We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

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.

0 of 0 items showing

1 of 3 pages

Home in Lee

4.9 out of 5 average rating, 252 reviews

Cozy Berkshires Cottage

Stay in a cozy Berkshires 1920's cottage! The bedroom occupies the entire second floor with peaceful views of the surrounding field and yard. The cottage is set back from the main road, easily accessible yet private. - Zoned air conditioning & heating makes every room comfortable year-round. - Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. - Ideal for couples, solo adventurers, business travelers, and furry friends (pets). (Note: MA requires 11.7% tax added to charges)

Rental unit in Copake Falls

4.92 out of 5 average rating, 299 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

Treehouse in Tyringham

5 out of 5 average rating, 268 reviews

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.

Home in Stockbridge

4.95 out of 5 average rating, 110 reviews

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.

Cottage in Great Barrington

4.93 out of 5 average rating, 266 reviews

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.

Rental unit in Canaan

4.99 out of 5 average rating, 144 reviews

Mountain View Getaway

Come relax & enjoy panoramic mountain and pond views. Marvel at the dramatic lighting effects on Mercer Mt from sunrise-sunset from your private deck or bright living room. Fully equipped kitchen, grill on the deck, short scenic drive to a wide variety of restaurants & endless cultural venues in the surrounding quaint villages of Berkshire County Mass and Columbia County NY. Near hiking trails, skiing, apple picking & farm stores. Queechy Lake swimming, NYS boat launch for car top boats.

Cabin in Stockbridge

4.87 out of 5 average rating, 206 reviews

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.

Guesthouse in Lenox

4.92 out of 5 average rating, 194 reviews

Modern Barn with Loft at House on Golden Hill

Featuring 35 foot cedar ceilings, large windows, and skylights, The Barn is an oversized two-bedroom apartment with loft at House on Golden Hill, a 1790's farmhouse property in Lenox. The Barn is a detached dwelling with large secluded outdoor space and reserved parking for 3 cars. Situated next to the property's river, the barn provides sweeping mountain views and an idyllic Berkshires experience. Centrally located in the Berkshires and minutes from downtown Lenox and Tanglewood.

Farm stay in Pittsfield

4.99 out of 5 average rating, 168 reviews

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.

Home in Stockbridge

4.95 out of 5 average rating, 120 reviews

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!

Guesthouse in Stockbridge

4.95 out of 5 average rating, 212 reviews

Modern studio with views of the treetops

Our Stockbridge studio is located at the heart of the Berkshires, just north of the center of town. It is a new, modern, second floor studio suitable for up to four adults with views of the surrounding woods, a large kitchenette and comfortable, spacious living space for relaxing in your home away from home. There is a full bath and a private entrance. It is perfect for a weekend getaway or a seasonal stay, whatever your heart desires.

Guesthouse in Stockbridge

4.93 out of 5 average rating, 122 reviews

Modern barn in the heart of the Berkshires

Modern, renovated, historic dairy barn in the heart of the Berkshires. Located on 3.5 acres with beautiful views and close to everything. 1.5 miles to Main St Stockbridge/Red Lion Inn, 5 minutes to Tanglewood, 5 minutes to the Stockbridge Bowl and beautiful hiking trails, under 10 minutes to Lenox . This is the perfect base for exploring the Berkshires or a great getaway for relaxing and enjoying nature.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Stockbridge vacation rentals

Free parking on premises

Air conditioning

Stay near Stockbridge's top sights

Kripalu Center For Yoga & Health122 locals recommend

Norman Rockwell Museum343 locals recommend

The Mount, Edith Wharton's Home167 locals recommend

Shakespeare & Company134 locals recommend

Berkshire Botanical Garden118 locals recommend

The Red Lion Inn117 locals recommend

Other great vacation rentals in Stockbridge

Guesthouse in Stockbridge

4.88 out of 5 average rating, 17 reviews

Light-filled Carpenter's Cottage in Stockbridge

Home in West Stockbridge

5 out of 5 average rating, 40 reviews

Berkshires Forest Retreat with Hot Tub

Home in Stockbridge

4.98 out of 5 average rating, 42 reviews

Secluded Family Home in Serene Stockbridge Woods

Cabin in West Stockbridge

4.99 out of 5 average rating, 74 reviews

Modern Cabin near Tanglewood

Guesthouse in Great Barrington

4.95 out of 5 average rating, 92 reviews

Sweet Victorian in Housatonic

Home in West Stockbridge

5 out of 5 average rating, 32 reviews

Beautiful And Private Home Centrally Located

Home in Great Barrington

4.9 out of 5 average rating, 91 reviews

Quiet home on the hill.

Home in Great Barrington

5 out of 5 average rating, 63 reviews

House in beautiful Berkshires

Quick stats about vacation rentals in Stockbridge

Total rentals
130 properties
Nightly prices starting at
$90 before taxes and fees
Total number of reviews
4.1K reviews
Family-friendly rentals
80 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
20 properties have a pool

Frequently Asked Questions

Are there pet-friendly vacation rentals in Stockbridge?
Four-legged friends are welcome in Stockbridge. Choose from more than 30 vacation rentals for guests traveling with pets.
Are there family-friendly vacation rentals in Stockbridge?
Stockbridge has more than 80 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Stockbridge?
Experience the best of Stockbridge with our house rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Stockbridge have wifi?
Absolutely! We offer over 70 house rentals with wifi in Stockbridge. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Stockbridge?
Yes! Work meets play with ease at over 50 vacation rentals in Stockbridge featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Stockbridge vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Stockbridge, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Stockbridge have a gym?
Absolutely! We offer over 10 house rentals with a gym in Stockbridge. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in Stockbridge have a bbq area?
Absolutely! We offer over 10 cabin rentals with a bbq area in Stockbridge. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Hotel Rentals in Stockbridge?
Enhance your stay in our Hotel Rentals with the most popular amenities: over 20 homes with air conditioning, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
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.

Destinations to explore