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Search Ski Hotels in The Berkshires

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Check availability on The Berkshires Ski Hotels

Tonight
24 Oct - 25 Oct
Tomorrow
25 Oct - 26 Oct
Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov

Our top choices for The Berkshires ski hotels

Two Adirondack chairs facing a river with a forested hill in the background.
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
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.

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.
£74
includes taxes & fees
1 Nov - 2 Nov
The Yankee Inn
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A lakeside lodge with a dock, fishing rods, and outdoor seating.
A lodge with a large building and a dock by a lake, surrounded by forest.
A lakeside dock with kayaks and a covered boat ramp.

2. 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.
£91
includes taxes & fees
22 Nov - 23 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A modern hotel lobby with seating areas, tables, and a reception desk.
A hotel room with two beds, a desk, a chair, a TV, and a window with curtains.
A kitchenette with a microwave, coffee maker, and coffee cups.
A coffee station with two coffee machines and a variety of coffee pods and cups.

3. 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.
£75
includes taxes & fees
12 Nov - 13 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A snow-covered outdoor area with a patio, seating, and a covered dining area.
A modern living room with a fireplace, comfortable seating, and a large window with curtains.
A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.
A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.

4. 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.
£131
includes taxes & fees
27 Oct - 28 Oct
The Cornell Inn, Lenox & The Berkshires
A spacious hotel lobby with multiple seating areas, large windows, and a television.
Pool
A hotel room with a wooden desk, a flat-screen TV, a coffee maker, a blue chair, and a lamp.
Living area

5. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
  • Ski the Berkshires and warm up in the indoor pool after hitting nearby slopes at this art deco hotel nestled in rural Lenox.
£91
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn & Suites Berkshires-Lenox
A building entrance with a large planter with purple flowers and a small tree.
A spacious room with a large window, a brick wall, a sofa set, and a patterned carpet.
A library with bookshelves, a television, and two armchairs.
A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.

6. Hotel On North

Hotel On North
Pittsfield
£100
includes taxes & fees
15 Nov - 16 Nov
Hotel On North
A reception area with a fireplace, seating, and a doormat with the logo "Quality".
A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.
A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.
A hotel room with a bed, a desk, a television, a microwave, and a sofa.

7. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
Lee
  • Ski Lee's winter magic with cosy comfort just minutes from thrilling slopes, plus complimentary breakfast to fuel your adventures.
£77
includes taxes & fees
22 Nov - 23 Nov
Quality Inn Lee - Lenox South
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".
A garden with wooden Adirondack chairs and a stone pathway.
A spacious lobby with a fireplace, seating area, and a bar.

8. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Alpine retreat with ski adventures awaits at Berkshire Mountain Lodge in the snow-capped mountains.
£88
includes taxes & fees
22 Nov - 23 Nov
Berkshire Mountain Lodge
A multi-story building with a balcony, a pond with rocks, and a tree.
A living room with a sofa, armchair, coffee table, and a patterned rug.
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.
£112
includes taxes & fees
27 Oct - 28 Oct
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.
A hotel room with a wooden dresser, a television, a microwave, and a mirror.
A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.
A row of white plastic chairs on a covered outdoor area with a white building in the background.

10. Monument Mountain Motel

Monument Mountain Motel
Great Barrington
  • Scenic Berkshires ski retreat offers winter thrills just minutes from Butternut Mountain and Great Barrington's charm.
£50
includes taxes & fees
1 Nov - 2 Nov
Monument Mountain Motel
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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 dining area with round tables set for two, a fireplace, and a mural on the wall.
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.
A white two-story house with a front door, windows, and a chimney.
A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.

The Old Inn On The Green

The Old Inn On The Green
Great Barrington
£261
includes taxes & fees
1 Nov - 2 Nov
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 dining room with a large table set for a meal, surrounded by ornate chairs.
A room with a grand piano, a chessboard, a horse statue, and a blue armchair.

Hampton Terrace Inn

Hampton Terrace Inn
Lenox
£194
includes taxes & fees
11 Nov - 12 Nov
Hampton Terrace Inn
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.
A modern apartment with a living room, kitchenette, and dining area.
A compact living space with a kitchenette, a dining area, and a sofa.
A hotel room with two beds, a nightstand with a lamp, and a window with curtains.

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
£83
includes taxes & fees
25 Oct - 26 Oct
The Central Downtown Inn & Suites
A two-story house with a brick entrance and a white facade.
A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.
A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.
A neatly arranged bedroom with a bed, bedside table, and a dresser.

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
£338
includes taxes & fees
12 Nov - 13 Nov
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 dining area with a table set for two, a view of a green landscape through large windows, and outdoor seating with a view.
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 bedroom with a large bed, a fireplace, a bathtub, and a window with a view of greenery.

Devonfield Inn B&B

Devonfield Inn B&B
Lee
£308
includes taxes & fees
2 Nov - 3 Nov
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.
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Top The Berkshires Hotel Reviews

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"The parking lot was being resurfaced and we could not find a handicap spot near the door. It was inconvenient, and one handicap spot was filled by a car without a handicap placard."
Marcia 1-night trip
Posted 8 hours ago
Hampton Inn & Suites Berkshires-Lenox
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Wonderful staff , great location ! Fresh brownies offered at check in , specialty cocktails in the evening , lovely breakfast in the morning:)"
Sandra 1-night trip
Posted 11 hours ago
The Cornell Inn, Lenox & The Berkshires
Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"Very easy check in. Clean and safe."
James Kevin 3-night trip
Posted 11 hours ago
Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

10/10 Excellent
"I would prefer more flexibility making reservations. Online and by phone, I wanted two rooms for two people. I was forced to request two rooms for THREE people to work around the algorithm that allowed only one room for two people. Also I was forced to accept two rooms in the same price range, when I wanted one premium king, not two. I left another hotel due to their inflexibility, and I will choose one with a personal approach next time."
Joan 2-night trip
Posted 13 hours ago
The Yankee Inn
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good
"Forgot the woman’s name who checked us in but she was so helpful and friendly with awesome dinner suggestions. Locations was great to walk around town"
Monica 2-night trip
Posted 14 hours ago
Hotel Downstreet, an Ascend Collection Hotel
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Clean large room. Nice bathroom Walling distance to downtown and many restaurant options."
Denise 1-night trip
Posted 15 hours ago
Quality Inn Great Barrington
The Red Lion Inn

The Red Lion Inn

8/10 Good
"Absolutely great location! An older property- the lobby and hallways seemed dark and aging (yes it’s historic). Our room was surprisingly cheerful! I’d stay here again!!"
carole 1-night trip
Posted 19 hours ago
The Red Lion Inn
Hotel On North

Hotel On North

10/10 Excellent
"Staff is awesome and this dog friendly hotel doesn’t feel dirty or different than any other boutique hotel."
Vicki 1-night trip
Posted 3 days ago
Hotel On North
FairBridge Inn Express

FairBridge Inn Express

10/10 Excellent
"This motel was well-cared for and a good value compared to anywhere close boy on our early-October Saturday night in the busy Berkshires!"
Richard 1-night trip
Posted 9 days ago
FairBridge Inn Express

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