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

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.

stylish Berkshires Retreat

Lee MA

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

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 10-minute drive of Hawley Bog Preserve and Parker Hill.

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.

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.

Charming Farmhouse - quiet, private & peaceful

Worthington MA

Located in Worthington, this vacation home is a 4-minute drive from Hiram H. Fox Wildlife Management Area and 6 minutes from Fox Den Wildlife Management Area.

Enjoy comfortable elegance in this secluded grand home located in town

Lenox MA

Located in Lenox, this vacation home is in a rural location, within a 15-minute walk of Ventfort Hall Mansion and Gilded Age Museum and Lenox Library.

Stockbridge Village in Summer

Stockbridge MA

With a stay at this vacation home in Stockbridge, you'll be on a river, within a 15-minute drive of Tanglewood Music Center and Housatonic River.

Kitchen

Washer

Brookside Mountain Retreat | 13BR | Heated Pool, Hot Tub + Game Room

Stephentown NY

Located in Stephentown, this vacation home is in a rural location, a 4-minute drive from Taconic Ridge State Forest and 6 minutes from Zema's Nursery.

Cozy Riverside Berkshires Retreat

Great Barrington MA

$284 nightly

$317 total

Sep 9 - Sep 10

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

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Hinsdale MA

With a stay at this vacation home in Hinsdale, you'll be steps from Ashmere Lake and a 4-minute drive from Bas Ridge Golf Course.

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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.