Family-friendly holiday rentals in West Stockbridge

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Top-rated family-friendly rentals in West Stockbridge

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite

Loft in Great Barrington

4.99 out of 5 average rating, 316 reviews

The Old Red Barn

Renovated studio in barn built circa 1830, centrally located to all activities in the Berkshires. Bright and sunny space with views of fields and spectacular sunsets. Open upstairs loft bedroom with pine floors, catherial ceiling, exposed beams, full kitchen , bathroom and washer and dryer. The Berkshires are beautiful in the fall , come stay ! 5 minute drive to town. Walk to the Green River , hike the trails. We provide all basic household supplies. We invite all to enjoy our old red barn.

Guest favourite

Chalet in Otis

4.94 out of 5 average rating, 378 reviews

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Guest favourite

Cabin in Chatham

4.9 out of 5 average rating, 123 reviews

Cozy Secluded Cabin w. wood stove near Berkshires

The Red House is surrounded by acres of forest and is close to conservation areas with hiking trails. Minutes to antiquing, Kripalu, Norman Rockwell Museum, The Mount, Tanglewood, Skiing, Shakespeare & Co. You’ll love my place because of the peace, quiet and seclusion. Located up an old dirt country road. Relax by the wood stove (bring wood), in the sun room or explore nearby Spencertown, Chatham or West Stockbridge. Many ski slopes nearby & a small lake! If visiting in winter, 4wd recommended.

Guest favourite

Guest suite in South Lee

4.92 out of 5 average rating, 202 reviews

Sunny Riverside Apartment

The Berkshires are a perfect spot for a getaway week or weekend. You will enjoy this cozy 2-story apartment, easily accessible to all that the region has to offer. The apartment has a fully equipped kitchen, dining space, living area, and two bedrooms, overlooking the Housatonic River. Every town in South County is 5-15 minutes drive, and in 50 minutes you could be at The Clark Museum or Mass MOCA in North County. Several ski areas are nearby, and Kripalu is just an easy 10 minute drive.

Guest favourite

Home in Lenox

4.93 out of 5 average rating, 223 reviews

The Berkshire Quintessential Cape downtown Lenox

The quintessential Cape located on a quiet dead-end street in the center of Lenox. This completely renovated home has beautiful oak floors throughout. Decorators white painted walls with high ceilings & an abundant amount of windows allowing this well kept home to be flooded with beautiful light. First floor bedroom and full bath. Upstairs has two large bedrooms with shared bath. Open living and dining with wood burning fireplace. A quick stroll into town, Tanglewood & Canyon Ranch.

Guest favourite

Rental unit in Great Barrington

4.93 out of 5 average rating, 190 reviews

Secluded but not isolated Berkshire Retreat

1.5 bedroom 1.5 bath self contained apartment (apprx. 950 sq ft ) attached to the main house set on a secluded 5.5 acre lot 2.9 miles from downtown Great Barrington . There is a CB2 day bed in the living room that sleeps an additional 2 people comfortably. Extra charge of $25/night +tax if the extra bedroom is used in 2 person reservations. $20 extra cleaning fee for reservations of 4 or more. During heating season not suitable for children under 5 because of pellet stove. .

Guest favourite

Cottage in Craryville

4.91 out of 5 average rating, 515 reviews

Columbia County Getaway - Raspberry Ridge Cottage

Affordable, pet and family friendly country cottage in the Hudson Valley off TSP; close to Berkshires and Hudson. Amenities are high speed reliable internet, landscaped grounds, hilltop gazebo with dining deck, grill, fire pit. Cosy wood-stove inside. Backyard chicken coop with fresh eggs. Go 'tree-bathing' on the deck. Woodland setting with open fields. Perfect for a low-key weekend getaway. Hosts live next door. Chief Martindale Diner walking distance. Ample parking.

Guest favourite

Cottage in Copake Falls

4.91 out of 5 average rating, 339 reviews

Beautiful cottage at the foot of the Birkshires

Come stay with us in our beautiful cozy cottage, on a small lot located in the heart of Copake Falls, walking distance to Taconic State Park. Enjoy great farm to table dining, ski the Berkshires (just under 10 minutes to Catamount Resort), hike to Bash Bish Falls, bike the Harlem Valley Rail Trail, and swim in the spring fed iron ore pit during the open season.

Guest favourite

Home in Stockbridge

4.97 out of 5 average rating, 101 reviews

Greek Revival Farmhouse

Set on 2 acres, our home is a short walk to Norman Rockwell Museum and Chesterwood. All rooms have hardwood floors except the tiled bathrooms. We recently updated the kitchen, and previously remodeled both bathrooms with a 'vintage modern' aesthetic. Our home is furnished with a mix of antiques, vintage items and contemporary pieces.

Guest favourite

Home in Chatham

4.93 out of 5 average rating, 196 reviews

Beautiful Lake/Mountain Views. Bright Sunlit Home.

Home Away From Home! Spectacular views with large windows and decks to enjoy the view of the lake, mountains or the stunning fall foliage. This relaxing getaway has everything you need to enjoy your stay. Cook a gourmet meal, build a warm fire, take a walk to the country store or just read a book in one of its many quiet spots.

Guest favourite

Home in New Lebanon

4.99 out of 5 average rating, 360 reviews

The old sawmill from 1771

The oldest house in town, fully renovated. Beautiful two-story living room with leafy, private back deck for meals outside. Kitchen with stone counters, gas cook top, and dishwasher; two bathrooms with warm floors. Floorboards upstairs a foot wide; queen size bed with view over the trees, creek and porch.