South Orleans Rentals

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602 Houses

9 Woodridge Road 99912

South Orleans house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$200

A Contemporary Gem w/Cape Character, Dog Friendly!

South Orleans house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$142

Pristine waterfront oasis, plus game room, jacuzzi and home office!

South Orleans house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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$343

Close to Pleasant Bay & Beaches!

South Orleans house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$146

Explore Downtown and Pleasant Bay!

South Orleans house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$150

Great rentals within 20 miles that match your search

Cliff Cottage By The Pond

Dennis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$148

Raised Split Ranch Single House in South Dennis

Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$401

Perfect for two families!

Orleans house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 11

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Price per night from

$737

4 Bedroom Cape with Swimming Pool

Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$589

4br - 1350ft2 - Nature Lover's Hideaway

Wellfleet house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$328

High End-suite style cottage 5 min bike ride to amazing Craigville Beach.

Centerville cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$344

Sunset View Cottage

Truro cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Charming isolation getaway” What a wonderful stay we had at the Sunset View Cottage. The cottage is charming, rustic, and comes with all the basic necessities. There’s a screened in sitting area with a twin bed for those that like sleeping in the cool night breeze. We loved the pond, the boat, the kayak and the raft. The dock was a wonderful place to have breakfast; and it was also where we saw the Neowise comet and a few shooting stars! The pond itself is a gem because it offers very shallow waters for those learning to swim or dogs who like to fish, and deeper waters for jumping off the raft, floating around or swimming. Just to manage expectations, this is not a location for people who don’t like rustic accommodations or are afraid of bugs. It is a non-insulated cottage right near a pond surrounded by trees. It has comfortable beds, fans, screens, running hot water, a hammock, strong internet, a gas grill, and an outdoor shower. This suited our needs and made us extremely happy. In addition Christine and her family made us feel very welcome there & even pointed out the wild blueberries that we enjoyed picking. So grateful that they are open to sharing a slice of their heaven with us! We will surely be back.

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Price per night from

$328

Private Contemporary Cape Set on a Hilltop

Chatham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$344

Home Near Oceanside Beaches Dog Friendly!

Wellfleet house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$167

Classic Cape Great Location! Dog Welcome!

Wellfleet house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$163

2 min walk to the beach - 30 Union Wharf#3

Dennis Port condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$287

Hardings Beach Chatham Cape Cod

Chatham house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$279

28-2 Greyneck Road Harwich MA

West Harwich condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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$516

Home Away From Home

South Dennis cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

“South Dennis House” The house we rented was perfect for my family. My girls were happy they each had their own bed! The house had everything we needed. We enjoyed the short travel time to all of the Dennis area beaches. The owners were very friendly and helpful. We had a wonderful time.

Responds fast! avg. 2 hours 18 minutes

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Price per night from

$245

Nice clean house 1/4 mile walk to Sesuit Harbor!

Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$516

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Price per night from

$395

Cozy Beach Home - Walk Everywhere Beach and Fun!

South Yarmouth townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$115

Charming Cape Cod Cabin

Eastham house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$287

Central air conditioning, New House - Bayside Close to Campground Beach

Eastham house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“A great family vacation!” This was a great house! The sleeping accomodations were perfect for my family. The house had everything we needed and the location was ideal for staying in Eastham. The bike path had several entrances near the home and being pm the bay side of the cape allowed my wife and I to relax on the beach even with small children. Having a screened in porch too was a huge benefit of the house. Nice to have dinner outside without being dinner for the local Mosquitos.

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$573

Central air conditioning, New Eastham House - Steps to Beach

Eastham house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Great comfortable beach house” My wife and 2 children & I have been staying at this house for 7+ years, and it is a close walk of approximately 600 yards to a great Bay beach. This allows you to easily return for lunch. The house is comfortable for 2 families, as we always have another family of 4 visit us there. The beach is ideal for young children, and the house has all of the amenities of home. We look forward to another Summer Vacation in 2011.

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$745

“Great time!!” This wonderful home was great for our Cape vacation! The home is beautiful and the owner's pride and love for their home shows throughout the property. The owners were excellent to work with, very professional and very responsive to inquiries. The house is beautifully decorated and extremely well stocked with everything we needed to make our vacation perfect. We appreciated all the amenities - inside and out, the huge rear deck was one of our favorite places to relax and enjoy the quiet area and the beautiful landscaping, we could even hear the waves at night. The location was very convenient to restaurants, shops and beaches and is centrally located to exploring anywhere on the Cape. We are looking forward to calling this our "home away from home" again!!!

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$395

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Price per night from

$733

Cape Cod 2 BD cottage (June $1200wk) private beach in W. Hyannisport

West Hyannisport house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Our family enjoyed a memorable reunion week in this beach neighb” We spent the week walking to aves, swimming at Squaw Island, golfing, tennis, and dining out at some great restaurants. This beach house has central air, a new gas grill and outdoor shower. All musts for our vacation rental requests. Nice quiet area with great Cape Cod experiences. The house is clean and comfortable. Great master bed. Near boats to the vineyard and Nantucket. We plan on another family reunion vacation at this beach house again this summer.

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Price per night from

$264

Dennis Port walk to beach!

Dennis Port house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

“Adorable beachy cottage” Wonderful little cottage. Comfortable slept 4 of us, all the conveniences of home but must bring your own linens/towels/washcloths. Great location, walk to beach, good restaurants. Fireplace provided good heat.

Responds fast! avg. 1 hour 26 minutes

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Price per night from

$229

High-end Brewster ,Mass. Bay view town home

Brewster apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$409

Pleasant Forest Shores cottages #2 : So. Chatham

South Chatham cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$102

CapeCod nrOcean quiet woods ac Sleeps12, dsl

Truro house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

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Price per night from

$982

Responds fast! avg. 28 minutes

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Price per night from

$287

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Price per night from

$900

Quiet and comfortable 3 bedroom cape

Eastham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$327

Spectacular Private Waterfront and Beachfront Home

Wellfleet cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Unforgettable” Heaven on earth at Drew and Heather's ! Very pleasant house, with all facilities, and a hudge sundeck. High tide, and it's like a private pool at 30 ft. Low tide, and a wonderful sandbeach appears 6 hours for fantastic walks. Can you imagine nicer bike rides very early in the morning to PB's restaurant and baker at highway 6 (about 20 mn ), for a wonderful croissant breakfast ! So much to say about the stay at Wellfleet, Just come and see by yourself. It's sure, I'll be back (from France)

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Price per night from

$310

Pleasant Forest Shores cottages #3 : So. Chatham

South Chatham cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$115

Pleasant Forest Shores cottages #Apt : So. Chatham

South Chatham cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$75

Viewing 38 of 602
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