Orleans Vacation Rentals

(36 rentals)
Sunny, Charming, 5 BR, Kid-Friendly, Updated Farmhouse w/AC

$491

avg/night

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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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Hidden Gem with pool

3 BR | 2 BA | Sleeps 6 | Quick View

$429

avg/night

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Key Amenities

  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

Beautiful, clean house with great outdoor space. Pool being installed and available starting Memorial Day-pictures will be added.This house is on a quiet lane 8 mins driving to both Nauset (ocean) and Skaket (bay) beaches. 1 mile from Orleans center with shopping and dining.Master bedroom with ...

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Property Type

Orleans House

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Orleans Beach Bungalow

2 BR | 1 BA | Sleeps 6 | Quick View

$285

avg/night

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Key Amenities

  • Kid Friendly

About this property

Sunny and cozy cottage is just 2/10 mile from Priscilla Beach in East Orleans. This charming home offers a full length back deck, living room open to kitchen with bar seating, two bedrooms and a loft. Mini-Split A/C in the living room to keep you cool on hot summer days. It's just a 5 minute stroll ...

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Property Type

Orleans Bungalow

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Orleans - Skaket (ASP-428)

3 BR | 1 BA | Sleeps 6 | Quick View

Distance to beach: 0.2 miles to Skaket

$229

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 with ...

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Property Type

Orleans House

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East Orleans - Nauset (ASP-448)

3 BR | 1.5 BA | Sleeps 6 | Quick View

Distance to beach: 0.2 miles to Nauset

$271

avg/night

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Key Amenities

  • Kid Friendly

About this property

Charming period home located only 2/10ths of a mile from gorgeous Nauset Beach on The Atlantic. Enjoy the sunny deck, comfortable furnishings, wonderful country kitchen and spacious backyard. Attached apartment also available for rent.

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Property Type

Orleans House

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Orleans - Skaket (ASP-530)

4 BR | 2.5 BA | Sleeps 8 | Quick View

Distance to beach: 0.2 miles to Skaket

$432

avg/night

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Key Amenities

  • Kid Friendly

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 with ...

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Property Type

Orleans House

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Orleans - Skaket Beach (ASP-771)

2 BR | 1 BA | Sleeps 4 | 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! Sweet and cozy 2-bedroom house just 2/10ths of a mile from gorgeous Skaket Beach on Cape Cod Bay. Corner lot on a quiet road with 3 A/C units, new stove & refrigerator, fresh bedding, outdoor shower. An ideal setting for the smaller gathering just steps to the sand! Separate bunk ...

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Property Type

Orleans House

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Orleans - Bakers Pond (ASP-1204)

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 0.2 miles to Bakers Pond

$217

avg/night

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Key Amenities

  • Kid Friendly

About this property

Recently renovated, 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 ...

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Property Type

Orleans House

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Nauset Beach Charmer

4 BR | 1.5 BA | Sleeps 8 | Quick View

$471

avg/night

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Key Amenities

  • Kid Friendly

About this property

New Rental for Summer 2021! Wonderful one-level cottage 3/10 mile to Nauset Beach. This 4 bedroom 1.5 home is updated, immaculate and is the perfect place to make memories for years to come. Main level offers a spacious and sunny open floor plan with vaulted ceilings and a fully equipped kitchen, spacious ...

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Property Type

Orleans House

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Orleans (ASP-1087)

3 BR | 3 BA | Sleeps 7 | Quick View

Distance to beach: 1 miles to Skaket

$327

avg/night

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Key Amenities

  • Kid Friendly

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 from ...

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Property Type

Orleans House

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Coastal Chic Getaway

3 BR | 2 BA | Sleeps 6 | Quick View

$436

avg/night

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Key Amenities

  • Kid Friendly

About this property

New rental for Summer 2021! Light and bright East Orleans cape convenient to both Nauset Beach and Main Street shops and restaurants. Main level features a spacious living room with cathedral ceilings and plenty of seating and a flat screen TV, a large fully equipped kitchen, a sunny dining room that ...

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Property Type

Orleans House

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East Orleans - Mill Pond (ASP-478)

2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 0.0 miles to Mill Pond

$171

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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Orleans - Crystal Lake (ASP-1129)

4 BR | 3 BA | Sleeps 10 | Quick View

Distance to beach: 0.8 miles to Crystal Lake

$418

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, and ...

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Property Type

Orleans House

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East Orleans - Nauset (ASP-447)

3 BR | 1.5 BA | Sleeps 6 | Quick View

Distance to beach: 0.2 miles to Nauset

$243

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 patio with ...

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Property Type

Orleans House

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Orleans (ASP-1166)

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 0.0 miles to Mayflower Point

$230

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 or kayaking. ...

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Property Type

Orleans House

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Orleans (ASP-1147)

1 BR | 1 BA | Sleeps 2 | Quick View

Distance to beach: 0.3 miles to Nauset Harbor

$160

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 features a brand new kitchen, queen sofabed and A/C unit. The bedroom has a king (easily converted into 2 twins, ...

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Property Type

Orleans House

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Orleans - Waterfront on Bakers Pond (ASP-1205)

4 BR | 4 BA | Sleeps 8 | Quick View

Distance to beach: 0.0 miles to Bakers Pond

$540

avg/night

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Key Amenities

  • Kid Friendly

About this property

2013 WATERFRONT HOME! Gorgeous 3-level contemporary home with 180 degree view of a beautiful 32-acre lake and conservation lands. With water views from every room, 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 .3 mile to a sandy beach/boat ...

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Property Type

Orleans House

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Orleans - Lakefront Retreat (ASP-1181)

3 BR | 2 BA | Sleeps 8 | Quick View

Distance to beach: 0.0 miles to Pilgrim Lake

$392

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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Orleans - Namequoit River (ASP-550)

1 BR | 1 BA | Sleeps 2 | Quick View

Distance to beach: 4 miles to Nauset

$174

avg/night

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Key Amenities

  • Kid Friendly

About this property

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 fans ...

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Property Type

Orleans House

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Orleans - Bakers Pond (ASP-1250)

3 BR | 2 BA | Sleeps 7 | Quick View

Distance to beach: 0.1 miles to Bakers Pond

$235

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 comfortable furnishings, ...

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Property Type

Orleans House

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Orleans - Town Cove (ASP-1256)

4 BR | 2 BA | Sleeps 8 | Quick View

Distance to beach: 0.0 miles to Town Cove

$463

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 out ...

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Property Type

Orleans House

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2/10 Mile to Nauset Beach, New In-Ground Saltwater Pool & Hot Tub

$1057

avg/night

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Key Amenities

  • Kid Friendly
  • Private Pool

About this property

NEW HEATED IN-GROUND SALTWATER POOL AND HOT TUB!! Large home just 2/10ths of a mile via a private beach path to Nauset Beach. All three bedrooms are oversized and include their own bathroom. Enjoy two spacious master bedroom suites, one on each floor, and both with king-size beds. The first floor master ...

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Property Type

Orleans House

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East Orleans Water View Getaway

$371

avg/night

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Key Amenities

  • Kid Friendly

About this property

Immaculate home sleeps 6 in a private location with beautiful water views. Tastefully decorated and spotless, this 1600 square foot home has 2 queen bedrooms on the main level and a loft space with a double and a twin bed. The main level includes a sunny fully equipped eat-in kitchen with quartz counters ...

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Property Type

Orleans House

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East Orleans - Barley Neck (ASP-1270)

2 BR | 1.5 BA | Sleeps 4 | Quick View

Distance to beach: 2 miles to Nauset Beach

$298

avg/night

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Key Amenities

  • Kid Friendly

About this property

Just Listed! Bright, sunny and spacious two bedroom contemporary home located in the Barley Neck area of East Orleans. Loaded with artistic charm featuring cathedral ceilings, wonderful open kitchen and dining area, separate living room and wood floors throughout. Enjoy spending time on the large wrap ...

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Property Type

Orleans House

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East Orleans (ASP-1155)

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to Nauset

$337

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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4/10ths Mile to Skaket Beach

4 BR | 2 BA | Sleeps 8 | Quick View

$741

avg/night

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Key Amenities

  • Beachfront
  • Kid Friendly
  • Oceanfront

About this property

**$500 off for June 26-July 3, 2021** Welcome to your perfect Cape Cod vacation at Namskaket Retreat! Nestled in the bayside Orleans neighborhood of Namskaket, this beautifully updated historic home is just ½ mile to Skaket Beach and convenient to the Cape Cod Rail Trail and Orleans Center. Nickerson ...

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Property Type

Orleans House

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Orleans (ASP-943)

4 BR | 2.5 BA | Sleeps 10 | Quick View

Distance to beach: 0.2 miles to Pilgrim Lake/Nauset

$336

avg/night

View Details

Key Amenities

  • Kid Friendly

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, Pilgrim ...

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Property Type

Orleans House

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East Orleans - Ocean Harbor Association (ASP-1142)

4 BR | 2.5 BA | Sleeps 10 | Quick View

Distance to beach: 0.2 miles to Mill Pond

$496

avg/night

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Key Amenities

  • Kid Friendly
  • Pet Friendly

About this property

Salt waterfront home located in the Ocean Harbor Association in East Orleans. This newly-furnished 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 ...

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Property Type

Orleans House

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South Orleans - Uncle Seth's Pond (ASP-1272)

4 BR | 2.5 BA | Sleeps 8 | Quick View

Distance to beach: 0.7 miles to Pleasant Bay

$521

avg/night

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Key Amenities

  • Kid Friendly

About this property

NEW LISTING! Nature abounds throughout this beautiful and serene setting on Uncle Seth's Pond. Enjoy the lovely views and freshwater access from your own shoreline! This custom built 4 bedroom, 2 1/2 bath home with central-air conditioning offers a spacious living room that leads out to an expansive deck ...

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Property Type

Orleans House

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East Orleans - Snow Shore (ASP-1159)

2 BR | 2.5 BA | Sleeps 6 | Quick View

Distance to beach: 0.2 miles to Snow Shore

$289

avg/night

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Key Amenities

  • Kid Friendly

About this property

'Rose Cottage' is an absolutely lovely, light and bright expanded cottage located on almost an acre in the desirable Snow Shore area of East Orleans. Recently renovated with two bedroom suites (one on each level), separate sitting/sleeping alcove, multiple decks, and skylights. This wonderful vacation ...

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Property Type

Orleans House

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Orleans - Skaket (ASP-429)

2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 0.2 miles to Skaket

$164

avg/night

View Details

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 with ...

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Property Type

Orleans House

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Orleans - Skaket Beach (ASP-1268)

3 BR | 2.5 BA | Sleeps 8 | Quick View

Distance to beach: 0.8 miles to Skaket Beach

$421

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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Orleans - Nauset Beach (ASP-1251)

3 BR | 1 BA | Sleeps 6 | Quick View

Distance to beach: 0.8 miles to Nauset Beach

$176

avg/night

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Key Amenities

  • Kid Friendly

About this property

On the way to Nauset Beach! Charming classic Cape Cod pine paneled cottage tucked away in 6-acre Nauset Farms Condominiums. This sweet, well loved cottage offers new ductless A/C, flat screen TV and brand new living room sofa. A great vacation spot close to the East Orleans village and only 3/4 of a mile ...

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Property Type

Orleans House

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Rock Harbor Hideaway

3 BR | 1 BA | Sleeps 6 | Quick View

$303

avg/night

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About this property

Immaculate and beautifully renovated three bedroom home perfectly located between Orleans Main Street and Rock Harbor. The home is set back from the road and offers privacy and the charm of Cape Cod. Main level with living room, dining room, fully equipped kitchen, two bedrooms (both with TVs) and one ...

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Property Type

Orleans House

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3 bed 3/10 mi to Mill Pond and Nauset Inlet

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 0.3 miles to Mill Pond

$437

avg/night

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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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Orleans (ASP-1210)

2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 0.0 miles to Mayflower Point

$212

avg/night

View Details

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

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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

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!