The Best Ski Hotels in Stockbridge, MA from NT$2,736 in 2026

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Our top choices for Stockbridge ski hotels

1. 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

Suite, Private Bathroom (RedBird Suite) | View from room

Suite, Private Bathroom (Parlour Suite) | Premium bedding, iron/ironing board (on request), WiFi (free)

2. 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

Superior Room, 1 King Bed, Jetted Tub | Jetted tub

Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

42-inch flat-screen TV with cable channels, TV

Superior Room, 1 King Bed, Jetted Tub | Desk, laptop workspace, iron/ironing board, WiFi (free)

3. 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

Grand Villa, 3 Bedrooms | Iron/ironing board, cribs (free), WiFi, bed sheets

4. 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

5. 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

Standard Room, 1 King Bed, Non Smoking | Desk, iron/ironing board, cribs (surcharge), rollaway beds (surcharge)

6. 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

Room, 2 Queen Beds, Non Smoking | Iron/ironing board, cribs (free), rollaway beds (surcharge), WiFi (free)

Iron/ironing board, cribs (free), rollaway beds (surcharge), WiFi (free)

7. 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

Standard Apartment, Private Bathroom (Greylock - No Pets)

Superior Suite, Private Bathroom (Honeymoon - Pets Allowed)

Deluxe Suite, Private Bathroom (Garden - Pets Allowed) | Miscellaneous

8. 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

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Top Stockbridge Hotel Reviews

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!"

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."

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"

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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Room 1

Change your mind

Treat yourself

Be picky

Check availability on Stockbridge Ski Hotels

Our top choices for Stockbridge ski hotels

1. The Red Lion Inn

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

3. The Yankee Inn

4. Holiday Inn Club Vacations Oak 'n Spruce Resort

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

6. Quality Inn Lee - Lenox South

7. Monument Mountain Motel

8. Shaker Mill Inn

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

Choose what matters most at ski hotels in Stockbridge

Top Stockbridge Hotel Reviews

Quality Inn Great Barrington

Hotel On North

Vacation Village in the Berkshires

Howard Johnson by Wyndham Lenox

The Red Lion Inn

Explore a world of travel with Expedia

Find Ski Hotels in Stockbridge, MA

Change your mind

Treat yourself

Be picky

Check availability on Stockbridge Ski Hotels

Our top choices for Stockbridge ski hotels

1. The Red Lion Inn

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

3. The Yankee Inn

4. Holiday Inn Club Vacations Oak 'n Spruce Resort

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

6. Quality Inn Lee - Lenox South

7. Monument Mountain Motel

8. Shaker Mill Inn

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

Choose what matters most at ski hotels in Stockbridge

Top Stockbridge Hotel Reviews

Quality Inn Great Barrington

Hotel On North

Vacation Village in the Berkshires

Howard Johnson by Wyndham Lenox

The Red Lion Inn

Explore a world of travel with Expedia