A person snowboarding down a snowy slope.

Find Ski Hotels in The Berkshires, MA

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on The Berkshires Ski Hotels

Tonight
Oct 6 - Oct 7
Tomorrow
Oct 7 - Oct 8
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for The Berkshires ski hotels

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.

1. The Yankee Inn

The Yankee Inn
Lenox
  • Embrace winter magic at this mountainside retreat offering an indoor pool, hot tub, and direct access to Bousquet Ski Area.
￥16,732
￥18,690 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
A reception area with a fireplace, seating, and a doormat with the logo "Quality".
A hotel room with a bed, a desk, a television, a microwave, and a sofa.
A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.
A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.

2. Quality Inn Lee - Lenox South

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.
￥14,625
￥16,336 total
includes taxes & fees
Nov 1 - Nov 2
Quality Inn Lee - Lenox South
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
A modern hotel lobby with a seating area, a sofa, and a large window with curtains.
A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.
A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.

3. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
  • Ski adventures await in Great Barrington with mountain activities and a cozy indoor pool retreat after exploring Butternut slopes.
￥22,675
￥25,327 total
includes taxes & fees
Nov 2 - Nov 3
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.
A spacious living room with large windows, a fireplace, and a variety of seating options.
An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.
Indoor pool

4. Vacation Village in the Berkshires

Vacation Village in the Berkshires
Williamstown
  • Explore ski paradise at Jiminy Peak with mountainside hot tubs and slope-view relaxation at this Williamstown family retreat.
￥13,615
￥16,940 total
includes taxes & fees
Nov 1 - Nov 2
Vacation Village in the Berkshires
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A dining area with large windows, wooden furniture, and a view of a lake.
A lodge with a large building and a dock by a lake, surrounded by forest.
A lakeside lodge with a dock, fishing rods, and outdoor seating.

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

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.
￥18,247
￥20,382 total
includes taxes & fees
Nov 1 - Nov 2
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A modern hotel lobby with seating areas, tables, and a reception desk.
A breakfast area with a counter, coffee machine, and a display of pastries.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A coffee station with two coffee machines and a variety of coffee pods and cups.

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

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
  • Winter adventures await at riverside Holiday Inn Express in Great Barrington, steps away from premier ski slopes and hiking trails.
￥14,996
￥16,751 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".
A spacious lobby with a fireplace, seating area, and a bar.

7. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Alpine retreat with ski adventures awaits at Berkshire Mountain Lodge in the snow-capped mountains.
￥13,532
￥18,641 total
includes taxes & fees
Oct 18 - Oct 19
Berkshire Mountain Lodge
A snow-covered outdoor area with a patio, seating, and a covered dining area.
A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.
A dining area with a glass table, red walls, and framed artwork.
A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.

8. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
  • Crackling fireplaces warm rooms just minutes from Tanglewood's winter concerts in this historic B&B.
￥24,223
￥27,784 total
includes taxes & fees
Oct 27 - Oct 28
The Cornell Inn, Lenox & The Berkshires
A building with a porch and multiple windows, surrounded by purple flowers.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
A café with a display case, a frozen food section, and a marketplace sign.

9. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
South Lee
  • Alpine ski resort getaway awaits with 4 pools, mini-golf, and endless winter adventures in the beautiful Berkshires.
￥17,616
￥22,763 total
includes taxes & fees
Oct 8 - Oct 9
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A building entrance with a large planter with purple flowers and a small tree.
A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.
A spacious room with a large window, a brick wall, a sofa set, and a patterned carpet.
A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.

10. Hotel On North

Hotel On North
Pittsfield
￥17,640
￥19,704 total
includes taxes & fees
Nov 1 - Nov 2
Hotel On North
View all properties

Choose what matters most at ski hotels in The Berkshires

Resort
4 stars
5 stars
Spa
Family-friendly

4-star ski hotels in The Berkshires

A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.
A hotel room with two beds, a nightstand with a lamp, and a window with curtains.
A modern apartment with a living room, kitchenette, and dining area.
A compact living space with a kitchenette, a dining area, and a sofa.

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
￥15,627
￥17,455 total
includes taxes & fees
Oct 18 - Oct 19
The Central Downtown Inn & Suites
A dining area with round tables set for two, a fireplace, and a mural on the wall.
A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.
A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.
A room with two brown leather armchairs, a wooden side table with a lamp, a potted plant, and a window with a view of a snowy landscape.

The Old Inn On The Green

The Old Inn On The Green
Great Barrington
￥45,794
￥55,259 total
includes taxes & fees
Nov 1 - Nov 2
The Old Inn On The Green
A white house with a balcony, green shutters, and a front door with a decorative glass panel. There are two large flower pots on the steps.
A grand staircase with red carpeted steps and a wooden handrail, leading to a landing with a vase of flowers and a framed picture.
A traditional living room with a fireplace, a grand piano, plush seating, and a bookshelf.
A room with a grand piano, a chessboard, a horse statue, and a blue armchair.

Hampton Terrace Inn

Hampton Terrace Inn
Lenox
￥40,299
￥45,014 total
includes taxes & fees
Nov 4 - Nov 5
Hampton Terrace Inn
A two-story house with a brick entrance and a white facade.
A dining area with tables set for a meal, surrounded by large windows offering a view of trees and a garden.
A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.
A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.

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 Chesterwood
Stockbridge
￥57,294
￥69,308 total
includes taxes & fees
Nov 6 - Nov 7
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A large, two-story house with a well-maintained lawn and a fence.
A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.
A house with a fire pit in the yard, outdoor seating, and a large window overlooking the yard.
A dining area with a table set for two, a view of a green landscape through large windows, and outdoor seating with a view.

Devonfield Inn B&B

Devonfield Inn B&B
Lee
￥58,269
￥65,086 total
includes taxes & fees
Nov 2 - Nov 3
Devonfield Inn B&B
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 properties

Top The Berkshires Hotel Reviews

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Delightful and charming! When you go to an inn that is over 200 years old you don’t know what to expect and everything was a wonderful surprise. Super clean, stylish, and staff that was warm and friendly. We had what we believe was the smallest room in the Inn, not much over 100 ft.², and it was perfect for a one night stay. The breakfast options were a real treat!"
F. Cole 1-night trip
Posted 1 hour ago
The Cornell Inn, Lenox & The Berkshires
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Love the fireplace in our room! The amenities always make this place worth the money, and the views to top it all off!!"
Jennifer 1-night trip
Posted 12 hours ago
Vacation Village in the Berkshires
Hotel On North

Hotel On North

10/10 Excellent
"Beautiful boutique hotel. We will be back!"
Rebecca 1-night trip
Posted 17 hours ago
Hotel On North
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Beautiful location plenty of activities and very convenient having the country store on site! Also the onsite restaurant was amazing!"
Jeffrey 1-night trip
Posted 17 hours ago
Jiminy Peak Mountain Resort
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"The staff was very pleasant and helpful. Breakfast was good. They had delicious and fresh muffins. Parking was right outside our door."
Leslie 2-night trip
Posted 22 hours ago
Quality Inn Great Barrington
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Great staff, heated bathroom floors."
Ellen 3-night trip
Posted 1 day ago
The Red Lion Inn
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent
"My impression s? It’s a quiet rural area, but I am impressed how quiet the motel was. Not all the time, but occasionally it get noisy. I also liked the area."
Casey A 4-night trip
Posted 6 days ago
Best Western Plus Berkshire Hills Inn & Suites

Explore a world of travel with Expedia