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Orleans Holiday Rentals

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    Travellers to Orleans are booking May dates now. Secure your holiday rental today, and have the perfect trip.
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    3 Bedroom by Nauset Beach1 / 18
    (4)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    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 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
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    • Balcony
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    • Waterfront
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    When it's time for your next vacation, make this prime lakefront Orleans home yours, and enjoy beautiful views in a secluded, tranquil setting with close proximity to town. You'll have access to private and public docks and two kayaks. Ideal for large families, couples, or groups, this home offers...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
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    For the ultimate Cape Cod retreat, stay at this charming shingle-style cottage in Orleans. You'll have stunning views of the water just out your back door, a cozy interior with a fireplace, and plenty of outdoor space on the deck and sunroom - complete with a gas grill. Located in the ocean town of...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Walk to Nauset Beach and National Seashore from this charming home!1 / 26
    (1)Terrible
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Enjoy dining al fresco on the patio with a gorgeous ocean view at this cozy Cape Cod home. Grab one of the two beach chairs and head to Nauset beach, just a few blocks away - you'll be relaxing in no time! Additional area beaches are nearby and you're also not far from the fishing mecca of Mill...
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    Orleans, Cape Cod 02643
    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 across...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    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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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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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, 3 Bathrooms, Sleeps 6 Quick View
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    'Rose Cottage' is an absolutely lovely, light and bright expanded cottage located on almost an acre in the desirable Snow Shore area of East Orleans. Recently renovated with two bedroom suites (one on each level), separate sitting/sleeping alcove, multiple decks, and skylights. This wonderful...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Absolutely charming Cape located in the very desirable Briar Springs area of East Orleans. Situated on a very beautiful and spacious lot, this home is light and bright throughout, offers lovely furnishings and is meticulously kept evoking the feeling of a true vacation get-away. The first floor...
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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 8 Quick View
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    Brand new renovation! Light and bright expansive ranch that has been beautifully and thoughtfully upgraded throughout. This architech-designed 'green' home is pristine and feels brand new! A few of its many highlights are its wonderful great room offering additional living space, inviting deck...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    #503 - the Ocean Loft: This beautiful fully-renovated barn loft is a perfect place to spend time relaxing and soaking up the summer sun poolside. Brand new wood floors, multiple skylights and exposed beams makes this bright and airy loft an ideal place to spend time recharging from a long day at...
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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 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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    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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    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    JUST LISTED! Waterfront on Skaket Beach! TWO-bedroom ground level condo in 4-unit waterfront building. Enjoy the sandy shore of Cape Cod Bay right outside your door. There are 2 twins in one bedroom, bunkbeds (twins) in the other and a twin daybed tucked in the corner of the living room. This...
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    Orleans, Cape Cod 02653
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Comfortable 4 bedroom home located on a quiet dead end road just a short distance from Rock Harbor and the Cape Cod Rail Trail. For the 2017 season: both bathrooms updated, hardwood flooring, water filtration system, Wifi Internet access 55inch TV, DVD . Central Air! Also enjoy relaxing in the...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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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 8 Quick View
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    2 miles to Skaket Beach, 2 King Beds, 3 ACs & WIFI 'Ready to Rent for the 2018 Season' This is a classic Cape Cod home in a private location between the Bay and the Atlantic with cooling cross breezes, close proximity to Skaket Beach and Orleans center. This three bedroom, two bath property...
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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 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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    ENCHANTING COTTAGE LESS THAN A MILE FROM ROCK HARBOR IN ORLEANS!1 / 25
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    $1850 Rate include all charges. No hidden fees! Enchanting Orleans Vacation Cottage only 0.9 miles to picturesque Rock Harbor Beach. This property is bright, cheery, and a wonderful summer retreat on Cape Cod! Features include a remodeled kitchen with dishwasher, a cozy living area with...
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    Orleans, Cape Cod 2653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Crystal Lake Waterfront! Enjoy fresh water swimming right outside your door! This wonderful, private spot is ideal for the extended family offering 5 bedrooms plus an office/den, including an incredibly spacious master bedroom suite and two other bedrooms that open out onto a screened porch that...
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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 8 Quick View
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    Cosy, welcoming home in South Eastham. Our traditional Cape Cod house features 4 bedrooms, 2 baths, and a fully finished basement with easy access to beaches, the Cape Cod Bike Trail, shopping and restaurants. All bedrooms have window A/C units. We are on a quiet wooded lane, just one mile from...
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    Orleans, Cape Cod
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    A VERY SPECIAL HOME FOR 6 VERY SPECIAL GUESTS IN NAUSET HEIGHTS!1 / 24
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Reviewed 11 July 2017
    My husband, three children and I just returned from an incredible week vacationing here — we only wished we could have stayed longer. Beautifully decorated and well located, the...
    Reviewed 13 June 2017
    This is an excellent location for all Orleans beaches with access to the private resident’s beach which is wide open, clean and just stunning. The property itself provides...
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    About this property
    $1875-$2275 Rates include all charges - no hidden fees! Recently purchased by new owners, this beach cottage has undergone a face lift to maximize the exterior and interior space and to completely redefine the meaning of rustic from its 20th century images of musty rugs and knotty pine. The new...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    $1800-$1950 Rates include all charges. No hidden fees! Lovely Cape Cod Vacation Bungalow located in Orleans. The perfect Cape retreat near Skaket Beach and less than .5 mile to Orleans Town Center and Rock Harbor! The bright, nautical-themed living room features a flat screen TV, DVD player, and a...
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    Orleans, Cape Cod 2653
    Cabin Holiday Rental - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
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    Brand New Home, Heated Pool, Sleeps 12, Linens & Towels Included! Peak Summer Weekly Rate: $10,000 (Rents Saturday - Saturday during peak season) This brand new East Orleans home, provides the highest level of modern amenities in a great location close to Nauset Beach and Orleans Center. The custom...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
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    About this property
    This brand new luxury 3 bedroom home with central AC sleeps 8. It is a state of the art home built in 2014 with views of Crystal Lake in Orleans. Direct deeded access to Crystal lake comes with the home through short path down from the property to the water. You won't find another rental like this...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 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 association...
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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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    NEW LISTING! Charm oozes throughout this adorable duplex condo with 180 degree water views of Town Cove. This lovely spot is in a quiet in-town location within walking distance of shops, restaurants, live theatre and baseball games! Two bedrooms, one with a queen and slider to deck; the other has a...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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, 2 Bathrooms, Sleeps 6 Quick View
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    $1575-$2175 ($100 less if not bringing pet) Rates include all charges - no hidden fees! This delightfully redone 2.5 bedroom/1.5 bath home located in a sought-after East Orleans location is bright and open with an unbeatable location! The front door leads directly into a large living room cooled by...
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    Orleans, Cape Cod 2653
    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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    About this property
    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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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Light and bright spacious beach house sitting on the edge of a marsh at the end of a sandy lane-- just 2/10ths of a mile from Skaket Beach! This wonderful spot offers panoramic marsh views with peeks out to the waters of Cape Cod Bay. The recently renovated main floor consists of a lovely kitchen...
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
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    Renovated Gem on Town Cove in Orleans with hot tub, walk to town Peak Summer Weeks: $4,400 - $5,400 Please note:  This property rents Sunday to Sunday in summer for full-week or multiple week terms only, but is available during the shoulder-season for 3-night minimum. This Orleans home is located...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    About this property
    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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    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Waterfront 4 Bedroom on Crystal Lake in Orleans. This well appointed 4 bedroom has recently been fully updated. It has central AC throughout the home and it is quite spacious! Upper and lower floors all have lake front views. The main level has an eat in kitchen with mini bar with seating for 4....
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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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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    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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    ORLEANS 3 BEDROOM 2 BATH VERY CLOSE TO NAUSET BEACH!1 / 22
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed 31 May 2017
    My husband and I rented this wonderful, warm and inviting contemporary home for a week and didn't want to leave. It is conveniently located in East Orleans where you'll find...
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    $1795-$2595 Rates include all charges - no hidden fees! This beautifully decorated three bedroom, two bathroom East Orleans home with bright, open contemporary style and is located just a mile to Nauset Beach! Upon entry to this home you will find soaring ceilings with wood beams, charming wood...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    About this property
    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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    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
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 10
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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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    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Private Outdoor Pool (Unheated)
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    About this property
    Beautiful historic home, private mini estate. Heated Pool, Central AC, Sleeps 13, Linens & Towels Included, Pets considered! Peak Summer Weekly Rates: $9,500 - $11,000 Rents Saturday - Saturday during peak season Please click on the 'Virtual Tour' to see a 3D tour of the home The interior of this...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 13
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Smoking allowed
    About this property
    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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