Find Ski Hotels in Stockbridge, MA
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on Stockbridge Ski Hotels
Our top choices for Stockbridge ski hotels
8.8 out of 10, Excellent, (1,004 reviews)
- Step into winter wonderland at this historic hotel, where skiing adventures and mountain relaxation unite just steps from scenic trails.
"We stayed in winter"
Teresa
The price is NT$4,954
NT$6,946 total
includes taxes & fees
May 17 - May 18
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
9.2 out of 10, Wonderful, (111 reviews)
- 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. "
Robert
The price is NT$9,789
NT$11,842 total
includes taxes & fees
May 25 - May 26
9.2 out of 10, Wonderful, (1,003 reviews)
- 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."
Nicholas
The price is NT$3,271
NT$3,653 total
includes taxes & fees
May 6 - May 7
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
8.6 out of 10, Excellent, (1,000 reviews)
- Nestled near premier ski areas, this cozy retreat offers mountain adventures and a fitness center for year-round active stays.
"Great location to the ski area we were visiting."
John
The price is NT$3,219
NT$3,596 total
includes taxes & fees
May 7 - May 8
9.6 out of 10, Exceptional, (449 reviews)
- 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."
Deborah
The price is NT$3,451
NT$3,786 total
includes taxes & fees
May 6 - May 7
9.0 out of 10, Wonderful, (849 reviews)
- 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?!"
Candice
The price is NT$2,164
NT$2,417 total
includes taxes & fees
May 12 - May 13
8.4 out of 10, Very Good, (1,006 reviews)
- 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."
Ashley
The price is NT$2,674
NT$2,987 total
includes taxes & fees
May 12 - May 13
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
9.0 out of 10, Wonderful, (1,004 reviews)
- 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."
Anonymous traveler
The price is NT$3,907
NT$4,364 total
includes taxes & fees
May 11 - May 12
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.
Top Stockbridge Hotel Reviews
The Red Lion Inn
10/10 Excellent
Explore a world of travel with Expedia
- Golf Hotels in Pittsfield
- 4 Star Hotels in Lenox
- Hotels near Goose Pond Reservation
- Richmond Hotels
- Golf Hotels in Lanesborough
- Great Barrington Hotels
- Hotels near National Shrine of the Divine Mercy
- Four Seasons Hotels in Monterey
- Family Hotels in Sheffield
- Lenox Hotels
- Hotels with smoking rooms in Lee
- Family Hotels in Monterey
- Pet-Friendly Hotels in Pittsfield
- Hotel Wedding Venues Hotels in Stockbridge
- Hotels near Bousquet Ski Area
- Hotels with an Indoor Pool in Lenox
- Hotels with smoking rooms in Great Barrington
- Hotels near Tanglewood Music Center
- Hotels with Hot Tubs in Lee
- Cheap Hotels in The Berkshires
- Stockbridge Hotels
- South Lee Hotels
- Resorts & Hotels with Spas in Hancock
- Hotels near Chesterwood
- Historic Hotels in Richmond
- Country Houses in Beartown State Forest
- Cheap Hotels in Pittsfield
- Hotels near Ski Butternut
- Hotels with an Indoor Pool in Pittsfield
- Resorts & Hotels with Spas in Great Barrington
- Resorts & Hotels with Spas in Sheffield
- Hotels with a Pool in Sheffield
- Hotels near Guido's Marketplace
- Hotel Wedding Venues Hotels in Great Barrington
- Lee Hotels
- B&B in Great Barrington
- Hotels near Walter J. Koladza
- Pet-Friendly Hotels in The Berkshires
- Hotels with Bars in Pittsfield
- Hotels near Mahaiwe Performing Arts Center
- Hotels with a Pool in Stockbridge
- 4 Star Hotels in Great Barrington
- Hotels near Herman Melville's Arrowhead
- Romantic Hotels in Lenox
- Hotels near Furnace Brook Winery at Hilltop Orchards
- Pet-Friendly Hotels in Lee
- Hotels with an Indoor Pool in The Berkshires
- Boutique Hotels in The Berkshires
- Casino Hotels in Great Barrington
- Historic Hotels in Lenox
- Family Hotels in The Berkshires
- Inns in Beartown State Forest
- B&B in Stockbridge
- Hotels near Tyringham Cobble
- Hotels with a Pool in Great Barrington
- Flights from Louisville (LOU) to Pittsfield (PSF)
- Flights to Stockbridge
- Flights from Charleston (CRW) to Pittsfield (PSF)
- Flights to South Lee
- Flights from Walter J. Koladza
- Flights from Sydney (SYD) to Pittsfield (PSF)
- Flights from Phoenix (PHX) to Great Barrington (GBR)
- Flights to Alford
- Flights from Houston (HOU) to Pittsfield (PSF)
- Flights from Denver (DEN) to Great Barrington (GBR)
- Flights from Washington (DCA) to Pittsfield (PSF)
- Flights from Houston (IAH) to Great Barrington (GBR)
- Flights from Dallas (DFW) to Great Barrington (GBR)
- Flights from South Egremont
- Flights from Watertown (ART) to Pittsfield (PSF)
- Flights from Lee
- Flights from Portsmouth (PSM) to Pittsfield (PSF)
- Flights from Chicago (ORD) to Great Barrington (GBR)
- 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