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Vacation rentals in West Stockbridge

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Top-rated vacation rentals in West Stockbridge

Guests agree: these stays are highly rated for location, cleanliness, and more.

Cottage in Great Barrington
Artist Cottage
Enchanting, private, romantic, retro style, artsy, cottage & lodge building with fireplaces and outdoor hot tub and shower area in a quaint, quiet, neighborhood nested at the base of Flag Rock and near nature trails and downtown Great Barrington. Perfect for a romantic get-away. Open retro style kitchen with wood stove and TV is stocked with utensils and pans for cooking with gas oven and retro appliances. Upstairs bedroom with ensuite large bathroom with soaking tub and message chair.
$186 per night
Home in Lee
1817 Berkshire Farmhouse- Close to Everything.
We are nestled at the foot of October Mountain State Forest, yet close to the centers of Lee, Lenox, & Pittsfield. Our charming house was built in 1817- original wood beams, wood floors, and quite a history. Whether you enjoy skiing, exploring local restaurants & downtowns, venturing outdoors or experiencing the local art scene, the Berkshires has something for everyone. Our little farmhouse serves as the perfect "home base" for all of your Berkshire adventures.
$139 per night
Guesthouse in Lenox
The Granary at House on Golden Hill
The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.
$97 per night

Stay near West Stockbridge's top sights

No. Six Depot Roastery & Cafe82 locals recommend
Chesterwood63 locals recommend
Shaker Mill Tavern4 locals recommend
Rouge Restaurant34 locals recommend
Public Market6 locals recommend
Turn Park Art Space10 locals recommend

Other great vacation rentals in West Stockbridge

Home in Lenox
Berkshire, MA Getaway! Mile to town
$225 per night
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
$303 per night
Guest suite in Austerlitz
Rustic-Modern Studio - Near Hudson, Chatham, & GB
$95 per night
Vacation home in Great Barrington
Home in Great Barrington. Steps from downtown!
$184 per night
Home in New Lebanon
The old sawmill from 1771
$125 per night
Home in Stockbridge
Cozy cottage by the brook
$139 per night
Guesthouse in Canaan
Airy cottage with meadow views in The Berkshires
$160 per night
Apartment in Great Barrington
Private En Suite in Beautiful Victorian
$107 per night
Cabin in Canaan
Rustic Barn Studio Apartment
$145 per night
Home in Lee
Cozy Berkshires Cottage
$134 per night
Home in West Stockbridge
West Stockbridge MA gem, in town and facing lake
$250 per night
Home in West Stockbridge
Retreat to Nature, Sunset Views by Evergreen Home
$169 per night

Destinations to explore