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Orleans Luxury Holiday Homes

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    Travellers to Orleans are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    33 Matching Rentals in OrleansView all 224 rentals
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    Stunning Ocean Front Luxury Home1 / 19
    (2)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Executive Waterfront Luxury Home. A/C; Heated Pool & Elevator1 / 29
    (1)Excellent
    4 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    10 Bedrooms, 8 Bathrooms, Sleeps 24 Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    About this property
    30 Chestnut is a bright, charming home in a private, wooded location only steps from a rustic beach on Little Pleasant Bay, where you can take evening walks or explore the shoreline in our double kayak. This is a quiet, serene environment with a large patio where you can cook dinner on the grill,...
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    East Orleans, Orleans 02653
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    4 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    • Hot Tub
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    Private Orleans resort with water views, heated pool & spa; sleeps 15 (linens included) Peak Summer Weekly Rates: $16,000- $17,800 Rents Sunday to Sunday during peak season The new Massachusetts state and local taxes apply to stays starting July 1 or later. Book in June and save!   Please click on...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 15
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    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    Newly Renovated Luxury Waterfront Home, Kayak to Nauset Beach and Pochet Island! -Linens Included- Rents from Saturday to Saturday in July and August $9,500-$9,800/week PRIME SUMMER WEEKLY RATE Please click on the 'Virtual Tour' to see a 3D tour of the home Be one of the first to stay at this...
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    East Orleans, Orleans 02643
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    5 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Private Orleans resort-style compound with heated pool & spa, fire pit and cabana (linens included) Peak Summer Weekly Rates: $16,650-$18.500 Rents from Sunday to Sunday during peak weeks The new Massachusetts state and local taxes apply to stays starting July 1 or later. Book in June and save!...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 16
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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    About this property
    Come to your very own private resort on Cape Cod. Located directly on Nauset Harbor on the Eastham\Orleans town line, The Jeremiah House is the place to be for your quintessential Cape Cod getaway. This luxury home is the perfect convergence of classic old Cape Cod architecture and charm with...
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    Orleans, Cape Cod 02642
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    5-Bedroom Grand Villa, Overlooks Nauset Beach and the Atlantic Peak Summer Weekly Rates: $12,600- $14,000 Rents Saturday to Saturday Linens Included NEW Listing for 2019! Please click on the 'Virtual Tour'tab to take a 3D tour of the home PLEASE NOTE: The new Massachusetts state and local taxes...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Luxurious Orleans Home with Private Salt Pool, Sleeps 10, Linens included Peak Summer Weekly Rate: $9,500 Rents Saturday to Saturday during peak season PLEASE NOTE: The new Massachusetts state and local taxes apply to stays starting July 1 or later. Book in June and save! Located on a large...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Stunning cape contemporary style waterfront home with walls of glass and panoramic salt water views from most every room. Association Dock for access to Town Cove and beyond. This home was completely renovated with designer high-end kitchen, gleaming hardwood floors, custom fireplace, and every...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    95 Nauset Heights Road (ID #18053) ~ Oceanfront Five Bedroom Home ~ Nauset Heights Area 2019 Season! Breath-taking, panoramic Atlantic views from Nauset Heights! A Classic Cape Cod Jewel. Rambling ocean front cottage boasts casual and comfortable charm. The ocean at your doorstep! Outside of the...
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    East Orleans, Orleans 02653
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    Path to Skaket Beach1 / 41
    (3)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Contemporary home with private setting just 3/10 mile walk through a private neighborhood association path to Skaket Beach. Back yard overlooks an active cranberry bog! Near the Cape Cod Bike Trail and less than a mile to Rock Harbor fishing fleet. There are 3 decks and a fully screened porch with...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    5-BR Beach House Directly On Nauset Beach, Best Views on the East Coast Peak Summer Weekly Rate: $8,500-$9,500 Rents Saturday to Saturday Linens included   PLEASE NOTE: The new Massachusetts state and local taxes apply to stays starting July 1 or later. Book in June and save! Perched on the...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    NEW FOR 2019 SEASON. 4 bedroom, 3 bath home surrounded by water views! Woods Cove out front with views of the Atlantic and outer Nauset Beach. Rachel Cove in the back yard that leads to Town Cove. Large living room with flat screen tv leads to back deck overlooking the cove. Gourmet kitchen with...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    Newly updated, heated pool, sleeps 12: 051-O1 / 34
    (1)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Grill
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    Pet friendly
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    Reviewed 18 September 2018
    Orleans was new for our group of 12 family and friends that travel to the Cape every year. Loved it, we were located 1 mile from Nauset Beach, bars and restaurants close to the...
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    East Orleans; magnificent updated historic home, heated pool, A/C, perfect family vacation; Sleeps 13 Peak Summer Weekly Rates: $11,500 - $12,500 Rents Saturday - Saturday during peak season Please click on the 'Virtual Tour' to see a 3D tour of the home   PLEASE NOTE: The new Massachusetts...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 13
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    4 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    Meticulous Modern East Orleans Home, Water Views Peak Season Weekly Rate: $9,000-$9,500 Rents from Sunday to Sunday during peak weeks   PLEASE NOTE: The new Massachusetts state and local taxes apply to stays starting July 1 or later. Book in June and save! The height of modern luxury in East...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 15
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    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    About this property
    Updated East Orleans 6 Bedroom Home with Pool (linens included) Peak Summer Weekly Rates: $7,300 - $8,900 Rents Sunday to Sunday during peak season. Linens included PLEASE NOTE: The new Massachusetts state and local taxes apply to stays starting July 1 or later. Book in June and save! NEW Kitchen...
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    East Orleans, Orleans 02643
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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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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    About this property
    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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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Resplendent in South Orleans, Heated Pool, Sleeps up to 12 Peak Summer Weekly Rates: $9,800 - $10,200   Linens and Bed Making Included Rents Saturday to Saturday in Peak Summer Pets Considered NEW Listing for 2019! Welcome to sumptuous summer living in this magnificent six-bedroom retreat...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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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....
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Located overlooking the sands of Nauset Beach, this spotless vacation home is as true a Cape Cod experience as you could ever find. Complete with 5 bedrooms and 3 full baths, 2 spacious decks for relaxing and grilling, outdoor shower, wireless Internet, AC on the main level, 4 TVs and all the bells...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    Elevated ocean views, walk to Nauset Beach. Linens included. Peak Summer Weekly Rates: $4,500 - $5,200 Rents Saturday to Saturday during peak season   PLEASE NOTE: The new Massachusetts state and local taxes apply to stays starting July 1 or later. Book in June and save! This spacious East Orleans...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Great location. Short walk down Beach Road to Nauset Beach, which many call the best Cape Cod beach. Spacious master bedroom on top floor. Beautiful view toward Nauset Beach from upper deck. Contemporary style. Beautiful lawn and plantings. East Orleans is part of the Quiet East Side of the...
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    East Orleans, Orleans 02653
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    New to the Rental Market for Summer 2018. Large 4 bedroom, 5 bath home sleeps 14. Perfect for 2 families! First floor has a large open living room with TV, master with king bed and own bath, plus bedroom #2 with twin bunk beds. There is a second full bath off the kitchen area. Second floor has...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Secluded East Orleans gem, close to Nauset Beach, sleeps 10 (linens incl)   Peak Summer Weekly Rates: $3,900 - $5,700 Rents Saturday to Saturday during peak season PLEASE NOTE: The new Massachusetts state and local taxes apply to stays starting July 1 or later. Book in June and save! Please...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    First floor master suite and fully equipped separate guest suite make this newer custom Cape an ideal property for two families. The spacious design and top quality appointments in this builders own home assure you a comfortable, relaxing, and memorable vacation you'll truly enjoy. Granite...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    Waterfront Retreat with Scenic Water Views of Woods Cove, and Nauset Beach in Orleans to the Coast Guard Station in Eastham. This lovely contemporary 5 bedroom, 4 bath, 3 level home is set on a private and environmentally beautiful spot in Orleans. Launch your kayak at the water's edge. The first...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Rare Blend of Classic Charm and Spacious Modern Upscale Accommodations, Sleeps 10 Peak Summer Weekly Rates:  $7,200-$7,500 Rents Saturday to Saturday in Peak Season Linens Included   PLEASE NOTE: The new Massachusetts state and local taxes apply to stays starting July 1 or later. Book in June and...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    20 Hayward Lane, East Orleans (ID# 108991) Close to Nauset Beach MeetingHouse Pond, Pleasant Bay and Village of East Orleans 2018 Season! 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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Prestigious location within Quanset Harbor Club Association. Built on 1.3 acres and only 3 houses away from the community’s private beach on beautiful Pleasant Bay. This is the perfect property to enjoy all that Cape Cod has to offer. Home is newly furnished with a new gourmet kitchen with high end...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    170 Pochet Rd, East Orleans Pochet Association NEW 2019! Pochet Association! Unique and beautiful, light and bright, lovely gardens, multiple decks and patios, inside 4 bedrooms, 2 baths, eat in kitchen, separate dining, living room, family room, lots of spaces to relax and enjoy, just 1/10th of...
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    East Orleans, Orleans 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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