Chatham Vacation Rentals

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USA > Massachusetts > Chatham

Make Chatham your next getaway—choose from 17 great vacation rentals

Although some of the towns on Cape Cod have lost a bit of their historic charm over the years, Chatham in the Lower Cape has managed to maintain its quaint appeal. With myriad mom-and-pop shops tucked along a pedestrian-friendly and well-maintained main street, Chatham retains its unique allure among Cape towns. And our Chatham vacation rentals allow you to enjoy all the historic sites and Cape Cod flavor while living like a local!

Explore Chatham house rentals, apartments, condo rentals, and more

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House rentals

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Apartments

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Condo rentals

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Chatham vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Whale's Tales
3 Bed | 2.5 Bath | Sleeps 8

Whale's Tales - Chatham, MA

$541 avg / night
Chatham Charmer
3 Bed | 2 Bath | Sleeps 7

Chatham Charmer - Chatham, MA

$639 avg / night
Cozy Cape Time
4 Bed | 2 Bath | Sleeps 8 (6 Adults Max)

Cozy Cape Time - Chatham, MA

$508 avg / night
Earles Way Point
3 Bed | 2 Bath | Sleeps 6

Earles Way Point - Chatham, MA

$473 avg / night
A Chatham Pearl on Oyster River
3 Bed | 2 Bath | Sleeps 6

A Chatham Pearl on Oyster River - Chatham, MA

$528 avg / night

View 12 more homes

Recent Chatham vacation rental reviews

Very clean home and convenient to all locations without being in a busy area. Would stay again.
Lou G. | Aug 2022
The kitchen is not well equipped or organized for the size of the home. Pots and Pans as well as plates and cups feel like someones leftovers and hodgepodge. Outside of that the place was well situated in Chatham and very comfortable.
TANYA N. | Aug 2022
We loved our stay! It is very well done, in a perfect location! We really enjoyed the bikes and hammock! Can’t wait to return. Thank you!
Cynthia T. | Aug 2022
Chatham Frequently Asked Questions

Yes, 26 of our Chatham homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 123 of our Chatham vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Chatham vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Chatham team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Chatham, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

Things to Do in Chatham, MA

Chatham offers plenty of fun for singles, couples, and families alike! Head to the Main Street gazebo for summer concerts featuring local artists. The Cape Cod Baseball League boasts star collegiate players, and the Chatham Anglers are one of its top teams.

Colonial history buffs will be in heaven in Chatham, especially when it comes to historic homes. The Atwood House Museum, built in 1752, is the oldest structure in town and boasts historic documents, vintage tools, a period herb garden and a lighthouse turret. The Caleb Nickerson House, circa 1772, is a classic example of colonial architecture, with wooden wainscoting and pine board floors. The Josiah Mayo House, circa 1820 (and thus downright modern by comparison), transports visitors to the past and celebrates Chatham's first postman.

Had enough of historic homes? The Chatham Railroad Museum sits in the town's railroad depot and boasts locomotives from the 1939 New York World's Fair as well as a wooden caboose from the early 1900s. Or, pay a visit to the cast-iron Chatham Lighthouse, established by Thomas Jefferson, which has protected ships since 1808.

Chatham Beaches & Outdoor Adventures

When you book one of our Cape Cod summer rentals in Chatham, you're never far from the water - and the town offers six saltwater beaches to please everyone in your party. Chatham Lighthouse Beach, with its eponymous historic lighthouse, is the most popular during the warmer months. Harding‘s Beach boasts warmer and calmer waters, due to its position on Nantucket Sound. Schoolhouse Pond and Forest Beach are great for families with small children, and Oyster Pond Beach is conveniently close to town. Dogs are welcome in the early morning and evening on Pleasant Bay Beach (perfect for guests staying in one of our pet-friendly Chatham rentals!), and Pleasant Street Beach is also close to nearby Harwich. After a long day, wash your cares (and sand) away at your Chatham vacation rental.

Day Trips from Chatham

Chatham sits on the Lower Cape and is the perfect gateway to other towns along the coast from Eastham, aka "The Gate", to quaint Harwich to gay-friendly Provincetown. It's also a short drive to Harwich Port to catch the ferry to the picturesque islands of Nantucket and Martha's Vineyard.

Whether historic architecture, windswept beaches, or simply visions of a relaxing weekend getaway draws you here, you'll find a true gem on the Cape when you make one of our Chatham rentals your home-away-from-home!