Find Adventure Hotels in Stockbridge, MA

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Check availability on Stockbridge Adventure Hotels

Next weekend
29 May - 31 May
In two weeks
5 Jun - 7 Jun

Our top choices for Stockbridge adventure hotels

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,002 reviews)
"Room was clean. Breakfast was fresh and the area was pristine. All staff was pleasant. "
United States
Melinda
The price is AED 404
AED 451 total
includes taxes & fees
28 May - 29 May
Best Western Plus Berkshire Hills Inn & Suites
Property amenity

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (625 reviews)
"Beautiful outdoor space. "
United States
Jairo
The price is AED 653
AED 729 total
includes taxes & fees
4 Jun - 5 Jun
Courtyard by Marriott Lenox Berkshires
TV

NEW RENO - Historic Loft w/views of the Berkshires

NEW RENO - Historic Loft w/views of the Berkshires
New Lebanon
9.8 out of 10, Exceptional, (13 reviews)
"Place was nice, decent value, comfy and cozy. Would stay again."
United States
John
The price is AED 309
AED 815 total
includes taxes & fees
27 May - 28 May
NEW RENO - Historic Loft w/views of the Berkshires
Interior

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AED 569
AED 1,423 total
includes taxes & fees
28 May - 29 May
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Gift shop

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (5 reviews)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
United States
Jen B.
The price is AED 430
AED 919 total
includes taxes & fees
27 May - 28 May
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Beach

2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
8.4 out of 10, Very Good, (12 reviews)
"Great location and property. thank you"
United States
Christine P.
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (14 reviews)
"Great location and nice size house for a family of 5. We had a couple hiccups but the host responded quickly and handled things promptly. "
United States
Jennifer L.
The price is AED 744
AED 1,163 total
includes taxes & fees
25 May - 26 May
Cozy Riverside Berkshires Retreat
Indoor pool, a heated pool

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Hancock
9.4 out of 10, Exceptional, (6 reviews)
"Convenience to slopes and restaurants really great….,had a nice stay"
United States
Thomas S.
The price is AED 430
AED 919 total
includes taxes & fees
27 May - 28 May
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
A heated pool

Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby

Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby
Hancock
9.6 out of 10, Exceptional, (5 reviews)
"Great location on mountain and great communication by unit owner."
United States
Marc F.
Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very Good, (10 reviews)
"Kind and responsive host."
United States
Javier
The price is AED 591
AED 2,005 total
includes taxes & fees
25 May - 26 May
Comfortable Berkshires retreat on mtn resort, SISO
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Top Stockbridge Hotel Reviews

The Yankee Inn

The Yankee Inn

8/10 Good
"Excellent value, I had a great experience. The breakfast was a cut above, but they didn't include any fresh fruit. Maybe that's nit-picking. I'd recommend it, especially to families. Lots of good restaurants nearby."
judith 1-night trip
Posted 20 hours ago
The Yankee Inn

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