Chatham Vacation Rentals

Name: Hudson Valley and The Berkshires getaway
Address: Hillsdale

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Vacation Rentals in Chatham

Lakefront Luxe: Private Dock, Game Rm, Near Hudson

Located in Coxsackie, this vacation home is on the waterfront, a 1-minute drive from Sleepy Hollow Lake and 6 minutes from Hudson River Islands State Park.

Pool

Kitchen

Spectacular views and close to Great Barrington.

Located in Great Barrington, this vacation home is within a 5-minute drive of Housatonic River and Housatonic River Walk.

Pool

Kitchen

Berkshire Village Carriage House - Super Private!!

$223

includes taxes & fees

$200 per night

Dec 30 - Dec 31

Located in Lanesborough, this vacation home is in the mountains, within a 15-minute drive of Crane Museum of Papermaking and Berkshire Athenaeum.

Kitchen

Free WiFi

Antique Farmhouse Totally Restored

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.

Hot Tub

Kitchen

Berkshire Ski House on Lake Garfield w/HT By Great Barrington

Located in Monterey, this vacation home is within a 5-minute drive of Beartown State Forest and Bidwell House Museum.

Hot Tub

Kitchen

Beautiful Berkshire Farm House on 160+ Acres

Located in Great Barrington, this vacation home is on the waterfront, within a 15-minute drive of W.E.B. Du Bois Boyhood Homesite and Mahaiwe Performing Arts Center.

Kitchen

Washer

Private Estate, Heated YEARROUND Outdoor Pool

With a stay at this vacation home in Great Barrington, you'll be within a 15-minute drive of W.E.B. Du Bois Boyhood Homesite and Mahaiwe Performing Arts Center.

Pool

Kitchen

3 Bedroom Lakefront Home with Hot Tub & Fireplace

Located in Wynantskill, this vacation home is on the waterfront, within a 10-minute drive of Kinloch Park Dog Park and Joseph L Bruno Stadium.

Hot Tub

Kitchen

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

With a stay at this vacation home in Lenox, you'll be within a 5-minute drive of Wyndhurst Golf & Club and Berkshire Scenic Railway Museum.

Pool

Kitchen

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Located in Lenox, this vacation home is within a 15-minute walk of Pleasant Valley Wilderness Sanctuary and Kennedy Park.

Kitchen

Washer

A Grand property in Historic Stockbridge

A stay at this vacation home places you in the heart of Stockbridge, steps from Housatonic River and Mission House.

Kitchen

Washer

Hudson Valley and The Berkshires getaway

Located in Hillsdale, this vacation home is within a 15-minute drive of W.E.B. Du Bois Boyhood Homesite and Hillsdale Town Hall.

Kitchen

Washer

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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.