Pittsfield Vacation Rentals

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Vacation Rentals in Pittsfield

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 Riverside Berkshires Retreat

Great Barrington MA

$326 nightly

$364 total

Jul 30 - Jul 31

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

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.

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

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

Chatham NY

$339 nightly

$380 total

Jul 28 - Jul 29

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

Hearts Desire is your private escape.

Lanesborough MA

With a stay at this vacation home in Lanesborough, you'll be on a lake, within a 10-minute drive of Jiminy Peak Mountain Resort and Cheshire Reservoir.

Hot Tub

Kitchen

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

Hawley MA

Located in Charlemont, this vacation home is in the mountains, within a 15-minute drive of Hawley Bog Preserve and Swift River.

Kitchen

Washer

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

Quiet Cabin On Over 12 Acres Of Woods!

Becket MA

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

Kitchen

Washer

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

stylish Berkshires Retreat

Lee MA

$396 nightly

$442 total

Jul 28 - Jul 29

Total with taxes and fees

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

Kitchen

Washer

3 Bedroom Lakefront Home with Hot Tub & Fireplace

Wynantskill NY

When you stay at this vacation home in Wynantskill, you'll be on the waterfront, within a 15-minute drive of Palace Theater and MVP Arena.

Hot Tub

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.