Vacation Rentals in Stockbridge

Welcome to our family get-away which we also rent. Set on 2 acres in the Stockbridge hamlet of Glendale, the house is conveniently located - just a short walk to...

This brand new Beautiful, 3 bedroom, four season cottage with library, sleeping loft, located by Lake Mahkeenac in Stockbridge, Massachusetts.

Book Early For Fall foliage 2008. Come visit our newly furnished home with a spacious 2 story living room and gaze out of the row of glass doors facing the lake.

Newly renovated spacious studio near Stockbridge town hall and Chime tower. Property overlooks golf course in tranquil garden setting.

Enjoy the scenic views and serenity or explore the local waterways by launching your canoe on the brook running through this 4.8 acre property.

Charming 3 story cottage in a unique setting. Furnished 3 bedroom. 2 bathroom house with front/back porches, a part of larger estate in Stockbridge, in heart of the...

A 2 acre hilltop location overlooking beautiful Berkshire Mountains and Botanical Gardens, this historical central entrance colonial, built in 1800's, has updated...

Charming & spacious 1930s cottage style house surrounded by 3 acres of lawn, trees and perennial beds in the beautiful estate area at the West end of Main Street in...

Beautifully furnished, recently renovated Stockbridge home centrally located 3 miles from Tanglewood, 1 mile from Norman Rockwell.

The last house on a quiet street ending at a suspension footbridge crossing the Housatonic river. This turn of the century home is artist owned.

Newly renovated cabin in wooded community with wall to wall carpeting, washer and dryer. Walk to town beach. 1.5 miles to Tanglewood.

Unique architect's home set in 4 acres private estate, 5 minute walk to Tanglewood. This unique home (lots of wood, glass and stone) offers 4 bedrooms (1 king, 2...

Secluded, romantic, woodsy location 1 mile from Tanglewood. 3 miles form Stockbridge and Lenox. Stone fireplace, cathedral ceilings, screened porch.

Stunning home on best street in Stockbridge. Eighteen secluded acres at end of private road. Adjacent to Beartown State Forest.

6 acre very private hilltop location, overlooking beautiful Berkshire Mountains. The large open living room with fireplace is perfect for entertaining / dinning.

This lovely, bright, newly constructed studio apartment is prefect for a writer's /Artist retreat, a couple looking for a weekend getaway or a small family vacation...

This charming and unique property located across the street from the Red Lion Inn started life in the nineteenth century as a carriage house but has been in...

The Cottage is located on 2 acres with mountain views one mile from Main Street, Stockbridge; less than 5 minutes from Tanglewood, Norman Rockwell, The Marians, and...

This modern architect-designed three bedroom/ two bath home (sleeps 6) sits high on a bluff on 22 acres with wonderful southern and western mountain views featuring...

This three-bedroom/2.5-bath home is the perfect vacation rental with all the comfort and amenities of an expensive resort. Enjoy 16 acres of total privacy, extensive...