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Orleans Luxury Rentals

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    Travelers to Orleans are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    43 Matching Rentals in Orleans
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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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    5 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    4 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    About this property
    Private Orleans resort with water views, heated pool & spa; sleeps 15 (linens included) Peak Summer Weekly Rates: $15,900- $17,800 Rents Sunday to Sunday during peak season Come enjoy Thanksgiving on the Cape! Sit by the fire pit after a wonderful family dinner.   Please click on the 'Virtual...
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    Orleans, Cape Cod 02653
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 15
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    Stunning Ocean Front Luxury Home1 / 19
    (2)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Reviewed April 24, 2018
    Describing this house as stunning is not hyperbole! This truly IS a stunning house in a perfect location. We have booked a week in 2018 making this the fifth year in a row that...
    Reviewed October 2, 2016
    We have stayed in the house for the past 3 years and have just booked it for a week in 2017. It is well-equipped, immaculately clean and large enough for our 3 generation family...
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    About this property
    Windswept is of the most sought-out and beautiful locations on the Cape. This Cape Cod beach house borders Nauset Beach, the National Seashore. Nauset Beach is 15 mile long, excellent for swimming and surfing. The views from the Great Room and the adjacent deck will move you... the sound of the...
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    East Orleans, Orleans 02653
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 16
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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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    Reviewed April 22, 2018
    We just had a glorious week enjoying the incredible views, the majestic house and pool, and of course the natural beauty of the Cape. We have rented our fair share of properties...
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    About this property
    This 6000 sq-ft luxury Estate is a gracious oasis of tranquility with mesmerizing views suitable for family vacations & executive corporate retreats. This luxurious estate features four large Master Bedroom Suites, Elevator, A dinning room that seats 16, Large Living Room, Great Room, Game/Media...
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    East Orleans, Orleans 02653
    Rental Home - 4 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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    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
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    95 Nauset Heights Road (ID #18053) ~ Oceanfront Five Bedroom Home ~ Nauset Heights Area 2018 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
    Rental Home - 5 Bedrooms, 2 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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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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 This spacious East Orleans home is located just off Nauset Beach in the desirable Grand View neighborhood. This neighborhood is characterized by...
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    Orleans, Cape Cod 02653
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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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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    Reviewed 1 week ago
    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: $9,500 - $12,000 Rents Saturday - Saturday during peak season Please click on the 'Virtual Tour' to see a 3D tour of the home   The interior of this beautiful 1920...
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    Orleans, Cape Cod 02653
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 13
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    6 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    About this property
    Cape Cod elegance describes this beautiful, expansive home which sits peacefully at the end of the cul-de-sac adjacent to a cranberry bog. Ideal for the larger gathering with its great room with soaring cathedral ceiling, gorgeous eat-in kitchen, spacious TV loft, screened porch, deck and patio....
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    Orleans, Cape Cod 02653
    Rental Home - 6 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
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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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...
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    Orleans, Cape Cod 02653
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Nauset Heights! Classic Cape Cod beach house overlooking the Atlantic. Expansive great room with fieldstone fireplace, wrap around porch, and views from practically every room! FRIDAY to FRIDAY rental.
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    Orleans, Cape Cod 02653
    Rental Home - 6 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sweeping Views, Central AC with Pool1 / 43
    (1)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Reviewed August 14, 2018
    The location is wonderful with views for days. Easy access to Nauset, East Orleans businesses and all the Cape has to offer. Our family of six stayed for one week and we...
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    Access to small private beach and kayak launch in East Orleans This beautiful and well appointed 5 bedroom has recently been fully remodeled. There are sweeping views of Nauset Harbor stretching all the way to Nauset Light. Beautifully redone with an architect's eye, it boasts full central AC,...
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    Orleans, Cape Cod 02653
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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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 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
    Rental Home - 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:  $5,900-$7,200 Rents Saturday to Saturday in Peak Season Linens Included & Pets Considered NEW Listing for 2018! Originally built in 1800 with a recent addition, this historic property's...
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    Orleans, Cape Cod 02653
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    8 Stony Island Way, Orleans MA (ID# 96304) 2018 Season! Waterfront on Woods Cove with views out to Nauset Marsh. A great launch site for canoes or kayaks to explore Nauset Marsh and the beach. 5 bedroom, 4.5 bath home in East Orleans on 2.5 acres adjacent to 5 acres of conservation with privacy and...
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    East Orleans, Orleans 02653
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Newer & Stunning 5800 sq ft estate in Orleans, Tonset Area, Sleeps 12 Peak Summer Weekly Rates: $6,900 - $7,500 Rents Saturday to Saturday during peak season Linens Included beds not made Please click on the 'Virtual Tour' to see a 3D tour of the home All weekly rentals include access to Ocean...
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    East Orleans, Orleans 02643
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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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
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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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, it...
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    Orleans, Cape Cod 02653
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Home sleeps 14 close to Nauset Beach 2018 Season, NAUSET BEACH only 2/10 of a mile away! 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...
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    Orleans, Cape Cod 02643
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    55 Barley Neck Rd (ID #131073) ~ Waterviews, Private Pool, Central A/C ~ Meetinghouse Pond 2018 Season! Sweet Retreat on Barley Neck in East Orleans! This bright and airy home has gentle slopping views of Meeting House Pond, a private pool, new screen room and patio/outdoor fire pit. Close to the...
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    East Orleans, Orleans 02653
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Meticulous Modern East Orleans Home, Water Views, Pets Considered Peak Season Weekly Rate: $8,000-$8,500 Rents from Sunday to Sunday during peak weeks The height of modern luxury in East Orleans, this home has tremendous views of Nauset Inlet and the Atlantic Ocean beyond. The first thing you'll...
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    Orleans, Cape Cod 02653
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 14
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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
    Rental Home - 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
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    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 NEW Kitchen for 2018! Fully remodeled kitchen with high end appliances. It's the best of all worlds at this unique East Orleans...
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    East Orleans, Orleans 02643
    Rental Home - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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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
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    2013 WATERFRONT HOME! Gorgeous 3-level contemporary home with 180 degree view of a beautiful 28-acre lake and conservation lands. 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...
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    Orleans, Cape Cod 02653
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    3 BR | 3.5 BA | Sleeps 8 Built by the present owner's grandfather in the 1930's, this home is as close to the water as you can get. All rooms have views of beautiful Pleasant Bay. The ground floor boasts a new, fully-equipped, kitchen, a guest half bath, a large living room, a den/breakfast nook, a...
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    Orleans, Cape Cod 02653
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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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: $7,500-$7,900 Rents Saturday to Saturday Linens included NEW Listing for 2018! Perched on the dunes overlooking the open Atlantic you'll find this stunning beach house with easy access to Nauset...
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    Orleans, Cape Cod 02653
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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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
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Spacious Nauset Beach Home Sleeps 14+, 5 minute walk to beach, hot tub (Linens Included) This HUGE home is nestled just off the Atlantic in East Orleans, under a half mile from famous Nauset Beach.  The spacious home boasts 4000 square feet and 3 levels of living space, 5 bedrooms and 5 full...
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    East Orleans, Orleans 02643
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    63 Briar Spring Road in East Orleans (ID #18264) ~ Waterfront Three Bedroom Home ~ Pochet Inlet Area 2018 Season Wonderful views! This updated home overlooks beautiful Pochet Inlet. Newly built in 2014, this property offers a spacious and open LR/DR/KIT located on the second level with a bonus room...
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    Location Information
    Orleans, Cape Cod 02653
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Path to Skaket Beach1 / 41
    (3)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Parking
    • Washer
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Washer
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Open updated home only 1/10th of a mile to The River that leads out to Pleasant BAY 2018 Season! 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 the...
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    Orleans, Cape Cod 06543
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    11 Surf Boat Lane 183381 / 17
    (1)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Balcony
    • Wi-Fi
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    • Cable/satellite TV
    • Patio
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    11 Surf Boat Lane, East Orleans MA (ID# 18338) ~ Nauset Heights 2018 Season! Gorgeous new Kitchen!Casual living in Nauset Heights! Follow down road to the path that takes you through dunes to the ever so popular Nauset Beach on the Atlantic Ocean. Large contemporary 4BR/ 2.5BA home. Main level...
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    East Orleans, Orleans 02653
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
    • Hot Tub
    • Patio
    • Washer
    • Wi-Fi
    • DVD Player
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    29 Nauset Road, East Orleans, MA (ID# 18082) ~ Nauset Heights 2018 Season! 'The White Heron' is a wonderful and large Nauset Heights home just steps to Nauset Beach! Spectacular views of the ocean and gorgeous sunrises are enjoyed from every room and both decks! The main floor includes a spacious...
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    Location Information
    East Orleans, Orleans 02653
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 9
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Washer
    • Grill
    • Cable/satellite TV
    • Patio
    • Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Huge yard with fire pit, finished basement with toys and games, central AC 'Lucky Enough,' a charming and spacious ranch on Pochet Neck, has everything your family needs for the perfect summer getaway. Fully-equipped for kids of all ages, this vacation home has a finished basement with family room...
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    Location Information
    Orleans, Cape Cod 02653
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • DVD Player
    • Grill
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Updated, Spacious & Private, Sleeps 12 with Carriage House and Pool Peak Summer Weekly Rates:  $9,450 - $10,500 Rents Saturday to Saturday in peak season Linens Included   NEW Listing for 2018! A short stroll from a saltwater landing on Nauset Inlet you'll discover this vacation treasure in...
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    Location Information
    Orleans, Cape Cod 02653
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Parking
    • Washer
    • Wi-Fi
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Orleans, Cape Cod 02653
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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