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Holiday Homes and Apartments Orleans, MA

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    Holiday Homes and Apartments Orleans, MA
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    247 Holiday Rentals in Orleans
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    Studio / 1 Bathroom / Sleeps 3
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    About this property
    East Orleans Studio has it all. Take one of the deeded private paths to Nauset Beach from this couples getaway located at the end of a private road. The amenities for this spotless getaway include, a King size bed, Double size sleeper sofa (for an overnight guest), Full kitchen with D/W, Full bath... View all property information
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    4 Bedrooms / 2 Bathrooms / Sleeps 7
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    About this property
    This quintessential Cape Cod home was built in 1775 and has been in the same family for almost 200 years. Charming beyond words this home sits at the end of Tonset Road and looks out over Nauset Inlet to the Atlantic Ocean beyond. Stone walls and meadows surround this time tested property. The... View all property information
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    1 / 16
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    WATERFRONT COTTAGE! Nestled on two acres in Mayflower Point is this absolutely lovely, newly renovated cottage. Light and bright with cottage character throughout, painted exposed beams, skylights and glorious views out to Pleasant Bay. Take the path to the water to kayak or canoe, walk to... View all property information
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    1 / 24
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    This vibrant and stylish 3BR/2BA classic home built in the 1800's is 6/10 mile to Skaket Beach. Pure old Cape Cod- perfect craftsmanship and the amenities we have all become accustomed to. The home is updated and in excellent condition but still retains much of its unique character and charm both... View all property information
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    5 Bedrooms / 4 Bathrooms / Sleeps 10
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    17 Blue Heron Way - Watefront on Namequoit River Waterfront compound with fabulous views of the Namequoit River and direct access to Pleasant Bay. This property has plenty of room for the extended family with a main house and guest cottage together sleeping up to 12 people. The main house has 3... View all property information
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    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    About this property
    NEW CONSTRUCTION! Gorgeous 3-level contemporary home overlooking conservation land and beautiful 28-acre Bakers Pond. 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 .3 mile to... View all property information
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    About this property
    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... View all property information
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    1 Bedroom / 1 Bathroom / Sleeps 2
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    About this property
    Quaint second floor apartment in South Orleans. This bright and cheerful, freshly renovated home offers an open floor plan with high ceilings in the kitchen, dining and living room area with ceiling fan, full bathroom, and separate bedroom with king size bed and window a/c. Amenities include... View all property information
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    4 Bedrooms / 2 Bathrooms / Sleeps 7
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    About this property
    Antique farm house on a very spacious and private lot in East Orleans. Pochet Inlet is close by for canoeing or fishing. This house is pet friendly. Additional amenities include: room fans, lobster pot, outdoor shower (private/hot water), heat, outdoor furniture, coffeemaker. View all property information
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    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    About this property
    14 Captains Row This 3 bedroom, 3 bath tri-level home is just 1/2 mile to Rock Harbor & a short drive to Skaket Beach in Orleans! AC units in all bedrooms and dining room. One bedroom with full bath on lower level, living room, dining and kitchen on main floor, and two bedrooms, two baths on the... View all property information
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    3 Bedrooms / 1 Bathroom / Sleeps 6
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    About this property
    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. Additional amenities include: beach chairs, crock pot, room fans, lobster pot,... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Enjoy the views overlooking Reuben’s Pond from this comfy 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... View all property information
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    4 Bedrooms / 2 Bathrooms / Sleeps 10
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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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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    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
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    20 Deerwood Lane, East Orleans, MA Fresh listing in East Orleans with central A/C. Walk to restaurants or Sundae School after a relaxing day at Nauset Beach. This dog friendly (with homeowner approval) home features lots of room with 4 bedrooms, hardwood floors throughout and central a/c with... View all property information
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    3 Bedrooms / 3 Bathrooms / Sleeps 7
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    With its great views of Cape Cod Bay across Namskaket Marsh from upper and lower decks, this charming 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 from the living/dining... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    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... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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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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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    Just 3/10 mile to Fresh Water Pilgrim Lake or 3 miles to Nauset Beach. This lovely three bedroom, two bath home sleeps eight and sits on a wonderful 1.6 acre lot. The first floor offers a fully equipped kitchen, dining area, welcoming living room, game/reading room, laundry, full bath, and master... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    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... View all property information
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    5 Bedrooms / 2 Bathrooms / Sleeps 10
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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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    7 Bedrooms / 4 Bathrooms / Sleeps 10
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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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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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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. Enjoy the spacious screened-in porch and all amenities. Additional amenities include: room fans, lobster pot, outdoor shower (private/hot water), heat, dehumidifier,... View all property information
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    This wonderful 4-bedroom, dog-friendly, vacation home is located only 200 yards from Skaket Beach. This great spot offers a fully equipped kitchen, living room, sun room, two bedrooms and full bath on the first level and two bedrooms and full bath on the second level. Enjoy the nicely maintained... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    Chill out 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. Bedrooms have air-conditioning for your comfort. Perfect for... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    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 a 5-minute drive to... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    Well-maintained home privately located 8/10th's of a mile from Baker's Pond. This lovely home is surrounded by mature trees and lush plantings. Enter from the side deck past the entryway on the first floor where you will find a fully equipped kitchen, ample dining area, cozy living room with queen... View all property information
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    Wonderful custom home with all the amenities-- only a half-mile from Pah Wah Pond and its conservation area that leads out to a beach on Little Pleasant Bay. Built in 2011, this air-conditioned 3200-sq. ft. upscale home has excellent accommodations for 8 guests with 2 master bedrooms (one up, one... View all property information
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    3 Bedrooms / 3 Bathrooms / Sleeps 10
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    About this property
    20 Hayward Lane, East Orleans Enjoy this lovely, large, sun-filled home in charming East Orleans on a spacious, 1.5 acre private property with saltwater views of Frostfish Cove (leading to Little Pleasant Bay) from almost every room. Relax and watch the boats go by from the large main-level deck,... View all property information
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    Country living in a private enclave, walk to water, on two acres! Crystal Lake, clear with sandy bottom, is an 0.4 mile walk. Nauset Beach, the Cape s best, is three miles away, no traffic lights. Just 0.1 mile walk to a conservation area with a mile of waterfront, and deeded access to a cove where... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Spotless home in a lovely quiet setting near the bike path. There are two living spaces and a first floor laundry and half bath. The first floor bedroom has a queen size bed. On the second floor there are two bedrooms with a queen bed and two twin beds and a full bath. Large two level deck. There... View all property information
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Dishwasher
    • Dryer
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    • Gym
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Large, beautiful 4 bedroom, 3-1/2 bathroom, Colonial style home just 6/10ths of a mile from popular Nauset Beach on the oceanside. This attractively furnished home has a remodeled kitchen, bright sun room, separate dining room, full livingroom, and a full bathroom. All the bedrooms are on the... View all property information
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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Grill
    • Waterfront
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
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    About this property
    Waterfront on Cape Cod Bay! This 2 bedroom, 1 bath condo Sits on the Dunes of Skaket Beach. The private stairway takes you to the fabulous deck and entrance of the top floor of condominium with views from Dennis to Provincetown! Enjoy watching the sunset from the deck after a long day playing in... View all property information
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    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Beautiful 4 bedroom home on private cul de sac in East Orleans. Pristine landscaped yard with swing set and hammock. Big kitchen that opens to the family room. Open den with tv and couches. Full bath, washer & dryer on the first floor. Upstairs has 3 large bedrooms with high ceilings and lots of... View all property information
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    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Under 1 mile to Skaket Beach 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 amenities. Convenient to the bike trail, shopping, and beaches. Main level includes living area, dining room, kitchen, Master... View all property information
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Dishwasher
    • Dryer
    • Grill
    • Satellite TV
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Bright and newly remodeled beach house located at the end of a sandy lane only 2/10ths of a mile from Skaket Beach on Cape Cod Bay. Enjoy the panoramic salt marsh views and peeks out the The Bay. The brand new kitchen, two living areas, flat-screen TV and multiple decks make this home a great spot... View all property information
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    $1,117
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    3 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Lovely 3 Bedroom home with a beautiful private yard just 1 mile to Skaket Beach or 3 miles to Nauset. All the extras you would want in a home including wireless internet, washer and dryer, air conditioning and an outdoor shower! Bedrooms 1 and 2 both offer a queen size bed. An additional... View all property information
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    $1,085
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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Grill
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Clean, comfortable and cozy cottage overlooking Rock Harbor Marsh. Wonderful screened in porch for your evening pleasure. 2 Bedrooms, 1 Bath. 1 Double, 2 Twins Additional amenities include: outdoor shower (private/hot water), outdoor furniture, room fans, lobster pot, coffeemaker. View all property information
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    5 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Satellite TV
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Cape Cod elegance describes this beautiful, expansive home which sits peacefully at the end of the cul-de-sac overlooking the natural beauty of a multi-acre cranberry bog and pond. Ideal for the larger gathering with its great room with soaring cathedral ceiling, gorgeous eat-in kitchen, spacious... View all property information
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Beautifully furnished historic home in the Nauset Heights area of East Orleans. Walk to private Association beach or to Nauset Beach (public/lifeguards) on the Atlantic in minutes. Sliders from open dining room and living room to large screened porch overlooking expansive backyard. There is also a... View all property information
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    5 Bedrooms / 3 Bathrooms / Sleeps 12
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    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Large, welcoming home for your family reunion or large group. Fully equipped, spacious home near Pleasant Bay beaches and boating. Very private yard recessed from quiet cul de sac street. BBQ/grill on deck with two tables and seating for outdoor dining. Living room, family room and sunroom all... View all property information
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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Dryer
    • Grill
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Beautiful 2 bedroom home in the Tonset area of East Orleans with a great swimming area a mile down the street, a boat or kayak launch 3/10 of mile away, and only 2 miles to Nauset Beach or everything Main Street in Orleans has to offer. The home is situated on a corner lot with a large backyard and... View all property information
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    3 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Adorable cottage located in a wonderful East Orleans neighborhood near Mill Pond and Snow Shore Landing. The interior of this cottage is as cute as a button. Updates include new outdoor furniture, mattresses, and brand-new ductless AIR-CONDITIONING. Just steps away from Robert's Cove for great... View all property information
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    6 Bedrooms / 5 Bathrooms / Sleeps 12
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Lovely expansive home with pool and privacy near Crystal Lake and Kents Point.58 Keziahs Lane . 'Fields Cove' is a lovely 6000+ sq ft expansive home enjoying privacy and enchanting waterviews out over the in-ground pool to a salt water cove leading out to Little Pleasant Bay. Pool is heated on... View all property information
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    $894
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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Grill
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    197 Rock Harbor Road, Orleans, MA Rustic cottage overlooking the Rock Harbor Marsh. Wonderful screened in porch for your evening pleasure. 2 Bedrooms, 1 Bath. 1 Double, 2 Twins. NO PETS ALLOWED. $800 per week in season. $55 Vacation Rental Damage Coverage, $60 Handling Fee (fee s non-refundable).... View all property information
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    $2,298
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    3 Bedrooms / 1 Bathroom / Sleeps 5
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    • Air Conditioning
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This immaculate newly renovated Cape Cod vacation cottage is located in a desirable area of Orleans just minutes to Skaket Beach and just a five minute drive to downtown Orleans and its popular shops. Situated on 2 acres with beautiful open land, trees and plantings, this cottage offers a cozy... View all property information
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