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Vacation Rentals & Houses in Chatham

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1,320 houses

Chatham Cape Cod Vacation Rental (13059)

Chatham house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$459

Walk to Ridgevale Beach From Family Friendly Home

West Chatham house

3 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$487

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

$769

Chatham Cape Cod Vacation Rental (8233)

Chatham house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$502

Captain's Haven

West Chatham cottage

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$201

South Chatham Cape Cod Vacation Rental (2400)

Chatham house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$344

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

Chatham house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$133

Chatham Cape Cod Vacation Rental (4385)

Chatham house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$415

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. 38 minutes

Price per night from

$447

South Chatham Cape Cod Vacation Rental (4642)

Chatham house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$415

South Chatham Cape Cod Vacation Rental (9577)

South Chatham house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$415

Chatham Cape Cod Vacation Rental (4983)

Chatham house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$230

Chatham Cape Cod Vacation Rental (9068)

Chatham house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$258

South Chatham Cape Cod Vacation Rental (3388)

Chatham house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$344

Chatham Cape Cod Vacation Rental (11498)

Chatham house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$702

Chatham Cape Cod Vacation Rental (7102)

Chatham house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$372

41 Captains Walk 102234

North Chatham house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$437

Chatham Cape Cod Vacation Rental (2973)

Chatham house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$258

South Chatham Cape Cod Vacation Rental (1011)

Chatham house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$415

Chatham Cape Cod Vacation Rental (10226)

Chatham house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$559

Chatham Cape Cod Vacation Rental (4489)

Chatham house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$387

South Chatham Cape Cod Vacation Rental (76)

Chatham house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$244

Chatham Cape Cod Vacation Rental (8716)

Chatham house

3 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$545

West Chatham Cape Cod Waterfront Vacation Rental (20)

Chatham house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$222

South Chatham Cape Cod Vacation Rental (5025)

Chatham house

4 bedrooms / 4 bathrooms / sleeps 11

Price per night from

$545

South Chatham Cape Cod Vacation Rental (3991)

Chatham house

3 bedrooms / 4 bathrooms / sleeps 7

Price per night from

$445

Chatham Cape Cod Vacation Rental (1936)

Chatham house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$230

Pleasant Forest Shores cottages #2 : So. Chatham

South Chatham cottage

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$103

14 Hallet Lane Chatham Cape Cod ~ Sand Simeon

Chatham house

6 bedrooms / 7 bathrooms / sleeps 16

Responds fast! avg. 2 hours 48 minutes

Price per night from

$1,263

Chatham Cape Cod Vacation Rental (2171)

Chatham house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$531

South Chatham Cape Cod Vacation Rental (135)

Chatham house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$244

South Chatham Cape Cod Vacation Rental (12170)

Chatham house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$344

South Chatham Cape Cod Vacation Rental (4643)

Chatham house

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$237

South Chatham Cape Cod Vacation Rental (4201)

Chatham house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$287

South Chatham Cape Cod Waterfront Vacation Rental (4963)

Chatham house

3 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$415

South Chatham Cape Cod Vacation Rental (4861)

Chatham house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$588

Chatham Cape Cod Vacation Rental (10327)

Chatham house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$230

South Chatham Cape Cod Vacation Rental (7129)

Chatham house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$445

Viewing 38 of 1,320
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
Walk to Ridgevale Beach From Family Friendly Home
Great visit

We visited for Labor Day weekend. We were 2 families with older kids, the youngest being 14. The 2 kind bedrooms accommodated the adults perfectly, and the bedroom with the 4 twins was great for the kids. The basement was comfy with the 2 couches, more than enough room, and we threw down an aero bed for that one extra straggler. The kitchen was well appointed as were the beach chairs and cooler and beach towels, that was a nice surprise. The house was super clean and there were cleaning supplies and garbage bags, toilet paper, paper towels all on hand. It's been my experience that the owners usually leave a small supply and you have to purchase the rest yourself, so that was a great, thank you for that! I did have a couple of questions upon arrival and the hosts were quick to respond. you can definitely walk to the beach, but it's far if you have a lot to schlep a lot of stuff, and if you do drive it's $20/day to park, that didn't thrill me. But if you rent a SUP or little sunfish from the rental shop, you don't have to pay for parking. Found that out after the fact, but happy to pass it on. Overall this was a fantastic experience and I would highly recommend a stay here. … see more
201 Main Street Chatham Cape Cod ~ Sandpiper
Beautiful, Cozy and Relaxing Weekend!

My Husband and I along with 3 other couples enjoyed a long weekend in this beautiful home. We thoroughly enjoyed the downstairs entertainment room with the pool table, movie theater screen and bar. The house had everything we needed and more. The location of the house is well within walking distance to downtown Chatham and is right across the street from a beautiful beach. The location is superb and the views are great! The outside area is also wonderful, and although it was snowy and cold during our stay, we did enjoy an evening hot tub which was such a treat! The owners were very helpful and responsive as was the property manager. We hope to return soon! … 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
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

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