Chatham Vacation Rentals

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Vacation Rentals in Chatham

Catskill Cottage Walk to Downtown & River Views

Catskill NY

With a stay at this vacation home in Catskill, you'll be just steps from Greene County Council on the Arts and Avalon Lounge.

Kitchen

Washer

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Stockbridge MA

With a stay at this vacation home in West Stockbridge, you'll be within a 5-minute drive of Tanglewood Music Center and Stockbridge Bowl.

Kitchen

Washer

Modern Luxurious Cabin, Catskills - The Tiny Nook

Catskill NY

$437 nightly

$472 total

Nov 2 - Nov 3

Total with taxes and fees

Located in Catskill, this vacation home is in a rural location, within a 10-minute drive of Cairo Town Hall and Angelo Canna Town Park.

Kitchen

Free WiFi

Beautiful New Build 1-bedroom home with Central Air ,on charming Copake Lake

Copake Lake NY

Located in Hillsdale, this vacation home is on a lake, within a 5-minute drive of Copake Lake and Mosquito Island.

Kitchen

Washer

Secluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay

East Chatham NY

Located in East Chatham, this vacation home is in the mountains, within a 15-minute drive of Queechy Lake and The Mac-Haydn Theatre.

Hot Tub

Kitchen

Riverside Retreat in the Berkshires

Great Barrington MA

$253 nightly

$282 total

Oct 26 - Oct 27

Total with taxes and fees

Located in Great Barrington, this vacation home is on a river, a short 4-minute walk from Monument Mountain Reservation and within 1 minutes by car from Housatonic River.

Kitchen

Washer

Enjoy comfortable elegance in this secluded grand home located in town

Lenox MA

Located in Lenox, this vacation home is in a rural location, within a 15-minute walk of Ventfort Hall Mansion and Gilded Age Museum and Lenox Library.

Kitchen

Washer

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield MA

With a stay at this vacation home in Pittsfield, you'll be on the waterfront, just steps from Pontoosuc Lake and a 4-minute drive from Onota Lake.

Kitchen

Washer

Great Barrington, Cabin Sleeps 14, Walk To Town

Great Barrington MA

A stay at this vacation home places you in the heart of Great Barrington, within a 10-minute walk of Housatonic River Walk and Housatonic River.

Kitchen

Washer

Gorgeous Hudson River Estate-with Pool and Winter Jacuzzi

Coxsackie NY

When you stay at this vacation home in Athens, you'll be on the beach, just steps from Hudson River and Hudson River Islands State Park.

Pool

Hot Tub

stylish Berkshires Retreat

Lee MA

With a stay at this vacation home in Lee, you'll be within a 10-minute drive of Tanglewood Music Center and Housatonic River.

Kitchen

Washer

Hilltop Escape with Views & Hot Tub

New Marlborough MA

Located in Great Barrington, this vacation home is a 4-minute drive from Dry Hill and 5 minutes from New Marlborough Town Hall.

Hot Tub

Kitchen

Don't see what you're looking for?

See all available properties in Chatham

View all properties

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.