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Holiday Rentals and Homes in Orleans, MA

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    All 186 Rentals in Orleans
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    €1,653
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    1 Bedroom / 1 Bathroom / Sleeps 3
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    About this property
    1 bedroom - Queen size bed 1 bathroom - stall shower sofa bed - double size open living, dining & kitchen dishwasher refrigerator microwave 2 burner range top toaster oven coffee pot cable TV - DVD wireless internet AM-FM radio - disc player iron & board gas fireplace beach chairs &... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    About this property
    Nice contemporary home with open floor plan located on a natural wooded lot in a pleasant and peaceful neighborhood of South Orleans. Enter into a welcoming first floor that offers a wonderful open living room, dining area and kitchen, and full bathroom with shower and laundry. The second floor has... View all property information
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    Bright, open and very spacious Cape centrally located on a cul-de-sac not far from Skaket Beach, Rock Harbor, The Cape Cod Rail Trail and Orleans Center. A wonderful, very well maintained home-- with a large deck ideal for eating summer meals or reading a book. Now with A/C units in the living room... View all property information
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    1 / 9
    1 Bedroom / 1 Bathroom / Sleeps 3
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    About this property
    Adorable cottage located in a beautiful, quiet area about 3/10ths of a mile from Nauset Harbor. The cozy living/dining/kitchen area features new appliances, a window A/C unit and queen sofa bed. The bedroom has two twin beds (easily converted into a king) and an A/C unit. A separate laundry area... View all property information
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    Pleasant Bay beach. (Private) is only a 3 minute walk away. Located on a private road, our unique, contemporary Cape Cod home offers a secluded setting, and lovely landscaping. The home is completely redecorated with a casually elegant Cape motif for your convenience and relaxation, including air... View all property information
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    1 / 8
    4 Bedrooms / 2 Bathrooms / Sleeps 7
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    About this property
    Antique farm house on a very spacious and private lot in East Orleans. Pochet Inlet is close by for canoeing or fishing. This house is pet friendly. Additional amenities include: room fans, lobster pot, outdoor shower (private/hot water), heat, outdoor furniture, coffeemaker. View all property information
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    €2,158
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    1 / 21
    3 Bedrooms / 3 Bathrooms / Sleeps 7
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    About this property
    Just a 3 minute stroll to the dock at Meetinghouse Pond in East Orleans! Meetinghouse Pond is the inner most deep-water anchorage in Orleans and is connected to Little Pleasant Bay by a network of waterways which are navigable even at low tide. The dock is prefect for swimming , fishing and a... View all property information
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    €918
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    1 / 15
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Chill out and relax at this wonderful waterfront retreat located in Mayflower Point. This charming cottage offers wonderful views of Lonnie's Pond and Kent's Point and has its own path to Lonnie's River leading out to Pleasant Bay. Bedrooms have air-conditioning for your comfort. Perfect for... View all property information
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    €735
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    1 / 7
    Studio / 1 Bathroom / Sleeps 3
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    About this property
    East Orleans Studio has it all. Take one of the deeded private paths to Nauset Beach from this couples getaway located at the end of a private road. The amenities for this spotless getaway include, a King size bed, Double size sleeper sofa (for an overnight guest), Full kitchen with D/W, Full bath... View all property information
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    1 / 11
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Gym
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    About this property
    Quaint second floor apartment in South Orleans. This bright and cheerful, freshly renovated home offers an open floor plan with high ceilings in the kitchen, dining and living room area with ceiling fan, full bathroom, and separate bedroom with king size bed and window a/c. Amenities include... View all property information
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    €2,755
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    1 / 23
    5 Bedrooms / 4 Bathrooms / Sleeps 10
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    About this property
    17 Blue Heron Way - Watefront on Namequoit River Waterfront compound with fabulous views of the Namequoit River and direct access to Pleasant Bay. This property has plenty of room for the extended family with a main house and guest cottage together sleeping up to 12 people. The main house has 3... View all property information
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    €1,240
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    1 / 19
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    1800s Antique Victorian only 1 mile from the Beach! Front porch rockers and side deck overlook the beautiful yard and gardens. The living room, dining room and family/tv room are very welcoming on the main level. One bedroom with a Queen bed is also located downstairs. Three additional bedrooms... View all property information
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    €3,490
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    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    About this property
    As you wind down the long private driveway you begin to appreciate the privacy and natural beauty of East Orleans. Perfectly located close to Nauset Beach and the Village of East Orleans this spotless vacation home is the ideal place to enjoy the full summer days and soft quiet nights of beautiful... View all property information
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    4 Bedrooms / 2 Bathrooms / Sleeps 10
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    • Air Conditioning
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    About this property
    Ultimate privacy and Olde Cape Cod charm in one of the most pristine areas of East Orleans. This home is completely renovated, tastefully decorated, and comfortably furnished for your summer enjoyment. Central A/C, lots of light, extra rooms that ramble with nooks and cubbys and closets at every... View all property information
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    1 / 23
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Well-maintained home privately located 8/10th's of a mile from Baker's Pond. This lovely home is surrounded by mature trees and lush plantings. Enter from the side deck past the entryway on the first floor where you will find a fully equipped kitchen, ample dining area, cozy living room with queen... View all property information
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    €1,929
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    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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    €2,755
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    5 Bedrooms / 4 Bathrooms / Sleeps 11
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    • Pets allowed
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    About this property
    You will find that all your expectations are exceeded in this custom built Cape vacation dream home. The front door opens to an inviting and airy foyer complete with nautical décor and powder room. To the right you enter the large living room with ample seating and flat screen TV with DVD player.... View all property information
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    €1,286
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Spacious AIR-CONDITIONED two-bedroom home sleeping six tucked up on a quiet wooded knoll at Bakers Pond. This wonderful spot offers much privacy and is less than .1 mile to beautiful freshwater swimming and kayaking on the pond. This location feels removed from it all, yet is only a 5-minute drive... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Newly renovated sprawling ranch home located in the beautiful Briar Springs area of East Orleans. The highlights of this lovely, bright and open home are its spacious great room with vaulted ceiling whichs leads out to a large deck, a separate living/dining area, new granite kitchen, master bedroom... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
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    About this property
    Yes, we have WiFi. From the spectacular contemporary Cape its just short walk to Nauset Beach. On the way our guests pass over a scenic foot bridge spanning a tidal stream and walk over the dunes to Atlantic. Enjoy the breathtaking views from top deck area. House is perfectly located in private... View all property information
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    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    • Balcony
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    About this property
    Beautiful 4 bedroom home on private cul de sac in East Orleans. Pristine landscaped yard with swing set and hammock. Big kitchen that opens to the family room. Open den with tv and couches. Full bath, washer & dryer on the first floor. Upstairs has 3 large bedrooms with high ceilings and lots of... View all property information
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    €2,710
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    About this property
    World famous Nauset Beach is short walk from your door and the Village of East Orleans is the same distance in the other direction. You will find this home very spacious with a living room with game table, family room that boasts cathedral ceilings, dining room, large kitchen and 1/2 bath on the... View all property information
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    5 Bedrooms / 4 Bathrooms / Sleeps 10
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    • Waterfront
    • Water Views
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    About this property
    Beach, Kayaks, SUPs on Pristine Orleans Lake! $4,500 PRIME SUMMER WEEKLY RATE Please Note: This home rents Sunday to Sunday in peak summer months Expansive Waterfront Home on Crystal Lake in the heart of Orleans. Crystal Lake is a pristine fresh water lake located close to Orleans Center. The home... View all property information
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    €3,215
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    3 Bedrooms / 3 Bathrooms / Sleeps 10
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    About this property
    20 Hayward Lane, East Orleans Enjoy this lovely, large, sun-filled home in charming East Orleans on a spacious, 1.5 acre private property with saltwater views of Frostfish Cove (leading to Little Pleasant Bay) from almost every room. Relax and watch the boats go by from the large main-level deck,... View all property information
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    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    About this property
    Under 1 mile to Skaket Beach Just under 1 mile to Skaket Beach from this beautiful 3 bedroom, 3 bath home on the bayside of Orleans! Spacious home with all of the desired amenities. Convenient to the bike trail, shopping, and beaches. Main level includes living area, dining room, kitchen, Master... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    123 Areys Lane, Orleans -Property ID: 18226 Surrounded by serene woods, this inviting Cape has much to offer! It features a sunny breezeway/ den that connects to a large eat-in kitchen and spacious living/ dining areas. Three bedrooms (1st floor - queen, 2nd floor - 1 double bed, 3rd bedroom has 1... View all property information
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    €5,235
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Dryer
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    • Waterfront
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    About this property
    Experience the simpler days of Old Cape Cod in this charming and well-appointed home on the water. Salt air, sea breezes and sensational sunsets abound on this private beach at beautiful Skaket Beach. Imagine being able to enjoy swimming, fishing, clamming, boating and sunbathing without having to... View all property information
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    7 Bedrooms / 7 Bathrooms / Sleeps 16
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    • Private Outdoor...
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    About this property
    Main + Guest House, Pool, on Cove, Sleeps up to 16$12,800 PRIME SUMMER WEEKLY RATE (linens included) Please note: This property rents Sunday to Sunday in summer for full-week or multiple week terms only, but is available off-season for weekends and special events. This Orleans Estate is located in... View all property information
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    €1,745
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    3 Bedrooms / 1 Bathroom / Sleeps 6
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    About this property
    Secluded Cape Cottage, 3-5 Minute Walk to Beach$1,900 PRIME SUMMER WEEKLY RATE Book July 4th Week -- Stay an Extra Night at 50% Off! Please ask for details: 508 896-3241​ It's possibly one of the best values in Orleans. Located on the Bayside of Orleans, this well-maintained cottage is one of 4... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    Just 3/10 mile to Fresh Water Pilgrim Lake or 3 miles to Nauset Beach. This lovely three bedroom, two bath home sleeps eight and sits on a wonderful 1.6 acre lot. The first floor offers a fully equipped kitchen, dining area, welcoming living room, game/reading room, laundry, full bath, and master... View all property information
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    Cosy, welcoming home in South Eastham. Our traditional Cape Cod house features 4 bedrooms, 2 baths, and a fully finished basement with easy access to beaches, the Cape Cod Bike Trail, shopping and restaurants. Three bedrooms and the living room have window A/C units. We are on a quiet wooded lane,... View all property information
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Gym
    • Internet Access
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    • Smoking allowed
    • Suitable for children
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    • x
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    About this property
    Large, beautiful 4 bedroom, 3-1/2 bathroom, Colonial style home just 6/10ths of a mile from popular Nauset Beach on the oceanside. This attractively furnished home has a remodeled kitchen, bright sun room, separate dining room, full livingroom, and a full bathroom. All the bedrooms are on the... View all property information
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    4 Bedrooms / 2 Bathrooms / Sleeps 10
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    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    Salt waterfront home located in the Ocean Harbor Association in East Orleans. This newly-furnished home is set on over an acre of beautiful multi-level grounds with frontage and views of Little Cove. Enjoy kayaking right from your backyard, access to the association tennis courts or deepwater... View all property information
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    3 Bedrooms / 1 Bathroom / Sleeps 6
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    About this property
    Charming period home located only 2/10ths of a mile from gorgeous Nauset Beach on The Atlantic. Enjoy the sunny deck, comfortable furnishings, wonderful country kitchen and spacious backyard. Attached apartment also available for rent. Additional amenities include: room fans, lobster pot, cd,... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Enjoy the views overlooking Reuben’s Pond from this comfy 3-bedroom, 2-bath contemporary saltbox offering a bright and open floor plan and updated furnishings. Front-to-back living room with fireplace and a great screened porch open onto a spacious wraparound deck. This great vacation spot is... View all property information
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    3 Bedrooms / 1 Bathroom / Sleeps 6
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    About this property
    Very spacious one-level apartment only 2/10ths of a mile from gorgeous Nauset Beach on The Atlantic. Completely 'refreshed' with new rugs, new furniture and new gas grill. Step down to a second living area to the 'summer room' with a second TV which leads outside to a private patio with an outdoor... View all property information
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    7 Bedrooms / 4 Bathrooms / Sleeps 10
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    • x
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    About this property
    Charming Antique home with 6 bedrooms plus a den providing accommodations for up to 10 guests. Two kitchens, two living rooms, set on a huge lot in the lovely Barley Neck area of East Orleans. All the beds are new, it has been freshly painted and has a great yard. The barn has 2 miniature goats... View all property information
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    3 Bedrooms / 3 Bathrooms / Sleeps 7
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    • x
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    About this property
    With its great views of Cape Cod Bay across Namskaket Marsh from upper and lower decks, this charming home offers peace and privacy. Located on a cul-de-sac with a shady front yard, the house has skylights, sunlit rooms, an open loft with a sleep sofa and sliders to the decks from the living/dining... View all property information
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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    Clean, comfortable and cozy cottage overlooking Rock Harbor Marsh. Wonderful screened in porch for your evening pleasure. 2 Bedrooms, 1 Bath. 1 Double, 2 Twins Additional amenities include: outdoor shower (private/hot water), outdoor furniture, room fans, lobster pot, coffeemaker. View all property information
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    5 Bedrooms / 4 Bathrooms / Sleeps 10
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    About this property
    Enjoy easy access to a gorgeous private association beach and dock on Pleasant Bay from this well maintained property in the beautiful neighborhood of ''East Egg''. This incredibly spacious home offers lovely water views, central air, large kitchen, and game room with regulation pool table, perfect... View all property information
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    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    • x
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    About this property
    NEW CONSTRUCTION! Gorgeous 3-level contemporary home overlooking conservation land and beautiful 28-acre Bakers Pond. With water views from every room, this dramatic home has 3 exterior decks and a private path to the pond only 75 feet away. Set on a cul-de-sac on a private lane, it is .3 mile to... View all property information
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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    Adorable updated two bedroom cottage with a bright screened in porch, outdoor shower and A/C units. Located in the Pine Tree Cottage colony. The first bedroom has a full bedroom and the second has two twins and there is a full bathroom with a shower. This cottage is perfect for a family of four or... View all property information
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    3 Bedrooms / 1 Bathroom / Sleeps 6
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    • x
    • x
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    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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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Suitable for children
    • x
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    About this property
    20 Deerwood Lane, East Orleans, MA Fresh listing in East Orleans with central A/C. Walk to restaurants or Sundae School after a relaxing day at Nauset Beach. This dog friendly (with homeowner approval) home features lots of room with 4 bedrooms, hardwood floors throughout and central a/c with... View all property information
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    4 Bedrooms / 4 Bathrooms / Sleeps 14
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    • Private Outdoor...
    • Satellite TV
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    About this property
    This exceptional compound is one-of-a-kind with a Main House, Carriage House and private pool. The Main house has a restaurant quality kitchen which will bring out the Iron Chef in you. Ample seating in the dining area with separate bar. Entertaining is easy in the Living Room with HDTV and DVD,... View all property information
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • x
    • x
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    About this property
    Comfortable 4 bedroom home located on a quiet dead end road just a short distance from Rock Harbor and the Cape Cod Rail Trail. Enjoy the spacious screened-in porch and all amenities. Additional amenities include: room fans, lobster pot, outdoor shower (private/hot water), heat, dehumidifier,... View all property information
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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Suitable for children
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    About this property
    197 Rock Harbor Road, Orleans, MA Rustic cottage overlooking the Rock Harbor Marsh. Wonderful screened in porch for your evening pleasure. 2 Bedrooms, 1 Bath. 1 Double, 2 Twins. NO PETS ALLOWED. $800 per week in season. $55 Vacation Rental Damage Coverage, $60 Handling Fee (fee s non-refundable).... View all property information
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