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Orleans Holiday Homes

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    Travellers to Orleans are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    All 241 Rentals in Orleans
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    5 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    This 4 bedroom, 3 bath home sits on Namequoit River in Orleans with a private dock off the backyard offering direct access to Pleasant Bay. The first level of the home offers one bedroom with a king sized bed and one bedroom with a queen size bed. The second level features two additional bedrooms,...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    This is a lovely, beautifully furnished 4 bedroom, 3 bath East Orleans property just 500 yards away from Mill Pond Landing and only 2.5 miles from Nauset Beach. It features a well equipped, efficient kitchen for entertaining, a formal dining area, a den with large panel TV, and a comfortable...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Ocean Harbor Estates1 / 22
    (1)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Beautiful 4 bedroom home located in Ocean Harbor Estates that offers tennis, footpath to saltwater beach and boating access to Nauset Harbor and the Atlantic from Little Cove. A traditional Cape set up on a hill with a private back yard bordering a protected bird sanctuary. This home features 4...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    8 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    With its great views of Cape Cod Bay across Namskaket Marsh from upper and lower decks, this charming and newly renovated 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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 8 Bedrooms, 3 Bathrooms, Sleeps 7
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    238 Tonset Road, East Orleans (ID# 113528) 2018 Season! 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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Adorable cottage located in a wonderful East Orleans neighborhood near Mill Pond and Snow Shore Landing. The interior of this cottage is as cute as a button. Updates include new outdoor furniture, mattresses, and brand-new ductless AIR-CONDITIONING. Just steps away from Robert's Cove for great...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Perched beside a saltwater river overlooking Little Pleasant Bay, this 5BR/3BA Orleans home offers a picturesque haven for nature lovers. Bring your kayaks, or rent one locally, and enjoy an afternoon out on the water. Explore hiking trails around Kent's Point Nature Preserve, located across the...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    VERY CLOSE TO NAUSET BEACH!1 / 22
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    This beautifully decorated three bedroom, two bathroom East Orleans home with bright, open contemporary style and is located just a mile to Nauset Beach! Upon entry to this home you will find soaring ceilings with wood beams, charming wood floors, along with a tall brick fireplace, and sliders to...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    Great location near beach and town, newly renovated, sleeps 8 ** NEW for 2018! Complete Renovation with Upgrades! ** All new landscaping New sliding doors leading out to updated patio New carpets Updated paint throughout the home Outdoor shower! New furniture Some new beds New bedding Brand new...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    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, 100 feet away! Additional amenities: Beach Chairs
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    On the Waterfront of Nauset Heights1 / 43
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    BY THE SEA, featured in Coastal Living magazine, is a waterfront beach house on Nauset Beach. If you like sand dunes and salty air, this is a rare opportunity to vacation in Nauset Heights, a quintessential Cape Cod beach community. Step out the door to one of the country’s most beautiful beaches....
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Lovely Cape Cod Vacation Bungalow located in Orleans. The perfect Cape retreat near Skaket Beach and less than .5 mile to Orleans Town Center and Rock Harbor! The bright, nautical-themed living room features a flat screen TV, DVD player, and a sleeper sofa. The kitchen if fully equipped with...
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    Orleans, Cape Cod 2653
    Cabin Holiday Rental - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    20 Deerwood Lane, East Orleans, MA (ID# 120896) 2018 Season! Wonderful Home 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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    10 Bedrooms, 8 Bathrooms, Sleeps 24 Quick View
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    • Waterfront
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    • Hot Tub
    • Private Outdoor Pool (Unheated)
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    Orleans Estate (3 structures) with large heated pool, on Town Cove, Sleeps up to 24 Peak Summer Weeks from $24,500  Linens included   Please click on the 'Virtual Tour' to see a 3D tour of the home Please note:  This property rents Sunday to Sunday in summer for full-week or multiple week terms...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 10 Bedrooms, 8 Bathrooms, Sleeps 24
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    JUNE SPECIAL!! FROM JUNE 2ND-30TH - SAVE AS MUCH AS 30% OFF THE RENTAL RATE!! DEPENDING ON THE NUMBER OF WEEKS YOU BOOK! PLEASE CALL TO RECEIVE DISCOUNT! This very special 4 bedroom, 3 bath vacation rental features handsome wood floors and central air-conditioning. Located on a wooded lot, you can...
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    Orleans, Cape Cod 2653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
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    Walking distance to Meetinghouse Pond, Passive Solar This 3 bed, 2.5 bath retreat with central A/C is hidden away down a semi private drive in East Orleans. It has large sliding glass doors down one side of the home off the living room offering lots of light. Mid-century modern decor fills this...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Secluded Cape Cottage, 3-5 Minute Walk to Beach Peak Summer Weekly Rates: $2,100 Rents Saturday - Saturday during peak season It's possibly one of the best values in Orleans. Located on the Bayside of Orleans, this well-maintained cottage is one of 4 homes on a 25 acre family estate located...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Newly renovated ranch located on a cul-de-sac in the desirable Brick Hill area of East Orleans. Fresh, bright and open with Central Air Conditioning! Enjoy the newer furnishings throughout and all amenities. A great spot convenient to the sandy shore of Nauset Beach and The East Orleans Village.
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Hilltop Home1 / 16
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Peeks of the Atlantic Ocean from this hilltop home in East Orleans! Full of Cape Cod charm with a screened/enclosed sun porch that overlooks an expansive yard. Enjoy your privacy with over an acre of land just waiting for kites, volleyball, soccer, croquet, or shoot some hoops in the basketball...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Walk to Meetinghouse Pond, 3 season porch, pet friendly This beautiful Cape Cod home sits on Barley Neck, a small peninsula just a few minutes drive to Nauset Beach. Surrounded by Meeting House Pond and Little Pleasant Bay, this area is harbored from the Atlantic Ocean by Pochet Island. From this...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    ID#134634,14 Linda s Lane, Orleans 2018 Season! Great location not far away Nauset Harbor, Nauset Beach the Atlantic Ocean and Skaket Beach on Cape Cod Bay watch the sun set over the cape! Located on Lindas lane last house on the left very private yard home sitting on the hill side. Home offers an...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    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....
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Located in desirable East Orleans, Nauset Heights, this beautiful 3 bedroom, 1 bath home is a walk to the Outer North Nauset beach by way of Nauset Heights Association access & a great salt water inlet off the ocean. Private Nauset beach access is just 3/10ths of a mile away, Priscilla Landing...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Unheated)
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    Luxurious Orleans Home with Private Salt Pool, Sleeps 10 (linens included) Peak Summer Weekly Rates: $9,000 - $9,500 Rents Saturday to Saturday during peak season Located on a large private lot in South Orleans, this luxurious property provides the highest level of amenities and diverse indoor and...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Skaket Beach at just 1000 ft!! This gorgeous Orleans vacation rental home is located in the perfect spot for you to enjoy Cape Cod. At this lovely home you will be just 2/10ths of a mile from beautiful private access to Skaket Beach in Orleans on Cape Cod Bay. This home is located on an old Cape...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
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    Our home is located in a quiet upscale neighbourhood close to all amenities. Walk to grocery store, downtown shopping, library, tennis courts and town field. Less than a 5 minute drive to ocean and bay. Quick access to highway and all the surrounding Cape towns. Relax and unwind at With the...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    7 Mallard Drive, Orleans MA( ID# 49614) Close to Skaket Beach 2018 Season! Wonderful home near Skaket Beach, A/C, private yard, quiet neighborhood! 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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 miles to Skaket Beach, 2 King Beds, 3 ACs & WIFI This is a classic Cape Cod home in a private location between the Bay and the Atlantic with cooling cross breezes, close proximity to Skaket Beach and Orleans center. This three bedroom, two bath property with a private yard is 2 miles from...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Beautiful and spacious 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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Skaket Beach at just 2/10ths of a mile, gorgeous marsh views and has been completely renovated & newly furnished in 2013! This rental home is perfect for the family. It has a lovely deck area with deck furniture to enjoy the stunning views, central a/c to keep you comfortable, 3 bedrooms , 1 full...
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    Orleans, Cape Cod 02753
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    This spacious home has it all - spectacular water views from almost every room. Just a short walk to Nauset Beach and multiple decks to enjoy ocean views! The house is well equipped and furnished and offers great living space for a family vacation. With 5 bedrooms and 3.5 baths, this spacious home...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 9
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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!
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    New and upscale with guest house, walk to Skaket Beach SAVE $400/WEEK!  Rates shown reflect a $400/week adjustment for open weeks only. Rents Saturday - Saturday during peak season Linens not included   This home is about a 10 minute walk or a very short drive to Skaket Beach. It's also less than...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Smoking allowed
    About this property
    Built in 2013, this beautiful home abuts conservation land and sits at the end of a cul de sac offering great peace and quiet for your vacation. The interior is clean and nicely decorated and offers amenities like Wifi, cable tv and Central A/C, (central a/c also in lower level). The first floor...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Great privacy in East Orleans! Enjoy this lovely 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 gracefully...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Fall in Love with this expansive 4-BR. Bow Roof House located on a country road in desirable Orleans, within walking distance to Pah Wah landing, where you can launch your boat, kayaks or canoes, or sail to the Outer Beach. The Pah Wah Point hiking trails and a sandy beach at Little Pleasant Bay...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to Cape Cod and enjoy being just a few blocks from the beach at this adorable three-bedroom duplex for six. Located in the small town of Orleans, you'll have lots of room plus a great outdoor space at this home, complete with a nice patio, grill, and outdoor shower. This home is located in...
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    Orleans, Cape Cod 02643
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Heated)
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    Kid friendly
    Smoking allowed
    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, it...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    244 Tonset Road, East Orleans (ID#125800) 2018 Season! Adorable vacation rental located in East Orleans. This property has a screened porch overlooking the private back yard located in a nice neighborhood equidistant to Nauset Beach on the Atlantic Ocean and Skaket Beach watch the sun set over...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    *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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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Cable/satellite TV
    • Grill
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy this gorgeous custom 3 bedroom, 2 bath East Orleans vacation rental that is located just 1/10th of a mile from some of Cape Cod s best inner water ways off of Pleasant Bay and minutes from Nauset Beach & East Orleans Village. This rental home has been tastefully designed with high-end...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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