Chatham Vacation Rentals

Compare 16 vacation rentals. Enter your trip dates to get started.
USA > Massachusetts > Chatham

Make Chatham your next getaway—choose from 16 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


House rentals

View 14 House rentals


View 1 Apartments

Condo rentals

View 1 Condo rentals

Chatham vacation rentals for every getaway

Dog-friendly Hot tub Internet
Couple's Paradise by the Sea 3D Tour
1 Bedroom | 1 Bath | Sleeps 2

Couple's Paradise by the Sea - Chatham, MA

From $109
A Chatham Pearl on Oyster River 3D Tour
3 Bedroom | 2 Bath | Sleeps 6

A Chatham Pearl on Oyster River - Chatham, MA

From $201
B By the Sea 3D Tour
2 Bedroom | 1 Bath | Sleeps 4

B By the Sea - Chatham, MA

From $233
Chatham Getaway 3D Tour
2 Bedroom | 1 Bath | Sleeps 5

Chatham Getaway - Chatham, MA

From $175
Charming Downtown Chatham Condo 3D Tour
1 Bedroom | 1 Bath | Sleeps 2

Charming Downtown Chatham Condo - Chatham, MA

From $153

View 11 more homes

Recent Chatham vacation rental reviews

Beautiful grounds, spacious suite, friendly owners, quiet environment, bike paths nearby. Would stay here again next time I'm on the Cape.
Stephen R. | May 2022
My wife and I loved all of it. Our ONLY concern is that the fire alarm went off in the middle of the night and we were on edge going back to sleep because we were concerned it would happen again. Thankfully it didn't. The following morning we cooked breakfast and the alarm went off again for about 15 to 20mins. Other than that, the place is immaculate. We would definitely stay again...
Ariel R. | May 2022
Immaculately clean, perfect cozy size for our little family of three, incredible sized yard with view of the sunset over the marsh, walking distance to a lovely beach. What else could you need?!
Sarah E. | May 2022

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!