Pittsfield Vacation Rentals

Name: Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Price range: $726 total

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Vacation Rentals in Pittsfield

Cozy Riverside Berkshires Retreat

Great Barrington MA

$270 nightly

$302 total

Apr 24 - Apr 25

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

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

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Lanesborough MA

With a stay at this vacation home in Lanesborough, you'll be within a 10-minute drive of Crane Museum of Papermaking and Barrington Stage Company.

Hot Tub

Kitchen

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Pittsfield MA

Located in Pittsfield, this vacation home is on a lake, within a 5-minute drive of Pittsfield Dog Park and Crane Museum of Papermaking.

Hot Tub

Kitchen

Home in Great Barrington

Great Barrington MA

$288 nightly

$321 total

Apr 21 - Apr 22

Total with taxes and fees

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

Kitchen

Washer

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 a 4-minute drive from Tanglewood Music Center and 8 minutes from National Shrine of the Divine Mercy.

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 15-minute drive of Tanglewood Music Center and National Shrine of the Divine Mercy.

Pool

Kitchen

Berkshires Lakefront Retreat

Becket MA

With a stay at this vacation home in Becket (Sherwood Forest), you'll be within a 15-minute drive of Pyramid Lake and Jacob's Pillow.

Kitchen

Washer

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.

Kitchen

Washer

4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi

East Otis MA

With a stay at this vacation home in Otis, you'll be on the waterfront, just steps from Otis Reservoir and a 5-minute drive from County Beach.

Kitchen

Washer

Vintage BARN Apartment-POOL-HotTub-FirePit-Hiking-Museums-Theater-Pets welcome!

Pownal VT

With a stay at this vacation home in Pownal, you'll be in the mountains, just steps from Green Mountain National Forest and a 5-minute drive from Solomon Wright Library.

Pool

Hot Tub

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stockbridge MA

$650 nightly

$726 total

Apr 21 - Apr 22

Total with taxes and fees

With a stay at this vacation home, you'll be centrally located in Stockbridge, a 4-minute drive from National Shrine of the Divine Mercy and 11 minutes from Tanglewood Music Center.

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.