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Find Ski Hotels in The Berkshires, MA

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Check availability on The Berkshires Ski Hotels

Tonight
Oct 21 - Oct 22
Tomorrow
Oct 22 - Oct 23
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

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 swimming pool with a surrounding deck, a stone wall, and a building in the background.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

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.
NT$3,460
NT$3,864 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.
A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.
A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

2. 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.
NT$4,658
NT$5,203 total
includes taxes & fees
Nov 2 - Nov 3
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A hotel patio with outdoor seating and a fire pit.
A modern kitchen with a marble countertop, stainless steel appliances, and a variety of food items displayed on the counter.
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.
A modern reception area with a green textured wall, a reception desk, and a coffee machine.

3. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
NT$4,147
NT$4,632 total
includes taxes & fees
Nov 8 - Nov 9
Hilton Garden Inn Lenox Pittsfield
A snow-covered outdoor area with a patio, seating, and a covered dining area.
A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.
A dining area with a glass table, red walls, and framed artwork.
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.
NT$4,976
NT$5,708 total
includes taxes & fees
Oct 27 - Oct 28
The Cornell Inn, Lenox & The Berkshires
A modern hotel lobby with seating areas, tables, and a reception desk.
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.
A kitchenette with a microwave, coffee maker, and coffee cups.

5. 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.
NT$2,918
NT$3,260 total
includes taxes & fees
Nov 17 - Nov 18
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A lakeside dock with kayaks and a covered boat ramp.
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.

6. 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.
NT$3,721
NT$4,156 total
includes taxes & fees
Nov 15 - Nov 16
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A spacious hotel lobby with multiple seating areas, large windows, and a television.
A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.
A wooden cabinet with a coffee maker and a white container.
A gym with exercise equipment including treadmills, a stationary bike, and free weights.

7. 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.
NT$3,556
NT$3,972 total
includes taxes & fees
Oct 30 - Oct 31
Hampton Inn & Suites Berkshires-Lenox
A building with a porch and multiple windows, surrounded by purple flowers.
A living room with a sofa, armchair, coffee table, and a patterned rug.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.
A café with a display case, a frozen food section, and a marketplace sign.

8. 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.
NT$3,794
NT$4,872 total
includes taxes & fees
Oct 29 - Oct 30
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
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 kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.
A hotel room with a sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.

9. 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.
NT$3,004
NT$3,356 total
includes taxes & fees
Nov 15 - Nov 16
Quality Inn Lee - Lenox South
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 garden with wooden Adirondack chairs and a stone pathway.
A spacious lobby with a fireplace, seating area, and a bar.

10. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Alpine retreat with ski adventures awaits at Berkshire Mountain Lodge in the snow-capped mountains.
NT$2,780
NT$3,829 total
includes taxes & fees
Nov 22 - Nov 23
Berkshire Mountain Lodge
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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 cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.
A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.
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
NT$9,404
NT$11,348 total
includes taxes & fees
Nov 11 - Nov 12
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 room with a grand piano, a chessboard, a horse statue, and a blue armchair.
A dining room with a large table set for a meal, surrounded by ornate chairs.
A grand staircase with red carpeted steps and a wooden handrail, leading to a landing with a vase of flowers and a framed picture.

Hampton Terrace Inn

Hampton Terrace Inn
Lenox
NT$7,098
NT$7,929 total
includes taxes & fees
Nov 17 - Nov 18
Hampton Terrace Inn
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.
A compact living space with a kitchenette, a dining area, and a sofa.
A covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.
A modern apartment with a living room, kitchenette, and dining area.

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
NT$3,210
NT$3,586 total
includes taxes & fees
Nov 2 - Nov 3
The Central Downtown Inn & Suites
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
NT$12,385
NT$14,982 total
includes taxes & fees
Nov 5 - Nov 6
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 house with a fire pit in the yard, outdoor seating, and a large window overlooking the yard.
A bedroom with a large bed, a fireplace, a bathtub, and a window with a view of greenery.
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
NT$11,966
NT$13,365 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.
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Top The Berkshires Hotel Reviews

The Yankee Inn

The Yankee Inn

8/10 Good
"Efficient & comfortable. Very good value."
brian 1-night trip
Posted 8 hours ago
The Yankee 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 1 day ago
Hotel On North
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"Clean room. Comfortable beds. Good breakfast. Staff were nice and professional."
Melissa 1-night trip
Posted 1 day ago
Hampton Inn & Suites Berkshires-Lenox
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"-"
Serena 1-night trip
Posted 3 days ago
Quality Inn Great Barrington
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 6 days ago
FairBridge Inn Express

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