Orleans Vacation Rentals

(42 rentals)
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Key Amenities

  • Kid friendly

About this property

Beutiful place to relax we had the best view from the masters bedroom, we offers breakfast and bed. This its beutiful cottage house we rental vacation summers second floor includes 2 rooms with magnificent views you will and enjoy a peaceful place

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Property Type

Orleans Cottage

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Spacious 2,500 square ft. family home with abundant natural light nestled in a private association of 20 homes in easy walking distance (0.3 miles) to a saltwater pond (Meetinghouse Pod). Our house is on a 0.7 acre lot with a large, wooded backyard offering privacy in a neighborhood surrounded by Pleasant ...

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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

$297

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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2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 0.2 miles to Bakers Pond

$237

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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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to Nauset

$360

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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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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2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 0.2 miles to Skaket

$200

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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Key Amenities

  • Kid friendly
  • Oceanfront
  • Pet friendly
  • Rentals by owner

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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3 BR | 2.5 BA | Sleeps 8 | Quick View

Distance to beach: 0.8 miles to Skaket Beach

$449

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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4 BR | 2.5 BA | Sleeps 10 | Quick View

Distance to beach: 0.6 miles to Skaket

$410

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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5 BR | 3.5 BA | Sleeps 11 | Quick View

Distance to beach: 1 miles to Nauset

$805

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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3 BR | 2 BA | Sleeps 7 | Quick View

Distance to beach: 0.1 miles to Bakers Pond

$261

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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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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4 BR | 3 BA | Sleeps 11 | Quick View

Distance to beach: 3 miles to Nauset Beach

$557

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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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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2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 0.0 miles to Mayflower Point

$232

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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3 BR | 2 BA | Sleeps 8 | Quick View

Distance to beach: 0.0 miles to Pilgrim Lake

$416

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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2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 0.0 miles to Mill Pond

$186

avg/night

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Key Amenities

  • Kid friendly

About this property

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 sandy ...

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Property Type

Orleans House

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3 BR | 2.5 BA | Sleeps 10 | Quick View

Distance to beach: 0.2 miles to Mill Pond

$566

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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3 BR | 4 BA | Sleeps 8 | Quick View

Distance to beach: 0.0 miles to Bakers Pond

$599

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 10 | Quick View

Distance to beach: 0.8 miles to Crystal Lake

$447

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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6 BR | 4 BA | Sleeps 12 | Quick View

$1054

avg/night

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Key Amenities

  • Kid friendly
  • Pool
  • Private pool

About this property

Fabulous two home property with a pool! This unique property is perfect for larger and multi-generational groups with two houses connected by a covered walkway. Gorgeous heated pool and jacuzzi and large patio with stone fireplace provide perfect outdoor living. The property sleeps 12 with 6 bedrooms ...

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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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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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5 BR | 3.5 BA | Sleeps 10 | Quick View

Distance to beach: 1 miles to Nauset

$963

avg/night

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Key Amenities

  • Kid friendly

About this property

Let nature surround you in this sprawling contemporary where an artists touch and peeks of the Atlantic Ocean are present throughout. Enter this home into the large living, dining space with vaulted ceilings & large sliders all around. Down the hall from the living area you will find a full bath with ...

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Property Type

Orleans House

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2 BR | 2 BA | Sleeps 6 | Quick View

$359

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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$484

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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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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5 BR | 3 BA | Sleeps 10 | Quick View

1

Distance to beach: 2 miles to Nauset Beach

$600

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

"The Perfect Vacation Rental"

We have been visiting the Cape for many years , decades. Always renting a new location.I know now that we never found the right house until I came across this treasure, 2 yrs ago. This home is well constructed, ...

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4 BR | 3 BA | Sleeps 10 | Quick View

1

Distance to beach: 0.1 miles to Nauset Beach

$1012

avg/night

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Key Amenities

  • Kid friendly
  • Pool
  • Private pool

About this property

Smell the sea air and listen to the soothing rhythm of the ocean at Sea Mist!  A short 2/10ths of a mile from one of the most beautiful beaches on Cape Cod, this property brings together easy access to Nauset Beach with the luxury of a salt-water heated pool that includes a hot tub and sun shelf.  ...

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Property Type

Orleans House

"Beautiful House, Would Move in if We Could"

This home was absolutely gorgeous from top to bottom, and we would move here if we could. The larger bedroom on the second floor has fantastic sunrise views, and I can’t think of a better way to wake ...

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5 BR | 2 BA | Sleeps 10 | Quick View

Distance to beach: 0.0 miles to Atlantic Ocean

$725

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 8 | Quick View

$461

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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3 BR | 2 BA | Sleeps 6 | Quick View

$683

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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3 BR | 1 BA | Sleeps 6 | Quick View

Distance to beach: 0.2 miles to Skaket

$271

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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4 BR | 2 BA | Sleeps 6 | Quick View

$360

avg/night

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Key Amenities

  • Kid friendly
  • Pet 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. Linens and Towels are provided.

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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

"Nice place"

Two of us had plenty of room the place was very clean and comfortable. We had a great stay and will be back.

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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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1 BR | 1 BA | Sleeps 2 | Quick View

Distance to beach: 0.3 miles to Nauset Harbor

$173

avg/night

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Key Amenities

  • Kid friendly

About this property

Adorable guest house located in a beautiful, quiet area about 3/10ths of a mile from Nauset Harbor. Consisting of 528 square feet, the cottage offers much! The cozy living/dining/kitchen area , includes a queen sofabed and A/C unit. The bedroom has a king (easily converted into 2 twins, if you prefer) ...

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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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4 BR | 3 BA | Sleeps 9 | Quick View

Distance to beach: 3 miles to Pleasant Bay Beach

$490

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 | 4.5 BA | Sleeps 8 | Quick View

Distance to beach: 5 miles to Nauset Beach

$929

avg/night

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Key Amenities

  • Kid friendly

About this property

Enjoy your own private SALTWATER POOL! Pristine Contemporary Cape with central A/C and enclosed saltwater pool. This 4-bedroom, 4.5 bath home is designed for today's living with an inviting open floor plan and great vacation feel throughout. Wonderful updated kitchen with island, spacious living ...

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Property Type

Orleans House

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About this property

Suitable for 2 families or extended family. 2 Kitchens, 2 entrances. Sleeps 10.

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Property Type

Orleans House

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Orleans Vacation Rentals

Find your ideal Orleans vacation rental today


The population of this Lower Cape town swells during the summer for good reason. Orleans has easy access to so many things that people booking vacation rentals covet. We have an outstanding selection of vacation houses perfect for adventure-seeking travelers. One of the best and most underrated parts of staying in Orleans is the easy access via route 6 to Outer Cape spots like Eastham and Wellfleet, as well other Lower Cape spots like Chatham. But you don't have to leave town if you book a vacation rental in Orleans. Let's have a look...

Orleans, MA travel advice


Summer in Orleans, Massachusetts is great, regardless of where your rental is located. But perhaps better than most places, "shoulder season" (meaning Spring and early Fall) in Orleans is a treat. Most of the restaurants, shops, and boutiques in Village Center stay open during shoulder season. And the town has some great trails for walking and biking, plus the town reduces the restrictions of having dogs at the beach. So, it's easy to see why people book vacation rentals in Orleans during the summer and the surrounding shoulder season months, as well.

Activities and beaches


Get your tide chart ready because Orleans has some of the Cape's most diverse bodies of water as well as some of its best beaches. Skaket Beach and Rock Harbor sit on Cape Cod Bay -- so if book a vacation rental near here, but sure to catch a sunset!

While on the west end of town there's Nauset Beach and Mill Pond. Nauset Beach is on the south end of the Cape Cod National Seashore, which attracts travelers from around the country and the globe. Parking is $20/day the last time we checked but if buy admission to one beach on the CC National Seashore, you can visit them all without paying.

You can't miss Pleasant Bay and Little Pleasant Bay which are accessible to the east of Route 28. This is a water-lover's paradise with everything you could ever want in one place, including some diverse wildlife.

There's a great local art scene here, too. Vacationers and year round residents love the galleries dotted around Route 6A nad Main Street including Trove Art Gallery & Boutique, the Frying Pan Gallery, Left Bank Gallery, and Coastal Craft Gallery.


Outdoor attractions


Outdoor activities rule in Orleans! There's something for all vacationers in this Lower Cape town. Ever heard of renting a catboat? You can try that or rent a kayak or paddleboard to navigate Orleans's waterways. Some of the best include Cape Kayaking, Arey's Pond Boat Yard, Goose Hummuck, or Pleasant Bay Community Boating, all town favorites.

If deep-sea fishing is your idea of the perfect vacation activity, try Dragonfly Sportfishing for a a fishing charter -- hopefully you'll see striped bass or bluefin tuna!

There are boating centers, and yacht clubs in Orleans too. If you book an Orleans vacation rental, check out Blue Claw Boat Tours. Captain Rob will help you do it right with a tour from Orleans to Chatham Harbor. Definitely on our list of "musts".


Recommended food and restaurants in Orleans


Many of Orleans's top restaurants are clustered just south of the rotary connecting route 6 and route 28. There is something for most travelers for sure, so here's the deal on a few of our recommendations:

Land Ho! -- first off, classic name for a pub and grub place on the Cape. This spot right on Main Street is great for a beer and for some laid back apps and main dishes. It's popular with locals and seasonal visitors staying in vacation rentals, alike. Plus, it just turned 50!

The knack is one of the first restaurants you see as you get off the Orleans rotary from Route 6. It's known for its modern airy accommodations, burgers, and lobster rolls -- or as the locals say "lobstah rolls".

If you want more of a bar scene on your vacation, try Mahoney's Atlantic Bar & Grill. It's styling but not upscale and it has a vibrant bar scene (by Cape standards!) and is a good dinner spot with a full menu.

For some people, it's not a vacation until you've had a rockin' breakfast. For that, check out the Hole-in-One on route 6A, which has great donuts and coffee. But the show here are the muffins -- mocha fudge is a must!

We're calling right now: the best coffee joint on the Cape is Sunbird -- pretty great logo too. The lunch is sneaky great (esp for families) at this local favorite. They've made a great transition during/after the pandemic too so it's easy to order online and pick up outside.

A list of restaurants in Orleans wouldn't be complete without mentioning Hot Chocolate Sparrow on Old Colony way. Its got ice cream, coffee, espresso, sweets and, um, hot chocolate for days...


Orleans vacation rentals on Cape Cod Vacation Rentals


Booking Orleans vacation cottages and homes is super easy on CapeCodVacationRentals.com. You can save significantly over booking a hotel or an inn. Plus, you'll have all the comforts and space of home in your vacation rental. Our inventory of houses in this Lower Cape town can't be beat. Happy planning!