A person snowboarding down a snowy slope.

The Berkshires Hotel Guide - Ski Hotels in The Berkshires, Massachusetts

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Check availability on The Berkshires Ski Hotels

Tonight
23 Sept - 24 Sept
Tomorrow
24 Sept - 25 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct

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 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 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.
€114
includes taxes & fees
28 Sept - 29 Sept
The Yankee Inn
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.
A garden with wooden Adirondack chairs and a stone pathway.
A spacious lobby with a fireplace, seating area, and a bar.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Alpine retreat with ski adventures awaits at Berkshire Mountain Lodge in the snow-capped mountains.
€97
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge
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 dining area with large windows, wooden furniture, and a view of a lake.
A lakeside dock with kayaks and a covered boat ramp.

3. 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.
€124
includes taxes & fees
29 Sept - 30 Sept
The Black Swan Lee - Lenox, an Ascend Collection Hotel
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A modern hotel with a large entrance, multiple floors, and a well-lit facade.
A snack bar with shelves of snacks and a refrigerated display.
A modern cafe with a counter, seating area, and large windows.

4. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
  • Warm up on the slopes at Bousquet Ski Area, just minutes away from this cosy Pittsfield retreat with an indoor pool and hot tub.
€111
includes taxes & fees
21 Oct - 22 Oct
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.
A row of white plastic chairs on a covered outdoor area with a white building in the background.
A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.
A hotel room with a wooden dresser, a television, a microwave, and a mirror.

5. 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.
€75
includes taxes & fees
28 Sept - 29 Sept
Monument Mountain Motel
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.
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.

6. 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.
€102
includes taxes & fees
27 Sept - 28 Sept
Vacation Village in the Berkshires
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 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.

7. Hotel On North

Hotel On North
Pittsfield
€131
includes taxes & fees
24 Sept - 25 Sept
Hotel On North
A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.
A hotel reception area with framed artwork, a coffee machine, and a sign indicating 'Quality by Choice Hotels'.
A hotel room with a bathroom, a bed, a desk, and a nightstand.
A hotel room with a wooden desk, a television, a mirror, and a bathroom visible through an open door.

8. Quality Inn Great Barrington

Quality Inn Great Barrington
Great Barrington
  • Experience snowy adventures in Great Barrington with daily manager's reception and a hearty breakfast before hitting the slopes.
€99
includes taxes & fees
18 Oct - 19 Oct
Quality Inn Great Barrington
A building with a porch and multiple windows, surrounded by purple flowers.
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.
A living room with a sofa, armchair, coffee table, and a patterned rug.

9. 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.
€131
includes taxes & fees
29 Sept - 30 Sept
Holiday Inn Club Vacations Oak 'n Spruce Resort
A large house with a covered patio area featuring outdoor seating and a fire pit.
A sunlit room with large windows, a stone floor, and two rocking chairs.
A cozy lounge area with plush seating, a fireplace, and large windows offering a view of the outdoors.
A corner dining area with a wooden table set for four, surrounded by upholstered chairs.

10. The Whitlock

The Whitlock
Lenox
€135
includes taxes & fees
29 Sept - 30 Sept
The Whitlock
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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 hotel room with two beds, a nightstand with a lamp, and a window with curtains.
A compact living space with a kitchenette, a dining area, and a sofa.

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
€96
includes taxes & fees
24 Sept - 25 Sept
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 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 traditional living room with a fireplace, a grand piano, plush seating, and a bookshelf.

Hampton Terrace Inn

Hampton Terrace Inn
Lenox
€252
includes taxes & fees
24 Sept - 25 Sept
Hampton Terrace Inn
A dining area with round tables set for two, a fireplace, and a mural on the wall.
A white two-story house with a front door, windows, and a chimney.
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
€347
includes taxes & fees
5 Oct - 6 Oct
The Old Inn On The Green
A large, two-story house with a well-maintained lawn and a fence.
A bedroom with a large bed, a fireplace, a bathtub, and a window with a view of greenery.
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 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
€428
includes taxes & fees
24 Sept - 25 Sept
Devonfield Inn B&B
A two-story house with a brick entrance and a white facade.
A neatly arranged bedroom with a bed, bedside table, and a dresser.
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.

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
€545
includes taxes & fees
12 Oct - 13 Oct
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

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 less than an hour ago
Hotel Downstreet, an Ascend Collection Hotel
Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"I am disappointed that it has been over two weeks and I have yet to receive my room deposit back. They told me 7-10 days"
Graham 2-night trip
Posted 20 hours ago
Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

10/10 Excellent
"The room was spacious, clean and comfortable. I will definitely stay there again."
William 2-night trip
Posted 2 days ago
The Yankee Inn
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Even in the off season it was beautiful."
Karen 1-night trip
Posted 2 days ago
Jiminy Peak Mountain Resort
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"This is a wonderful, historic inn. Check out the Red Lion Den for music. We heard a terrific local group. We ate in the Tavern and the food was tasty. This is not a luxurious place. It dates back to the 1700s. But it is really charming. My friends and I stayed in a suite in an out building. We had a low-ceiled living room downstairs, which was a. great place to talk and catch up. The bedroom situation was a little funky because the bathroom was right next to the bed in one of two sleeping areas upstairs and the door really squeaked when it opened and closed. But that was about our only complaint. I'd be delighted to return."
Gerald 1-night trip
Posted 2 days ago
The Red Lion Inn
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent
"Good"
Kauan 1-night trip
Posted 4 days ago
Howard Johnson by Wyndham Lenox

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