South Orleans Rentals

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1,136 Houses

Topside MainHouse

South Orleans house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$1,230

Topside BoatHouse on Pleasant Bay

South Orleans boathouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$493

9 Woodridge Road 99912

South Orleans house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$201

A Contemporary Gem w/Cape Character, Dog Friendly!

South Orleans house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$143

Fire Pit, Outdoor Shower, Near Jacknife Beach!

South Orleans house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$182

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

South Orleans house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$344

Charming three bedroom home, only 2 miles to Jackknife Beach in Chatham

South Orleans house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$142

Close to Pleasant Bay & Beaches!

South Orleans house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$147

Private Lake Access, Great for Families!

South Orleans house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$280

Explore Downtown and Pleasant Bay!

South Orleans house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$136

Great rentals within 20 miles that match your search

Connors Cottage

West Hyannisport house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$201

In the Heart of Brewster. Min to Bay Beaches

Brewster house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Price per night from

$494

Luxurious & Spacious Waterfront Home on Swimmable Private Beach. Pet OK.

Barnstable house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$1,312

Barnstable Village Private Pool

Barnstable house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 3

“Great place to stay” The home was clean and well maintained. The pool was a huge hit with my niece and the rest of the family. We were in a great location, close to a beach, some shops and restaurants.

Price per night from

$457

Walk to Town, Chatham Bars Carriage House

Chatham apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 3

Price per night from

$603

Beautiful vacation home for rent

Dennis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$525

Perfect for two families!

Orleans house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 11

Price per night from

$738

4 Bedroom Cape with Swimming Pool

Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$603

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

Centerville cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$345

Charming 3 bdrm cottage - walk to beach

Dennis Port house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$247

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.

Price per night from

$329

Renovated Cape Cod Home -10 Minutes To Beaches & Ctr

Hyannis Port house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

Price per night from

$371

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.

Price per night from

$574

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.

Price per night from

$746

“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!!!

Price per night from

$396

Price per night from

$735

Beautiful Home - Great Price, Wi Fi, Flat Screen

Yarmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$201

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.

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

Price per night from

$230

Classic Cape Cod cottage on a quiet lane

Eastham cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Perfect location” We had a wonderful time on vacation in this house. It was spacious and sunny and the yard was huge. Location was perfect walking distance to bay beach and fresh water pond. Also close driving to all of the fun in Eastham. The owners were super helpful with all my questions....and I often repeated questions and asked a lot. Thanks for a great vacation. Sharon

Price per night from

$148

Spectacular Waterfront Townhome - Oyster Pond #25

Chatham house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$873

Summer Fun in Eastham

Eastham cottage

  • 1 bathroom
  • sleeps 2

Price per night from

$115

Vacation Home Away from Home!

Truro house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$295

High-end Brewster ,Mass. Bay view town home

Brewster apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$410

CapeCod nrOcean quiet woods ac Sleeps12, dsl

Truro house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

Price per night from

$984

The Cape Cod Cottage with Beach Pass

Eastham cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$295

Responds fast! avg. 24 minutes

Price per night from

$287

Serene Pond Setting

Truro cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$345

Viewing 38 of 1,136
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