Pittsfield Vacation Rentals

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Vacation Rentals in Pittsfield

Cozy Riverside Berkshires Retreat

Great Barrington MA

$285 nightly

$300 total

Jun 15 - Jun 16

Total with taxes and fees

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

Kitchen

Washer

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

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

Chatham NY

$339 nightly

$380 total

Jun 11 - Jun 12

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.

The Meadows House @ Otis Ridge w/ 7-person hot tub

Otis MA

Located in Otis, this vacation home is in the mountains, a 2-minute drive from Otis Ridge and 5 minutes from Old Baldy Wildlife Sanctuary.

Hot Tub

Kitchen

Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown

Pownal VT

With a stay at this vacation home in Pownal, you'll be steps from Green Mountain National Forest and a 3-minute drive from Mountain Meadow Preserve.

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

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

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.

Peace and quiet on the lake

Becket MA

With a stay at this vacation home in Becket (Sherwood Forest), you'll be within a 10-minute drive of Pyramid Lake and Jacob's Pillow.

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 Tanglewood Music Center and Lenox Arts Center.

Kitchen

Free WiFi

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

Great Barrington MA

Located in Great Barrington, this vacation home is within a 5-minute drive of Ski Butternut and Lake Buel.

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.

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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.