Luxury Vacation Rentals in Orleans

(35 rentals)
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4 BR | 3 BA | Sleeps 8 | Quick View

Distance to beach: 60 miles to Pleasant Bay

$915

avg/night

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Key Amenities

  • Kid friendly

About this property

Nestled along the picturesque shores of Pleasant Bay, this charming summer rental offers the perfect retreat for those seeking a serene coastal getaway. With its classic New England charm and stunning waterfront location, this home exudes warmth, character, and timeless appeal. Boasting 4 bedrooms, 3 ...

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Property Type

Orleans House

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Key Amenities

  • Kid friendly
  • Oceanfront

About this property

This beautiful, sunny farmhouse located near the heart of Orleans is an antique home that has modern updates inside and a gorgeous surrounding yard. Very private with ample parking. Walking path to Gould Pond for birdwatching and nature walks.The house is open, airy, very clean and well cared for. ...

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Property Type

Orleans House

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5 BR | 3.5 BA | Sleeps 11 | Quick View

Distance to beach: 1 miles to Nauset

$836

avg/night

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Key Amenities

  • Kid friendly

About this property

Cape Cod elegance describes this expansive, fully air-conditioned home sitting peacefully on 2.4 acres in the desirable Pochet area of East Orleans. Beautifully renovated in 2022 with new furnishings throughout makes this 5 bedroom, 3.5 bath home ideal for the larger gathering. The open kitchen/dining/living ...

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Property Type

Orleans House

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Key Amenities

  • Rentals by owner

About this property

Enjoy spectacular water views from almost every room of this 3 Bedroom, home that sleeps 7. Minutes from town, wake up to the calm, crystal smooth waters with sightings of seals, launch your kayak right from the property...wind down after a great day on the beach to cocktails on the expansive deck complete ...

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Property Type

Orleans House

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5 BR | 2 BA | Sleeps 10 | Quick View

Distance to beach: 0.0 miles to Atlantic Ocean

$687

avg/night

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Key Amenities

  • Kid friendly

About this property

Incredible spot! Expansive Cape cottage on a bluff in Nauset Heights overlooking Nauset Inlet and the Atlantic with upper level deck and a private stairway down to the beach. Casual Old Cape Cod with pine panelling throughout. The main floor bedrooms consist of a large bedroom with queen bed and a second ...

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Property Type

Orleans House

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4 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 0.0 miles to Town Cove

$629

avg/night

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Key Amenities

  • Kid friendly

About this property

'Westwinds' is a wonderful, classic expansive ranch located on beautiful Town Cove. Set far off the road, this very special property is surrounded by meadows, woodlands, and lovely waterfront views. Enjoy direct saltwater access from the property-- ideal for kayaking, canoeing, fishing and sailing ...

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Property Type

Orleans House

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5 BR | 3 BA | Sleeps 10 | Quick View

Distance to beach: 2 miles to Nauset Beach

$628

avg/night

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Key Amenities

  • Kid friendly

About this property

Beautiful FIVE-bedroom home with A/C and full amenities only minutes from Nauset Beach and East Orleans village! Ideal for larger gatherings and/or extended families, this meticulous, well-appointed, and beautifully decorated home offers two separate gathering spaces, two separate bedroom wings, air-conditioning, ...

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Property Type

Orleans House

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3 BR | 4 BA | Sleeps 8 | Quick View

Distance to beach: 0.0 miles to Bakers Pond

$606

avg/night

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Key Amenities

  • Kid friendly

About this property

Contemporary 3-level home with water views from every room and a private path to the pond only 75 feet away. Set on a cul-de-sac on a private lane only .5 mile to Nickerson Park biking and hiking paths and 3 miles to Skaket Beach on the Bay. Relax in air-conditioned comfort in this 2800 sq. ft. open-concept ...

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Property Type

Orleans House

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4 BR | 3 BA | Sleeps 11 | Quick View

Distance to beach: 3 miles to Nauset Beach

$600

avg/night

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Key Amenities

  • Kid friendly

About this property

Wonderful East Orleans property with newer furnishings and central A/C, perfect for family and friends of all ages. Enjoy this terrific 4 bedroom home that affords space for everyone. The main house has a spacious king bedroom on the 1st floor with a full bath and walk-in shower. The 2nd floor features ...

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Orleans House

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3 BR | 2.5 BA | Sleeps 10 | Quick View

Distance to beach: 0.2 miles to Mill Pond

$578

avg/night

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Key Amenities

  • Kid friendly

About this property

Salt waterfront home located in the Ocean Harbor Association in East Orleans. This 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 boating access and swimming ...

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Property Type

Orleans House

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$571

avg/night

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Key Amenities

  • Beachfront
  • Kid friendly

About this property

Sweet beach house tucked on a sandy lane, just minutes to both Priscilla Landing inlet and Nauset Beach. The home offers three bedrooms with one king and two others each with a queen bed. There is also one and a half baths. There are window A/C's throughout the house for your comfort and electric ...

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Orleans House

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3 BR | 2 BA | Sleeps 6 | Quick View

$564

avg/night

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Key Amenities

  • Kid friendly

About this property

This beautiful 3 bedroom 2.5 bathroom Crystal Lake home has high end finishes throughout and a location that can't be beat! Crystal Lake Haven has peeks of Crystal Lake and direct access to the lake via the property in front of it. The main level offers a large eat in kitchen/living area with ...

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Property Type

Orleans House

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4 BR | 3 BA | Sleeps 9 | Quick View

Distance to beach: 3 miles to Pleasant Bay Beach

$558

avg/night

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Key Amenities

  • Kid friendly

About this property

Waterfront with Private Dock on Namequoit River! Enjoy incredible views and access to the beautiful salt water of Pleasant Bay right from your own backyard! This spacious 3 bedroom + loft, 3 bath property sleeping 9 is a wonderful vacation spot to call your home away from home. The first level offers ...

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Property Type

Orleans House

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4 BR | 2 BA | Sleeps 8 | Quick View

$499

avg/night

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Key Amenities

  • Kid friendly

About this property

Overlooking Orleans Town Cove and with direct access to the water, this beautifully remodeled home is your perfect Cape Cod vacation retreat! Light and bright, with beautiful hardwood floors and an open floor plan, the main level has a large, fully equipped kitchen with granite counters and breakfast ...

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Property Type

Orleans House

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4 BR | 3 BA | Sleeps 10 | Quick View

Distance to beach: 0.8 miles to Crystal Lake

$472

avg/night

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Key Amenities

  • Kid friendly

About this property

Crystal Lake-- 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, ...

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Property Type

Orleans House

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3 BR | 2.5 BA | Sleeps 8 | Quick View

Distance to beach: 0.8 miles to Skaket Beach

$453

avg/night

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Key Amenities

  • Kid friendly

About this property

Light & bright 3-bedroom + den home with central A/C near Skaket Beach! Lovely 2900 sq. ft. Cape on a quiet lane 8/10 mile from the sandy shores of Cape Cod Bay. Main level features a spacious main bedroom with full bath and laundry area, a large living room, separate den (with queen pullout), an ...

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Property Type

Orleans House

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Key Amenities

  • Beachfront
  • Kid friendly
  • Oceanfront

About this property

Located just 2/10th's of a mile from bay-side Skaket Beach is this sweet 3 bedroom, 1 full bath (tub/shower combination) home offering beautiful tidal marsh views and a spacious deck to enjoy the outdoors. With Central A/C, the property is set back at the end of a sandy lane and is close to the Cape ...

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Property Type

Orleans House

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Key Amenities

  • Kid friendly

About this property

This Cape Cod home is perfect for the beach lover, boater, kayaker or paddle boarder with proximity to Mill Pond and boating to the outer beach! Beautiful home offers 3 spacious bedrooms and two full baths on two levels. Main level features a sunny living room with gas fireplace and flat screen TV ...

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Property Type

Orleans House

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3 BR | 2 BA | Sleeps 8 | Quick View

Distance to beach: 0.0 miles to Pilgrim Lake

$411

avg/night

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Key Amenities

  • Kid friendly

About this property

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 swim float for boating, fishing or swimming. The main deck, overlooking the water with comfortable outdoor furniture and gas grill, ...

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Property Type

Orleans House

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Spacious 2,500 sq ft. family home with abundant natural light in a private association of 20 homes in close proximity to saltwater pond - 0.7 acre lot with large, wooded backyard offering privacy in neighborhood surrounded by Pleasant Bay inlets, coves, and “rivers” - Located in East Orleans, ...

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Property Type

Orleans House

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4 BR | 2.5 BA | Sleeps 10 | Quick View

Distance to beach: 0.6 miles to Skaket

$399

avg/night

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Key Amenities

  • Kid friendly

About this property

Walk to Skaket Beach! Spacious home with A/C, tucked away at the end of a quiet cul-de-sac. Only .6 miles to the sandy shore of Cape Cod Bay via a neighborhood path. Offering great privacy on 1.3 acres, the highlights of this home are its wonderful family room with cathedral ceiling and wood stove, new ...

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Property Type

Orleans House

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2 BR | 2 BA | Sleeps 6 | Quick View

$379

avg/night

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Key Amenities

  • Kid friendly

About this property

Sunny 1960's style contemporary ranch in a gorgeous, private setting offers your perfect Cape Cod vacation! This one level home has 2 bedrooms and 2 updated full bathrooms with walk-in showers, a fully equipped kitchen, cozy living room and large dining room overlooking private yard. Primary Bedroom ...

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Property Type

Orleans House

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3 BR | 2 BA | Sleeps 6 | Quick View

$375

avg/night

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Beautiful summer rental close to shopping, tennis courts, playground and bike trail. Short drive to bay side beaches and ocean. All the amenities of home. Guests will be asked to provide their own linens. Towels are provided.

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Property Type

Orleans House

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 0.0 miles to Mayflower Point

$363

avg/night

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Key Amenities

  • Kid friendly

About this property

Chill out (now with central A/C!) 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. Enjoy its own path down a slope to Lonnie's River that leads out to Pleasant Bay. Perfect for boating ...

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Property Type

Orleans House

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3 BR | 1.5 BA | Sleeps 6 | Quick View

Distance to beach: 0.1 miles to Skaket Beach

$357

avg/night

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Key Amenities

  • Kid friendly

About this property

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 wireless ...

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Property Type

Orleans House

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to Nauset

$351

avg/night

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Key Amenities

  • Kid friendly

About this property

Great privacy in East Orleans! Enjoy this lovely 3-bedroom, 2-bath contemporary home 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 tucked up ...

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Property Type

Orleans House

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2 BR | 1 BA | Sleeps 4 | Quick View

$343

avg/night

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Key Amenities

  • Beachfront
  • Kid friendly
  • Rentals by owner

About this property

Enjoy breathtaking sunsets over Cape Cod Bay from this private, direct beachfront rental on kid-friendly, Skaket Beach in Orleans. Charming 2nd floor apartment with stunning views. Living area, 2 bedrooms, 1 bath and kitchenette. Very clean, cozy & simple. Max 4 people. Sorry no pets allowed.

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Property Type

Orleans Apartment

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3 BR | 1 BA | Sleeps 6 | Quick View

Distance to beach: 0.2 miles to Skaket

$336

avg/night

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Key Amenities

  • Kid friendly

About this property

Location, Location! Sweet and cozy 2-bedroom Plus bunkhouse just 2/10ths of a mile from gorgeous Skaket Beach on Cape Cod Bay. Corner lot on a quiet sandy road with 3 ductless A/C units, new stove & refrigerator, and outdoor shower. An ideal setting for the smaller gathering just steps to the sand! ...

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Property Type

Orleans House

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3 BR | 1.5 BA | Sleeps 6 | Quick View

Distance to beach: 0.2 miles to Nauset

$336

avg/night

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Key Amenities

  • Kid friendly

About this property

Walk to Nauset Beach! Once part of the historic Mayo Duck Farm and a 2/10 mile from beautiful Nauset Beach and the Atlantic Ocean. This home's furnishings have been refreshed, and include a flat screen television. Steam up the lobster in the country kitchen. Have your morning coffee on the back deck ...

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Property Type

Orleans House

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3 BR | 1.5 BA | Sleeps 6 | Quick View

Distance to beach: 0.2 miles to Nauset

$307

avg/night

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Key Amenities

  • Kid friendly

About this property

Very spacious one-level apartment only 2/10ths of a mile from gorgeous Nauset Beach on The Atlantic. NOW WITH A/C units! Completely refreshed with new rugs, new furniture and new gas grill. Step down to a second living area to the 'summer room' with a second TV which leads outside to a private ...

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Property Type

Orleans House

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3 BR | 2 BA | Sleeps 7 | Quick View

Distance to beach: 0.1 miles to Bakers Pond

$273

avg/night

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Key Amenities

  • Kid friendly

About this property

''Hilltop'' is a bright and airy newly-renovated home with easy access to beautiful Bakers Pond. Tucked up on a hill in a quiet neighborhood, this home has living areas on 3 levels, a fully-equipped kitchen and dining area (with bay windows) and opens to a large wraparound deck. Fresh ...

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Property Type

Orleans House

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3 BR | 1 BA | Sleeps 6 | Quick View

Distance to beach: 0.2 miles to Skaket

$248

avg/night

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Key Amenities

  • Kid friendly

About this property

Location, Location! Popular duplex cottages very close to Skaket Beach on Cape Cod Bay. Simple and beachy, each unit has a private deck and central air-conditioning! Both share the enclosed outdoor shower. No washer/dryer, but there's a clothesline for bathing suits and towels. Each unit has a bath ...

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Property Type

Orleans House

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2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 0.2 miles to Bakers Pond

$238

avg/night

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Key Amenities

  • Kid friendly

About this property

Spacious two-bedroom, one level home with CENTRAL AIR-CONDITIONING sleeping six tucked up on a wooded knoll at Bakers Pond. This spot offers much privacy and is less than .1 mile to beautiful freshwater swimming and kayaking on the pond. This location feels removed from it all, yet is only a 5-minute ...

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Property Type

Orleans House

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2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 0.0 miles to Mayflower Point

$237

avg/night

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Key Amenities

  • Kid friendly

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 little Pleasant Bay. Two bedrooms, one with a queen bed, the other with a bunk-bed ...

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Property Type

Orleans House

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About this property

Cozy Orleans one bedroom bungalow in historic Rock Harbor. Immaculately restored with granite counters and beautiful hardwood floors, tile bath, and high quality construction. Set within the tranquil beauty of Rock Harbor Creek and just 0.2 miles to Rock Harbor & Cape Cod Bay and .9 miles to the Cape ...

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Property Type

Orleans Cottage

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Orleans Vacation Rentals