Pittsfield Vacation Rentals

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Vacation Rentals in Pittsfield

Spectacular views and close to Great Barrington.

Located in Great Barrington, this vacation home is within a 5-minute drive of Housatonic River and Housatonic River Walk.

Berkshire Village Carriage House - Super Private!!

$227

includes taxes & fees

$203 per night

Jan 21 - Jan 22, 2025

Located in Lanesborough, this vacation home is in the mountains, within a 15-minute drive of Crane Museum of Papermaking and Berkshire Athenaeum.

Berkshire Ski House on Lake Garfield w/HT By Great Barrington

Located in Monterey, this vacation home is within a 5-minute drive of Beartown State Forest and Bidwell House Museum.

Beautiful Berkshire Farm House on 160+ Acres

Located in Great Barrington, this vacation home is on the waterfront, within a 15-minute drive of W.E.B. Du Bois Boyhood Homesite and Mahaiwe Performing Arts Center.

Peace and quiet on the lake

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.

Private Estate, Heated YEARROUND Outdoor Pool

With a stay at this vacation home in Great Barrington, you'll be within a 15-minute drive of W.E.B. Du Bois Boyhood Homesite and Mahaiwe Performing Arts Center.

Quintessential 6-BR Berkshires Lodge

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

3 Bedroom Lakefront Home with Hot Tub & Fireplace

Located in Wynantskill, this vacation home is on the waterfront, within a 10-minute drive of Kinloch Park Dog Park and Joseph L Bruno Stadium.

Amore Estate - beautiful room with many places to explore and relax in.

With a stay at this vacation home in Lenox, you'll be within a 5-minute drive of Wyndhurst Golf & Club and Berkshire Scenic Railway Museum.

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Located in Lenox, this vacation home is within a 15-minute walk of Pleasant Valley Wilderness Sanctuary and Kennedy Park.

A Grand property in Historic Stockbridge

A stay at this vacation home places you in the heart of Stockbridge, steps from Housatonic River and Mission House.

Charlemont Retreat on Chickley River w/ EV Charger

Located in Charlemont, this vacation home is in a rural location, within a 15-minute drive of Mohawk Trail State Forest and Zoar Outdoor/Deerfield Valley Canopy Tours.

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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.