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Holiday Rentals in Orleans

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    Travellers to Orleans are booking September dates now. Secure your holiday home today, and have the perfect trip.
    All 231 Rentals in Orleans
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    22 Uncle Vicks Way 184011 / 14
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    About this property
    Enjoy the comfort of this conveniently located and well-appointed newer home. Nauset Beach (oceanside) with full amenities (restrooms, outdoor showers, Liam's for seafood, burgers, ice cream and more) is just a short drive (3.5 mi) from the house. Skaket Beach on the Cape Cod Bay with its long...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Enjoy easy access to a gorgeous private association beach and dock on Pleasant Bay from this well maintained property in the beautiful neighborhood of ''East Egg''. This incredibly spacious home offers lovely water views, central air, large kitchen, and game room with regulation pool table, perfect...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 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 6
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    Studio 2 in Holly Tree Cottages at Nauset Beach1 / 23
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    *If you can't find the dates available that you are looking for, we also have a second studio you may be interested in. Send us an inquiry and we will try to help you find the dates you want.* Sea Wind is a studio in “Holly Tree Cottages” available by world-renowned Nauset Beach. It offers high...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Waterfront on Nauset Harbor! Classic Cape located on an incredible property overlooking the water and beyond. Enjoy the lovely living area with fieldstone fireplace, relaxing on the spacious deck or taking the path to the shore's edge. Current updates include new carpeting throughout house,...
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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 9 Quick View
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    This recently remodeled 3 bedroom just 1.5 miles or a 5 minute drive from Nauset Beach offers lots of open living space inside and out. 3 living rooms and a lower level entertainment area give this home room for the whole family to gather together or spread out for different activities. The outside...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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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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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    26 Winslow Drive, Orleans (ID# 18543) ~ South Orleans 2017 season ! Located in South Orleans and close to Chatham for shopping and dining! This home is less than ½ mile to the beaches on Pleasant Bay and overlooks scenic Uncle Seth’s Pond. This contemporary home with an abundance of glass offers...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Cape Cod ~Cozy  Relaxing Vacation Apt.1 / 6
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Lovely Summer Rental in East Orleans. Approximently 0.5 miles from Nauset Beach. This apartment will sleep 4. One seperate bedroom with queen bed. Bathroom and shower. Murphy bed available.in sitting area. Comfortable sitting area with Direct TV, WiFi, washer and dryer, microwave among the...
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    Orleans, Cape Cod 02653
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Terrace
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    Classic Nauset Heights home sitting directly on the bluff with magnificent views of Nauset Beach, the Atlantic Ocean and Nauset Marsh. Short walk to bay and ocean beaches. Vintage, rustic cottage character in unbelievable location. Great value for view. Wooden farmhouse style floors throughout...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
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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 2017 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, 3 Bathrooms, Sleeps 8 Quick View
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    Bright, open and very spacious Cape centrally located on a cul-de-sac not far from Skaket Beach, Rock Harbor, The Cape Cod Rail Trail and Orleans Center. A wonderful, very well maintained home-- with a large deck ideal for eating summer meals or reading a book. Now with A/C units in the living room...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    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 only...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    15 Mill Pond Road, East Orleans, MA ID# 18164 ~ Mill Pond Area 2017 Season! Beautifully decorated home in the desirable Mill Pond area and with central air!. This comfortable home has an updated ktichen with new appliances, countertops, and flooring. Gorgeous Great Room with Cathedral Ceiling and...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Convenient to Skaket Beach for saltwater activities. The property features three bedrooms and two baths, sleeping 6 comfortably. The first level of the home features a kitchen, livingroom, dining area, full bathroom and one bedroom with a queen sized bed. The second level offers an additional full...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 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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    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 barn...
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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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    Charming period home located only 2/10ths of a mile from gorgeous Nauset Beach on The Atlantic. Enjoy the sunny deck, comfortable furnishings, wonderful country kitchen and spacious backyard. Attached apartment also available for rent. Additional amenities include: room fans, lobster pot, cd,...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Newly decorated, charming East Orleans escape just a mile and a quarter to fabulous Nauset Beach on The Atlantic. This sweet two bedroom home is located on a cul de sac convenient to East Orleans Village. Enjoy grilling on the patio with family and friends and the outdoor shower to wash all that...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lovely three bedroom contemporary Cape with an open floor plan located in a private cul de sac neighborhood. Features wireless internet, deck and private outdoor shower and is near the bike trail. Two bedrooms are on the first floor. One with a trundle bed and the other with two twins. Upstairs...
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    Orleans, Cape Cod
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    ASP-5501 / 15
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Charming modern waterfront cottage-- now with A/C!-- located in the exclusive Mayflower Point section of Orleans where the Namequoit River meets Little Pleasant Bay. The secluded area boasts scenic water views, quiet nights and sounds of birds. The living space has a new whole-house fan, ceiling...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    Priscilla Landing1 / 26
    (6)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    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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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Nauset Beach!! At this lovely East Orleans vacation rental home you can enjoy the best of Cape Cod. This 4 bedroom, 2 bath home has everything you need for a comfortable stay here in East Orleans. There are A/C units, WIFI internet access,, outdoor grill and plenty of outdoor living space. 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 8 Quick View
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    244 Tonset Road, East Orleans (ID#125800) Reduced rate for the week of 8/12-8/19! 2017 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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Skaket Beach at just 1000 ft!! This gorgeous Orleans vacation rental home is located in the perfect spot for you to enjoy Cape Cod. At this lovely home you will be just 2/10ths of a mile from beautiful private access to Skaket Beach in Orleans on Cape Cod Bay. This home is located on an old Cape...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Newly renovated sprawling ranch home located in the beautiful Briar Springs area of East Orleans. The highlights of this lovely, bright and open home are its spacious great room with vaulted ceiling whichs leads out to a large deck, a separate living/dining area, new granite kitchen, master bedroom...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Step back in time in this classic turn of the century cottage with views of Cape Cod Bay. Located on a wonderful property with an expansive yard, a screened-in porch and a path down to the sandy shore of Cape Cod Bay, 100 feet away! Additional amenities include: beach chairs, crock pot, room fans,...
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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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    Located in desirable East Orleans, Nauset Heights, this beautiful 3 bedroom, 1 bath home is a walk to the Outer North Nauset beach by way of Nauset Heights Association access & a great salt water inlet off the ocean. Private Nauset beach access is just 3/10ths of a mile away, Priscilla Landing...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Very spacious and nicely appointed home with two living rooms perfect for the larger get-together. Located on a wooded lot close to Little Pleasant Bay and the Paw Wah Pond boat ramp. Enjoy the nice deck and all amenities, including a refurbished kitchen and new flat-screen TV-- plus CENTRAL A/C!...
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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 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 and has its own path to Lonnie's River leading out to Pleasant Bay. Perfect for boating or kayaking. Many...
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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 7 Quick View
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    Charming Cape, just off historic Town Cove. With two bedrooms down, one up, plus a child's nook, this comfortable home can accommodate 7 guests. Features bathrooms up and down; a sunny family room/dining area; fully-equipped kitchen; and a cozy living room with fireplace. Only a short walk to Asa's...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    This cute 2 bedroom, 2 bath waterfront condo sits on beautiful Skaket Beach in Orleans. It is a second floor, end unit with unobstructed views of Cape Cod Bay. The property features two bedrooms, one with a queen sized bed and one with two twin sized beds, as well as a double pull out sleeper sofa...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Adorable updated two bedroom cottage with a bright screened in porch, outdoor shower and A/C units. Located in the Pine Tree Cottage colony. The first bedroom has a full bed and the second has two twins and there is a full bathroom with a shower. This cottage is perfect for a family of four or a...
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    Orleans, Cape Cod
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Luxury 6 BR Home W/ 60 Foot Private Pool1 / 23
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    6 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Internet Access
    • Patio
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    This warm and inviting 6 bedroom, 4 bath home sprawls over 4 stories of comfortable rooms with spacious, open living areas and a private, fully fenced back yard. Perfectly located in South Orleans, the house is just minutes from the Lower Cape villages of Chatham, Brewster and Orleans. A beautiful...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 16
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Recently renovated home tucked up on a knoll located in a very pleasant East Orleans neighborhood. The addition of a new second floor consists of two spacious bedrooms that look out to a scenic pond across the way and a nice bath. The rest of the home offers comfortable furnishings with all...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
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    7 Mallard Drive, Orleans MA( ID# 49614) Close to Skaket Beach 2017 Season! Wonderful home near Skaket Beach, A/C, private yard, quiet neighborhood! Just under 1 mile to Skaket Beach from this beautiful 3 bedroom, 3 bath home on the bayside of Orleans! Spacious home with all of the desired...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    7 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    About this property
    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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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Smoking allowed
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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 their own deck. Unit 1 has three bedrooms (#428); Unit 2 has two bedrooms (#429). Both share the enclosed outdoor shower. Brand new Central AC! Additional...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
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    WATERFRONT on Bakers Pond! Take the path from the patio to your private pondfront to enjoy swimming, fishing and kayaking on this lovely freshwater pond. Designed as an airy contemporary cabin on 3 levels-- all with sunset water views-- this home has beautiful pine panelling and hardwood fir floors...
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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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    Lovely 3 bedroom, 1.5 bath East Orleans Cottage located in a quiet and private area of East Orleans convenient to great waters for kayaking, paddle boarding, walking along the water edge and Nauset Beach. This cute cottage has WIFI, flat screen TV, nice deck and yard, outdoor shower, A/C, cooking /...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    This immaculate home is located in a quiet neighborhood with just a .2 mile walk down a sandy path to Skaket Beach. It is also close to the bike trail and nearby shopping and restaurants. The home features an open floor plan with skylites, a spacious screened porch with seating, and a large back...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Three bedroom with A/C * Wireless Internet * NO Pets Accepted 2017 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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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Skaket Beach at just 2/10ths of a mile, gorgeous marsh views and has been completely renovated & newly furnished in 2013! This rental home is perfect for the family. It has a lovely deck area with deck furniture to enjoy the stunning views, central a/c to keep you comfortable, 3 bedrooms , 1 full...
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    Orleans, Cape Cod 02753
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Set on a rise in a quiet South Orleans neighborhood, this single-level home offers plenty of privacy and living space: a living room opening to the backyard deck, a dining room, kitchen breakfast bar, and a family room leading to a sunroom that also opens to the backyard deck. Ductless A/C,...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    6 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    • Waterfront
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    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This one of a kind, magnificent, 6 bedroom estate is perfectly situated on Little Pleasant Bay and on nearly 4 acres of pristine, wooded land with 170 feet of sandy beach front. Stunning views from almost every place in the home, multi-level decks. The property consists of the main house, an...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 16
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