Stockbridge Vacation Rentals

Name: Classic Stockbridge Cottage
Address: Stockbridge

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Vacation Rentals in Stockbridge

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.

Pet friendly

Outdoor Space

Fox Hollow Luxury Ranch Laurel Lake

With a stay at this vacation home in Lenox, you'll be on a lake, within a 10-minute drive of Tanglewood Music Center and The Mount.

Pool

Pet friendly

Hearts Desire is a furnished whole house in a small, colorful garden center.

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 Mount Greylock State Reservation.

Hot Tub

Fireplace

Berkshires sanctuary w/ outdoor living area & fire pit. Minutes from Tanglewood!

With a stay at this vacation home in Richmond, you'll be within a 10-minute drive of Tanglewood Music Center and Fairfield Brook WMA.

Pet friendly

Hot Tub

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.

Pet friendly

Hot Tub

Rockspring by AvantStay | Huge Berkshires Estate

With a stay at this vacation home in Stockbridge, you'll be within a 10-minute drive of Tanglewood Music Center and Berkshire Theatre Festival.

Near Tanglewood: Historic Summer Retreat

$135

per night

May 28 - May 29

When you stay at this vacation home in New Lebanon, you'll be in the mountains, within a 10-minute walk of New Lebanon Town Hall and Shatford Memorial Park.

Pet friendly

Fireplace

Sweet Cozy Victorian in Housatonic. Close to everything.

$250

per night

Jun 5 - Jun 6

With a stay at this vacation home in Housatonic, you'll be within a 15-minute drive of Tanglewood Music Center and Art et Industrie.

Pet friendly

Free WiFi

Renovated 9-BR 1800s Inn 8-Min to Catamount

Located in Great Barrington, this vacation home is a 5-minute drive from W.E.B. Du Bois Boyhood Homesite and 8 minutes from Mahaiwe Performing Arts Center.

Pet friendly

Fireplace

Dancing Horse Lodge

With a stay at this vacation home in Pittsfield, you'll be in the mountains, within a 15-minute drive of Tanglewood Music Center and Guido's Marketplace.

Hudson Valley and The Berkshires getaway

Located in Hillsdale, this vacation home is within a 15-minute drive of W.E.B. Du Bois Boyhood Homesite and Hillsdale Town Hall.

Pet friendly

Washer

Classic Stockbridge Cottage

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

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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.