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Find Ski Hotels in The Berkshires, MA

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Check availability on The Berkshires Ski Hotels

Tonight
Sep 29 - Sep 30
Tomorrow
Sep 30 - Oct 1
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for The Berkshires ski hotels

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
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 modern hotel lobby with a seating area, a sofa, and a large window with curtains.
A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.

1. 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$6,181
NT$6,904 total
includes taxes & fees
Oct 7 - Oct 8
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
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 hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

2. 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$3,430
NT$3,831 total
includes taxes & fees
Oct 27 - Oct 28
The Yankee Inn
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 breakfast area with a counter, coffee machine, and a display of pastries.

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.
NT$3,779
NT$4,221 total
includes taxes & fees
Oct 19 - Oct 20
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 dining area with large windows, wooden furniture, and a view of a lake.
A lakeside lodge with a dock, fishing rods, and outdoor seating.
A lakeside dock with kayaks and a covered boat ramp.

4. 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$4,295
NT$4,798 total
includes taxes & fees
Oct 29 - Oct 30
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A reception area with a fireplace, seating, and a doormat with the logo "Quality".
A hotel room with a sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.
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.

5. 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$3,482
NT$3,889 total
includes taxes & fees
Oct 19 - Oct 20
Quality Inn Lee - Lenox South
A building entrance with a large planter with purple flowers and a small tree.
A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.
A library with bookshelves, a television, and two armchairs.
A spacious room with a large window, a brick wall, a sofa set, and a patterned carpet.

6. Hotel On North

Hotel On North
Pittsfield
NT$4,266
NT$4,766 total
includes taxes & fees
Oct 5 - Oct 6
Hotel On North
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 café with a display case, a frozen food section, and a marketplace sign.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

7. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
  • Alpine ski resort getaway awaits with 4 pools, mini-golf, and endless winter adventures in the beautiful Berkshires.
NT$3,715
NT$4,771 total
includes taxes & fees
Oct 18 - Oct 19
Holiday Inn Club Vacations Oak 'n Spruce Resort
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.
Indoor pool
A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.
A spacious living room with large windows, a fireplace, and a variety of seating options.

8. 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.
NT$3,024
NT$3,726 total
includes taxes & fees
Sep 30 - Oct 1
Vacation Village in the Berkshires
A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.
A modern cafe with a wooden accent wall, a coffee machine, and black chairs.
A reception area with a large landscape painting, a dark reception desk, and a potted plant.
A modern hotel building with the name "Hotel Downtown" on the facade.

9. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
North Adams
NT$4,295
NT$4,798 total
includes taxes & fees
Oct 14 - Oct 15
Hotel Downstreet, an Ascend Collection Hotel
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.
A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.
A reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.
A reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.

10. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
Pittsfield
  • Nestled near premier ski areas, this cozy retreat offers mountain adventures and a fitness center for year-round active stays.
NT$3,359
NT$3,752 total
includes taxes & fees
Oct 18 - Oct 19
Best Western Plus Berkshire Hills Inn & Suites
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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 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 covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.
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
NT$3,144
NT$3,511 total
includes taxes & fees
Sep 30 - Oct 1
The Central Downtown Inn & Suites
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$8,145
NT$9,098 total
includes taxes & fees
Oct 29 - Oct 30
Hampton Terrace Inn
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 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.

The Old Inn On The Green

The Old Inn On The Green
Great Barrington
NT$10,479
NT$12,645 total
includes taxes & fees
Oct 1 - Oct 2
The Old Inn On The Green
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 bedroom with a large bed, a fireplace, a bathtub, and a window with a view of greenery.
A house with a fire pit in the yard, outdoor seating, and a large window overlooking the yard.

Devonfield Inn B&B

Devonfield Inn B&B
Lee
NT$12,988
NT$14,507 total
includes taxes & fees
Oct 25 - Oct 26
Devonfield Inn B&B
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 dining area with tables set for a meal, surrounded by large windows offering a view of trees and a garden.
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
NT$16,401
NT$19,840 total
includes taxes & fees
Oct 12 - Oct 13
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"I typically do not reserve in motel with parking in front of each space due to security, I was mistaken at this facility. Pleasant neighborhood and the building was situated well off the main street."
Peter 1-night trip
Posted 15 hours ago
Quality Inn Great Barrington
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"One of the most unique establishments in the US. It brings one back to time when life was much simpler. Highly recomended."
Michael 1-night trip
Posted 21 hours ago
The Red Lion Inn
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Nice room. Exceptionally clean. Great staff"
Daniel 3-night trip
Posted 21 hours ago
The Yankee Inn
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Great location; walkable to restaurants. Spacious 7th floor room had a nice town and mountain view. All staff friendly and helpful. Bed was comfortable; room very clean. Breakfast was minimal and uninspiring."
Karl 1-night trip
Posted 6 days ago
Hotel Downstreet, an Ascend Collection Hotel
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Even in the off season it was beautiful."
Karen 1-night trip
Posted 8 days ago
Jiminy Peak Mountain Resort
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent
"Good"
Kauan 1-night trip
Posted 10 days ago
Howard Johnson by Wyndham Lenox

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