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Vacation Rentals & Houses in Chatham

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1,245 houses

Chatham Cape Cod Vacation Rental (13059)

Chatham house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$457

Quintessential Cape Cod Vacation Home in N.Chatham

Chatham house

5 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 2 hours 25 minutes

Price per night from

$768

Chatham Cape Cod Vacation Rental (8233)

Chatham house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$500

Captain's Haven

West Chatham cottage

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$199

South Chatham Cape Cod Vacation Rental (2400)

Chatham house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$343

#604: Great location - private, secluded near downtown & beach! Dog friendly!

Chatham house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 35 minutes

Price per night from

$132

Chatham Cape Cod Vacation Rental (4385)

Chatham house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$557

Beautiful sunsets in Chatham!

Chatham house

4 bedrooms / 3 bathrooms / sleeps 8

“Wonderful vacation home in great location, a cooks delight!!” Our family could not have been happier spending our vacation in the wonderful Chatham home. The kitchen is fully equipped and great room for family to congregate. The sunset on the pond was spectacular and owners were so pleasant to deal with. They were extremely accommodating. Great location for enjoying all cape beaches, hopping on the bike trails and enjoying Downtown Chatham. I would highly recommend!!

Responds fast! avg. 31 minutes

Price per night from

$523

South Chatham Cape Cod Vacation Rental (4642)

Chatham house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$414

South Chatham Cape Cod Vacation Rental (9577)

South Chatham house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$414

Chatham Cape Cod Vacation Rental (4983)

Chatham house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$229

Chatham Cape Cod Vacation Rental (9068)

Chatham house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$257

South Chatham Cape Cod Vacation Rental (3388)

Chatham house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$343

Chatham Cape Cod Vacation Rental (11498)

Chatham house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$700

Chatham Cape Cod Vacation Rental (7102)

Chatham house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$371

41 Captains Walk 102234

North Chatham house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$436

Chatham Cape Cod Vacation Rental (2973)

Chatham house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$257

South Chatham Cape Cod Vacation Rental (1011)

Chatham house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$414

Chatham Cape Cod Vacation Rental (10226)

Chatham house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$557

Chatham Cape Cod Vacation Rental (4489)

Chatham house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$386

South Chatham Cape Cod Vacation Rental (76)

Chatham house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$243

Chatham Cape Cod Vacation Rental (8716)

Chatham house

3 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$543

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

$543

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

$529

South Chatham Cape Cod Vacation Rental (135)

Chatham house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$243

South Chatham Cape Cod Vacation Rental (12170)

Chatham house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$343

South Chatham Cape Cod Vacation Rental (4643)

Chatham house

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$236

South Chatham Cape Cod Vacation Rental (4201)

Chatham house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$286

South Chatham Cape Cod Waterfront Vacation Rental (6972)

Chatham house

3 bedrooms / 3 bathrooms / sleeps 9

Price per night from

$443

South Chatham Cape Cod Waterfront Vacation Rental (4963)

Chatham house

3 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$414

South Chatham Cape Cod Vacation Rental (4861)

Chatham house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$586

Chatham Cape Cod Vacation Rental (10327)

Chatham house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$229

South Chatham Cape Cod Vacation Rental (7129)

Chatham house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$443

190 Countryside Drive 104737

Chatham house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$264

Spectacular Waterfront Townhome - Oyster Pond #32

Chatham house

2 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 20 minutes

Price per night from

$529

Viewing 38 of 1,245
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
Beautiful sunsets in Chatham!
Beautiful house with breathtaking sunsets

The house was located in a small private neighborhood. I was pleasantly surprised to see the house in person because the pictures did not show how big it really was. it was such a magnificent house, The kitchen looked like it came straight out of a HGTV home. I was also impressed by the master bathroom and how beautiful it was with its two shower heads and the jacuzzi tub. The owners were sweet and very helpful with the location we were living in and about the house and its technology. They also left a kind-hearted gift for us when we arrived.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

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