Family-friendly holiday rentals in West Stockbridge

4.92 out of 5 average rating, 145 reviews

Cabin in Chatham

Rustic Secluded Cabin near Berkshires. *wood stove

The Red House offers a peaceful secluded retreat, surrounded by acres of forest & with excellent hiking trails. Enjoy the tranquility of nature while being minutes from antiquing, Kripalu, the Norman Rockwell Museum, The Mount, Tanglewood, skiing, & Shakespeare & Co. You'll appreciate the serene privacy, situated on an old dirt road. Relax by the wood stove or in the sunroom. Nearby towns of Spencertown, Chatham, & West Stockbridge offer unique charm. 4WD vehicle is recommended for winter visits

FamilyKitchenHeating

4.95 out of 5 average rating, 275 reviews

An open living space with a high wood-beam ceiling is displayed. A large stone fireplace serves as a focal point, surrounded by comfortable seating. A kitchen island with stools offers additional space. Large windows allow natural light to fill the room, enhancing the inviting atmosphere.

Farm stay in New Lebanon

Barn Stay at Shadowbrook Farm

Welcome to the Shadowbrook Farm Stay. Tucked in the hills of upstate New York, this 1700's Shaker barn has been restored into a beautiful guest house. It sits upon a two hundred acre working pasture raised meat farm. This barn was used to hold, and milk cows for two hundred and fifty years. Guests will have access to portions of the farm lands which are highlighted on the maps provided in the Farm Stay manual. If you follow the farm road, you are able to meet every farm animal on the property!

FamilyKitchenDecor

4.97 out of 5 average rating, 106 reviews

Cabin in East Nassau

Fall Foliage Luxury Cabin & View Autumn Adventures

Welcome to our mountain retreat, nestled in the heart of nature and brought to you by Den Outdoors. 25 mins to Tanglewood, 35 mins to Jacobs Pillow, 15 mins to Jiminy Peak, 30 mins to The Clark, MASS MoCA, and the Berkshire region. 10 mins to a swimmable lake. 2.5 hrs from NYC and from Boston. Come experience all Autumn has to offer! Stunning views, no visible neighbors, Goodland wood fired hot tub, Breeo Fire pit, large Webber Grill, radiant floor, EV charging, and the MOST STUNNING view!

KitchenIndoor spacesLayout

4.89 out of 5 average rating, 252 reviews

Cabin in Stockbridge

Hip Stockbridge Cabin - A stroll to the lake

Welcome to our stylish cabin! Relax in the spacious yard & sunny deck. Cozy fieldstone fireplace, vaulted ceilings & skylights. The cottage features gorgeous pine wood walls & fantastic interior design. Unwind in the reading nook, relax in the en suite bedroom with skylight, or put on your favorite vinyl. Kids will adore the sleeping loft. Just a 9 minute walk or 2 minute drive to the public beach (the beautiful Stockbridge Bowl). BBQ grill, outdoor fire pit . Tanglewood minutes away.

FamilyIndoor spacesOutdoor spaces

4.94 out of 5 average rating, 207 reviews

A modern living area features large windows allowing natural light to fill the space. A cozy sofa and a comfortable chair invite relaxation, while a country-style table accommodates dining or work. The decor is enhanced by a colorful area rug and minimalistic furnishings.

Guest suite in Richmond

Berkshires/Pet Friendly/Tanglewood/Private Ranch

Pet-Friendly, Child-Friendly Getaway! Modern suite with full kitchen on private horse ranch. Wake to horses in the fields, hiking, breakfast on your patio. Perfect location for individuals, couples, families animal lovers. Near all ski areas (Jiminy Peak/Catamount/Bousquet /Butternut), shopping, museums (Norman Rockwell/Mass MoCA) wine tasting (Balderdash Cellars, Hilltop Orchards) Tanglewood, Jacobs Pillow, Miraval, Kripalu, Canyon Ranch. Trail Rides /Horse activities available by appt!

Indoor spacesFamilyComfort

Guesthouse in Great Barrington

A dining area features a wooden table surrounded by four black chairs. A vase with greenery is centered on the table. In the background, a cozy seating area with a sofa is visible, illuminated by natural light from a nearby window.

4.95 out of 5 average rating, 174 reviews

Sweet Victorian in Housatonic

Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newly renovated Victorian house in Housatonic. Tasteful clean furniture, organic new sheets, pillows and duvets. Lovely clean kitchen that is fully equipped to host dinners. Situated up on a hill in Housatonic this three bedroom is conveniently located to to Great Barrington, Lake Mansfield, Stockbridge, Butternut, Catamount, Tanglewood, Kripalu and Monument Mountain.

KitchenIndoor spacesAccuracy

4.99 out of 5 average rating, 317 reviews

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relaxing our wood-fired hot tub- we hope you enjoy your stay and will visit us again.

FamilyIndoor spacesLong stay

4.86 out of 5 average rating, 126 reviews

Home in West Stockbridge

Peaceful Stockbridge Cabin in the Woods

The Residence is a beautiful, secluded home in the Berkshire foothills. The 14-acre property includes hiking trails through the woods, a meadow, and a lovely babbling brook. Despite its secluded feel, the house just a short drive from many of the area's favorite attractions. The Residence provides a wonderful for base for enjoying all that the Berkshires have to offer, though guests may decide to spend much of their stay exploring the rustic beauty of the property itself.

KitchenIndoor spacesSkiing

4.96 out of 5 average rating, 112 reviews

An open living space features a large sectional sofa surrounding a central glass coffee table. A decorative chandelier hangs from the exposed wooden beams. Natural light streams in through multiple floor-to-ceiling windows, revealing views of the surrounding greenery.

Barn in East Chatham

Luxury Barn Retreat Near Hudson & the Berkshires

Set on eight private acres where New York meets the Berkshires, this architect-designed 19th-century barn combines soaring ceilings, original beams and contemporary comforts. Enjoy a chef’s kitchen, two fireplaces, designer interiors, peaceful outdoor spaces and access to nearby Queechy Lake. A private outdoor sauna will be ready for all stays beginning October 1, 2026. Minutes from Chatham and an easy drive to Hudson, Great Barrington and Tanglewood.

Indoor spacesKitchenBathroom

Barn in Town of Hillsdale

4.97 out of 5 average rating, 183 reviews

Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna

A private hilltop oasis in nature. Newly renovated barn with some luxury amenities including sauna & outdoor firepit & movie theater screen & hot tub & stock tank pool on a 15-acre hilltop w/ views & privacy in Hudson Valley / Berkshires. Fully stocked for cooking & tons of games. Near great shops & restaurants in Hudson & Great Barrington. We can point you to the best people to book for private massages or yoga classes right at the house.

FamilyIndoor spacesGetting around

4.97 out of 5 average rating, 159 reviews

A bright bedroom features a spacious bed with neutral bedding, framed by wooden walls and beams. Natural light fills the room through a large window, showcasing a glimpse of the outdoor area. A small side table and a decorative plant complement the simple, serene design.

Cabin in Chatham

The Upstate Cabin: A secluded getaway in the woods

Cozy cabin tucked away in the woods, 2.5 hours north of NYC and 2.5 hours west of Boston - where the Catskills meet the Berkshires. There's hiking in the summer, skiing in the winter, and total peace & quiet year-round. This entire cabin has been hand-lovingly restored and we can't wait to share the space with you. Follow us on Insta at @theupstatecabin to follow our upstate adventures and cabin transformation.

FamilyIndoor spacesLocation

A serene bedroom features a spacious bed dressed in soft linens and a colorful quilt. A cozy couch is positioned against the wall, offering a relaxation spot. Natural light is let in through multiple windows, highlighting the light blue paneled walls and white furniture.

4.97 out of 5 average rating, 141 reviews

Stylish Mid-century Modern Berkshires Cape

Stylish and design forward, yet entirely comfortable for families and kids. Fully renovated 4 bedroom, 2.5 bath home located in the heart of the Berkshires. Enjoy the large, sunny yard and deck with lots of seating and a large dining table - perfect for al fresco dinner and drinks! The house is decorated in mid century modern style with gorgeous design touches throughout!

KitchenFamilySleep quality

Popular amenities for West Stockbridge family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Cottage in Great Barrington

A charming cottage is framed by vibrant flowering shrubs and greenery. The front porch is adorned with decorative elements, while large windows invite natural light into the space. A wooden fence encloses the front garden, enhancing the quaint and inviting atmosphere.

4.93 out of 5 average rating, 352 reviews

Artist Cottage

FamilyKitchenBeach

4.96 out of 5 average rating, 307 reviews

The spacious living room features large windows that provide scenic views of the mountains and lake. A comfortable sectional sofa is complemented by a decorative throw and cushions. The ceiling is elevated with wooden beams, and stylish decor enhances the inviting atmosphere.

Home in Monterey

Jaw dropping mountain & lake views

FamilyIndoor spacesCondition

A spacious living area features a modern sectional sofa adorned with various cushions, positioned around a round coffee table. Exposed wooden beams and high ceilings create an open atmosphere. A staircase leads to an upper level, and natural light illuminates the well-equipped kitchen visible in the background.

4.88 out of 5 average rating, 107 reviews

Stonebridge Cabin: Modern Amenities, Enjoy Nature!

FamilyKitchenHiking

4.98 out of 5 average rating, 134 reviews

The spacious kitchen features an island with a wood countertop and built-in storage. Mint green cabinetry offers a serene ambiance. Natural light flows through large windows, illuminating the dining area with a wooden table and cozy seating, creating an inviting space for gatherings.

Home in Ghent

Luxe Retreat+Sauna+HotTub & Swimming on 12 acres

KitchenIndoor spacesComfort

4.96 out of 5 average rating, 107 reviews

A bright loft space features a spacious queen bed with light linens and decorative throw pillows. Skylights open the room to natural light, illuminating the cozy seating area and a kitchenette. A small dining table sits nearby, while a fireplace adds warmth to the ambiance.

Loft in Austerlitz

The Lookout Loft @Moonbeams: stay on 38 acres

KitchenIndoor spacesAccuracy

Superhost

Home in Hudson

4.91 out of 5 average rating, 148 reviews

Designer Home, Hot Tub, Private Yard, & Projector

KitchenIndoor spacesCheck-in

4.96 out of 5 average rating, 112 reviews

Home in Athens

Lake House close to Skiing & Indoor Hot Tub

FamilyIndoor spacesBeach

4.96 out of 5 average rating, 179 reviews

Home in Greenville

Greenville Getaway|Paws & Pines: Dog Park & HotTub

Indoor spacesFamilyHot tub

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 188 reviews

An open living area showcases rustic wooden beams and a cozy gas fireplace. A modern gray sofa faces the fireplace, complemented by a glass coffee table with a vase of pink flowers. Natural light floods in from the glass doors, leading to the lush green outdoor space.

Home in Stockbridge

Bright Stockbridge country home, near everything!

Indoor spacesKitchenAmenities

4.92 out of 5 average rating, 101 reviews

A modern kitchen features clean lines and natural light. The space includes a refrigerator, stove, and a dining table with two chairs. Soft white cabinetry is complemented by a wooden tabletop, while a window offers views of the outdoors, enhancing the open and airy feel.

Apartment in Stockbridge

Stockbridge private apartment

FamilyKitchenCheckout

4.99 out of 5 average rating, 385 reviews

A charming two-story red house is surrounded by lush greenery and colorful flowering plants. Sturdy steps lead up to the entrance, framed by vibrant shrubs and hydrangeas, creating a welcoming outdoor area that blends naturally with the landscape.

Home in New Lebanon

The old sawmill from 1771

Indoor spacesKitchenLaundry

4.99 out of 5 average rating, 138 reviews

A modern farmhouse bungalow is nestled among lush greenery along a brook. The red exterior is complemented by white trim and a front porch. A wooden bench sits by the water's edge, inviting relaxation amidst the tranquil natural surroundings.

Bungalow in Egremont

3-bedroom Berkshire bungalow on 2.5 peaceful acres

KitchenFamilyView

4.96 out of 5 average rating, 193 reviews

The rustic cabin is framed by lush greenery, with a welcoming front porch featuring wooden steps leading up to the entrance. Tall trees and landscaped shrubs create a serene setting. A stone chimney adds a touch of charm to the inviting exterior.

Cabin in Canaan

Newly Renovated Cabin in the Country

KitchenIndoor spacesCondition

Guesthouse in Stockbridge

A modern, renovated barn is set against a backdrop of lush greenery. Two brightly colored lounge chairs and a reclining chair are positioned on the grassy area, inviting relaxation. Large windows reflect the surrounding trees, emphasizing the tranquil outdoor setting.

4.91 out of 5 average rating, 171 reviews

Modern barn in the heart of the Berkshires

FamilyIndoor spacesAmenities

4.98 out of 5 average rating, 186 reviews

Farm stay in Saugerties

Catskills Family Retreat: Pool, Sauna and Animals!

FamilyIndoor spacesBiking

Cottage in Great Barrington

The rustic carriage house is surrounded by lush greenery, featuring a vibrant garden with various plants and flowers. A teal umbrella provides shade over an outdoor seating area, complemented by a stone pathway leading to the entrance, enhancing the inviting atmosphere of the setting.

4.93 out of 5 average rating, 155 reviews

Carriage house with Chef's Kitchen, close to town

KitchenFamilyCheck-in

Family-friendly home rentals with a pool

Superhost

A comfortable living room features a large sectional sofa and a wooden coffee table. A reclining chair is positioned nearby, while a flat-screen TV is mounted on the wall. Natural light enters through glass doors, which open to the outdoor area. Soft colors and warm tones create a cozy ambiance.

4.93 out of 5 average rating, 104 reviews

Berkshire Vacation Home in Lee

FamilyIndoor spacesWi-Fi

4.93 out of 5 average rating, 108 reviews

The exterior shows a modern home embraced by lush greenery. A wooden deck with a railing wraps around the entrance, complemented by well-maintained landscaping featuring shrubs and plants. Trees provide a natural backdrop, enhancing the tranquil rural setting.

Home in Pittsfield

Berkshire Getaway Ranch 3 acres + saltwater pool

KitchenIndoor spacesQuiet

4.98 out of 5 average rating, 107 reviews

A spacious white cottage is set against a vibrant green lawn, framed by blooming white flowers. Expansive trees surround the property, overlooking rolling hills that stretch towards a tranquil river in the distance under a clear blue sky.

Home in Coxsackie

Hudson River estate guest cottage

FamilyIndoor spacesHiking

5.0 out of 5 average rating, 111 reviews

A modern log cabin sits beneath a clear sky, featuring a spacious deck supported by sturdy beams. The exterior shows natural wood tones, surrounded by lush greenery and trees. A manicured lawn leads to a gravel driveway, providing access to the property.

Cabin in Craryville

The Copake Cabin - A rustic-modern retreat.

FamilyKitchenComfort

4.95 out of 5 average rating, 170 reviews

A clear view of a fenced swimming pool is surrounded by lush greenery and trees. A stone pathway leads to the pool area, with well-maintained flower beds in the foreground. Seating options are available near the pool for relaxation.

Cottage in Averill Park

Cozy cottage with pool, walking distance to lake

Indoor spacesFamilyLaundry

4.98 out of 5 average rating, 175 reviews

The exterior view of the guest house is framed by a large tree, showcasing the red brick barn-style structure. Outdoor seating areas are visible, along with a shaded patio featuring a red umbrella. The surrounding lawn is well-kept, leading to fenced paddocks in the background.

Farm stay in Red Hook

Sackett & Van Dam Guest House @ Little 9 Farm 1706

KitchenFamilyValue

Superhost

A spacious outdoor area is surrounded by vibrant planters filled with blooming flowers. Comfortable seating is arranged around a fire pit, with a green umbrella providing shade. A pink flamingo float is set nearby, alongside a wooden hot tub and a stock tank plunge pool.

Home in Hudson

4.94 out of 5 average rating, 196 reviews

Hudson getaway w/ hot tub+ plunge pool on 20 acres

FamilyKitchenBathroom