Vacation Rentals in Great Barrington

BOOK NOW FOR FALL FOLIAGE AND WINTER SKI SEASON!! Sparkling new home near Lake Buel with your own dock (pictured) in a peaceful lakefront community.

Literally one of the best locations in Great Barrington – a serene property on a tranquil, dead-end street in town. Housed in one of the finest buildings, this...

Literally one of the best locations in Great Barrington - a serene setting on a tranquil, dead-end street in town. Housed in one of the finest buildings, the...

Tranquil retreat for romance or family fun. Tastefully decorated, completely renovated, cathedral- ceiling cottage with every convenience, from a fully stocked...

House by the lake and just 20 minutes to culture( Tanglewood, Stockbridge Theater,Jacob' Pillow Dance). Feel the charm of Adirondack decor, casual, comfortable,...

Tastefully & comfortably furnished. Sparkling, spacious, sun-filled & private woods & landscaped lawns (front/back) --1.5 mi.

When you decide to visit Fran's Place, you will have the opportunity to create a fond memory that will last forever. This property is situated in the most popular...

Walk to downtown Great Barrington, hike the Appalachian Trail or kayak on the Housatonic River from this Historic Wyantenuck Cottage.

Sunny contemporary. Quiet, Private. Cheerful. Near all Berkshire cultural events and 4 minutes to town. Sky lights, views, walking trails, lots of windows, huge...

Enjoy Lake Buel from our wonderful, quiet lakefront home. You will feel truly at home here because that is what it is; our second home, Fabulous for family and...

Cozy, beautifully furnished, converted 18th Century barn, surrounded by one of the most beautiful gardens in the Berkshires. The 20x30 foot great room with cathedral...

Beautiful field and mountain views, private yard with deck and patio. 2 Miles from downtown Gt Barrington shops and restaurants.

This delightful, sun-filled three-bedroom/one-bath cape is situated on a quiet country road. This comfortable home has a backyard terrace, gardens, and all...

Located in beautiful scenic Southwestern Massachusetts, this year round, 4 bedroom, 2 bathroom cottage with access to one the great lakes of the Berkshires has been...

Beautiful park-like 1 1/2 acres. Private road. All amenities. Each room with A/C. 5 HDTVs with 60 inch in LR and large HDTV in all BR and Den- All with DVD.

This charming Cape style home is situated on 15+ acres of woods and lawns and perennial gardens. There are 3 bedrooms on the main floor, one with private bath and...

A private and centrally situated apartment suite for your Berkshire respite offers relaxation in an area filled with cultural activities:Tanglewood, Jacobs Pillow,...

Combine the cultural and natural wonders of the Berkshires by vacationing in this charming, original knotty pine cottage a short walk to swimming and boating on...

Perched on a gradual slope overlooking our Private Cove is this Cute, Imaginative, Unique Country Cottage that can accommodate 6 people.

Refurbished Lake Buel cottage in quiet, wooded community waits for you. Spacious living room with amenities, large eat-in kitchen fully stocked for cooking or dine...