A lake with a rocky shoreline and a forested island.

Western Massachusetts Hotel Guide - Ski Hotels in Western Massachusetts, Massachusetts

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Check availability on Western Massachusetts Ski Hotels

Tonight
6 Sept - 7 Sept
Tomorrow
7 Sept - 8 Sept
Next weekend
11 Sept - 13 Sept
In two weeks
18 Sept - 20 Sept

Our top choices for Western Massachusetts 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 hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
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.
€112
includes taxes & fees
22 Sept - 23 Sept
The Yankee Inn
A multi-story hotel with a prominent "Hotel Northampton" sign, featuring a classic architectural style with a brick facade and multiple windows.
An outdoor cafe with tables and chairs, surrounded by hanging flower baskets and a brick building in the background.
A hotel room with two beds, a TV, a desk, and a chair.
A hotel room with a desk, chair, lamp, and a large mirror. There is a staircase leading to an outdoor area with a railing.

2. Hotel Northampton

Hotel Northampton
Northampton
  • Alpine escape in the historic Hotel Northampton with nearby ski access and cosy fireside lounges.
€119
includes taxes & fees
7 Sept - 8 Sept
Hotel Northampton
A brick building with a green door, white porch chairs, and a pathway lined with pink flowers.
A hotel room with a bed, a sofa, a dining table, and a chair. There are two nightstands with lamps and a framed picture on the wall.
A modern hotel room with a bed, sofa, dining table, and chairs.
A brick building with a sign reading "The Ellery."

3. The Ellery

The Ellery
Northampton
  • Winter wonders await at this charming bed & breakfast near ski areas, where crackling lobby fireplaces and mountain adventures combine.
€138
includes taxes & fees
22 Sept - 23 Sept
The Ellery
A view of a red building by a waterway through a window.
A bar area with wooden stools, a long counter, and potted plants.
A yellow multi-story building with a water feature in front.
A wooden porch with a sign reading "OLD MILL" above a double door.

4. Old Mill Inn

Old Mill Inn
Hatfield
  • This historic, cosy bed & breakfast welcomes skiers with premium amenities and a perfect location for winter escapes.
€173
includes taxes & fees
8 Sept - 9 Sept
Old Mill 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 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.

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.
€123
includes taxes & fees
27 Sept - 28 Sept
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 modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.
A hotel room with a bed, a desk, a television, a microwave, and a sofa.

6. 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.
€97
includes taxes & fees
27 Sept - 28 Sept
Quality Inn Lee - Lenox South
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.
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

7. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Alpine retreat with ski adventures awaits at Berkshire Mountain Lodge in the snow-capped mountains.
€96
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.
A reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.
A hotel room with a patterned carpet, a sofa, a chair, a small table, a lamp, a television on a cabinet, and two framed pictures on the wall.
A reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.

8. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
Pittsfield
  • Nestled near premier ski areas, this cosy retreat offers mountain adventures and a fitness centre for year-round active stays.
€86
includes taxes & fees
8 Sept - 9 Sept
Best Western Plus Berkshire Hills Inn & Suites
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A modern cafe with seating areas, a coffee station, and large windows offering a view of greenery.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.
A modern hotel with a large entrance, multiple floors, and a well-lit facade.

9. 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.
€122
includes taxes & fees
10 Sept - 11 Sept
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A two-story house with a porch, a balcony, and a chimney.
A traditional living room with a green sofa, a yellow armchair, a wooden coffee table, and a patterned rug.
A traditional dining room with a wooden table, chairs, and a chandelier.
A dining room with a wooden table, chairs, a chandelier, and a fireplace.

10. Blooming Inn

Blooming Inn
Shelburne Falls
  • Embrace winter adventure at this rural guesthouse with on-site snowmobiling, sledding, and snow tubing near Shelburne Falls.
€136
includes taxes & fees
16 Sept - 17 Sept
Blooming Inn
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Choose what matters most at ski hotels in Western Massachusetts

Resort
4 stars
5 stars
Spa
Family-friendly

4-star ski hotels in Western Massachusetts

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
€384
includes taxes & fees
8 Sept - 9 Sept
Devonfield Inn B&B
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 hotel room with two beds, a nightstand with a lamp, and a window with curtains.
A covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
€95
includes taxes & fees
7 Sept - 8 Sept
The Central Downtown Inn & Suites
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 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.

The Old Inn On The Green

The Old Inn On The Green
Great Barrington
€343
includes taxes & fees
7 Sept - 8 Sept
The Old Inn On The Green
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 neatly arranged bedroom with a bed, bedside table, and a dresser.
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
€344
includes taxes & fees
28 Sept - 29 Sept
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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 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.
A room with a grand piano, a chessboard, a horse statue, and a blue armchair.

Hampton Terrace Inn

Hampton Terrace Inn
Lenox
€216
includes taxes & fees
10 Sept - 11 Sept
Hampton Terrace Inn
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 Western Massachusetts Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Enjoyed our stay and would highly recommend!"
Roger 2-night trip
Posted 7 hours ago
Vacation Village in the Berkshires
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Charming, updated throughout. Extremely clean and well appointed. Extremely delightful stay."
Colleen And mark 2-night trip
Posted 2 days ago
The Red Lion Inn
FairBridge Inn Express

FairBridge Inn Express

8/10 Good
"The exterior is scary. The lobby is a fright. Rooms however were clean and updated. I appreciate that. But the lot is a disgrace."
Janet 1-night trip
Posted 3 days ago
FairBridge Inn Express
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Staff at the front desk were welcoming, friendly, and helpful throughout my stay. The room was very clean. The bed was comfortable. The shower had good water pressure and plenty of hot water. The room was equipped with a refrigerator, microwave, and coffeemaker, as well as a TV, and the WiFi worked fine. The breakfast area in the office building had several tables, and included a "make-your-own-waffles" station (love that!), buffet-style scrambled eggs and sausage, as well pre-packaged muffins. Yogurt and other items were available in a refrigerator. Parking was in a a space right outside the room entrance on the first floor, which was ground level. The location is on Main Street (Route 7) in Great Barrington, but set back from the road so there's less traffic noise. There are restaurants and shops in easy walking distance of this motel, and it is an easy drive of 15 mins. or so to the nearby towns of Lenox, Lee (location of Mass. Turnpike exit/entrance), West Stockbridge, and Stockbridge that have their own shops, restaurants, sites, and venues of interest. I highly recommend this motel."
Janet L. 2-night trip
Posted 4 days ago
Quality Inn Great Barrington

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