Southfield Vacation Rentals

Name: Classic Stockbridge Cottage
Address: Stockbridge

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Vacation Rentals in Southfield

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

Newly Renovated Family House On Highland Lake with Dock

With a stay at this vacation home in Winsted, you'll be on the beach, just steps from Highland Lake and a 2-minute drive from Winchester Historical Society.

Outdoor Space

Free WiFi

Hilltown Nest is a wonderful place for family and friends to gather.

Located in Huntington, this vacation home is in the mountains, a 1-minute drive from Westfield River and 5 minutes from C.M. Gardner State Park.

Fireplace

Outdoor Space

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

$360

per night

Jun 3 - Jun 4

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.

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.

Pool

Pet friendly

Big farmhouse in the foothills of the Berkshires

$195

per night

Jun 24 - Jun 25

With a stay at this vacation home in Russell, you'll be within a 15-minute drive of Westfield River and Baystate Noble Hospital.

Pet friendly

Fireplace

Sweet Cozy Victorian in Housatonic. Close to everything.

$250

per night

Jun 2 - Jun 3

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

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.

Pet friendly

Fireplace

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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.