Chatham Vacation Rentals

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USA > Massachusetts > Chatham

Make Chatham your next getaway—choose from 7 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, and more

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House rentals

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Apartments

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Chatham vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
A Chatham Pearl on Oyster River 3D Tour
3 Bed | 2 Bath | Sleeps 6

A Chatham Pearl on Oyster River - Chatham, MA

From $233
Lucky Number Seven 3D Tour
2 Bed | 1 Bath | Sleeps 6

Lucky Number Seven - Chatham, MA

From $156
Bike the Beach 3D Tour
4 Bed | 2 Bath | Sleeps 9

Bike the Beach - Chatham, MA

From $177
Seashell Wishes-Salty Kisses 3D Tour
2 Bed | 1 Bath | Sleeps 5 (4 Adults Max)

Seashell Wishes-Salty Kisses - Chatham, MA

From $127
B By the Sea 3D Tour
2 Bed | 1 Bath | Sleeps 4

B By the Sea - Chatham, MA

From $150

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Recent Chatham vacation rental reviews

We recently spent a couple of nights in this spacious, meticulously clean and peaceful apartment, probably the nicest place we've ever stayed! We were lucky enough to meet the owner, who was so friendly and accommodating, while he was tending his beautifully manicured property, I can only imagine how gorgeous the grounds must be in the height of the season with the many hydrangea bushes and flowers in bloom. We will most definitely return to this absolutely spectacular rental!
Janet J. | Oct 2021
This house has a great location and amenities. Definitely would recommend it.
Gwendolyn C. | Oct 2021
One of the top 5 VRBO we've stayed at. Quiet, clean and centrally located for what we want to do. Great hosts and helpful with our only issue, an internet problem. Would recommend.
john b. | Oct 2021

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!