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Orleans Luxury Holiday Rentals

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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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    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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    Stunning Ocean Front Luxury Home1 / 19
    (2)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 16 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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    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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    • Cable/satellite TV
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    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   Please click on the 'Virtual Tour' to see a 3D tour of the home Your multi-generational or multi-family summer vacation has...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 15
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    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    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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    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: $16,900-$18.500 Rents from Sunday to Sunday during peak weeks Please click on the 'Virtual Tour' to see a 3D tour of the home Your multi-generational or multi-family...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 16
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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
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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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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    Smoking allowed
    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, 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
    Holiday Rental House - 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
    Holiday Rental House - 4 Bedrooms, 3 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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    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
    Holiday Rental House - 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 17 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: $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
    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 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 notice is the...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 15
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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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    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
    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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    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, minutes from...
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    East Orleans, Orleans 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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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 Originally built in 1800 with a recent addition, this historic property's superb post Colonial exterior belies its...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 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
    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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    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, 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, 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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    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
    Holiday Rental House - 5 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
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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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
    Holiday Rental House - 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
    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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    17 Blue Heron Way (ID# 121865) - Watefront on Namequoit River Summer 2019! Wonderful Waterfront compound with incredible 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...
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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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    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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    ORLEANS HISTORIC 1860'S PET-FRIENDLY HOME NEAR NAUSET BEACH!1 / 34
    (5)Excellent
    6 Bedrooms, 1 Bathroom, Sleeps 12 Quick View
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    Reviewed 12 May 2018
    This house is a delightful spot for a family vacation. Very private and surrounded by forest on 3 sides it is conveniently located near Nauset beach and a short drive from the...
    Reviewed 7 May 2018
    Updated traditional Cape classic. Large grounds with lots of space for kids and dogs to romp and run. Well-groomed garden with lovely flowers. Shade and sun throughout the...
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    Historic 1860's antique Cape Cod home, perfect for groups or families with kids and/or pets! Located in the Pochet area of East Orleans and just a short distance to Nauset Beach, the charming village of East Orleans, and the clear, warm water at Crystal Lake! This Pet Friendly home is set on over...
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    East Orleans, Orleans 2643
    Holiday Rental House - 6 Bedrooms, 1 Bathroom, Sleeps 12
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    Panoramic Views of the Atlantic1 / 26
    (6)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Reviewed 9 November 2016
    The house is designed perfectly for a couple of families who want to rent a beach house for a week or two. It is not only well-designed and practical, but is also spotless and...
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    About this property
    Priscilla Landing is on the Nauset Estuary and has private pathways to the Atlantic. The first floor has 3 bedrooms. One room has Queen sized bed with a private bath. Second room as 2 twins also with a private bath. The Master suite has a King sized bed, Private Bath with walk-in shower and a...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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