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Orleans Vacation Rentals

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    Travellers to Orleans are booking May dates now. Secure your vacation rental today, and have the perfect trip.
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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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    Orleans, Cape Cod
    1 / 17
    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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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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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    Orleans, Cape Cod 02653
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    This lovely 3 bedroom, 2 bath East Orleans vacation rental is located 1.9 miles to Nauset Beach in East Orleans and just 3/10ths of a mile to Nauset Farms Market, Sundae School Ice Cream and Zia s Pizzeria. At this private and quiet location you can enjoy the beautiful outdoor living area and... 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
    1 / 10
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    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
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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
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    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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    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    NEW LISTING!!! This is a well appointed 3000 square foot home in South Orleans, minutes from Rt. 28. Easy access towards Nauset and Skaket beach or Pleasant Bay. The downstairs includes a master suite with King bed and ensuite, full open kitchen and dining room, kids play room, laundry / mud room.... View all property information
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    Orleans, Cape Cod 02653
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    4 of 5 bubbles (1) Very good
    4 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
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    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Located in desirable East Orleans, Nauset Heights, this beautiful 3 bedroom, 1 bath home is a walk to the Outer North Nauset beach by way of Nauset Heights Association access & a great salt water inlet off the ocean. Private Nauset beach access is just 3/10ths of a mile away, Priscilla Landing... 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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    AT SKAKET BEACH! This charming renovated 1927 Cape has ample room for 6, a master bedroom with a vaulted ceiling and a private half-bath, plus a lovely wraparound porch with hammock. The sunny interior features newly-painted floors, comfy furnishings throughout and excellent amenities, including... 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
    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,... View all property information
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    Orleans, Cape Cod 02653
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    NEW LISTING! Pamper yourself in this grand 5 bedroom, 3 bath home located in an ultra private estate neighborhood overlooking Pilgrim Lake where you can swim and enjoy all non-motorized boating! Once you arrive at this expansive retreat in Orleans with 4 zoned central A/C, it will feel as though... 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
    20 Deerwood Lane, East Orleans, MA (ID# 120896) 2017 Season! 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... 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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    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
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    Orleans, Cape Cod 02653
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    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, 4 Bathrooms, Sleeps 14 | Quick View
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    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
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    Orleans, Cape Cod 02653
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    #502 The Lobsta Pot: East Orleans at its finest.  This quaint and FULLY RENOVATED cottage is a short walk to preservation land and a salt water bay worthy of kayaking.  Bring your bikes for a fast 10-minute ride to Nauset Beach or your kayaks for unending exploration in Town Cove, Mill Pond and... 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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    About this property
    Completely renovated 2 bedroom, 1 bath home on secluded acre at the end of a private road. Large private deck overlooks Duck Pond. Bird lovers Oasis! Stainless steel appliances, hardwood floors, washer/dryer, and spa shower. Large front and back yard great for play. Spotlessly clean. Walk to East... View all property information
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    Orleans, Cape Cod 02653
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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... 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
    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
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Walk to Nauset Beach from this wonderful home. Once part of the historic Mayo Duck Farm and a 2/10 mile walk from beautiful Nauset Beach and the Atlantic Ocean. This home has been completely "refreshed" for the 2014 season including some new furniture, new rugs and curtains, and even a new flat... View all property information
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    Orleans, Cape Cod 02653
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    5 of 5 bubbles (6) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Priscilla Landing is on the Nauset Estuary and has private pathways to the Atlantic. The first floor has 3 bedrooms. One room has Queen sized bed with a private bath. Second room as 2 twins also with a private bath. The Master suite has a King sized bed, Private Bath with walk-in shower and a... 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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    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
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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
    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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    Orleans, Cape Cod 02653
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    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    25 B Doane Road, East Orleans (ID# 106441) Nauset Heights 2017 Season! Adorable 2 bedroom cottage in Nauset Heights. Peeks of Mill Pond and around the corner from the landing. Cute, clean and charming 2 bedroom, 1 bath cottage with central air conditioning, part of the Pilgrim Lane cottages.... View all property information
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    Orleans, Cape Cod 02653
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Designed to look like an illustration from a children’s fairytale, this gracious and comfortable vacation home promises a magical vacation any time of the year. Enter through lush gardens into a surprisingly spacious, fully air conditioned home designed with relaxation, convenience, and fun in... View all property information
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    Orleans, Cape Cod 02653
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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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    6 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    Spacious 4 Acre private waterfront estate located in the prestigious and secluded Snow Point Association with private steps down to the water. Snow Point is a small peninsula of land in Orleans bordered by Rachel Cove, Town Cove and Woods Cove. You'll experience 180-degree views of the water from... View all property information
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    Orleans, Cape Cod 02653
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    4.5 of 5 bubbles (3) Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Contemporary home with private setting just 3/10 mile walk through a private neighborhood association path to Skaket Beach. Back yard overlooks an active cranberry bog! Near the Cape Cod Bike Trail and less than a mile to Rock Harbor fishing fleet. There are 3 decks and a fully screened porch with... View all property information
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    Orleans, Cape Cod 02653
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    Just 0.3 miles to Private Pleasant Bay Beach!! This 4 bedroom / 2 bath home features nice furnishings and amenities with access to a deeded path to a private beach on Pleasant Bay. It is about 3/10ths of a mile to the beach. The path is up a slight hill and wooded. The first floor features a... 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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    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... 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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    Newly Listed and Newly Updated, this is the rental you’ve been looking for!! Situated in a secluded wooded neighborhood, not far from shops and restaurants. Perfect home base, just 1.7 miles from popular Skaket Beach on Cape Cod Bay, 1 mile from Rock Harbor sunsets, and the bike path is just .3... 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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    Beautiful Open Layout with updated furnishings on Nauset Heights! Walk to Nauset Beach. Unique extras like large outdoor shower, original artwork, and private setting. See reviews and latest availability and pricing on our site: nausetrental For 2015: A/C in all Bedrooms, All new bedding,... View all property information
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    Orleans, Cape Cod 02643
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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: 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
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    Orleans, Cape Cod 02653
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    • x
    About this property
    26 Winslow Drive, Orleans (ID# 18543) ~ South Orleans 2017 season ! Located in South Orleans and close to Chatham for shopping and dining! This home is less than ½ mile to the beaches on Pleasant Bay and overlooks scenic Uncle Seth’s Pond. This contemporary home with an abundance of glass offers... 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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    • Grill
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    • Parking
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Three bedroom with A/C * Wireless Internet * NO Pets Accepted 2017 Season! Located on a quiet street in a private setting this 3 bedroom, 3 bath tri-level home is just 1/2 mile to Rock Harbor & a short drive to Skaket Beach and the local shops and restaurants in Orleans! AC units in all bedrooms... 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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    • Grill
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Location, Location! Popular duplex cottage very close to Skaket Beach on Cape Cod Bay. Simple and beachy, each side rents separately and has its own deck. Unit 2 (#429) with two bedrooms, has a new kitchen for the 2014 season. Unit 1 (#428) has three bedrooms. Both share the enclosed outdoor... View all property information
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    Orleans, Cape Cod 02653
    1 / 9
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Location, Location! Popular duplex cottage very close to Skaket Beach on Cape Cod Bay. Simple and beachy, each side rents separately and has their own deck. Unit 1 has three bedrooms (#428); Unit 2 has two bedrooms (#429). Both share the enclosed outdoor shower. Brand new Central AC! Additional... View all property information
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    Orleans, Cape Cod 02653
    1 / 19
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This recently renovated 2 bedroom,1 bath cottage is nicely appointed in a prime East Orleans location, convenient to beaches and shopping. It is situated across the street from Town Cove and Asa's Landing and offers views of the water. The cottage has lovely grounds and gardens to enjoy, as well as... View all property information
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    Orleans, Cape Cod 02653
    1 / 31
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Washer
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    244 Tonset Road, East Orleans (ID#125800) 2017 Season! Adorable cottage in East Orleans. This home has a screened porch overlooking the private back yard and is located in a nice neighborhood equidistant to Nauset and Skaket Beaches. 3 bedrooms 2 Full Baths, Master Bedroom with private bath.... View all property information
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    Orleans, Cape Cod 02653
    1 / 19
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Terrace
    • Balcony
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    About this property
    *If you can't find the dates available that you are looking for, we also have a second studio you may be interested in. Send us an inquiry and we will try to help you find the dates you want.* Beach Rose is a studio in “Holly Tree Cottages” available by world-renowned Nauset Beach. It offers high... View all property information
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    Orleans, Cape Cod 02653
    1 / 19
    3.5 of 5 bubbles (4) Average
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Parking
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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 6 | Quick View
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    1 / 7
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
    • DVD Player
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    • Patio
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    This small two bedroom home has all the quiet charm that you would expect for your cape cod vacation. Perfect for a couple or a small family, this home offers relaxation. - All reservations have a $60 reservation fee and a refundable security deposit. - Additional amenities include: coffee maker,... View all property information
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    Orleans, Cape Cod
    1 / 21
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Orleans, Cape Cod 02653