Vacation Rentals & Houses in Chatham

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Pleasant Forest Shores cottages #2 : So. Chatham

South Chatham cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$102

“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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Price per night from

$395

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

Hardings Beach Chatham Cape Cod

Chatham house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$279

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

Private Contemporary Cape Set on a Hilltop

Chatham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$344

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Price per night from

$395

Charming Beach House - Beautifully Updated & Immaculate. Walk to Nantucket Sound

South Chatham house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$430

Pleasant Forest Shores cottages #4 : So. Chatham

South Chatham cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$102

Great rentals within 20 miles that match your search

Mar y Sol: an Authentic Cape Cod cottage

West Yarmouth house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$202

Idyllic! King beds, pets, pond access, close to everything!

Harwich Port house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$318

Spacious waterfront townhouse at Cove at Yarmouth

West Yarmouth hotel apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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Price per night from

$403

Cape Cod Coastal Retreat

South Yarmouth house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$328

Cape Cod Retreat- RARE FIND-1 mile to Beach, A/C, Linens Included, Superhost

South Yarmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$339

8 minutes to Beach, Updated, Outdoor Shower, Fire pit, Grill, Fenced Yard

South Yarmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$288

Chequessett Beach House of Wellfleet

Wellfleet house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Golf within 30mins drive

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Price per night from

$1,092

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

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.

Match: Golf within 30mins drive

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Price per night from

$456

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

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Price per night from

$201

Perfect for two families!

Orleans house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 11

Match: Golf within 30mins drive

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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.

Match: Golf within 30mins drive

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Price per night from

$328

405 Lower County Rd Harwich Port MA

Harwich Port condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$196

The Berry Quaint Cottage

South Dennis cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Golf within 30mins drive

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Price per night from

$213

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

Match: Golf within 30mins drive

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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

Quaint 2 bdrm unit

Dennis Port house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$228

Topside BoatHouse on Pleasant Bay

South Orleans boathouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$492

Topside MainHouse

South Orleans house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Golf within 30mins drive

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Price per night from

$1,227

Cozy Beach Home - Walk Everywhere Beach and Fun!

South Yarmouth townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Golf within 30mins drive

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Price per night from

$115

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

Match: Golf within 30mins drive

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Price per night from

$201

Cliff Cottage By The Pond

Dennis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Golf within 30mins drive

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Price per night from

$148

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.

Match: Golf within 30mins drive

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Price per night from

$264

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

Match: Golf within 30mins drive

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Price per night from

$148

Responds fast! avg. 28 minutes

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Price per night from

$287

Match: Golf within 30mins drive

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Price per night from

$900

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