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Orleans Vacation Rentals

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    Travellers to Orleans are booking June dates now. Secure your vacation rental today, and have the perfect trip.
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Hilltop Home1 / 16
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Private, updated 2 bed, full A/C, adjacent Conservation land This is a unique ranch in beautiful East Orleans, neighboring the Orleans Conservation Area. At the end of the road you'll find nature trails in conservation land and along the saltwater estuary of Little Pleasant Bay, where you can walk...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    New bedroom suite, recently expanded living room, flat screen TV's and 2nd full bath! This quaint 3 bedroom, 2 full bathroom Cape Cod Vacation Cottage is located on a spacious corner lot located just 3/10 of a mile from beautiful Skaket Beach in Orleans. Enter into cheerful living room, here you...
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    Orleans, Cape Cod 2653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    Adorable cottage located in a beautiful, quiet area about 3/10ths of a mile from Nauset Harbor. The cozy living/dining/kitchen area features a brand new kitchen, queen sofa bed and A/C unit. The bedroom has a king bed (easily converted into 2 twins) and an A/C unit. A separate laundry area has a...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
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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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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Spectacular Location! An outstanding waterfront spot offering exceptional privacy. Want to unplug? This simple, rustic cottage (no wifi, no TV) is on a peninsula surrounded by salt water and has views of Mill Pond. Launch your kayak or boat from its shore to access Nauset Inlet and to the beautiful...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Designed to look like an illustration from a children’s fairytale, this gracious and comfortable vacation home promises a magical vacation any time of the year. Enter through lush gardens into a surprisingly spacious, fully air conditioned home designed with relaxation, convenience, and fun in...
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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 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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Our charming home is well appointed with all you need to have a great vacation. Air conditioned, fully furnished kitchen to make your meals, barbecue grill in the backyard. The deck is surrounded by mature trees and plants adding a beautiful setting for a relaxing vacation. A fabulous outdoor...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Salt waterfront home located in the Ocean Harbor Association in East Orleans. This newly-furnished home is set on over an acre of beautiful multi-level grounds with frontage and views of Little Cove. Enjoy kayaking right from your backyard, access to the association tennis courts or deepwater...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Charming 2-bedroom cottage in East Orleans, on a private lane off Tonset Road. The bedrooms have a queen, and 2 twins; full bathroom. Eat-in kitchen open to living room with ductless A/C unit to cool the cottage. Only a half-mile to Tonset Harbor beach for swimming and boating. Lovely outdoor...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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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    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
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 14
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    28 Kings Way, Orleans MA (ID# 95117) 2018 Season! Adorable 3 Bedroom, 2 Bath Cape style home close to Skaket Beach. Convenient to Nauset Beach, Orleans Town Center, and the bike trail. Main level includes large living area, eat in kitchen, bedroom with two twins and full bath. Second level has main...
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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 8 Quick View
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    Wonderful home in very private East Orleans setting! Screened-in porch off the well-equipped kitchen area to enjoy all our summer meals. There is even a large deck off kitchen for grilling and relaxing. There are (3) bedrooms on first level including (1) king bedroom suite, and also (2) Queens size...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Freshwater Lakefront! Wonderful, newly renovated cottage set on 1.5 acres on Pilgrim Lake! Bright and open with cathedral ceilings, large fireplace and walls of glass overlooking the lake. This great spot offers much privacy with access to the fresh water out your back door, along with...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Nauset Heights! Absolutely lovely, newly built guest house located just under a half mile from the sandy shore of Nauset Beach on The Atlantic. Designed with the cozy character of a barn with the finer amenities of today. Beautifully detailed throughout with authentic wide pine floors, sliding...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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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    Located right on the shore of beautiful Town Cove in Orleans. This family home has 3 bedrooms 2 baths and a view of the water which is special. This classic Cape Cod home is one floor living with all 3 bedrooms on the main floor. The master has a Queen with private bath with a walk-in shower, BR2...
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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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    Recently renovated, spacious two-bedroom home with CENTRAL AIR-CONDITIONING sleeping six tucked up on a wooded knoll at Bakers Pond. This spot offers much privacy and is less than .1 mile to beautiful freshwater swimming and kayaking on the pond. This location feels removed from it all, yet is...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    8 Hofe Road 183921 / 11
    (2)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    8 Hofe Road, Orleans MA (ID# 18392) ~ Close to Skaket Beach and Bike Trail 2018 Season! Quoted by a previous tenant this is the best rental for the money....! Spacious ranch minutes away from Skaket Beach and the Cape Cod Rail Trail! Sliders lead from the dining area to a large shaded deck which...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    4 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    • Cable/satellite TV
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    • Waterfront
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    • Private Outdoor Pool (Unheated)
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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 Open June weeks JUST REDUCED 20%! (click the rates tab for the new rates) Rents Sunday to Sunday during peak season   Please click on the 'Virtual Tour' to see a 3D...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 15
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    This 3 bedroom Cape Cod charm is bright and airy. This beautiful summer home is appointed with your comfort in mind and decorated with your love of Cape Cod at heart. Simple luxuries include hardwood floors, flat screen TV, DVD, Ping Pong Table and window A/C units in all of the bedrooms to keep...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    NOW WITH CENTRAL A/C! Comfortable 4-bedroom home located on a quiet dead end road just a short distance from Rock Harbor and the Cape Cod Rail Trail. Bathrooms recently updated, hardwood flooring, water filtration system, Wifi Internet access 55-inch TV, DVD. Enjoy the outdoors or relax in the...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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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, 2 Bathrooms, Sleeps 5 Quick View
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    Charming ranch on a quiet lane offering a idyllic setting right on Henson's Cove. There are many ways to enjoy the outdoors at this wonderful location. Bring your kayak or canoe to paddle Pleasant Bay, enjoy beautiful fresh water swimming at nearby Crystal Lake, walk the conservation land of Kents...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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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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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Location, Location! Popular duplex cottage very close to Skaket Beach on Cape Cod Bay. Simple and beachy, each side rents separately and has its own deck. Unit 2 (#429) with two bedrooms, has a new kitchen for the 2014 season. Unit 1 (#428) has three bedrooms. Both share the enclosed outdoor...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Completely renovated, absolutely gorgeous, Sea Captain's home located on over an acre in the highly sought after Nauset Heights area of East Orleans. Enjoy the light and breezy feeling throughout, the wonderful screened-in porch and the spacious deck with peeks of the ocean. A wonderful vacation...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Minute Walk to Nauset Beach, Ocean View1 / 24
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Unique Nauset Heights home with lookout deck, 250 yards to Nauset Beach ** Please note: $500 Minimum for off-season stays!** Classic Nauset Heights! Walk to Nauset Beach & Views of Atlantic Ocean! Unique extras like rain shower, summer reading library, mid-century artwork, mature gardens and 900...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Ideally located only a short stroll to Orleans Village and the Barley Neck Inn or a 10 minute bike ride to beautiful Nauset Beach, this newly renovated 2-bedroom is fully equipped for your total relaxation and enjoyment. Nestled among two acres of secluded woods and wetlands, 'Teal Pond' is located...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Sweeping Bay Views, Privacy, Two Full Kitchens  (Pets Considered)  Peak Summer Weekly Rates: $4,300 - $4,500 Rents Saturday - Saturday during peak season This unique vacation home is nestled between Rock Harbor to the east and Skaket beach to the west. The home has its own private boardwalk...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Three bedroom with A/C * Wireless Internet * NO Pets Accepted 2018 Season! Located on a quiet street in a private setting this 3 bedroom, 3 bath tri-level home is just 1/2 mile to Rock Harbor & a short drive to Skaket Beach and the local shops and restaurants in Orleans! There is an AC unit in...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    This charming and pristine contemporary ranch, nestled in a private wooded paradise-Mayflower Point, is minutes by foot to private salt and fresh water accesses for boating, swimming, or fishing. Launch a kayak at ''The River'', leading to Pleasant Bay and the outer beaches, or, if you prefer,...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedroom by Nauset Beach1 / 18
    (4)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    100 Yards from Water! Its hard to beat the location and value of this charming, well-appointed, 3 bedroom cottage on picturesque Nauset Heights with a short walk to both inland waterways and famous Nauset Beach. Set in a beautiful and relaxing setting - a perfect refuge. 3 Bedrooms. One Queen....
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, 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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    Bright and spacious ranch located on a wonderful, 1.2 acre level lot off a quiet lane the desirable Barley Neck area of East Orleans. With A/C units in the living area, loft and bedrooms, and brand new finishes and furnishings throughout! Two bedrooms are on the main floor, each with a Queen bed...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Superb Pleasant Bay Views, from Large, Luxurious, Secluded Orleans Vacation Home. Peak Summer Weekly Rates: $4,850 - $6,250 Rents Saturday to Saturday during peak season Linens Included Please click on the 'Virtual Tour' to see a 3D tour of the home Nestled in the woods of South Orleans on...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 10
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    At the end of a private lane lies your secluded vacation retreat on tranquil Pilgrim Lake. Just 60 feet from the decks and living room window is your private lakefront with boat dock for swimming, boating or fishing. The main deck, overlooking the water with comfortable outdoor furniture and gas...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Bike to Ocean and Bay beaches from this Orleans vacation home. Beautiful 3 bedroom, 1 bathroom, plus Outdoor Shower. Ranch style home. This home is a peaceful and charming property offering quick access to all of Cape Cods charm and activities. The open floor plan is perfect for entertaining with a...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    World famous Nauset Beach is short walk from your door and the Village of East Orleans is the same distance in the other direction. You will find this home very spacious with a living room with game table, family room that boasts cathedral ceilings, dining room, large kitchen and 1/2 bath on the...
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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 9 Quick View
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    6 mins to beach, open & airy living space, huge yard This recently remodeled 4 bedroom just 1.5 miles or a 5 minute drive from Nauset Beach offers lots of open living space inside and out. 2 living rooms and a lower level entertainment area give this home room for the whole family to gather...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Incredible spot! Expansive Cape cottage on a bluff in Nauset Heights overlooking Nauset Inlet and the Atlantic with a newer upper level deck and a private stairway down to the beach. Casual Olde Cape Cod with pine panelling throughout. The main floor bedrooms consist of a large bedroom with double...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Chill out (now with central A/C!) and relax at this wonderful waterfront retreat located in Mayflower Point. This charming cottage offers wonderful views of Lonnie's Pond and Kent's Point. Enjoy its own path down a slope to Lonnie's River that leads out to Pleasant Bay. Perfect for boating or...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pleasant Bay Retreat1 / 19
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Located 1/10 of a mile from the private saltwater beach on Pleasant Bay via an Association path, this multi-level contemporary offers a peaceful retreat on Shoal Pond in South Orleans. The main level is open and bright, with a wonderfully open great room, fireplace, dining area, kitchen, entry way,...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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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    7 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Charming Antique home with 6 bedrooms plus a den providing accommodations for up to 10 guests. Two kitchens, two living rooms, set on a huge lot in the lovely Barley Neck area of East Orleans. All the beds are new, it has been freshly painted and has a great yard. The barn has 2 miniature goats...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 10
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