Chatham Vacation Rentals

Compare 22 vacation rentals.
USA > Massachusetts > Chatham

Make Chatham your next getaway

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, condo rentals, apartments, and more

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House rentals

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Condo rentals

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Apartments

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Popular amenities for Chatham vacation rentals

Popular
Dog-friendly Hot tub Internet
Lucky Number Seven
2 Bedroom | 1 Bath | Sleeps 6

Lucky Number Seven - Chatham, MA

$271 avg / night
4.81 (70)
Charming Downtown Chatham Condo
1 Bedroom | 1 Bath | Sleeps 2

Charming Downtown Chatham Condo - Chatham, MA

$216 avg / night
4.79 (56)
Sea House
1 Bedroom | 1 Bath | Sleeps 4

Sea House - Chatham, MA

$201 avg / night
4.75 (28)
A Chatham Pearl on Oyster River
3 Bedroom | 2 Bath | Sleeps 6

A Chatham Pearl on Oyster River - Chatham, MA

$348 avg / night
4.0 (49)
Whale's Tales
3 Bedroom | 2.5 Bath | Sleeps 8

Whale's Tales - Chatham, MA

$400 avg / night
4.83 (12)

View 17 more homes

Recent Chatham guest reviews

We loved the view! It was so peaceful at this time of year.
Anita M. | Nov 2024
Spent a weekend here for a wedding in the area. Loved the apartment, cozy atmosphere and natural lighting gave the accommodation a relaxing vibe. Well appointed and close to all the main strip. Would gladly stay again.
Nate P. | Nov 2024
Furnishings, decor, location, and comfort are at the top of my list. I enjoyed my stay very much!
Susan C. | Nov 2024
Chatham vacation rental FAQ

Yes, 53 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. 202 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.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons 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!