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Stockbridge vacation rentals

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Top-rated vacation rentals in Stockbridge

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

Home in Stockbridge
Bright Stockbridge country home, near everything!
Berkshires charm in this fully renovated 1800's post and beam farmhouse set on 5 park-like acres. Features open plan living/dining/kitchen with gas cooktop and gas 3 sided fireplace, lovely sun room, master suite downstairs and 2 br, bath and sitting area upstairs. Spacious deck overlooking the expansive property Conveniently located between the charming towns of Stockbridge, Lenox & Great Barrington. We are surrounded by 4 ski areas, the closest is 10 minutes away! Many dining options too.
$186 per night
Home in Stockbridge
Hadley House: Lush Homesteading Experience with Hot Tub, Play Barn, Sleep Shack w/ Direct Access to the Konkapot for Kayaking: sleeps 8+
Hadley House: Lush Homesteading Experience w/ Hot Tub, Play Barn, Sleep Shack, Konkapot access for Kayaking: sleeps 8+. Amenities: 3+ bedrooms. 1.5 bath + outdoor shower w/ hot water, hot tub, party barn, bar, fire pit, patio w/ outdoor seating, tiki torches and grill. Flower, veggies and herb gardens, sleeping shack, chicken coop, kayaking, catch and release fishing. Spectrum wifi, (2) Smart TVs, stainless appliances, wood stove, front porch seating, washer/dryer, window unit AC throughout.
$100 per night
Cabin in Stockbridge
Hip Stockbridge Cabin - A stroll to the lake
Hello hip, glamping cabin! The decor is chic & bohemian cool! Enjoy the large yard & sunny deck. Fieldstone fireplace w/ vaulted ceilings & skylights. Cottage has beautiful pine throughout w/ fabulous interior design picks. Enjoy the sweet reading nook, master bedroom w/ skylights or put on a favorite record. Kids will love the cozy sleeping loft. A 8-10 minute walk or 2 minute drive to lake public beach (The lovely Stockbridge Bowl) Outdoor shower. BBQ grill, great outdoor space to play.
$208 per night

Stay near Stockbridge's top sights

Photo of Norman Rockwell Museum
Norman Rockwell Museum345 locals recommend
Photo of The Red Lion Inn
The Red Lion Inn118 locals recommend
Photo of Naumkeag
Naumkeag109 locals recommend
Photo of Kripalu Center For Yoga & Health
Kripalu Center For Yoga & Health122 locals recommend
Photo of Berkshire Botanical Garden
Berkshire Botanical Garden118 locals recommend
Photo of Michaels of Stockbridge
Michaels of Stockbridge7 locals recommend

Other great vacation rentals in Stockbridge

Rental unit in Stockbridge
Historic,Famous,Iconic, Unforgettable Berks Escape
$207 per night
Home in West Stockbridge
New! Berkshires Forest Retreat with Hot Tub
$337 per night
Rental unit in Stockbridge
Holmes Suite: PRIME Downtown Stockbridge
$98 per night
Guesthouse in Stockbridge
Modern barn in the heart of the Berkshires
$175 per night
Cottage in Great Barrington
Artist Cottage at the foot of Monument Mountain
$195 per night
Hotel room in Lenox
Standard King in Boutique Lenox Hotel
$95 per night
Rental unit in Canaan
Mountain View Getaway
$96 per night
Cottage in Great Barrington
Cozy Country Cottage w Fireplace near Ski Mtns!
$158 per night
Home in West Stockbridge
Retreat to Nature with Sunset Views
$186 per night
Home in Lee
1817 Berkshire Farmhouse- Close to Everything.
$151 per night
Private room in Lee
Comfortable living in 1870's house!
$70 per night
Treehouse in Lee
Gingerbread House Tower in the Berkshire Hills
$253 per night