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.

Guest favorite

Home in Lee

4.89 out of 5 average rating, 234 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)

Sep 13 – 20

$108 per night
Guest favorite

Apartment in Copake Falls

4.93 out of 5 average rating, 250 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!

Sep 14 – 21

$92 per night
Guest favorite

Treehouse in Tyringham

5.0 out of 5 average rating, 222 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.

May 13 – 20

$248 per night

Popular amenities for Stockbridge vacation rentals

Stay near Stockbridge's top sights

Norman Rockwell Museum344 locals recommend
Naumkeag109 locals recommend
The Red Lion Inn117 locals recommend
Berkshire Botanical Garden118 locals recommend
Kripalu Center For Yoga & Health122 locals recommend
Michaels of Stockbridge7 locals recommend

Other great vacation rentals in Stockbridge

Guest favorite

Home in Dalton

4.91 out of 5 average rating, 112 reviews

The Yellow House

Feb 12 – 19

$77 per night
Guest favorite

Loft in Great Barrington

4.99 out of 5 average rating, 296 reviews

The Old Red Barn

Apr 5 – 12

$139 per night
Guest favorite

Home in Stockbridge

4.95 out of 5 average rating, 103 reviews

Sun-filled, Charming Stockbridge Classic- In Town!

Nov 14 – 21

$241 per night
Guest favorite

Guest suite in South Lee

4.92 out of 5 average rating, 189 reviews

Sunny Riverside Apartment

May 27 – Jun 3

$155 per night
Guest favorite

Guest suite in Valatie

4.98 out of 5 average rating, 229 reviews

Guest Suite in Old Chatham Hunt Country

May 15 – 22

$79 per night
Guest favorite

Cottage in Great Barrington

4.93 out of 5 average rating, 234 reviews

Artist Cottage

Dec 14 – 21

$175 per night
Guest favorite

Apartment in Lenox

4.88 out of 5 average rating, 168 reviews

Station House 1E Private Room & Bath

May 4 – 11

$64 per night
Guest favorite

Cottage in West Stockbridge

4.98 out of 5 average rating, 106 reviews

Historic 1810 Farmhouse - Fully Renovated

Jun 8 – 15

$215 per night
Guest favorite

Home in Canaan

5.0 out of 5 average rating, 132 reviews

Country Cottage

Mar 12 – 19

$135 per night
Guest favorite

Guesthouse in Becket

4.93 out of 5 average rating, 257 reviews

Country Cabin

May 5 – 12

$106 per night
Guest favorite

Apartment in Canaan

5.0 out of 5 average rating, 81 reviews

Mountain View Getaway

Nov 18 – 25

$91 per night
Guest favorite

Home in Lee

5.0 out of 5 average rating, 33 reviews

GreenHouse

Sep 1 – 8

$119 per night

Quick stats about vacation rentals in Stockbridge

Total rentals

140 properties

Rentals with a pool

40 properties have a pool

Pet-friendly rentals

30 properties allow pets

Family-friendly rentals

80 properties are a good fit for families

Total number of reviews

3.5K reviews

Nightly prices starting at

$100 before taxes and fees

Frequently Asked Questions

  • Do house rentals in Stockbridge have air conditioning?

    Absolutely! We offer over 60 house rentals with air conditioning in Stockbridge. Enjoy a tailored experience with all the comforts you desire.

  • 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 boutique hotel rentals in Stockbridge?

    Experience the best of Stockbridge with our boutique 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 house rentals in Stockbridge have wifi?

    Absolutely! We offer over 60 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 60 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 40 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 bbq area?

    Absolutely! We offer over 40 house rentals with a bbq area in Stockbridge. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore