South Orleans Rentals

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1,139 Houses

Topside MainHouse

South Orleans house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$1,227

Topside BoatHouse on Pleasant Bay

South Orleans boathouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$492

9 Woodridge Road 99912

South Orleans house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$200

A Contemporary Gem w/Cape Character, Dog Friendly!

South Orleans house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$142

Fire Pit, Outdoor Shower, Near Jacknife Beach!

South Orleans house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$181

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

South Orleans house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$343

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

$146

Private Lake Access, Great for Families!

South Orleans house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$279

Explore Downtown and Pleasant Bay!

South Orleans house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$135

Great rentals within 20 miles that match your search

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

Barnstable house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$1,309

Raised Split Ranch Single House in South Dennis

Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$401

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

$456

Walk to Town, Chatham Bars Carriage House

Chatham apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 3

Price per night from

$602

Beautiful vacation home for rent

Dennis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$524

Glendon Beach Cottage #95 100 yds to the beach

Dennis house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Long Weekend” Great location to beach and local places to eat and drink. Easy access to the rest of the Cape. Pet friendly was a plus. The only downer was it stated it slept 6 but only room for 4, this made for some unhappy campers

Responds fast! avg. 8 minutes

Price per night from

$201

Perfect for two families!

Orleans house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 11

Price per night from

$737

4 Bedroom Cape with Swimming Pool

Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$602

4br - 1350ft2 - Nature Lover's Hideaway

Wellfleet house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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

Price per night from

$344

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

$328

Private Contemporary Cape Set on a Hilltop

Chatham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$344

Classic Cape Great Location! Dog Welcome!

Wellfleet house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$163

Across from Mayo Beach walk to downtown!

Wellfleet house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$120

Across from Mayo beach walk to downtown!

Wellfleet house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$124

Renovated Cape Cod Home -10 Minutes To Beaches & Ctr

Hyannis Port house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

Price per night from

$370

The Berry Quaint Cottage

South Dennis cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$213

Charming 2 bdrm 1 1/2 bath house

Dennis Port house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$194

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. 3 hours 57 minutes

Price per night from

$245

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

Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$516

Quintessential Cape Cod

West Yarmouth house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$745

Sunny Vacation Cottage in North Truro, MA

Truro cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$131

Great Place for a Cape Cod Vacation

Barnstable cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$1,145

Quaint 2 bdrm unit

Dennis Port house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$228

Ocean View Condo across from Beach with pool!

Dennis Port condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 34 minutes

Price per night from

$172

Chatham Beach Chic 5⭐ -5 min Walk to Beach! Cape Escape Hear the waves at Night!

South Chatham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$395

Price per night from

$395

Viewing 38 of 1,139
rentals in South Orleans

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