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Holiday Rentals and Villas in Orleans, MA

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    Travellers to Orleans are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 6
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 27
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    4 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Classic Nauset Heights 3 Bedroom home sitting directly on the bluff with magnificent views of Nauset Beach, the Atlantic Ocean, Nauset Marsh, Coast Guard Light, and Fort Hill. Short walk to bay and ocean beaches. Vintage cottage character in unbelievable location. Great value for view. Full... 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
    1 / 14
    5 of 5 stars (1) Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    This private gem sits at the end of a sandy lane wrapped in trees and bathed in sunlight. The front deck welcomes you to sit and relax and enjoy the peace and quiet and plan your next days adventure. Located less the 2 miles from Nauset Beach and slightly farther from Cape Cod Bay, this Cape... View all property information
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    Orleans, Cape Cod 02653
    1 / 16
    5 of 5 stars (2) Excellent
    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
    5 of 5 stars 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...
    5 of 5 stars Reviewed 5 May 2015
    Alden Road Cottage was very suitable for my family of 4. The 3 bedrooms were spacious and could sleep 2. Still warm enough to use the outdoor shower. Living room and dining area...
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    1 / 16
    4 of 5 stars (1) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Renovated ranch with semi-finished lower level walkout tucked up on a hill in the lovely Brick Hill area of East Orleans. This nice vacation home is fresh and bright offering newer furnishings and convenience to the East Orleans Village and Nauset Beach. Three bedrooms accommodate 6 guests, with... View all property information
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    Orleans, Cape Cod 02653
    4 of 5 stars Reviewed 19 August 2014
    What a great cottage rental! Location is perfect. Close to Nauset Beach yet tucked away from traffic. We felt safe and cozy. Rooms are spacious and tastefully decorated. Layout is...
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    1 / 22
    4 of 5 stars (1) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    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
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    Orleans, Cape Cod 02653
    1 / 25
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Located right on the shore of beautiful Town Cove in Orleans. This family home has 3 bedrooms 2 baths and a view of the water which is special. This classic Cape Cod home is one floor living with all 3 bedrooms on the main floor. The master has a Queen with private bath with a walk-in shower, BR2... View all property information
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    Orleans, Cape Cod 02653
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    1 / 19
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    20 Deerwood Lane, East Orleans, MA (ID# 120896) Wonderful Home 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... View all property information
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    Orleans, Cape Cod 02653
    1 / 21
    4 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    32 Pond Road, Orleans -( ID: 18315) This charming Cape has an open floor plan that leads to a great screened-in sun room. Quaint furnishings lends itself to easy summer living. 3 A/C units in the home. Close to Crystal Lake, center of town and East Orleans Village. It is only a short distance to... View all property information
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    Orleans, Cape Cod 02653
    1 / 17
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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
    1 / 25
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    About this property
    Walk to the water from this private 4 bedroom, three bath home. Just 2 houses away from a private path to Little Pleasant Bay! Nestled within two acres on a gorgeous country dead end road. The sandy beach of Crystal Lake is only .4 mile walk away, Pilgrim Lake less than a mile, and a short... View all property information
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    Orleans, Cape Cod 02653
    1 / 15
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Three bedroom Cape Cod Cottage for rent. Waterview sunsets. Private location on quiet cul-de-sac. 2.9 miles to Nauset Beach, voted Best Beach on Lower Cape. Walk to Asa's Landing for boating and water activities. Three bedroom, One and half baths, sleeps six. Upper level master bedroom and half... View all property information
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    Orleans, Cape Cod 02653
    1 / 9
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
    • Terrace
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    • Balcony
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    New for the 2016 Season: New Oven, new floors, new roof, new chimney and painting! Unique 3 bedroom home tucked in a wooded path to Nauset Beach. This home offers peeks of the Atlantic from the living room and small viewing deck and distant sounds of the Ocean. Also a second spacious deck for... 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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    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 / 16
    4 of 5 stars (1) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    10 Shorewood Drive, Orleans MA (ID# 18402) ~ Near Bakers Pond Bright and airy home in quiet neighborhood with easy access to Bakers Pond (26 acre kettle pond stocked with trout) or Nickerson State Park a block away where you can enjoy fresh water activities and hiking. Comfortable furnishings,... View all property information
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    Orleans, Cape Cod 02653
    1 / 13
    3 of 5 stars (1) Average
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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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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    Orleans, Cape Cod 02653
    3 of 5 stars Reviewed 1 week ago
    The setting and view of the bay were perfect. Inside was uncomfortable old rickety furniture crammed in all rooms.
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    1 / 30
    5 of 5 stars (1) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    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
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    Orleans, Cape Cod 02653
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    1 / 18
    3 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... View all property information
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    Orleans, Cape Cod 02653
    1 / 19
    3.5 of 5 stars (4) Average
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Located 1/10 of a mile from the private saltwater beach on Pleasant Bay via an Association path, this multi-level contemporary offers a peaceful retreat on Shoal Pond in South Orleans. The main level is open and bright, with a wonderfully open great room, fireplace, dining area, kitchen, entry way,... View all property information
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    Orleans, Cape Cod 02653
    1 / 19
    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... View all property information
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    Orleans, Cape Cod 02653
    1 / 17
    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... View all property information
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    Orleans, Cape Cod 02653
    1 / 17
    4 of 5 stars (2) Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    10 Daley Terrace, Orleans MA (ID# 18332) ~ Close to town, baseball fields This quaint & cozy ranch is set on a hill in a residential neighborhood & within walking distance to the center of town, public tennis courts and the Orleans Fire Birds baseball games. AC units in the living room and two of... View all property information
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    Orleans, Cape Cod 02653
    1 / 15
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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. Now with central air-conditioning for your comfort! Perfect for... View all property information
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    Orleans, Cape Cod 02653
    1 / 21
    4.5 of 5 stars (3) Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Spotless vacation home with in-ground pool. This home offers amenities and location at an affordable price. 5 bedroom and 3 1/2 baths, 2 kitchens, extra freezer and fridge, 2 living rooms, sun room, large deck, and a groomed yard make this the perfect home for a large family vacation. Less than a... 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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    36 Collins Lane, East Orleans (ID# 114103) Gorgeous 5 bedroom home with Central A/C and all the amenities. First floor features a luxury eat in kitchen with granite countertops and stainless appliances, great dining room, and living area with gas fireplace. First floor bedrooms include a spacious... View all property information
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    Orleans, Cape Cod 02653
    1 / 9
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    This exceptional vacation home is all you are looking for and more. Swim, boat, fish, or just relax on the sandy shore of Pleasant Bay just 150 yards from your front door! Quiet, private with 2 decks, the back yard sings of wildlife and privacy, comfortably furnished, extensive reading, music, +... View all property information
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    Orleans, Cape Cod 02653
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    20 Hayward Lane, East Orleans (ID# 108991) Close to Nauset Beach MeetingHouse Pond, Pleasant Bay and Village of 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... View all property information
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    Orleans, Cape Cod 02653
    1 / 19
    2 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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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    26 Winslow Drive, Orleans MA (ID# 18543) ~ South Orleans 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 lovely views... View all property information
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    Orleans, Cape Cod 02653
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    3 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 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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    Orleans, Cape Cod 02653
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    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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    Orleans, Cape Cod 02653
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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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    Orleans, Cape Cod
    1 / 14
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Enjoy a beautiful setting at this Orleans vacation rental. There are 2 bedrooms, 1 bathroom, a lovely deck area and gorgeous landscaping. Within a quick drive to Nauset Beach, Orleans Village with restaurants and shops yet set in a quiet spot. There is Cable / Satellite TV, cooking / serving... 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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    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... View all property information
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    Orleans, Cape Cod 02653
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Wi-Fi
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    • x
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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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    Orleans, Cape Cod 02653
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • Pet-friendly
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    • x
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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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    Orleans, Cape Cod 02653
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Porch
    • Outdoor Dining Area
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    • Pet-friendly
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    • x
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    • x
    About this property
    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... View all property information
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    Orleans, Cape Cod 02653
    1 / 20
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    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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    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Internet Access
    • Patio
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    • Porch
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Ultimate privacy and Olde Cape Cod charm in one of the most pristine areas of East Orleans. This home is completely renovated, tastefully decorated, and comfortably furnished for your summer enjoyment. Central A/C throughout the home, lots of natural light, extra rooms that ramble with nooks and... 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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    • Grill
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    • Pet-friendly
    • Child-friendly
    • ?
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    • x
    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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    Orleans, Cape Cod 02653
    1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    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. Light and bright throughout, this custom home features an open floor plan, gleaming hardwood floors and full amenities-- including A/C! The well-equipped kitchen with large... View all property information
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    Orleans, Cape Cod 02653
    1 / 6
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
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    • x
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    • x
    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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    Orleans, Cape Cod 02653
    1 / 14
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
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    • Washer
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    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... View all property information
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    Orleans, Cape Cod 02653
    1 / 14
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    22 Uncle Vicks Way, , MA (ID# 18401) 2016 Cape Cod Summer Vacation. A charming Cape ranch located close to town and the East Orleans Village. This home offers a lovely private setting, nice country furnishings and a lower level family room. Ideal vacation home with 3 bedrooms and 2 bathrooms and... View all property information
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    Orleans, Cape Cod 02653
    1 / 14
    2 Bedrooms, Sleeps 6 | Quick View
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    • x
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    • x
    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 11 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    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
    1 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • DVD Player
    • Washer
    • Grill
    • Air Conditioning
    • Patio
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Bright, open and very charming home on a well maincured lot with spacious patio and yard. Close to fresh water swimming at Bakers Pond, or go hiking, biking, or swimming at nearby Nickerson State Park. Two bedrooms on the main floor plus lower level with 2 twins. New ductless AC, kitchen, sofas,... View all property information
    Location Information
    Orleans, Cape Cod 02653