Chatham Vacation Rentals

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Our top choices for Chatham vacation rentals

9.6 out of 10, Exceptional, (30)
"CutePrivateGreat outdoor showe "
United States
Stephanie D.
The price is ¥14,191
¥52,209 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach
9.6 out of 10, Exceptional, (102)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
The price is ¥17,933
¥68,771 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
10.0 out of 10, Exceptional, (116)
"Comfortable and terrific location"
United States
Barry L.
The price is ¥28,069
¥76,385 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
8.6 out of 10, Excellent, (26)
"This was a very nice place to stay, the location was perfect. A short walk to town and centrally located on the Cape as a whole. This home had all of the amenities need for a comfortable stay."
United States
Jeffrey A.
The price is ¥33,527
¥84,041 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham

Aparthotel in Brewster

Brewster Green Resort
3.5 star property
9.4 out of 10, Exceptional, (121)
"Loved your location. We were originally placed in one of the townhomes, but when the locks/key didn't work, we were upgraded to the stand-alone house #106, which was wonderful! We loved the entire house - kitchen was great and stocked perfectly and all the rooms were big and comfortable. We hope to be back again soon!"
United States
Kathleen
The price is ¥29,473
¥33,732 total
includes taxes & fees
Dec 28 - Dec 29
Brewster Green Resort
9.8 out of 10, Exceptional, (7)
"Great location, walk to beach. Close to restaurants and pirate's cove mini golf. Beds were comfy. In-house laundry was convenient. Great outdoor shower. "
United States
Amanda W.
The price is ¥20,116
¥79,955 total
includes taxes & fees
Dec 28 - Dec 29
Charming House by the Beach with Patio, Grill, FirePit

Aparthotel in West Yarmouth

The Cove at Yarmouth by Westgate Resorts
3.0 star property
9.2 out of 10, Wonderful, (243)
"Great place to stay. Clean, friendly and accommodating!"
United States
Mike
The price is ¥20,091
¥22,993 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Cove at Yarmouth by Westgate Resorts
9.8 out of 10, Exceptional, (178)
"Great location, clean property!"
United States
Lisa B.
The price is ¥13,894
¥48,743 total
includes taxes & fees
Dec 30 - Dec 31
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
10.0 out of 10, Exceptional, (75)
"Beautiful views in a quiet and private location. Cottage had everything we needed and nicely appointed."
United States
Janice H.
The price is ¥21,754
¥67,374 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

Condo in Harwich port

The Nantucket Room Unit - #2
9.8 out of 10, Exceptional, (49)
"amazing location and cute place to stay!"
United States
Adriana A.
The price is ¥19,493
¥34,990 total
includes taxes & fees
Dec 28 - Dec 29
The Nantucket Room Unit - #2
9.0 out of 10, Wonderful, (62)
"Clean, beautiful, great location "
United States
Jennifer B.
The price is ¥11,072
¥50,548 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Quaint condo near private beach access with fireplace - close to dining
10.0 out of 10, Exceptional, (1)
"Great house with comfy beds. Would consider staying again. "
United States
Susan C.
The price is ¥21,676
¥73,905 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Lovely House 5 Min to Beach with Deck, Grill, Garage
9.6 out of 10, Exceptional, (4)
"The home was clean, cool and comfortable. Booking was easy and effortless! Can’t wait to go back!"
United States
Kim S.
The price is ¥24,247
¥79,152 total
includes taxes & fees
Dec 28 - Dec 29
Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!
10.0 out of 10, Exceptional, (18)
"Just a great location, and a very comfortable place. We loved the porch bed and chair. We are looking forward to returning."
United States
David B.
The price is ¥30,053
¥76,695 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus

Aparthotel in Bass River

Riverview Resort
3.0 star property
9.2 out of 10, Wonderful, (173)
"The staff was very helpful and upgraded us to a room with a view. The amenities were perfect. We definitely would go back there."
United States
John
The price is ¥32,786
¥37,523 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Riverview Resort
10.0 out of 10, Exceptional, (41)
"Great clean place. Host was very quick to respond. I would definitely recommend staying here. "
United States
Ginnie W.
The price is ¥29,332
¥53,562 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA
10.0 out of 10, Exceptional, (3)
"The property is just beautiful. It is in such a nice area and we really enjoyed our stay! Thank you so much"
United States
Hailey B.
The price is ¥27,913
¥79,956 total
includes taxes & fees
Jan 4 - Jan 5, 2026
WALK to the Beach + FirePit, Bikes, Paddleboards - Modern House
9.8 out of 10, Exceptional, (9)
"Great property. It looks like it was recently renovated and done really well. Convenient to the beaches and restaurants, and golf. We love Brewster. "
United States
Garret J.
The price is ¥27,757
¥66,750 total
includes taxes & fees
Dec 29 - Dec 30
Stylish 2nd floor Ocean Edge condo
10.0 out of 10, Exceptional, (13)
"We rented this house for a family vacation and would without a doubt rent it again! Everything you can possibly need was at the house. If you needed anything additional the host was very responsive and there to assist. We loved the time we got to spend here together. "
United States
Cara B.
The price is ¥27,913
¥104,302 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Walk to the Beach - Modern Home w/ FirePit, Bikes, Office, Grill + More!
2.0 star property
9.0 out of 10, Wonderful, (2)
"Very cute cottage. Very clean and grounds well manicured. "
United States
Anonymous traveler
The price is ¥20,142
¥50,663 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chatham Hotel Reviews

Find out more about Chatham

Search for holiday rentals in Chatham on Expedia! You can easily find your home rentals, villas, holiday apartments in Chatham using one of the methods below:

  • View our selection of featured holiday rentals in Chatham
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Look no further and take a look at our great range of rental properties in Chatham!

Frequently asked questions

Can I find a vacation rental in Chatham?

Yes, you can find vacation rentals in Chatham close to Chatham Railroad Museum, or you can select a more secluded option if you'd like a relaxing place to stay. Visitors like the popular beaches and waterfront in Chatham. While you're here, grab a bite or have a drink at the seafood restaurants.

What are some of the best vacation rentals that Chatham has to offer?

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!: Visitors give good reviews to this Chatham vacation home rental, which is located in the city center and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 9 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Chatham?

With 277 Expedia vacation rentals, you're sure to find just the right place for your Chatham stay.

What can I see and do in Chatham?

Cultural attractions include Gallery Antonia and Monomoy Theatre, whereas Chatham Lighthouse Beach and Ridgevale Beach are a couple of picturesque spots to enjoy the outdoors. While here, Chatham Lighthouse and Cape Cod Beaches are other places worth a visit.

What are vacation rentals like in Chatham?

Vacation rentals are privately owned properties you can stay in for several days or longer in Chatham. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for family trips or small group gatherings.