Vacation Rentals & Houses in Chatham

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1,124 houses

Chatham Cape Cod Vacation Rental (13059)

Chatham house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$586

Quintessential Cape Cod Vacation Home in N.Chatham

Chatham house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$778

South Chatham Cape Cod Vacation Rental (2400)

Chatham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$429

Price per night from

$144

Chatham Cape Cod Vacation Rental (4385)

Chatham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$557

South Chatham Cape Cod Vacation Rental (4642)

Chatham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$429

South Chatham Cape Cod Vacation Rental (9577)

South Chatham house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$500

Chatham Cape Cod Vacation Rental (4983)

Chatham house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$229

South Chatham Cape Cod Vacation Rental (3388)

Chatham house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$371

Chatham Cape Cod Vacation Rental (7102)

Chatham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$500

41 Captains Walk 102234

North Chatham house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$543

Chatham Cape Cod Vacation Rental (2973)

Chatham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$314

South Chatham Cape Cod Vacation Rental (1011)

Chatham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$500

Chatham Cape Cod Vacation Rental (4489)

Chatham house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$600

South Chatham Cape Cod Vacation Rental (76)

Chatham house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$286

Chatham Cape Cod Vacation Rental (8716)

Chatham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$786

West Chatham Cape Cod Waterfront Vacation Rental (20)

Chatham house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$221

South Chatham Cape Cod Vacation Rental (5025)

Chatham house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 11

Price per night from

$600

Chatham Cape Cod Vacation Rental (1936)

Chatham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$229

Pleasant Forest Shores cottages #2 : So. Chatham

South Chatham cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$102

Chatham Cape Cod Vacation Rental (2171)

Chatham house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$600

South Chatham Cape Cod Vacation Rental (135)

Chatham house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$357

South Chatham Cape Cod Vacation Rental (4643)

Chatham house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$257

South Chatham Cape Cod Vacation Rental (4201)

Chatham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$357

South Chatham Cape Cod Waterfront Vacation Rental (4963)

Chatham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$486

Chatham Cape Cod Vacation Rental (10327)

Chatham house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$257

South Chatham Cape Cod Vacation Rental (7129)

Chatham house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$514

Spectacular Waterfront Townhome - Oyster Pond #32

Chatham house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 51 minutes

Price per night from

$571

South Chatham Cape Cod Vacation Rental (3631)

Chatham house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$429

South Chatham Cape Cod Vacation Rental (3802)

Chatham house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$257

Chatham Cape Cod Vacation Rental (7899)

Chatham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$500

“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!!!

Responds fast! avg. 2 hours 24 minutes

Price per night from

$315

Pleasant Forest Shores cottages #3 : So. Chatham

South Chatham cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$115

South Chatham Cape Cod Vacation Rental (10339)

Chatham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$329

296 Main Street 133687

Chatham house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$979

Chatham Cape Cod Waterfront Vacation Rental (12273)

Chatham house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$514

Chatham Cape Cod Waterfront Vacation Rental (2172)

Chatham house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$2,021

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.

Price per night from

$638

Viewing 38 of 1,124
rentals in Chatham

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About Chatham

Located at the "elbow" of Cape Cod, Chatham has earned the reputation of a premier New England vacation spot. The area is known for its wide range of art galleries, beautiful beaches, and amazing views of the coast. In fact, this small town has been named one of America's Dozen Distinct Destinations by The National Trust for Historic Preservation. You'll find rows of art galleries and many unique boutique shops along Main Street, in addition to some of the best restaurants on the Cape like The Chatham Squire.

There's plenty to do outside of this strip as well, so be sure to make time for some of these must-see attractions and destinations:

  • Chatham Fish Pier: In addition to the great coast views, this pier offers great photo opportunities, especially of local fishermen unloading their catch for the day.
  • Chatham Lighthouse: Take one of the free tours of the lighthouse before climbing to the top of it yourself.
  • Watch the Seals: A few local business offer one-hour seal watching cruises.
  • Art Galleries: Chatham is home to over a dozen art galleries including the Chatham Art Gallery and the Potts Gallery of Fine Art.
  • Railroad Museum: This free museum gives visitors a look into the history of Cape Cod's former railroad industry.
  • Go to the Beach: Chatham is home to several great beaches, many of which are within walking distance of one another. Be sure to check out Chatham Lighthouse Beach.

Whether you're looking for a spacious home with a pool and high-end amenities, or a luxury condo just steps from the ocean and all the shopping and galleries Chatham has to offer, there's a vacation rental in the area that has everything you're looking for.

Top Destination reviews

South Chatham Cape Cod Vacation Rental (2400)
Beautiful place!

Beautiful home in an excellent location! The owners attention to detail was impressive! Couldn't ask for anything more! Can't wait to go back! … see more
South Chatham Cape Cod Vacation Rental (8975)
Loved this house, didn’t want to leave.

This was our first time in South Chatham after coming here for 50 years and many rentals. The owners have thought of everything (except maybe a 10x13 baking dish and a hair dryer). I loved the views, the proximity to the beach, the comfy beds, the beautiful garden,The very well equipped kitchen. … see more
Beach Chic Chatham 5⭐ Private-Newly Renov'd-Hear Waves at Night-5m Walk to Beach
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!!!see more
Chatham Cape Cod Waterfront Vacation Rental (10325)
Ideal rental for extended families!

Loved our week at 111 Barcliff! House has everything we could have hoped for! The flow allowed more privacy for us and our children than we expected. Beautiful property and beautiful view! … see more
16612: Stunning views of Nantucket Sound, wrap around deck, walk to beach!
Beautiful spot

Great location on the Cape , easy walk to ocean , in the evening spotted a wild coyote to be careful with small dogs an children . … see more
16631: Spacious, New Construction, Supreme Location, Central A/C!
Beautiful spacious house!

The house was perfect. Beautiful, spacious, updated. We very much enjoyed our time here. The house exceeded all expectations! … see more

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