South Orleans Rentals

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949 Houses

Topside BoatHouse on Pleasant Bay

South Orleans boathouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$492

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

Fire Pit, Outdoor Shower, Near Jacknife Beach!

South Orleans house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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$181

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

South Orleans house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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$343

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

South Orleans house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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$142

Close to Pleasant Bay & Beaches!

South Orleans house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$146

Private Lake Access, Great for Families!

South Orleans house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

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$279

Explore Downtown and Pleasant Bay!

South Orleans house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$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

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$1,309

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.

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$456

Walk to Town, Chatham Bars Carriage House

Chatham apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 3

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$602

Beautiful vacation home for rent

Dennis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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$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

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$201

4 Bedroom Cape with Swimming Pool

Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$602

4br - 1350ft2 - Nature Lover's Hideaway

Wellfleet house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$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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$344

Charming 3 bdrm cottage - walk to beach

Dennis Port house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$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.

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$328

Classic Cape Great Location! Dog Welcome!

Wellfleet house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$163

Across from Mayo Beach walk to downtown!

Wellfleet house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$120

Across from Mayo beach walk to downtown!

Wellfleet house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$124

Renovated Cape Cod Home -10 Minutes To Beaches & Ctr

Hyannis Port house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

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$370

The Berry Quaint Cottage

South Dennis cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$213

Charming 2 bdrm 1 1/2 bath house

Dennis Port house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$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

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$245

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

Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$516

Quintessential Cape Cod

West Yarmouth house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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$745

Sunny Vacation Cottage in North Truro, MA

Truro cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$131

Great Place for a Cape Cod Vacation

Barnstable cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$1,145

Quaint 2 bdrm unit

Dennis Port house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$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

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$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

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$395

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$395

Cozy Beach Home - Walk Everywhere Beach and Fun!

South Yarmouth townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$115

Glendon Beach Cottage #97 100 yds to the beach

Dennis Port house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$201

Glendon Beach Cottage #93 100 yds to the beach

Dennis Port house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Cozy & private by the sea!” My husband & I were looking to stay somewhere quiet & private for our week get-a-way. We were not looking to be entertained, we were looking to relax. This was the right choice for our vacation!. The cottages are nearby each other but separate from each other providing privacy from the neighboring cottages. We stayed in cottage #93 on the end & felt more "secluded" from the driveway/roadway. The beach was a short walk from the cottage - no need to bring the car! There were a number of trips made in the morning to the pretty beach location coffee in hand or a chair, drink & book later in the day. The beach is a rare find during "high season" since there is no fee to use. The cottage itself is small-ish as expected w/2 bedrooms, 1 bathroom, 1 common area for kitchen/living space & a nice size front deck w/a picnic table. Easy enough for simple vacation living. When we arrived, we encountered a couple of issues @ the cottage that were an indication of the previous inhabitants & their negligent & destructive living habits. One call to Jamie and the issues were handled promptly. The Property Management Team came to the property & addressed all concerns immediately! All in all, my husband & I will surely be looking to return to this cottage for another stay - maybe even bring the grandkids next time!

Responds fast! avg. 8 minutes

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$201

3bd 2 bath steps to private association beach

Dennis Port house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$622

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rentals in South Orleans

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