Chatham Vacation Rentals

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Vacation Rentals in Chatham

Pet Friendly Riverfront Home in Great Barrington

Great Barrington MA

$267 nightly

$298 total

Dec 7 - Dec 8

Total with taxes and fees

Located in Great Barrington, this vacation home is on a river, a 4-minute walk from Monument Mountain Reservation and within a 5-minute drive of Housatonic River.

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

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Lanesborough MA

With a stay at this vacation home in Lanesborough, you'll be within a 10-minute drive of Crane Museum of Papermaking and Barrington Stage Company.

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Pittsfield MA

Located in Pittsfield, this vacation home is on a lake, within a 5-minute drive of Pittsfield Dog Park and Crane Museum of Papermaking.

Hot Tub

Kitchen

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Lee MA

With a stay at this vacation home in Lee, you'll be within a 15-minute drive of Tanglewood Music Center and Greenock Country Club.

Kitchen

Washer

Berkshire House Stay

Lee MA

$989 nightly

$1,105 total

Dec 20 - Dec 21

Total with taxes and fees

With a stay at this vacation home in Lee, you'll be within a 15-minute drive of Tanglewood Music Center and Housatonic River.

Kitchen

Washer

Falls Reach In The Heart of Copake

Copake Falls NY

When you stay at this vacation home in Copake Falls, you'll be in the mountains, within a 5-minute drive of Taconic State Park and Callan Family Care.

Amore Estate - beautiful room with many places to explore and relax in.

Lenox MA

With a stay at this vacation home in Lenox, you'll be within a 10-minute drive of Tanglewood Music Center and Wyndhurst Golf & Club.

Pool

Kitchen

Modern Luxurious Cabin, Catskills - The Tiny Nook

Catskill NY

$316 nightly

$341 total

Dec 9 - Dec 10

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

Charming Catskill getaway walking distance to Main St. Pet-friendly!

Catskill NY

With a stay at this vacation home in Catskill, you'll be a 5-minute walk from Thomas Cole National Historic Site and 7 minutes by foot from Greene County Council on the Arts.

Kitchen

Washer

A Grand property in Historic Stockbridge

Stockbridge MA

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

Kitchen

Washer

General Williams Estate House Lenox/Stockbridge

Stockbridge MA

This family-friendly vacation home is 5.4 mi (8.7 km) from Tanglewood Music Center and 1.5 mi (2.5 km) from Berkshire Theatre Festival.

Pool

Kitchen

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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.