Vacation Rentals & Houses in Chatham

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172 houses

“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

296 Main Street 133687

Chatham house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

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$1,000

Former Chatham Bed and Breakfast

Chatham b&b

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

“Classic cape cod experience” Beautiful property well located on the cape non commercial sector. Tastefully appointed overall fantastic.

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$638

15 Bobbies Lane 43070

South Chatham house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“wonderful” very neat and clean. great location, worked out well for me and my family. the people at William Raveis rental were very friendly and easy to work with.i would highly recommend them and the house.

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$193

Private Contemporary Cape Set on a Hilltop

Chatham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$344

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$395

Spectacular Waterfront Townhome - Oyster Pond #25

Chatham house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

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$871

Walk to Town, Chatham Bars Carriage House

Chatham apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 3

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$602

Spectacular Waterfront Home - Oyster Pond 31&32

Chatham house

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 12

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$1,086

29 Forest Beach Road Extension 104441

South Chatham house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$464

76 Williamsburg Avenue 144347

South Chatham house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

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$171

Stunning home with water views and spectacular sunsets

North Chatham house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 16

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$2,863

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

Cape Cod Luxury Oceanfront 5bdrm Vacation Home

Chatham house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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$983

Fantastically located Chatham house - New patio, refurbished

Chatham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$253

Great rentals within 20 miles that match your search

Beachfront Home

West Yarmouth house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

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$1,731

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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$339

Chequessett Beach House of Wellfleet

Wellfleet house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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$1,092

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

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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$201

Perfect for two families!

Orleans house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 11

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$737

4br - 1350ft2 - Nature Lover's Hideaway

Wellfleet house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$328

Renovated Cape Cod Home -10 Minutes To Beaches & Ctr

Hyannis Port house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

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$370

405 Lower County Rd Harwich Port MA

Harwich Port condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$196

Great Place for a Cape Cod Vacation

Barnstable cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$1,145

Glendon Beach Cottage #97 100 yds to the beach

Dennis Port house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 8 minutes

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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

Cliff Cottage By The Pond

Dennis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$148

In the Heart of Brewster. Min to Bay Beaches

Brewster house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

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$493

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

Beautiful Home - Great Price, Wi Fi, Flat Screen

Yarmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$201

High-end Brewster ,Mass. Bay view town home

Brewster apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$409

The Cape Cod Cottage with Beach Pass

Eastham cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

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$295

Quiet and comfortable 3 bedroom cape

Eastham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$327

Steps to Campground Road Beach! A/C, Wifi, Outdoor Shower, Grill

Eastham cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Great Location! Great Time!” We were so happy to find this rental. The cottage is a gem...well maintained and nicely decorated with a cute beachy theme. It's in a great setting that provided nice privacy and some shade from the summer sun. Love the outdoor shower! The cottage is located so near to the beach that the kids were able to walk there safely by themselves. The owners were very professional to work with and the transaction went seamlessly. We look forward to returning in 2012!

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$659

Unique & Private 3 Bedroom Brewster Home

Brewster house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$328

Cape Cod Cottage, 4 bedrooms, 2 baths, Eastham, MA

Eastham cottage

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“Great Cottage” I spent a weekend in this cottage and had an overall excellent experience. It is in a great location and is within a close trip to the beach. The cottage was clean, comfortable, and has enough rooms and beds for many people. I will definitely come back next time I am in the Cape.

Responds fast! avg. 3 hours 27 minutes

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$332

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