Chatham Vacation Rentals

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Vacation Rentals in Chatham

Cozy Riverside Berkshires Retreat

Great Barrington MA

$284 nightly

$317 total

Jun 17 - Jun 18

Total with taxes and fees

When you stay at this vacation home in Great Barrington, you'll be on a river, within a 15-minute drive of Norman Rockwell Museum and National Shrine of the Divine Mercy.

Kitchen

Washer

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Chatham NY

$338 nightly

$379 total

Jul 13 - Jul 14

Total with taxes and fees

Located in Chatham, this vacation home is a 5-minute drive from The Mac-Haydn Theatre and 8 minutes from Hudson Chatham Winery.

Washer

Dryer

120-Acre Private Estate: Heated Pool, Fire Pit, Apple Orchard, Catskills Views

East Chatham NY

Located in East Chatham, this vacation home is within a 15-minute drive of Queechy Lake and New Lebanon Library.

Pool

Kitchen

Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!

Austerlitz NY

Located in Hillsdale, this vacation home is in the mountains, within a 15-minute drive of Hillsdale Town Hall and Ebenezer II Gifts and Antiques.

Kitchen

Washer

Large Barn styled vacation home that fits groups with space to spare.

Craryville NY

With a stay at this vacation home in Copake Lake, you'll be on the waterfront, just a 1-minute walk from Copake Lake and 13 minutes by foot from Mosquito Island.

Kitchen

Washer

BRAND NEW 4 story home minutes from Warren St w/ a King Suite!

Hudson NY

With a stay at this vacation home in Hudson, you'll be within a 10-minute drive of Olana State Historic Site and Hudson Area Library.

Kitchen

Washer

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Great Barrington MA

With a stay at this vacation home, you'll be centrally located in Great Barrington, within a 10-minute drive of Monument Mountain and Housatonic River.

Hot Tub

Kitchen

Catskill Stay w/ Deck & Fire Pit

Catskill NY

With a stay at this vacation home in Catskill, you'll be within a 15-minute drive of Olana State Historic Site and Lumberyard Contemporary Performing Arts.

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

Spacious Living, Covered Porch & Forest Setting | Beaver Creek by AvantStay

Stockbridge MA

With a stay at this vacation home in Stockbridge, you'll be within a 10-minute drive of National Shrine of the Divine Mercy and Tanglewood Music Center.

Kitchen

Free WiFi

All the comforts of home

Hudson NY

$138 nightly

$155 total

Jun 30 - Jul 1

Total with taxes and fees

Located in Hudson, this vacation home is on a lake, within a 10-minute drive of Hudson River Islands State Park and FASNY Museum of Firefighting.

Hot Tub

Kitchen

Imagine Being Lakeside, Kayaks/Fishing/EV Charger

Lenox MA

When you stay at this vacation home in Lenox, you'll be near the beach, within a 15-minute drive of Tanglewood Music Center and National Shrine of the Divine Mercy.

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.