) to the boat ramp on Quanset Pond with access to the saltwater of Pleasant Bay. Accepts dog with $50 pet surcharge. Additional amenities... View all property information
    Location Information
    Orleans, Cape Cod 02653
    1 / 16
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Wi-Fi
    • Outdoor Dining Area
    • Grill
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Holly Tree Cottages Quarterdeck Guest House. A fantastic location only 1/10th of a mile from gorgeous Nauset Beach on The Atlantic! Listen to the waves breaking on a quiet evening, or enjoy an early morning walk on the dunes. You'll love eating breakfast in the sunny family dining room or on the... View all property information
    Location Information
    Orleans, Cape Cod 02653
    1 / 17
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Wi-Fi
    • Satellite TV
    • Porch
    • DVD Player
    • Washer
    • Grill
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Walk to Skaket Beach! Spacious home tucked away at the end of a quiet cul-de-sac only 6/10ths of a mile from the sandy shore of Cape Cod Bay. Offering great privacy on 1.3 acres, the highlights of this home are its wonderful family room with cathedral ceiling and wood stove, brand-new kitchen,... View all property information
    Location Information
    Orleans, Cape Cod 02653
    1 / 17
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Grill
    • Outdoor Dining Area
    • DVD Player
    • Porch
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Step back in time in this classic turn of the century cottage with views of Cape Cod Bay. Located on a wonderful property with an expansive yard, a screened-in porch and a path down to the sandy shore of Cape Cod Bay. Additional amenities include: beach chairs, crock pot, room fans, lobster pot,... View all property information
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    Orleans, Cape Cod 02653
    1 / 25
    3 Bedrooms, 4 Bathrooms, Sleeps 7 | Quick View
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    • Porch
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    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Truly a one-of-a-kind contemporary home on Little Pleasant Bay! Set on over an acre of wooded land, this light and bright beach home has multiple decks, a screened porch and views of the water from nearly every room. Sliders in the living room and kitchen/dining area open to a large wrap-around... View all property information
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    Orleans, Cape Cod 02662
    1 / 20
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
    • Air Conditioning
    • Washer
    • Satellite TV
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    • Outdoor Dining Area
    • DVD Player
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Absolutely charming Cape located in the very desirable Briar Springs area of East Orleans. Situated on a very beautiful and spacious lot, this home is light and bright throughout, offers lovely furnishings and is meticulously kept evoking the feeling of a true vacation get-away. The first floor... View all property information
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    Orleans, Cape Cod 02653
    1 / 19
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Satellite TV
    • Grill
    • Washer
    • Porch
    • Patio
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Completely renovated, absolutely gorgeous, Sea Captain's home located on over an acre in the highly sought after Nauset Heights area of East Orleans. Enjoy the light and breezy feeling throughout, the wonderful screened-in porch and the spacious deck with peeks of the ocean. A wonderful vacation... View all property information
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    Orleans, Cape Cod 02653
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
    • Washer
    • Satellite TV
    • Grill
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    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    238 Tonset Road, East Orleans (ID# 113528) Charming home near Town Cove and Asa s Landing. This beautifully decorated, pristine 3 bedroom home also has an adorable 1 bedroom cottage right next door. Perfect for the group that needs a little privacy or extra room. Equipped with central air and... View all property information
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    Orleans, Cape Cod 02653
    1 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Parking
    • Internet Access
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    • Air Conditioning
    • Satellite TV
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    • Patio
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    61 Captain Linnell Road, Orleans, MA (ID# 100002) Near Skaket Beach Spacious, beautifully updated, dog friendly home near Skaket Beach. Large granite and stainless kitchen opens to dining area, living area and office. Sliders to deck, brick patio, back yard and fire pit. First floor bedroom with... View all property information
    Location Information
    Orleans, Cape Cod 02653
    1 / 24
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Grill
    • Internet Access
    • Air Conditioning
    • Washer
    • Satellite TV
    • Parking
    • DVD Player
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    4 High St., East Orleans, MA (ID# 125934) CLose to Nauset Beach 2016 Lovely home near Nauset Beach. 4 bedrooms all on second floor with central air on upper floor only. Open kitchen/sitting area as well as living room, dining room and laundry on first floor. Large deck and huge flat back yard... View all property information
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    Orleans, Cape Cod 02653
    1 / 13
    3 of 5 stars (1) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • DVD Player
    • Satellite TV
    • Washer
    • Internet Access
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Listen to the waves in this historic home or walk to Nauset Beach! Home was once part of the Mayo Duck Farm and at one point a restaurant with a huge local following. Now devided into 2 separate rental units. Located 2/10 of a mile from the Atlantic and Nauset Beach this vacation spot is... View all property information
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    Orleans, Cape Cod 02653
    1 / 22
    1 of 5 stars (1) Terrible
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
    • Grill
    • Patio
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Enjoy dining al fresco on the patio with a gorgeous ocean view at this cozy Cape Cod home. Grab one of the two beach chairs and head to Nauset beach, just a few blocks away - you'll be relaxing in no time! Additional area beaches are nearby and you're also not far from the fishing mecca of Mill... View all property information
    Location Information
    Orleans, Cape Cod 02643