A lake with a rocky shoreline and a forested island.

Ski Hotels & Resorts in Western Massachusetts from NZ$192

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Check availability on Western Massachusetts Ski Hotels

Tonight
22 Oct - 23 Oct
Tomorrow
23 Oct - 24 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Our top choices for Western Massachusetts ski hotels

A multi-story hotel with a prominent "Hotel Northampton" sign, featuring a classic architectural style with a brick facade and multiple windows.
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.
An outdoor cafe with tables and chairs, surrounded by hanging flower baskets and a brick building in the background.

1. Hotel Northampton

Hotel Northampton
Northampton
  • Alpine escape in the historic Hotel Northampton with nearby ski access and cosy fireside lounges.
NZ$292
includes taxes & fees
25 Oct - 26 Oct
Hotel Northampton
A brick building with a green door, white porch chairs, and a pathway lined with pink flowers.
A modern hotel room with a bed, sofa, dining table, and chairs.
A modern hotel room with a dining area, a sofa, a bed, and a TV.
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.

2. The Ellery

The Ellery
Northampton
  • Winter wonders await at this charming bed & breakfast near ski areas, where crackling lobby fireplaces and mountain adventures combine.
NZ$249
includes taxes & fees
9 Nov - 10 Nov
The Ellery
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
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.

3. The Yankee Inn

The Yankee Inn
Lenox
  • Embrace winter magic at this mountainside retreat offering an indoor pool, spa pool, and direct access to Bousquet Ski Area.
NZ$192
includes taxes & fees
20 Nov - 21 Nov
The Yankee Inn
A view of a red building by a waterway through a window.
A yellow multi-story building with a water feature in front.
A modern living room with a wooden dining table, leather sofa, and a large window.
A bar area with wooden stools, a long counter, and potted plants.

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.
NZ$352
includes taxes & fees
29 Oct - 30 Oct
Old Mill Inn
A lodge with a large building and a dock by a lake, surrounded by forest.
A dining area with large windows, wooden furniture, and a view of a lake.
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.

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.
NZ$225
includes taxes & fees
15 Nov - 16 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.
A reception area with a large landscape painting, a dark reception desk, and a potted plant.
A modern cafe with a wooden accent wall, a coffee machine, and black chairs.
A modern interior with a large window, a wooden table, and bar stools.

6. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
North Adams
NZ$234
includes taxes & fees
11 Nov - 12 Nov
Hotel Downstreet, an Ascend Collection Hotel
A multi-story hotel with a classic facade, large windows, and a prominent entrance.
A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.
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.

7. Hotel On North

Hotel On North
Pittsfield
NZ$246
includes taxes & fees
22 Nov - 23 Nov
Hotel On North
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 reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.
A modern cafe with a counter, seating area, and large windows.

8. 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 spa pool.
NZ$194
includes taxes & fees
22 Nov - 23 Nov
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
An outdoor patio area with seating, a fire feature, and a view of the building's exterior.
A modern bar area with a long counter, multiple bar stools, and a wooden accent wall.
A modern bar area with a long counter, multiple screens, and a seating area with metal chairs.
A modern reception area with a wooden reception desk, seating area with sofas and chairs, and large windows providing natural light.

9. Courtyard by Marriott West Springfield

Courtyard by Marriott West Springfield
West Springfield
  • Winter sports enthusiasts find alpine charm in this well-appointed hotel with premium ski trails and pristine snow nearby.
NZ$264
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott West Springfield
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.
A spacious lobby with a fireplace, seating area, and a bar.
A garden with wooden Adirondack chairs and a stone pathway.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

10. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Alpine retreat with ski adventures awaits at Berkshire Mountain Lodge in the snow-capped mountains.
NZ$208
includes taxes & fees
22 Nov - 23 Nov
Berkshire Mountain Lodge
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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 dining area with a table set for two, a view of a green landscape through large windows, and outdoor seating with a view.
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
NZ$725
includes taxes & fees
2 Nov - 3 Nov
Devonfield Inn B&B
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 traditional living room with a fireplace, a grand piano, plush seating, and a bookshelf.
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
NZ$430
includes taxes & fees
17 Nov - 18 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 covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.
A compact living space with a kitchenette, a dining area, and a sofa.

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
NZ$194
includes taxes & fees
29 Oct - 30 Oct
The Central Downtown Inn & Suites
A white two-story house with a front door, windows, and a chimney.
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 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.

The Old Inn On The Green

The Old Inn On The Green
Great Barrington
NZ$615
includes taxes & fees
5 Nov - 6 Nov
The Old Inn On The Green
A two-story house with a brick entrance and a white facade.
A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.
A dining area with tables set for a meal, surrounded by large windows offering a view of trees and a garden.
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
NZ$682
includes taxes & fees
6 Nov - 7 Nov
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 Western Massachusetts Hotel Reviews

The Yankee Inn

The Yankee Inn

8/10 Good
"Efficient & comfortable. Very good value."
brian 1-night trip
Posted 14 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
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"-"
Serena 1-night trip
Posted 4 days ago
Quality Inn Great Barrington

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