Chatham Vacation Rentals

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Vacation Rentals in Chatham

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.

Cozy Riverside Berkshires Retreat

Great Barrington MA

$284 nightly

$317 total

Sep 1 - Sep 2

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

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

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.

Amazing Backyard Escape, 10 Minutes from Stockbridge | Cordelia by AvantStay

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

Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10

Stockbridge MA

With a stay at this vacation home in Stockbridge, you'll be within a 10-minute drive of Tanglewood Music Center and Berkshire Botanical Garden.

Modern Luxurious Cabin, Catskills - The Tiny Nook

Catskill NY

$320 nightly

$346 total

Sep 15 - Sep 16

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.

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

Great Barrington MA

Located in Great Barrington, this vacation home is in a rural location, within a 5-minute drive of W.E.B. Du Bois Boyhood Homesite and Mahaiwe Performing Arts Center.

Pool

Kitchen

NEW RENO Historic Creamery in Berkshires w/hot tub

New Lebanon NY

$542 nightly

$550 total

Sep 14 - Sep 15

Total with taxes and fees

With a stay at this vacation home in New Lebanon, you'll be within a 5-minute drive of New Lebanon Library and Shatford Memorial Park.

Antique Farmhouse Totally Restored

Sheffield MA

Located in Sheffield, this vacation home is in a rural location, within a 5-minute drive of Mount Riga State Park and Mount Everett State Reservation.

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.

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Great Barrington MA

Stay at this vacation home in Great Barrington. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Ski Butternut and Lake Buel are located nearby.

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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.