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The Berkshires Hotels

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Featured The Berkshires Ski Hotels

See all 112 Hotels in The Berkshires
Black Swan Inn, an Ascend Collection Hotel

Black Swan Inn, an Ascend Collection Hotel

435 Laurel St, Lee
3.0 out of 5.0
4.2 out of 5 (105 reviews)
First time we have ever had issues We have been going to this property for many years. This was the first time we have ever had issues. The room was beautiful . But had only a few hangers in the closet. When I called and asked for more I was told "we don't have any more". The following morning I left a note for the cleaning service ...
  Aug 17, 2017

$92

$92
Days Inn Great Barrington

Days Inn Great Barrington

372 Main Street, Great Barrington
2.0 out of 5.0
3.7 out of 5 (107 reviews)
Good hotel close to town.This was a quick overnight getaway for us. The hotel was a great value for its proximity to town and area shops. We walked to town in the evening and had a nice dinner at "The Well", and returned to the town the following day to poke in the various shops.
  Aug 18, 2017

$129

$129
Holiday Inn Express Hotel & Suites Great Barrington

Holiday Inn Express Hotel & Suites Great Barrington

415 Stockbridge Rd, Great Barrington
2.5 out of 5.0
4.3 out of 5 (58 reviews)
Good for a night or twoIt is a typical prefab hotel on the edge of town. If you have a choice request a room that does NOT have a view of: a blank wall about 20' away. It is a beautiful town and they it what they came up with? Honestly.
  May 1, 2017

$140

$140
Berkshire Valley Inn

Berkshire Valley Inn

2541 Hancock Rd, Williamstown
2.5 out of 5.0
4.3 out of 5 (50 reviews)
Nice experienceOlder but nicely rentivated. Owners are very nice, helpful and pleasant. Any questions we had about attractions and directions they were there to help. Good breakfast, more than expected at a normal continental. Very clean. Traveling with older parents, was nice not to have to worry about ...
  Aug 19, 2017

$89

$89
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

37 Corey Rd, Hancock
2.5 out of 5.0
3.8 out of 5 (136 reviews)
Too shortJust an overnight fly by. Looks like lots to do and the hotel is comfortable and clean. Can't take drinks from the bar to the room and pub closes at 10.
  Aug 17, 2017

$149

$149
Hilton Garden Inn Lenox/Pittsfield

Hilton Garden Inn Lenox/Pittsfield

1032 South Street, Pittsfield
3.0 out of 5.0
4.6 out of 5 (18 reviews)
Great hotel. Comfortable and clean. Pool and excercise room were super clean.
  Jul 1, 2017

$119

$119
Vacation Village in the Berkshires

Vacation Village in the Berkshires

276 Brodie Mountain Rd, Hancock
3.0 out of 5.0
4.1 out of 5 (221 reviews)
Loved ItGreat place to stay if you like all the comforts of home and then some. Jacuzzi tub was awesome to have. Loved having a private deck. Bathroom was large and clean. Very comfortable. Will be returning next year.
  Aug 17, 2017

$135

$135
Crowne Plaza Pittsfield-Berkshires

Crowne Plaza Pittsfield-Berkshires

1 West St, Pittsfield
3.5 out of 5.0
3.5 out of 5 (120 reviews)
Good LocationThought it was a little pricey. Would have felt better if they offered free continental breakfast
  Aug 15, 2017

$99

$99
Monument Mountain Motel

Monument Mountain Motel

247 Stockbridge Rd, Great Barrington
2.5 out of 5.0
4.3 out of 5 (53 reviews)
Cute motel in the BerkshiresThis motel is exactly as described online. The room was comfortable and clean and the staff was helpful and friendly.
  Aug 17, 2017

$70

$70
Berkshire Inn

Berkshire Inn

150 W Housatonic St, Pittsfield
2.0 out of 5.0
3.5 out of 5 (48 reviews)
a nice motelA nice motel with a pleasant staff willing to assist with all my requests,
  Aug 17, 2017

$75

$75
Wagon Wheel Inn

Wagon Wheel Inn

484 Pittsfield Rd, Lenox
2.0 out of 5.0
3.6 out of 5 (66 reviews)
Great value This hotel is clean and tidy, and what it lacks in modern updates you save in price. If you are like me and really only use a hotel room as a place to crash after a long day of activities, it's perfect and won't break the bank. I love that it's owned and maintained by a local family. It's also great ...
  Aug 18, 2017

$50

$50
White Horse Inn

White Horse Inn

378 South St, Pittsfield
3.0 out of 5.0
4.6 out of 5 (41 reviews)
New England Weekend.John and Jeanie were wonderful B&B hosts. From arrival time, to our departure, they were pleasant and accommodating. The room (which was upgraded for us) was beautifully decorated, spacious and comfortable. Although, this was my first experience in a B&B, my boyfriend confirmed this was a top experience. ...
  Nov 21, 2016

$155

$155
Travelodge Great Barrington Berkshires

Travelodge Great Barrington Berkshires

400 Stockbridge Rd, Great Barrington
2.0 out of 5.0
3.1 out of 5 (81 reviews)
Great location, excellent value.Terrific hotel staff.! Welcoming and couldn't be friendlier. While a short drive to downtown Great Barrington, there are some excellent restaurants a short walk away in the adjacent plazas. While it's not a "new" building and motel, it's well kept, clean and set back from the main road - reducing ...
  Jun 30, 2017

$77

$77
Hampton Inn & Suites Berkshires Lenox

Hampton Inn & Suites Berkshires Lenox

445 Pittsfield Rd, Lenox
2.5 out of 5.0
4.6 out of 5 (108 reviews)
Last minute trip to western mass for work. Booked the hotel last minute and they upgraded me to a suite. It was very clean and very comfortable. I will definitely stay here again when in the area.
  Aug 17, 2017

$118

$118
Howard Johnson Express Inn - Lenox

Howard Johnson Express Inn - Lenox

462 Pittsfield Rd, Lenox
2.0 out of 5.0
3.4 out of 5 (172 reviews)
We Come Back Every YearAlways a nice experience for our yearly Berkshire 3 day weekend
  Aug 17, 2017

$69

$69
Lenox Inn

Lenox Inn

525 Pittsfield Rd, Lenox
2.0 out of 5.0
3.4 out of 5 (111 reviews)
Why pay more...especially if you're not using muchHotel staff were very pleasant and the room was cleaned daily.
  Mar 20, 2017

$55

$55
The Spring's Inn

The Spring's Inn

94 Route 7, New Ashford
2.0 out of 5.0
3.0 out of 5 (44 reviews)
Present owner renovating...very neat and clean...Historic motel,allowed to deteriorate, now slowly being restored by determined owner. Pets allowed . Comfortable beds and clean, well lit bathrooms. Needs new towels and a small freezer in the fridge.
  Jul 27, 2016

$64

$64
The Orchards Hotel

The Orchards Hotel

222 Adams Rd, Williamstown
3.5 out of 5.0
4.2 out of 5 (62 reviews)
facilities chargefor some reason management decided to add an additional 'facilities' charge onto the bill. never had this before. the pool , by the way was closed early.
  Aug 17, 2017

$199

$199
Wyndham Bentley Brook

Wyndham Bentley Brook

1 Corey Road, Hancock
3.0 out of 5.0
4.5 out of 5 (24 reviews)
Relaxing spot, nice propertyApartment had everything in it we could want/need. Close to Mt. Greylock so hiking opportunities are abundant. Not many restaurants nearby but it is the Berkshires. Country Store on property with basics. People in room next to us were loud snorers but that's not Wyndham's responsibility. We don't ...
  Jul 5, 2017
Map

Recently booked Ski Hotels in The Berkshires

Best Western Plus Berkshire Hills Inn & Suites
2.5 out of 5.0
Last booking: 1 hour ago
Jiminy Peak Mountain Resort
2.5 out of 5.0
Last booking: 2 hours ago
The Villager Motel
2.0 out of 5.0
Last booking: 2 hours ago
Howard Johnson Express Inn - Lenox
2.0 out of 5.0
Last booking: 5 hours ago
Holiday Inn Express Hotel & Suites Great Barrington
2.5 out of 5.0
Last booking: 5 hours ago
Crowne Plaza Pittsfield-Berkshires
3.5 out of 5.0
Last booking: 7 hours ago
Shaker Mill Inn
2.5 out of 5.0
Last booking: 7 hours ago
Super 8 Lee/Berkshires/Outlet Area
2.0 out of 5.0
Last booking: 8 hours ago
Cozy Corner Motel
2.0 out of 5.0
Last booking: 8 hours ago

The Berkshires Ski Resorts Information

Carve up the slopes with reservations at The Berkshires ski resorts.
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Strap on your ski boots, slip into your snow pants, and brave the fresh powder on black diamond trails when you make reservations here on Expedia.com. Our The Berkshires ski hotels turn up the heat on your adventures at the chilly slopes.

Whether you’re flaunting your Shaun White-inspired half-pipe tricks or still trying to figure out how to do a “pizza,” book a stay at a ski-in-ski-out resort. There’s nothing better than staying at a The Berkshires ski hotel right on the slopes to easily access both the chair lift and hot chocolate in the lodge. After sledding, cross-country skiing, and snowshoeing in The Berkshires, cozy up around the fireplace in your ski chalet.

Calling all ski bunnies and snowboarding pros: we offer deals on ski resorts in The Berkshires here on Expedia. You’ll slide right into our unbeatable deals with a ton of hotels to choose from and personalized recommendations to help you create the perfect mountain trip. Spend more of your hard-earned cash on new gear for your adventures skiing in The Berkshires and less on your accommodation. From accommodations with fireplaces to rooms with a view of the trails, we have a ski hotel meeting all your needs and price range. Book one of 112 ski hotels today and get ready to carve up the slopes tomorrow.