A lake with a rocky shoreline and a forested island.

Ski Hotels & Resorts in Western Massachusetts from AU$154

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Check availability on Western Massachusetts Ski Hotels

Tonight
1 Oct - 2 Oct
Tomorrow
2 Oct - 3 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

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 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 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.

1. 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.
AU$170
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 modern hotel room with a dining area, a sofa, a bed, and a TV.
A modern hotel room with a bed, sofa, dining table, and chairs.
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.
AU$203
includes taxes & fees
28 Oct - 29 Oct
The Ellery
A multi-story hotel with a prominent "Hotel Northampton" sign, featuring a classic architectural style with a brick facade and multiple windows.
A hotel lobby with a glass vase of white flowers on a table, red chairs, and a wooden reception desk.
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.

3. Hotel Northampton

Hotel Northampton
Northampton
  • Alpine escape in the historic Hotel Northampton with nearby ski access and cosy fireside lounges.
AU$198
includes taxes & fees
12 Oct - 13 Oct
Hotel Northampton
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 lodge with a large building and a dock by a lake, surrounded by forest.
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.
AU$186
includes taxes & fees
1 Nov - 2 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
An outdoor patio area with seating, a fire feature, and a view of the building's exterior.
A hotel room with two beds, a large window with a view of trees, and a wall mural.
A modern reception area with a wooden reception desk, seating area with sofas and chairs, and large windows providing natural light.
A modern bar area with a long counter, multiple screens, and a seating area with metal chairs.

5. 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.
AU$216
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott West Springfield
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 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.

6. Old Mill Inn

Old Mill Inn
Hatfield
  • This historic, cosy bed & breakfast welcomes skiers with premium amenities and a perfect location for winter escapes.
AU$295
includes taxes & fees
28 Oct - 29 Oct
Old Mill Inn
An indoor swimming pool with clear water, tiled floors, and a blue wall.
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.
A modern cafe with a counter, seating area, and large windows.

7. 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.
AU$159
includes taxes & fees
1 Nov - 2 Nov
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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 library with bookshelves, a television, and two armchairs.
A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.

8. Hotel On North

Hotel On North
Pittsfield
AU$180
includes taxes & fees
1 Nov - 2 Nov
Hotel On North
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.

9. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Alpine retreat with ski adventures awaits at Berkshire Mountain Lodge in the snow-capped mountains.
AU$159
includes taxes & fees
18 Oct - 19 Oct
Berkshire Mountain Lodge
A reception area with a fireplace, seating, and a doormat with the logo "Quality".
A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.
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.

10. 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.
AU$176
includes taxes & fees
21 Oct - 22 Oct
Quality Inn Lee - Lenox South
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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 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 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
AU$158
includes taxes & fees
7 Oct - 8 Oct
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 traditional living room with a fireplace, a grand piano, plush seating, and a bookshelf.
A dining room with a large table set for a meal, surrounded by ornate chairs.
A room with a grand piano, a chessboard, a horse statue, and a blue armchair.

Hampton Terrace Inn

Hampton Terrace Inn
Lenox
AU$410
includes taxes & fees
1 Nov - 2 Nov
Hampton Terrace Inn
A large, two-story house with a well-maintained lawn and a fence.
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 house with a fire pit in the yard, outdoor seating, and a large window overlooking the yard.
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
AU$610
includes taxes & fees
1 Nov - 2 Nov
Devonfield Inn B&B
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 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 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
AU$504
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 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
AU$665
includes taxes & fees
1 Nov - 2 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 Red Lion Inn

The Red Lion Inn

10/10 Excellent
"So glad we stayed here! Our room was decorated like a 1940s Norman Rockwell painting, but had every modern comfort. We were in Stevens House, a half-block from the main inn - the shared living areas were like a home and our en-suite room was super nice. We had one dinner in the inn that was fancy, but we usually ate at other good restaurants & the patisserie within 1 block. Many fun shops, and a good laundromat also within 1 block."
Ruth 3-night trip
Posted 3 hours ago
The Red Lion Inn
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good
"Staff very pleasant and helpful. On site restaurant was good and reasonably priced. Room was large with a nice view. Breakfast, which is continental, seemed a bit skimpy. Plenty of parking and in a great central area with many restaurants."
Francesca 1-night trip
Posted 22 hours ago
Hotel Downstreet, an Ascend Collection Hotel
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 3 days ago
Quality Inn Great Barrington

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