A nighttime view of a residential area with houses adorned with holiday lights.

Find Ski Hotels in Stockbridge, MA

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Check availability on Stockbridge Ski Hotels

Tonight
Sep 20 - Sep 21
Tomorrow
Sep 21 - Sep 22
Next weekend
Sep 25 - Sep 27
In two weeks
Oct 2 - Oct 4

Our top choices for Stockbridge ski hotels

1. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Step into winter wonderland at this historic hotel, where skiing adventures and mountain relaxation unite just steps from scenic trails.
NT$5,097
NT$7,274 total
includes taxes & fees
Sep 28 - Sep 29
The Red Lion Inn

2. 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
Stockbridge
  • Discover a skier's paradise nestled in the Berkshire mountains, with nearby slopes and après-ski comforts at this charming inn.
NT$16,436
NT$19,883 total
includes taxes & fees
Oct 12 - Oct 13
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

3. The Yankee Inn

The Yankee Inn
Lenox
  • Embrace winter magic at this mountainside retreat offering an indoor pool, hot tub, and direct access to Bousquet Ski Area.
NT$3,692
NT$4,124 total
includes taxes & fees
Sep 22 - Sep 23
The Yankee Inn

4. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
  • Alpine ski resort getaway awaits with 4 pools, mini-golf, and endless winter adventures in the beautiful Berkshires.
NT$3,723
NT$4,781 total
includes taxes & fees
Sep 23 - Sep 24
Holiday Inn Club Vacations Oak 'n Spruce Resort

5. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
  • Winter wonderland awaits at lakefront ski haven; fuel adventures with free breakfast and relax by panoramic waters.
NT$4,061
NT$4,536 total
includes taxes & fees
Sep 27 - Sep 28
The Black Swan Lee - Lenox, an Ascend Collection Hotel

6. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
Lee
  • Ski Lee's winter magic with cozy comfort just minutes from thrilling slopes, plus complimentary breakfast to fuel your adventures.
NT$3,490
NT$3,898 total
includes taxes & fees
Oct 19 - Oct 20
Quality Inn Lee - Lenox South

7. Monument Mountain Motel

Monument Mountain Motel
Great Barrington
  • Scenic Berkshires ski retreat offers winter thrills just minutes from Butternut Mountain and Great Barrington's charm.
NT$2,449
NT$2,736 total
includes taxes & fees
Sep 21 - Sep 22
Monument Mountain Motel

8. Shaker Mill Inn

Shaker Mill Inn
West Stockbridge
  • Step into winter adventures at this West Stockbridge bed & breakfast, where cross-country skiing trails and cozy relaxation await.
NT$4,742
NT$5,202 total
includes taxes & fees
Sep 21 - Sep 22
Shaker Mill Inn

9. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
  • Winter adventures await at riverside Holiday Inn Express in Great Barrington, steps away from premier ski slopes and hiking trails.
NT$3,787
NT$4,230 total
includes taxes & fees
Oct 19 - Oct 20
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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Choose what matters most at ski hotels in Stockbridge

Resort
4 stars
5 stars
Spa
Family-friendly

Top Stockbridge Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Staff was very friendly and helpful. The breakfast was very good with lots of tasty choices. Room was clean and comfortable. I would stay there again!"
Sandra 1-night trip
Posted less than an hour ago
Quality Inn Great Barrington
Hotel On North

Hotel On North

8/10 Good
"We loved staying there BUT we had two major hiccups: 1) the duvet covers are exceptionally heavy so we asked at the front desk for a blanket so we could use that instead. The answer we got back was that there had been some “event or something’ the day before and there were no blankets available. In that case, they brought us a second sheet and we used that instead of the duvet which worked out OK; 2) we stayed for two nights and they forgot to make up our room…which meant we came back to an unmade bed which was disappointing. We notified the front desk and while they were very apologetic they said the cleaning crew had left for the day so they couldn’t fix it. In general, it was clear they were short on staff. The youngish man on call to greet us could not have been less helpful and continued to be on other occasions. However, we encountered two other staff members and they were fine. Apart from that, we loved our room—very spacious with lots of character and the bathroom was also unusually large and well designed. Plugs are often a problem when we travel but our room had two perfectly placed plugs beside (not underneath!) each bed table (a big plus!). Parking behind the hotel is another huge plus—couldn’t be more convenient. We didn’t use the bar but did eat at the restaurant there one night (and their sister breakfast place down the street) and enjoyed both."
Linda 2-night trip
Posted 1 hour ago
Hotel On North
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Very clean, loved that there were large gas grills to bbq on. Everything was very clean and the staff was friendly and polite. Would upgrade next time to a bigger kitchen so we would have a full size stove not just a 2burner"
Charles 2-night trip
Posted 2 hours ago
Vacation Village in the Berkshires
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent
"Good"
Kauan 1-night trip
Posted 1 day ago
Howard Johnson by Wyndham Lenox
The Red Lion Inn

The Red Lion Inn

8/10 Good
"Bedding and bed were lovely. excellent to have good lighting at sink as well as a magnified mirror! Often lacking in places we have stayed. AC had trouble cooling the room down until we turned it on full blast. too much ambient light from floodlight on property next door and from hall (I finally turned off hallway light which helped. ) Common areas and halls need some brightening up with fresh, lighter paint--seemed dingy. Was terribly frustrating trying to make the Nespresso machine work. We do not own one and there were NO INSTRUCTIONS. You should assume people do not know how to operate any appliances like that and should have a card with directions. We gave up and went to the Tavern where we had lovely coffee and breakfast. Also had a great dinner in Tavern after our arrival. The patch burrata salad was superb. As was our waitress."
Judith 1-night trip
Posted 5 days ago
The Red Lion Inn

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