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Find ski hotels & lodging in Stockbridge, MA

Plan the perfect ski vacation from $100

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Check availability on Stockbridge Ski Hotels

Tonight
Dec 4 - Dec 5
Tomorrow
Dec 5 - Dec 6
This weekend
Dec 5 - Dec 7
Next weekend
Dec 12 - Dec 14

Top Stockbridge Ski Hotels

Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1000)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
$169 nightly
The price is $189
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Red Lion Inn
Business center
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
$414 nightly
The price is $462
Dec 18 - Dec 19
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Property grounds
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stockbridge
10.0 out of 10, Exceptional, (29)
"Great stay in a well appointed house close to trails, Stockbridge center, and a quick car trip to Lenox, Great Barrington, Tanglewood, Jacobs Pillow, and Shakespeare & Co. we enjoyed the morning walks, coffee at the Lost Lamb, drinks at the Red Lion Inn, dance at Jacob’s Pillow, music at Tanglewood, ice cream at High Lawn Farm, and just that Berkshire vibe! "
United States
Phillip F.
$764 nightly
The price is $853
Dec 6 - Dec 7
Total with taxes and fees
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Lobby sitting area
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, (1005)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
$93 nightly
The price is $104
Dec 7 - Dec 8
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Great stay!"
United States
Ann
$89 nightly
The price is $100
Dec 11 - Dec 12
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very Good, (978)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
$92 nightly
The price is $103
Dec 12 - Dec 13
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
Great Barrington
8.8 out of 10, Excellent, (702)
"Everything was wonderful....super clean rooms, check-in was fast and smooth, staff was on top of everything. We definitely will be back at Holiday Inn. "
United States
Tabitha
$107 nightly
The price is $120
Dec 7 - Dec 8
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Garden
Shaker Mill Inn

Shaker Mill Inn

2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (436)
"Nice place, easy check in"
United States
Robert
$106 nightly
The price is $117
Dec 7 - Dec 8
Total with taxes and fees
Shaker Mill Inn
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
9.0 out of 10, Wonderful, (1002)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
$101 nightly
The price is $113
Dec 14 - Dec 15
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Clean, pleasant staff and good breakfast. "
United States
Edward
$103 nightly
The price is $115
Dec 14 - Dec 15
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
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 Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"All of the above "
Lois 1-night trip
Posted 1 day ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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