Find Ski Hotels in Stockbridge, MA
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Sep 20 - Sep 21Tomorrow
Sep 21 - Sep 22Next weekend
Sep 25 - Sep 27In two weeks
Oct 2 - Oct 4Our top choices for Stockbridge ski hotels
1. The Red Lion Inn
The Red Lion InnStockbridge
- 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
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 ChesterwoodStockbridge
- 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
3. The Yankee Inn
The Yankee InnLenox
- 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
4. Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce ResortSouth 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 22 - Sep 23
5. The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
- 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
6. Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox SouthLee
- 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
7. Monument Mountain Motel
Monument Mountain MotelGreat 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
8. Shaker Mill Inn
Shaker Mill InnWest 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
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Top Stockbridge Hotel Reviews
The Yankee Inn
10/10 Excellent
"The room was very clean with a nice bathroom and close to Tanglewood!"
The Black Swan Lee - Lenox, an Ascend Collection Hotel
8/10 Good
"We enjoyed this Inn. Very scenic on Laural Lake. We enjoyed Mint Restaurant and had a fabulous time kayaking on the lake. It was a great place to celebrate my 59th birthday. Clean, organized and friendly. Would return."
Howard Johnson by Wyndham Lenox
10/10 Excellent
"Good"
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."
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- Visit South Lee
- Visit Lenox
- Frelinghuysen Morris House and Studio
- Lenox Mountain
- Visit Monterey
- Pleasant Valley Wilderness Sanctuary
- Bousquet Ski Area
- Greenock Country Club
- Visit West Stockbridge
- Visit Housatonic
- Visit Great Barrington
- Visit Lee
- National Shrine of the Divine Mercy
- Canoe Meadows Wildlife Sanctuary
- Mission House
- Berkshire Botanical Garden
- Animagic Museum of Animation
- South Lee Vacations
- Norman Rockwell Museum
- Lee Premium Outlets
- Charles H. Baldwin & Sons