Search Ski Hotels in The Berkshires
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20 Sept - 21 SeptTomorrow
21 Sept - 22 SeptNext weekend
25 Sept - 27 SeptIn two weeks
2 Oct - 4 OctOur top choices for The Berkshires ski hotels
1. 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.
₹11,122
₹12,423 total
includes taxes & fees
22 Sept - 23 Sept
2. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
- Alpine retreat with ski adventures awaits at Berkshire Mountain Lodge in the snow-capped mountains.
₹7,632
₹10,666 total
includes taxes & fees
1 Oct - 2 Oct
3. 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.
₹12,234
₹13,665 total
includes taxes & fees
27 Sept - 28 Sept
₹13,519
₹15,100 total
includes taxes & fees
18 Oct - 19 Oct
5. Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHGGreat Barrington
- Winter adventures await at riverside Holiday Inn Express in Great Barrington, steps away from premier ski slopes and hiking trails.
₹11,409
₹12,744 total
includes taxes & fees
19 Oct - 20 Oct
6. Quality Inn Great Barrington
Quality Inn Great BarringtonGreat Barrington
- Experience snowy adventures in Great Barrington with daily manager's reception and a hearty breakfast before hitting the slopes.
₹9,698
₹10,833 total
includes taxes & fees
18 Oct - 19 Oct
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.
₹7,378
₹8,242 total
includes taxes & fees
21 Sept - 22 Sept
8. Vacation Village in the Berkshires
Vacation Village in the BerkshiresWilliamstown
- Explore ski paradise at Jiminy Peak with mountainside hot tubs and slope-view relaxation at this Williamstown family retreat.
₹9,122
₹11,241 total
includes taxes & fees
22 Sept - 23 Sept
View all properties
4-star ski hotels in The Berkshires
₹9,399
₹10,498 total
includes taxes & fees
8 Oct - 9 Oct
₹20,987
₹23,443 total
includes taxes & fees
21 Sept - 22 Sept
₹31,639
₹38,179 total
includes taxes & fees
21 Sept - 22 Sept
₹42,090
₹47,014 total
includes taxes & fees
21 Sept - 22 Sept
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
₹49,517
₹59,902 total
includes taxes & fees
12 Oct - 13 Oct
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.
View all propertiesTop The Berkshires Hotel Reviews
Vacation Village in the Berkshires
10/10 Excellent
"Excelente A+, lo recomiendo"
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."
Hampton Inn & Suites Berkshires-Lenox
10/10 Excellent
"Hampton inns are always consistent in quality. The bed was very comfy!"
Howard Johnson by Wyndham Lenox
10/10 Excellent
"Good"
Hotel Downstreet, an Ascend Collection Hotel
10/10 Excellent
"Excellent location. Excellent adjacent restaurant "Door Prize". Will definitely stay again"
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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