Vacation Rentals & Houses in Chatham

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1,074 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

$779

South Chatham Cape Cod Vacation Rental (2400)

Chatham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$429

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

$443

Chatham Cape Cod Vacation Rental (4983)

Chatham house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$236

Chatham Cape Cod Vacation Rental (9068)

Chatham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$286

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

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

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

$857

West Chatham Cape Cod Waterfront Vacation Rental (20)

Chatham house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$243

South Chatham Cape Cod Vacation Rental (5025)

Chatham house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 11

Price per night from

$600

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

$214

South Chatham Cape Cod Vacation Rental (7129)

Chatham house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$514

Spectacular Waterfront Townhome - Oyster Pond #32

Chatham house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

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

$457

“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!!!

Price per night from

$395

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

$271

296 Main Street 133687

Chatham house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$1,000

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

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.

Price per night from

$193

Hardings Beach Chatham Cape Cod

Chatham house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$279

Pleasant Forest Shores cottages #Apt : So. Chatham

South Chatham cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$75

Private Contemporary Cape Set on a Hilltop

Chatham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$344

Viewing 38 of 1,074
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
Former Chatham Bed and Breakfast
Perfect for a family vacation!

My family has had the pleasure of staying at this home both when it was a B&B; and now, as rental. It is fantastic for extended families with plenty of space and still maintains all of the wonderful qualities of a quaint B&B.; All of the ammenities you could ever need are available to you. There is a great yard with deck and the outside shower is fantastic. It's close to the beach, has easy access to the center of Chatham and the central location on the Cape makes it easy for day trips. The owners take great care in making sure your stay is as comfortable as possible. Every year we wait anxiously for our summer vacation at this great home!see more

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