Restoration masterpiece-1885 schoolhouse. Exquisite suites w/frplcs and whrlpl baths. Spa rm w/jacuzzi for 2. Room dlvd. bkfst, king canopy beds.

Wilder House is a vintage inn in the historic village of Sheffield. 10 minutes from Great Barrington, the Berkshire School, and epic hikes, enjoy beautiful rooms in a walkable setting.

A luxury estate with 13 bedrooms, ensuite bathrooms and the latest technology; this property is ideal for weddings, retreats, and family gatherings!

Located in the Berkshires, across from Jiminy Peak skiing. Luxury condominium units with comforts of home and recreational amenities of a 4-season resort.

Rent The Kemble as your home for the weekend, host your dream wedding/reception (with up to 150 guests), then let the party continue with room to host 30 loved ones!

Waterfront, boutique-style cottage resort offering an all-season charming & tranquil escape with a touch of luxury surrounded by the Berkshire Mtns.

A retro inspired recently renovated historical road side inn

Idyllic and tranquil fully-furnished farmhouse on 4 acres. 5 bedrooms, 2 baths; sleeps 12. Screened porch overlooking gardens, stream, and wooded mountains.

Lovely 2,700 sq. ft. furnished 3 bedroom house, full kitchen, 2 baths, fireplace, 2 TVs, Netflix, A/C, laundry, BBQ, Gazebo, crib, garage. Private pond with kayaks. Sleeps 10.

The Central Downtown offers both short & long term stay accommodations for your time in the Berkshires.