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Orleans Holiday Homes

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    Travellers to Orleans are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 31
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This immaculate home is located in a quiet neighborhood with just a .2 mile walk down a sandy path to Skaket Beach. It is also close to the bike trail and nearby shopping and restaurants. The home features an open floor plan with skylites, a spacious screened porch with seating, and a large back... View all property information
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    Orleans, Cape Cod 02653
    1 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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
    1 / 19
    4 of 5 bubbles (1) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Breathtaking views of Nauset Harbor and tucked away at the end of a private drive. With cathedral ceilings and lots of windows, this cottage offers spectacular waterviews from almost every room. The sun rises over the dunes and harbor right into both sitting rooms and dining area...sunset is even... 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
    1800s Antique Victorian only 1 mile from the Beach! Front porch rockers and side deck overlook the beautiful yard and gardens. The living room, dining room and family/tv room are very welcoming on the main level. One bedroom with a Queen bed is also located downstairs. Three additional bedrooms... View all property information
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    Orleans, Cape Cod 02653
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Wonderful home in very private East Orleans setting! Screened-in porch off the well-equipped kitchen area to enjoy all our summer meals. There is even a large deck off kitchen for grilling and relaxing. There are (3) bedrooms on first level including (1) king bedroom suite, and also (2) Queens... View all property information
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    Orleans, Cape Cod 02653
    1 / 21
    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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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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
    Location Information
    Orleans, Cape Cod 02653
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    1 / 16
    4 of 5 bubbles (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Peeks of the Atlantic Ocean from this hilltop home in East Orleans! Full of Cape Cod charm with a screened/enclosed sunporch that overlooks an expansive yard. Enjoy your privacy with over an acre of land just waiting for kites, volleyball, soccer, croquet, or shoot some hoops in the basketball... View all property information
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    Orleans, Cape Cod 02653
    1 / 13
    3 of 5 bubbles (1) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Listen to the waves in this historic home or walk to Nauset Beach! Home was once part of the Mayo Duck Farm and at one point a restaurant with a huge local following. Now devided into 2 separate rental units. Located 2/10 of a mile from the Atlantic and Nauset Beach this vacation spot is... 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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    About this property
    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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    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Price Range $1690 - $1800 NEW LISTING! BOOK BEFORE MEMORIAL DAY AND SAVE $200 OFF THE WEEKLY RATE!! This idyllic 3 bedroom/1 bath home sits at the end of a quiet cul-de-sac. A down to the studs renovation was designed to maximize space and sunlight. Its cheerful interior combines whimsy and... View all property information
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    Orleans, Cape Cod 02653
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Nice 2 bedroom, 1.5 bath home so close you can WALK to your own private association beach on PLEASANT BAY. When you walk in the front door you go up a few stairs to get to the main level. The first level has a nice living room/dining room, a galley kitchen, and a relaxing 3 SEASON ROOM where you... View all property information
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    Orleans, Cape Cod 02653
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    4 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    Exceptional property with architectural designed Main House with Restaurant Quality Kitchen which includes a commercial 8 burner stove and separate grill for pancakes and bacon, Sub Zero refrigerator and wine cooler and 3 sinks. A large, granite center island, ample dining area and separate bar... 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 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
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    WATERFRONT on Bakers Pond! Take the path from the patio to your private pondfront to enjoy swimming, fishing and kayaking on this lovely freshwater pond. Designed as an airy contemporary cabin on 3 levels-- all with sunset water views-- this home has beautiful pine panelling and hardwood fir floors... View all property information
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    Orleans, Cape Cod 02653
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    5 of 5 bubbles (1) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Stunning Carriage House with Ocean Views in Nauset Heights. This home has an authentic feel of a post and beam barn. Superbly appointed with sliding barn doors, authentic wide pine floors and an enormous fieldstone fireplace. Home offers an amazing kitchen, one bedroom plus open loft and a view... View all property information
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    Orleans, Cape Cod 02653
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Skaket Beach at just 1000 ft!! This gorgeous Orleans vacation rental home is located in the perfect spot for you to enjoy Cape Cod. At this lovely home you will be just 2/10ths of a mile from beautiful private access to Skaket Beach in Orleans on Cape Cod Bay. This home is located on an old Cape... View all property information
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    Orleans, Cape Cod 02653
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    1 / 16
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Grill
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    About this property
    Price Range $2000-$3500 NEW LISTING! PROPERTY UNDERGOING COSMETIC UPGRADES! NEW PICTURES COMING SOON! The moment you arrive at this 3 bedroom, 3 bath classic cape with central a/c, you will immediately downshift into vacation gear. Sited on a knoll in East Orleans, the secluded front yard is ideal... 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
    Just a short distance to the center of Orleans, this well kept Saltbox style house is convenient to everything. It is only .3 miles to the bike path and 1.6 miles to Skaket Beach. The large grassy yard is private and spacious. The cute back deck comes equipped with an electric grill and outdoor... View all property information
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    Orleans, Cape Cod 02653
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    19 Uncle Harveys Way (ID #130652) ~ 3 Bedroom Home with WiFi and a/c units 2017 Season! Not far from town landing for launching your kayak. Three bedroom 2.5 bath home that sleeps 7. One king and 5 singles. About a 1.4 miles to Nauset Beach in Orleans. Spacious, airy and bright best describes this... View all property information
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    Orleans, Cape Cod 02643
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    This Orleans property features stunning views of Robert's Cove from almost every room in the house. This custom built home has a casual floor plan that takes advantage of the serene waterfront setting, as well as comfortable furniture for relaxing. Enjoy the pathway around Robert's Cove or bring... View all property information
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    Orleans, Cape Cod 02653
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    5 Bedrooms, 6 Bathrooms, Sleeps 16 | Quick View
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    About this property
    Private Orleans resort-style compound with heated pool & spa, fire pit and cabana (linens included) NEW Listing for 2017! (more photos to come as renovations are completed) Peak Summer Weekly Rates: $12,500 - $14,000 (Rents from Sunday to Sunday during peak weeks) Your multi-generational or... 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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    Price Range $1400 - $1700 This very special 3 bedroom, 2 bath vacation rental features handsome wood floors and central air-conditioning. Located on a wooded lot, you can paddle board, kayak, or boat in adjacent Areys Pond, swim in nearby Crystal Lake, body surf or soak up the sun. This private and... View all property information
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    Orleans, Cape Cod 2653
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    4 of 5 bubbles (2) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Price Range $1250-$1575 Enchanting Orleans Vacation Cottage only 0.9 miles to picturesque Rock Harbor Beach. This property is bright, cheery, and a wonderful summer retreat on Cape Cod! Features include a remodeled kitchen with dishwasher, a cozy living area with free-standing A/C unit, TV, DVD... View all property information
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    Orleans, Cape Cod 2653
    1 / 16
    4 Bedrooms, 5 Bathrooms, Sleeps 16 | Quick View
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    About this property
    Private Orleans resort with water views, heated pool & spa; sleeps 14 (linens included) NEW Listing for 2017! (more photos to come when renovations are complete, these photos are from the previous owner) Peak Summer Weekly Rates: $15,900- $16,900 JUST REDUCED -- weeks of July 2nd and 9th reduced... 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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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    27 Pond Road, Orleans (ID# 22347) 2017 Season! Nestled on a private 1.5-acre wooded lot, this charming and newly constructed home combine’s comfort with gracious living! The large kitchen features high-end appliances, marble counters, breakfast booth with bay windows and opens to the dining area... View all property information
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    Orleans, Cape Cod 02653
    1 / 15
    1 Bedroom, 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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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Masterfully Renovated across from Pleasant Bay (Linens Included) Peak Summer Weekly Rates: $3,500 - $3,800 (Rents Saturday - Saturday during peak season) This pristine property is located on Orleans Road in Orleans. Every room, every aspect of this newly renovated home is truly something special.... View all property information
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    Orleans, Cape Cod 02653
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    4 of 5 bubbles (2) Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    10 Daley Terrace, Orleans(ID# 18332) ~ Close to town, baseball fields 2017 Season! This cozy ranch is set on a hill in a residential neighborhood & within close 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 the... 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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    Bright and spacious ranch located on a wonderful, 1.2 acre level lot off a quiet lane the desirable Barley Neck area of East Orleans. With A/C units in the living area, loft and bedrooms, and brand new finishes and furnishings throughout! Two bedrooms are on the main floor, each with a Queen bed... 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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    Spectacular Location! An outstanding waterfront spot offering exceptional privacy. Want to unplug? This simple, rustic cottage (no wifi, no TV) is on a peninsula surrounded by salt water and has views of Mill Pond. Launch your kayak or boat from its shore to access Nauset Inlet and to the beautiful... 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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    Beach, Kayaks, SUPs on Pristine Orleans Lake! (Pets Considered) Please Note: This home rents Sunday to Sunday in peak summer months Peak Summer Weekly Rates: $4,600 - $4,900 Expansive Waterfront Home on Crystal Lake in the heart of Orleans. Crystal Lake is a pristine fresh water lake located close... 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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    Price Range $3800-$5500 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,... 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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    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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    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Rare opportunity to vacation in Nauset Heights right on the waterfront! Perfect Beach House for the beach loving family or couple. Walk out the door to one of Cape Cods most beautiful beaches. Swim, fish, sunbath or take gorgeous walks for miles along the National Seashore. This 3 bedroom home has... 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
    Price Range $********* Situated between Skaket Beach on the bay and Nauset Beach on the ocean, this beautifully renovated home is tucked in a quiet neighborhood. It is a short walk to playgrounds, public tennis courts, the town of Orleans for great shopping and dining to satisfy every palate, and... 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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    About this property
    This 3 bedroom, 1 bath Orleans home is within walking distance of picturesque Rock Harbor and Cape Cod Bay. The first bedroom features a king sized bed, the second a double sized bed and the third has one twin sized bed. The spacious living room also offers a pull out sleeper sofa for extra... 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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    • Pet-friendly
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    • x
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    • x
    About this property
    With its great views of Cape Cod Bay across Namskaket Marsh from upper and lower decks, this charming and newly renovated home offers peace and privacy. Located on a cul-de-sac with a shady front yard, the house has skylights, sunlit rooms, an open loft with a sleep sofa and sliders to the decks... View all property information
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    Orleans, Cape Cod 02653
    1 / 26
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    • Waterfront
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    • x
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    • x
    About this property
    63 Briar Spring Road in East Orleans (ID #18264) ~ Waterfront Three Bedroom Home ~ Pochet Inlet Area Wonderful views! This updated home overlooks beautiful Pochet Inlet. Newly built in 2014, this property offers a spacious and open LR/DR/KIT located on the second level with a bonus room on the... 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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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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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    Orleans, Cape Cod 02653
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
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    • Balcony
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    • Terrace
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    • x
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    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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    Orleans, Cape Cod 02653
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    This cute 2 bedroom, 2 bath waterfront condo sits on beautiful Skaket Beach in Orleans. It is a second floor, end unit with unobstructed views of Cape Cod Bay. The property features two bedrooms, one with a queen sized bed and one with two twin sized beds, as well as a double pull out sleeper sofa... 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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    • Pet-friendly
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    • x
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    • x
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    4 Seaview Rd East Orleans (ID #130778) ~ Oceanside Two Bedroom cottage ~ Mill Pond Area 2017 Season! Darling little Cape cottage. Enjoy simple summer living in this peaceful setting of cottages near Mill Pond. This property offers wireless internet, two comfortable bedrooms with A/C units, bright... View all property information
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    Orleans, Cape Cod 02653
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • x
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    • x
    About this property
    This 2 bedroom Orleans cottage is light and bright and offers close proximity to Skaket Beach! Located in a residential neighborhood, it features two bedrooms and two full baths, sleeping up to 5 comfortably. There is a fully equipped kitchen with eat in dining area, cozy living area with flat... View all property information
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    Orleans, Cape Cod 02653
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    5 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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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    3 of 5 bubbles (2) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    8 Hofe Road, Orleans MA (ID# 18392) ~ Close to Skaket Beach and Bike Trail 2017 Season! Quoted by a previous tenant this is the best rental for the money....! Spacious ranch minutes away from Skaket Beach and the Cape Cod Rail Trail! Sliders lead from the dining area to a large shaded deck which... View all property information
    Location Information
    Orleans, Cape Cod 02653