Stockbridge vacation rentals

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Top-rated vacation rentals in Stockbridge

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite
Home in Lee
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 5 – 12
$114 per night
4.89 out of 5 average rating, 234 reviews
Guest favorite
Loft in Great Barrington
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.
Apr 22 – 29
$137 per night
4.99 out of 5 average rating, 295 reviews
Guest favorite
Apartment in Copake Falls
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!
Aug 29 – Sep 5
$92 per night
4.93 out of 5 average rating, 247 reviews

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 Stockbridge
Sun-filled, Charming Stockbridge Classic- In Town!
May 5 – 12
$225 per night
4.95 out of 5 average rating, 103 reviews
Guest favorite
Tiny home in Chatham
Tiny House on 70 Private Acres in Hudson Valley
Jul 31 – Aug 7
$133 per night
4.99 out of 5 average rating, 176 reviews
Guest favorite
Cottage in West Stockbridge
Historic 1810 Farmhouse - Fully Renovated
May 4 – 11
$215 per night
4.98 out of 5 average rating, 106 reviews
Guest favorite
Cottage in Great Barrington
Newly built cottage on working farm
Nov 4 – 11
$100 per night
4.98 out of 5 average rating, 123 reviews
Guest favorite
Guest suite in Valatie
Guest Suite in Old Chatham Hunt Country
Mar 29 – Apr 5
$79 per night
4.98 out of 5 average rating, 229 reviews
Guest favorite
Home in Canaan
Country Cottage
Nov 6 – 13
$135 per night
5.0 out of 5 average rating, 131 reviews
Guest favorite
Home in Monterey
Charming cottage w/ gorgeous views.
Feb 17 – 24
$145 per night
4.92 out of 5 average rating, 306 reviews
Guest favorite
Chalet in Otis
Mid-Century Glass Octagon in the Berkshires
Nov 15 – 22
$352 per night
4.94 out of 5 average rating, 345 reviews
Guest favorite
Apartment in Sheffield
Hideaway with Spectacular Berkshire Views
Nov 1 – 8
$144 per night
5.0 out of 5 average rating, 318 reviews
Guest favorite
Home in Lee
Berkshire 4 season home
Apr 11 – 18
$161 per night
4.97 out of 5 average rating, 179 reviews
Guest favorite
Vacation home in Great Barrington
Home in Great Barrington. Steps from downtown!
Nov 30 – Dec 7
$191 per night
4.94 out of 5 average rating, 129 reviews
Guest favorite
Home in Lee
1817 Berkshire Farmhouse- Close to Everything.
Jun 5 – 12
$225 per night
4.9 out of 5 average rating, 202 reviews

Other great vacation rentals in Stockbridge

Guest favorite
Apartment in Stockbridge
Historic,Famous,Iconic, Unforgettable Berks Escape
Jan 22 – 29
$186 per night
4.96 out of 5 average rating, 85 reviews
Guest favorite
Home in Becket
Nerd Preservation Sanctuary
Oct 20 – 27
$80 per night
4.94 out of 5 average rating, 35 reviews
Guest favorite
Cottage in Stockbridge
Quiet 2 BR cottage in the heart of the Berkshires
Sep 21 – 28
$255 per night
5.0 out of 5 average rating, 21 reviews
Guest favorite
Guest suite in Great Barrington
Sweet 1-bedroom with salt water pool
May 19 – 26
$133 per night
5.0 out of 5 average rating, 41 reviews
Guest favorite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
Jun 5 – 12
$106 per night
4.99 out of 5 average rating, 101 reviews
Guest favorite
Home in Stockbridge
Relaxing Berkshire Retreat with Lake Access
May 11 – 18
$458 per night
5.0 out of 5 average rating, 31 reviews
Guest favorite
Cabin in West Stockbridge
Modern Cabin near Tanglewood
Dec 30 – Jan 6
$375 per night
4.98 out of 5 average rating, 41 reviews
Guest favorite
Home in West Stockbridge
Heart of the Berkshires - Bright, Cozy, Near Lake
Jun 2 – 9
$585 per night
5.0 out of 5 average rating, 52 reviews
Guest favorite
Home in West Stockbridge
Beautiful And Private Home Centrally Located
Dec 28 – Jan 4
$900 per night
5.0 out of 5 average rating, 16 reviews
Guest favorite
Home in West Stockbridge
Berkshires-Enjoy The Peak, private home
May 6 – 13
$595 per night
4.98 out of 5 average rating, 57 reviews
Guest favorite
Guesthouse in Lenox
Lenox - Sunny cottage nestled in the garden
Nov 7 – 14
$110 per night
4.9 out of 5 average rating, 51 reviews
Guest favorite
Home in Great Barrington
Quiet home on the hill.
Sep 5 – 12
$148 per night
4.93 out of 5 average rating, 67 reviews

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

  • 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 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 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.

  • 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 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.

  • 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