Find Ski Hotels in Stockbridge, MA from CA $104

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Our top choices for Stockbridge ski hotels

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,005 reviews)
  • cleanliness
    Step into winter wonderland at this historic hotel, where skiing adventures and mountain relaxation unite just steps from scenic trails.
"We stayed in winter"
United States
Teresa
The price is CA $196
CA $280 total
includes taxes & fees
May 17 - May 18
The Red Lion Inn

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, (111 reviews)
  • cleanliness
    Discover a skier's paradise nestled in the Berkshire mountains, with nearby slopes and après-ski comforts at this charming inn.
"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
The price is CA $422
CA $510 total
includes taxes & fees
May 25 - May 26
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,003 reviews)
  • cleanliness
    Embrace winter magic at this mountainside retreat offering an indoor pool, hot tub, and direct access to Bousquet Ski Area.
"Complimentary breakfast was good and then spent my days after at the mountain that was a quick 5 minute drive away with great skiing and snowboarding."
United States
Nicholas
The price is CA $135
CA $151 total
includes taxes & fees
May 10 - May 11
The Yankee Inn

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, (1,000 reviews)
  • cleanliness
    Nestled near premier ski areas, this cozy retreat offers mountain adventures and a fitness centre for year-round active stays.
"Great location to the ski area we were visiting."
United States
John
The price is CA $150
CA $167 total
includes taxes & fees
May 10 - May 11
Best Western Plus Berkshire Hills Inn & Suites

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (453 reviews)
  • cleanliness
    Step into winter adventures at this West Stockbridge bed & breakfast, where cross-country skiing trails and cozy relaxation await.
"Great location, clean, comfortable and delicious breakfast! Owner, John, gave us a complete tour of everything available in our room and the area. Great room with fireplace in sitting area, comfortable beds and kitchenette. Small town with shops, great bookstore, and restaurant within walking distance. Grounds look like they would be beautiful in spring, summer...we were there in January. Highly recommend."
United States
Deborah
The price is CA $149
CA $164 total
includes taxes & fees
May 13 - May 14
Shaker Mill Inn

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very good, (1,007 reviews)
  • cleanliness
    Experience snowy adventures in Great Barrington with daily manager's reception and a hearty breakfast before hitting the slopes.
"It is centrally located near literally EVERYTHING there is to do in Great Barrington outside of skiing."
United States
Ashley
The price is CA $115
CA $129 total
includes taxes & fees
May 13 - May 14
Quality Inn Great Barrington

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, (1,005 reviews)
  • cleanliness
    Winter wonderland awaits at lakefront ski haven; fuel adventures with free breakfast and relax by panoramic waters.
"Location is convenient to Lee Outlet Shopping, supermarket shopping, restaurants, ski area, and town area."
United States
Anonymous traveller
The price is CA $160
CA $179 total
includes taxes & fees
May 19 - May 20
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (849 reviews)
  • cleanliness
    Scenic Berkshires ski retreat offers winter thrills just minutes from Butternut Mountain and Great Barrington's charm.
"Nice hot shower. It isn't the ritz, but who needs the ritz?!"
United States
Candice
The price is CA $93
CA $104 total
includes taxes & fees
May 11 - May 12
Monument Mountain Motel

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (92 reviews)
  • cleanliness
    Warm up on the slopes at Bousquet Ski Area, just minutes away from this cozy Pittsfield retreat with an indoor pool and hot tub.
"hot tub was perfect after the day of skiing, everything very clean and new and lovely breakfast"
United States
Laura Pearson
The price is CA $161
CA $180 total
includes taxes & fees
May 17 - May 18
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (559 reviews)
"A nice little motel close to Catamount ski resort!"
United States
Benjamin
The price is CA $150
CA $168 total
includes taxes & fees
May 11 - May 12
The Little Lion
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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