Pittsfield Vacation Rentals

Name: Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
Address: Monterey

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Vacation Rentals in Pittsfield

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

$532

includes taxes & fees

$489 per night

Nov 24 - Nov 25

With a stay at this vacation home, you'll be centrally located in Hancock, within a 5-minute drive of Jiminy Peak Mountain Resort and Mountain Coaster.

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.

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

$511

includes taxes & fees

$511 per night

Dec 1 - Dec 2

Located in Valatie, this vacation home is on the waterfront, a 1-minute drive from Kinderhook Lake and 6 minutes from Valatie Family Care.

Secluded Family Home in Serene Stockbridge Woods

Located in South Lee, this vacation home is in a rural location, within a 5-minute drive of Berkshire Botanical Garden and Housatonic River.

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!!

$229

includes taxes & fees

$205 per night

Dec 22 - Dec 23

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

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

With a stay at this vacation home in West Stockbridge, you'll be within a 5-minute drive of Berkshire Botanical Garden and Tanglewood Music Center.

Cozy Home In The Berkshires, Pet Friendly with fenced in yard!

A stay at this vacation home places you in the heart of Adams, steps from Mount Greylock State Reservation and 7 minutes by foot from East Hoosac Quaker Meetinghouse.

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

With a stay at this vacation home in Otis, you'll be on the waterfront, just steps from Otis Reservoir and a 4-minute drive from County Beach.

Tranquil 3-BR Waterfront Retreat

Located in Becket, this vacation home is on the waterfront, within a 5-minute drive of Pyramid Lake and Jacob's Pillow.

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.

Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow

When you stay at this vacation home in Monterey, you'll be on a lake, within a 5-minute drive of Beartown State Forest and Bidwell House Museum.

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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.