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
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 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 swimming pool with a surrounding deck, a stone wall, and a building in the background.
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.
€105
includes taxes & fees
1 Nov - 2 Nov
The Yankee Inn
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 brick building with a sign reading "The Ellery."
A modern hotel room with a bed, sofa, dining table, and chairs.

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.
€126
includes taxes & fees
15 Nov - 16 Nov
The Ellery
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.

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.
€114
includes taxes & fees
15 Nov - 16 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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.
A hotel lobby with a glass vase of white flowers on a table, red chairs, and a wooden reception desk.

4. Hotel Northampton

Hotel Northampton
Northampton
  • Alpine escape in the historic Hotel Northampton with nearby ski access and cosy fireside lounges.
€148
includes taxes & fees
25 Oct - 26 Oct
Hotel Northampton
A view of a red building by a waterway through a window.
A wooden porch with a sign reading "OLD MILL" above a double door.
A bar area with wooden stools, a long counter, and potted plants.
A modern living room with a wooden dining table, leather sofa, and a large window.

5. Old Mill Inn

Old Mill Inn
Hatfield
  • This historic, cosy bed & breakfast welcomes skiers with premium amenities and a perfect location for winter escapes.
€179
includes taxes & fees
16 Nov - 17 Nov
Old Mill Inn
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.
A snack bar with shelves of snacks and a refrigerated display.
A modern hotel with a large entrance, multiple floors, and a well-lit facade.

6. 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.
€98
includes taxes & fees
22 Nov - 23 Nov
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A spacious hotel lobby with multiple seating areas, large windows, and a television.
A hotel room with a bed, a nightstand with a lamp and phone, a chair, and framed pictures on the wall.
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.

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.
€109
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn & Suites Berkshires-Lenox
A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.
A modern hotel building with the name "Hotel Downtown" on the facade.
A modern interior with a large window, a wooden table, and bar stools.
A modern cafe with a wooden accent wall, a coffee machine, and black chairs.

8. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
North Adams
€119
includes taxes & fees
12 Nov - 13 Nov
Hotel Downstreet, an Ascend Collection Hotel
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.
A garden with wooden Adirondack chairs and a stone pathway.

9. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Alpine retreat with ski adventures awaits at Berkshire Mountain Lodge in the snow-capped mountains.
€105
includes taxes & fees
22 Nov - 23 Nov
Berkshire Mountain Lodge
A two-story house with a large porch and multiple windows, surrounded by autumn foliage.
A modern kitchen with dark cabinetry, a coffee machine, and a built-in stove.
A modern kitchen with a central island, bar stools, a refrigerator, and a dining area with a sofa and a table.
A bedroom with a bed, two bedside tables, a window with a view of autumn trees, and wall-mounted sconces.

10. Shelburne Springs Hotel

Shelburne Springs Hotel
Shelburne Falls
€225
includes taxes & fees
26 Oct - 27 Oct
Shelburne Springs Hotel
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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 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.
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
€367
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 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 traditional living room with a fireplace, a grand piano, plush seating, and a bookshelf.

Hampton Terrace Inn

Hampton Terrace Inn
Lenox
€218
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 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.
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
€98
includes taxes & fees
26 Oct - 27 Oct
The Central Downtown Inn & Suites
A dining area with round tables set for two, a fireplace, and a mural on the wall.
A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.
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.

The Old Inn On The Green

The Old Inn On The Green
Great Barrington
€312
includes taxes & fees
1 Nov - 2 Nov
The Old Inn On The Green
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 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
€411
includes taxes & fees
5 Nov - 6 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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