Landoll's Mohican Castle, Christmas lights.

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Check availability on Stockbridge Adventure Hotels

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, (1,001 reviews)
"Breakfast was reasonable. We had issue with our room and the staff helpfully moved us to another room. Would stay again"
United States
Anandaraja
The price is AED 423
AED 473 total
includes taxes & fees
14 Jun - 15 Jun
Best Western Plus Berkshire Hills Inn & Suites
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 536
AED 1,365 total
includes taxes & fees
10 Jun - 11 Jun
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the 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 327
AED 830 total
includes taxes & fees
15 Jun - 16 Jun
NEW RENO - Historic Loft w/views of the Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (630 reviews)
"I enjoyed relaxing by the firepit. The only thing that could of made it a better stay would be free breakfast or at least coffee and tea. They have a Starbucks and area where you can purchase items but it was more like self serve and pay at reception desk."
United States
Elizabeth
The price is AED 731
AED 816 total
includes taxes & fees
22 Jun - 23 Jun
Courtyard by Marriott Lenox Berkshires
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (15 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is AED 817
AED 1,232 total
includes taxes & fees
11 Jun - 12 Jun
Cozy Riverside Berkshires Retreat
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 621
AED 1,157 total
includes taxes & fees
2 Jul - 3 Jul
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
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.
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Private kitchen

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
New Lebanon
8.0 out of 10, Very Good, (1 review)
"This location is great as an overnight trip. It’s centralized between ski resorts, restaurants near Pittsfield, MA and local NY. "
United States
Luz A.
The price is AED 645
AED 1,553 total
includes taxes & fees
10 Jun - 11 Jun
NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
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
Exterior

1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (4 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
The price is AED 775
AED 1,768 total
includes taxes & fees
10 Jun - 11 Jun
1789 Shaker Farmhouse in Berkshires/Hudson Valley
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.
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Top Stockbridge Hotel Reviews

The Red Lion Inn

The Red Lion Inn

8/10 Good
"It is a charming, historic hotel. Dinner in the tavern was delicious and service was very good. The only thing we didn't like was the mattress, which needs to be replaced as it has divits. Other than that, it's a cool place that is fun to explore. Wish we were here longer to try out the pool. We did enjoy getting a cocktail from the bar and sitting in rockers on the front porch, watching the traffic go by."
Nancy 1-night trip
Posted 1 day ago
The Red Lion Inn

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