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Holiday Rentals and Homes 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 / 28
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    Studio, 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
    1 / 26
    Studio, 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
    1 / 16
    4 of 5 bubbles (1) Very good
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    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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    Studio, 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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    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    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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    Orleans, Cape Cod 02653
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    4 of 5 bubbles (4) Very good
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    32 Pond Road, Orleans -( ID: 18315) 2017 Season! 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... View all property information
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    Orleans, Cape Cod 02653
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    Studio, 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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    1 / 30
    Studio, 4 Bathrooms, Sleeps 8 | Quick View
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    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
    1 / 36
    Studio, 4 Bathrooms, Sleeps 9 | Quick View
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    Elevated ocean views, walk to Nauset Beach. Linens included. Peak Summer Weekly Rates: $4,500 - $5,200 (Rents Saturday to Saturday during peak season) This spacious East Orleans home is located just off Nauset Beach in the desirable Grand View neighborhood. This neighborhood is characterized by... View all property information
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    Orleans, Cape Cod 02653
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    Studio, 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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    Studio, 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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    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    Nauset Heights! Absolutely lovely, newly built guest house located just under a half mile from the sandy shore of Nauset Beach on The Atlantic. Designed with the cozy character of a barn with the finer amenities of today. Beautifully detailed throughout with authentic wide pine floors, sliding barn... View all property information
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    Orleans, Cape Cod 02653
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    3.5 of 5 bubbles (4) Average
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    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
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    Studio, 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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    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    Charming modern waterfront cottage-- now with A/C!-- located in the exclusive Mayflower Point section of Orleans where the Namequoit River meets Little Pleasant Bay. The secluded area boasts scenic water views, quiet nights and sounds of birds. The living space has a new whole-house fan, ceiling... View all property information
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    Orleans, Cape Cod 02653
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    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    61 Captain Linnell Road, Orleans, MA (ID# 100002) Near Skaket Beach 2017 Season! Spacious, beautifully updated, dog friendly home near Skaket Beach on Cape Cod Bay. Large granite and stainless kitchen opens to dining area, living area and office. Sliders to deck, brick patio, back yard and fire... View all property information
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    Orleans, Cape Cod 02653
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    5 of 5 bubbles (1) Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
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    This warm and inviting 6 bedroom, 4 bath home sprawls over 4 stories of comfortable rooms with spacious, open living areas and a private, fully fenced back yard. Perfectly located in South Orleans, the house is just minutes from the Lower Cape villages of Chatham, Brewster and Orleans. A beautiful... View all property information
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    Orleans, Cape Cod 02653
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    1 / 21
    Studio, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Skaket Beach at just 2/10ths of a mile, gorgeous marsh views and has been completely renovated & newly furnished in 2013! This rental home is perfect for the family. It has a lovely deck area with deck furniture to enjoy the stunning views, central a/c to keep you comfortable, 3 bedrooms , 1 full... View all property information
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    Orleans, Cape Cod 02753
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    Studio, 1 Bathroom, Sleeps 6 | Quick View
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    Step back in time in this classic turn of the century cottage with views of Cape Cod Bay. Located on a wonderful property with an expansive yard, a screened-in porch and a path down to the sandy shore of Cape Cod Bay. Additional amenities include: beach chairs, crock pot, room fans, lobster pot,... 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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    5 of 5 bubbles (1) Excellent
    Studio, 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
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    Studio, 4 Bathrooms, Sleeps 10 | Quick View
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    Beautiful and spacious vacation home perfect for the extended family- set on an acre-plus lot on a quiet cul-de-sac offering association access to Pilgrim Lake (just a short 1/2 mile walk through the neighborhood), along with saltwater access to Arey's Pond less than 1/4 mile away! This rambling... View all property information
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    Orleans, Cape Cod 02653
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    4 of 5 bubbles (1) Very good
    Studio, 2 Bathrooms, Sleeps 7 | Quick View
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    10 Shorewood Drive, Orleans MA (ID# 18402) ~ Near Bakers Pond 2017 Season! 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... View all property information
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    Orleans, Cape Cod 02653
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    Studio, 3 Bathrooms, Sleeps 6 | Quick View
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    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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    Studio, 4 Bathrooms, Sleeps 10 | Quick View
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    Crystal Lake Waterfront! Enjoy fresh water swimming right outside your door! This wonderful, private spot is ideal for the extended family offering 5 bedrooms plus an office/den, including an incredibly spacious master bedroom suite and two other bedrooms that open out onto a screened porch that... View all property information
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    Orleans, Cape Cod 02653
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    Studio, 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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    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    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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    Studio, 4 Bathrooms, Sleeps 8 | Quick View
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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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    Orleans, Cape Cod 02653
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    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    Wonderful marsh front home on Bay. Sunsets from the open deck or screened porch. This home offers a large eat-in kitchen with sliding doors to the deck, a large living room, family room and three bedrooms with room for eight. There is newly sanded floors, new granite counter tops in the kitchen,... View all property information
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    Orleans, Cape Cod
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Absolutely wonderful young 4 bedroom, 3 full bath cape house with open floor plan on private and quiet cul de sac street off Beach Road. Only 0.8 mile from the magnificent Nauset Beach!- One of the best beaches in Cape Cod. The house has a soaring cathedral living room with grand brick fireplace,... View all property information
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    Orleans, Cape Cod 02653
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    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    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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    Studio, 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
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    Studio, 4 Bathrooms, Sleeps 14 | Quick View
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    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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    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    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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    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    This lovely East Orleans vacation rental home is located apprx. 1 mile to Nauset Beach and apprx. 8/10ths of a mile to East Orleans Village with Joe s Bar n Grill (BNI), Zia s PIzzeria, Sundae School Ice Cream and Nauset Farms Market. This home has 4 bedrooms, 2 bathrooms, a gorgeous outdoor patio... View all property information
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    Orleans, Cape Cod 02653
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    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    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
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    Studio, 3 Bathrooms, Sleeps 9 | Quick View
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    Walk to the water from this private 4 bedroom, three bath home. Just one house away from a waterview and 200 yards to deeded access to a cove off The River. 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... View all property information
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    Orleans, Cape Cod 02653
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    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    Delightful ranch located in the Nauset Heights area of East Orleans, just .2 miles away from Nauset Beach! The house is bright and cheerful with a nautical theme and features a deck offering peeks of the Atlantic Ocean. With four bedrooms and 2 baths, it sleeps 8 comfortably. The first floor... View all property information
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    Orleans, Cape Cod
    1 / 17
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    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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    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Terrace
    • Balcony
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    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
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    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
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    • Pet-friendly
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    • ?
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    • ?
    About this property
    Spend time in this classic waterfront getaway know as The "Boathouse" at "Topside". Enjoy water views from every room. You and your guests will feel like you are on your own private boat, sailing the blue water of Pleasant Bay. Swim directly from your steps leading into the water or spend the day... View all property information
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    Orleans, Cape Cod
    1 / 19
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Completely renovated, absolutely gorgeous, Sea Captain's home located on over an acre in the highly sought after Nauset Heights area of East Orleans. Enjoy the light and breezy feeling throughout, the wonderful screened-in porch and the spacious deck with peeks of the ocean. A wonderful vacation... View all property information
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    Orleans, Cape Cod 02653
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    Studio, 2 Bathrooms, Sleeps 10 | Quick View
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    • Washer
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Patio
    • Waterfront
    • Internet Access
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Prestigious location within Quanset Harbor Club Association. Built on 1.3 acres and only 3 houses away from the community’s private beach on beautiful Pleasant Bay. This is the perfect property to enjoy all that Cape Cod has to offer. Home is newly furnished with a new gourmet kitchen with high... 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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    • Pet-friendly
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    • x
    About this property
    This 3 Bedroom 2.5 bath retreat with Central AC is hidden away down a semi private drive in East Orleans. It has large sliding glass doors down one side of the home off the living room offering lots of light. Mid century modern decor fills this clean lined living space. Passive solar compliments... View all property information
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    Orleans, Cape Cod 02653
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    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    This 4 bedroom, 3 and a half bath rental sits in a quiet area of Orleans. It is a quarter mile to Pah Wah Landing Conservation area on Little Pleasant Bay and a short walk through the conservation area to the beach. Little Pleasant Bay has great kayaking and boating from nearby Portanimicut Launch... View all property information
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    Orleans, Cape Cod
    1 / 26
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
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    • Porch
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Floor plans, 90+ glowing reviews and a full pictorial coverage of 11 Freeman Lane await your viewing on our site: 'Briar Point Properties'. Open your door and walk 1/2 mile to Nauset Harbor Beach for a swim and spectacular Atlantic Ocean views. This popular home has a cool central air... View all property information
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    Orleans, Cape Cod 02653
    1 / 15
    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
    • Wi-Fi
    • Satellite TV
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Location Information
    Orleans, Cape Cod 02653