
Vacation rentals in Stockbridge
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Stockbridge
Guests agree: these stays are highly rated for location, cleanliness, and more.

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

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!

Gingerbread House Tower in the Berkshire Hills
Escape to this newly renovated, off-beat retreat for a magical stay. Part of Tyringham’s Gingerbread House located on the Santarella Estate in the Berkshires, Western Mass. This one-of-a-kind loft with tower bedchamber offers guests a fairytale experience. The open concept living space filled with plants brings the outdoors inside and offers ample room to relax. If looking for activity, guests can spend the day on the grounds, walking nearby trails, or exploring the many nearby Berkshire towns.

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 sleeping loft. A 9 minute walk or 2 minute drive to lake public beach (The lovely Stockbridge Bowl) . BBQ grill, outdoor fire pit . Gates of Tanglewood minutes aaway!

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.

The Coach House | Modern 2BR Loft + Views & Pool
Restored coach barn with 25-ft cedar ceilings, skylights, and mountain views—part of House on Golden Hill, a historic Lenox farmhouse compound. This airy 2BR + loft retreat blends rustic charm with modern ease. Enjoy a full kitchen, cozy living space, and outdoor area. Set beside a stream with seasonal pool access, it’s perfect for families, couples, or creative escapes. Centrally located and just minutes to downtown Lenox, Tanglewood, and trails—your Berkshires base for rest and inspiration.

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.

Historic,Famous,Iconic, Unforgettable Berks Escape
PICTURE IT...You can put yourself in the "famed" Norman Rockwell Main Street at Christmas Painting! That's Right,Cozy, Intimate,Magical and all to yourself.Fully equipped with all the comforts of home. Small Town Charm,Big time Historic setting in the heart of Downtown Stockbridge! Spend your afternoon sipping Tea or Wine looking out the iconic picture window Norman Rockwell installed himself. The one where the Christmas Tree Glows in a room that was Norman Rockwell's Studio from 1953-1957

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 relax by the firepit- we hope you enjoy your stay and will visit us again.

Private 2nd-floor studio on a working produce farm
Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or just relax out on the balcony and take in the views.

Sun-filled, Charming Stockbridge Classic- In Town!
Beautiful remodel on a classic old, well-appointed New England house located in the middle of town on a dead-end road leading to hiking trails for Laura's Tower. A quick walk to Downtown Stockbridge, Red Lion Inn, gas station, cafes, markets, shops... everything you need. A park sits directly across the street with open acreage, swings, sandbox, skate park. Parking available on site. Located within minutes of four season activities- happy to make recommendations!

The Cottage at The Barrington House
Welcome to the Cottage at the Barrington House! The Barrington House is nestled in the serene Berkshires Mountains - which have long been a sanctuary for weary city dwellers seeking breathing space, a perfect retreat for artists, writers and thinkers! It's sprawling grounds offer stunning views of lush valleys and distant peaks, while the interior features a fireplace, cozy reading nook, and unlimited windows that invite the natural world inside.
Popular amenities for Stockbridge vacation rentals
Stay near Stockbridge's top sights
Other great vacation rentals in Stockbridge

Historic Stockbridge Villa on 25 acres sleeps 16

The Blue Jay Cottage

Light-filled Carpenter's Cottage in Stockbridge

Charming Stockbridge Farmhouse- walk to town!

Berkshires Forest Retreat with Hot Tub

The Nest 5 min walk to downtown Great Barrington

Exceptional Stockbridge Retreat

Eliza Suite
Quick stats about vacation rentals in Stockbridge
Total rentals
140 properties
Nightly prices starting at
€ 94 before taxes and fees
Total number of reviews
4.8K reviews
Family-friendly rentals
90 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
30 properties have a pool
Frequently Asked Questions
Do hotel rentals in Stockbridge have air conditioning?
Absolutely! We offer over 20 hotel rentals with air conditioning in Stockbridge. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Stockbridge have a kitchen?
Absolutely! We offer over 70 house rentals with a kitchen in Stockbridge. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly house rentals in Stockbridge?
Four-legged friends are welcome in Stockbridge. Choose from more than 30 house rentals for guests traveling with pets.
Are there family-friendly house rentals in Stockbridge?
Stockbridge has more than 60 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in hotel rentals in Stockbridge?
Experience the best of Stockbridge with our hotel rentals, starting at about $990 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do hotel rentals in Stockbridge have wifi?
Absolutely! We offer over 20 hotel rentals with wifi in Stockbridge. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Stockbridge have free parking?
Absolutely! We offer over 70 house rentals with free parking in Stockbridge. Enjoy a tailored experience with all the comforts you desire.
Are there house rentals with a dedicated workspace in Stockbridge?
Yes! Work meets play with ease at over 30 house rentals in Stockbridge featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Stockbridge hotel rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 hotel rentals with pools in Stockbridge, available on Airbnb. Make a splash and soak up the sun in style!
What are the most popular amenities for Hotel Rentals in Stockbridge?
Enhance your stay in our Hotel Rentals with the most popular amenities: over 10 homes with free parking, over 20 homes with air conditioning, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Long Island Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Philadelphia Vacation rentals
- Mount Pocono Vacation rentals
- Jersey Shore Vacation rentals
- Ocean City Vacation rentals
- The Hamptons Vacation rentals
- Rentals with a fireplace Stockbridge
- Hotel rentals Stockbridge
- Rentals with a patio Stockbridge
- Rentals with breakfast Stockbridge
- Rentals with beach access Stockbridge
- Rentals with lake access Stockbridge
- Rentals with outdoor seating Stockbridge
- Rentals with a fire pit Stockbridge
- Rentals with a washer and dryer Stockbridge
- Family-friendly rentals Stockbridge
- Pet-friendly rentals Stockbridge
- Rentals with a hot tub Stockbridge
- Rentals with pools Stockbridge
- House rentals Stockbridge
- Hunter Mountain
- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- John Boyd Thacher State Park
- Bash Bish Falls State Park
- Kent Falls State Park
- Zoom Flume
- Catamount Mountain Ski Resort
- Bushnell Park
- Mount Greylock Ski Club
- Windham Mountain
- Norman Rockwell Museum
- Wintonbury Hills Golf Course
- Taconic State Park
- Mount Sugarloaf State Reservation
- Opus 40
- Mohawk Mountain Ski Area
- Beartown State Forest
- Mount Tom State Reservation
- Hunter Mountain Resort
- Bousquet Mountain Ski Area
- Hartford Golf Club
- Bright Nights at Forest Park