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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.
    1 / 28
    5 of 5 bubbles (3) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    5 of 5 bubbles (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Bright, sunny and updated new home in Nauset Heights with AC! This property is the perfect home base for family and friends to enjoy all that Orleans has to offer. Enjoy a beautiful light-filled living room with views of the ocean, which opens to an updated kitchen and dining room. Beautifully... View all property information
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    Orleans, Cape Cod 02653
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    #501 - Viking Cottage: new renovation, sunny secluded home with view & access to saltwater.  Enjoy the pleasures of a waterfront property -- Wake up to views of a peaceful Pleasant Bay inlet from this sun-filled, modern 3-bedroom cottage in the woods. Launch your kayak or canoe to explore beautiful... View all property information
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    Orleans, Cape Cod 02653
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Large wrap around deck provides spectacular views of Cape Cod Bay near Boat Meadow Landing. The Beach IS your front yard! Ideal for children. Relax swimming in the warmer Bay. Two kayaks provided for exploring the Bay and marsh. Take long walks along the water to Rock Harbor. Only a short 5 min.... View all property information
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    Orleans, Cape Cod 02642
    1 / 22
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    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.... View all property information
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    Orleans, Cape Cod 02653
    1 / 16
    4.5 of 5 bubbles (3) Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    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.... View all property information
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    Orleans, Cape Cod 02653
    4 of 5 bubbles Reviewed 8 September 2016
    This is the 3rd time we've rented this place. Comfortable, clean and close to the beach. A 10 minute walk to the outer end of Nauset, and minutes to the inlet. Nice little...
    5 of 5 bubbles Reviewed 20 May 2016
    My family of four (inc. two young children) loved the four nights we spent at this cottage. Nice, well-maintained property in a beautiful, quiet area and only 10 minutes walk to...
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    1 / 20
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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... View all property information
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    Orleans, Cape Cod 02653
    1 / 28
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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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... View all property information
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    Orleans, Cape Cod 02653
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    1 / 20
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
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    About this property
    Our home is located in a quiet upscale neighbourhood close to all amenities. Walk to grocery store, downtown shopping, library, tennis courts and town field. Less than a 5 minute drive to ocean and bay. Quick access to highway and all the surrounding Cape towns. Relax and unwind at With the... View all property information
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    Orleans, Cape Cod 02653
    1 / 30
    5 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    2013 WATERFRONT HOME! Gorgeous 3-level contemporary home with 180 degree view of a beautiful 28-acre lake and conservation lands. With water views from every room, this dramatic home has 3 exterior decks and a private path to the pond only 75 feet away. Set on a cul-de-sac on a private lane, it is... View all property information
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    Orleans, Cape Cod 02653
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Nice 2 bedroom, 1.5 bath home so close you can WALK to your own private association beach on PLEASANT BAY. When you walk in the front door you go up a few stairs to get to the main level. The first level has a nice living room/dining room, a galley kitchen, and a relaxing 3 SEASON ROOM where you... View all property information
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    Orleans, Cape Cod 02653
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This beautiful Cape Cod home sits on Barley Neck, which is small peninsula just a few minutes drive to Nauset Beach. Beach sticker for parking is included in your rental! It is surrounded by Meeting House Pond and Little Pleasant Bay. This area is harbored from the Atlantic Ocean by Pochet Island.... View all property information
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    Orleans, Cape Cod 02653
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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... View all property information
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    Orleans, Cape Cod 02653
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    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... View all property information
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    Orleans, Cape Cod 02653
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This lovely Contemporary Cape sits on almost an acre of land only 2/10ths of a mile from the sandy shore of Bakers Pond and 3/10 mile from Nickerson State Park (in Brewster). Light and bright throughout, this custom home features an open floor plan, gleaming hardwood floors and full amenities--... View all property information
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    Orleans, Cape Cod 02653
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    6 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    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.... View all property information
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    Orleans, Cape Cod 02653
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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... View all property information
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    Orleans, Cape Cod 02653
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    NEW LISTING! Charm oozes throughout this absolutely 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... View all property information
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    Orleans, Cape Cod 02653
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    1 / 22
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    1800s Antique Victorian only 1 mile from the Beach! Front porch rockers and side deck overlook the beautiful yard and gardens. The living room, dining room and family/tv room are very welcoming on the main level. One bedroom with a Queen bed is also located downstairs. Three additional bedrooms... View all property information
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    Orleans, Cape Cod 02653
    1 / 19
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    '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... View all property information
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    Orleans, Cape Cod 02653
    1 / 11
    2 Bedrooms, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    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... View all property information
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    Orleans, Cape Cod 02653
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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... View all property information
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    Orleans, Cape Cod 02653
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Charming remodeled 1930s cottage! This home is located in the desirable and scenic Mill Pond area in Orleans with a well kept yard and wrap-around deck. House is very comfortable with single story living. Three bedrooms (brand new mattresses) and 1 and a half baths are located off the main... View all property information
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    Orleans, Cape Cod 02653
    1 / 21
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This Pet friendly home is located just 0.8 miles from Nauset Beach. Enter into a charming, warm home that offers two spacious living areas. One is a bright great room with cathedral ceilings, sectional seating, big screen t.v and game table. Head into the living room where you will find a cozy... View all property information
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    Orleans, Cape Cod 02653
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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... View all property information
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    Orleans, Cape Cod 02653
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
    • Hot Tub
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    • Ocean Views
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    • x
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    • x
    About this property
    Beautiful waterfront vacation home with 180 degree unobstructed views of the Frostfish Cove, The River, Jack Knife Point and the mouth Pleasant Bay. This vacation home is about light-filled rooms virtually all with a view of the water, kayaking, canoeing, sailing, fishing and more: a most unique,... View all property information
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    Orleans, Cape Cod 02653
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    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... View all property information
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    Orleans, Cape Cod 02653
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    5 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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... View all property information
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    Orleans, Cape Cod 02653
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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... View all property information
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    Orleans, Cape Cod 02653
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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... View all property information
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    Orleans, Cape Cod 02653
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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... View all property information
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    Orleans, Cape Cod 02653
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    2 Bedrooms, Sleeps 6 | Quick View
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    About this property
    Only 1.8 miles to Nauset Beach and located In East Orleans Village! This renovated barn is private and cozy. You can walk into the village to get a morning coffee and newspaper, mail a postcard or grab a fresh made sandwich for your day * the beach. Stroll to dinner * one of the fine restaurants,... View all property information
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    Orleans, Cape Cod 02653
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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... View all property information
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    Orleans, Cape Cod 02653
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    5 Bedrooms, 4 Bathrooms, Sleeps 11 | Quick View
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    About this property
    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.... View all property information
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    Orleans, Cape Cod 02653
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Newly renovated ranch located on a cul-de-sac in the desirable Brick Hill area of East Orleans. Fresh, bright and open with Central Air Conditioning! Enjoy the newer furnishings throughout and all amenities. A great spot convenient to the sandy shore of Nauset Beach and The East Orleans Village.... View all property information
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    Orleans, Cape Cod 02653
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    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... View all property information
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    Orleans, Cape Cod 02653
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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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... View all property information
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    Orleans, Cape Cod 02653
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    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Just a short distance to the center of Orleans, this well kept Saltbox style house is convenient to everything. It is only .3 miles to the bike path and 1.6 miles to Skaket Beach. The large grassy yard is private and spacious. The cute back deck comes equipped with an electric grill and outdoor... View all property information
    Location Information
    Orleans, Cape Cod 02653
    1 / 15
    8 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Washer
    • DVD Player
    • Wi-Fi
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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... View all property information
    Location Information
    Orleans, Cape Cod 02653
    1 / 19
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Satellite TV
    • Grill
    • Wi-Fi
    • Washer
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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,... View all property information
    Location Information
    Orleans, Cape Cod 02653
    1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Washer
    • DVD Player
    • Patio
    • Wi-Fi
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Great privacy in East Orleans! Enjoy this lovely 3-bedroom, 2-bath contemporary saltbox offering a bright and open floor plan and updated furnishings. Front-to-back living room with fireplace and a great screened porch open onto a spacious wraparound deck. This great vacation spot is gracefully... View all property information
    Location Information
    Orleans, Cape Cod 02653
    1 / 21
    4 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    Amenities & Details
    • Private Outdoor...
    • DVD Player
    • Air Conditioning
    • Internet Access
    • Grill
    • Washer
    • Satellite TV
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This exceptional compound is one-of-a-kind with a Main House, Carriage House and private pool. The Main house has a restaurant quality kitchen which will bring out the Iron Chef in you. Ample seating in the dining area with separate bar. Entertaining is easy in the Living Room with HDTV and DVD,... View all property information
    Location Information
    Orleans, Cape Cod 02653
    1 / 30
    5 of 5 bubbles (1) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Satellite TV
    • Grill
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Washer
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Located on the bank of Rock Harbor Creek, this 5 BR, 4 Bath classic Cape has all you and your family are looking for this summer. The large second floor master suite overlooks the marsh with an attached private bedroom with 2 twins where the little ones can dream away, close to the folks. There is... View all property information
    Location Information
    Orleans, Cape Cod 02653
    1 / 22
    4 of 5 bubbles (1) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Washer
    • DVD Player
    • Internet Access
    • Parking
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    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... View all property information
    Location Information
    Orleans, Cape Cod 02653
    1 / 7
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Washer
    • Patio
    • Wi-Fi
    • DVD Player
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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: two new bathrooms, hardwood flooring, water filtration system, Wifi Internet access 55inch TV, DVD . Updated photos to come! Also enjoy relaxing in... View all property information
    Location Information
    Orleans, Cape Cod 02653
    1 / 12
    4 of 5 bubbles (1) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Ocean Views
    • Satellite TV
    • DVD Player
    • Washer
    • Balcony
    • Air Conditioning
    • Grill
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    PRICE REDUCTION! The only high season week still open from June 24 to July 1 has just been reduced by 20% to $2,500.00 plus a $100.00 cleaning fee. Thereafter the entire fall season is still open beginning Sept. 2 to Nov. 18 at moderate off-season prices, except 9/9 to 9/16. Yes, we have WiFi and... View all property information
    Location Information
    Orleans, Cape Cod 02653
    1 / 30
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Washer
    • DVD Player
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    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. Three bedrooms and the living room have window A/C units. We are on a quiet wooded lane,... View all property information
    Location Information
    Orleans, Cape Cod
    1 / 10
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Amenities & Details
    • Grill
    • Internet Access
    • DVD Player
    • Satellite TV
    • Parking
    • Air Conditioning
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    17 Center Place, Orleans MA (ID# 18374) Close to town, waterfront to pond 2017 Season! Charming waterfront cottage on scenic Boland Pond. A good location, only a short distance to the center of Orleans, not far from the bike trails and to Skaket and Nauset Beaches! 2 Bedrooms, 1 Bath. Sleeps a... View all property information
    Location Information
    Orleans, Cape Cod 02653