A lake with a rocky shoreline and a forested island.

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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

Superior Room, 1 King Bed, Jetted Tub | Jetted bathtub
Living area
Outdoor pool
Superior Room, 1 King Bed, Jetted Tub

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.
₹10,961
₹12,244 total
includes taxes & fees
22 Sept - 23 Sept
The Yankee Inn
Front of property
Terrace/patio
Reception
Room, 2 Double Beds

2. Hotel Northampton

Hotel Northampton
Northampton
  • Alpine escape in the historic Hotel Northampton with nearby ski access and cosy fireside lounges.
₹11,694
₹13,062 total
includes taxes & fees
7 Sept - 8 Sept
Hotel Northampton
Front of property
Deluxe Suite, 1 King Bed with Sofa bed
Deluxe Suite, 1 King Bed with Sofa bed
Front of property

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.
₹13,783
₹15,396 total
includes taxes & fees
20 Sept - 21 Sept
The Ellery
Exterior
Exterior
Studio Suite, Non Smoking, River View | Living area
Restaurant

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.
₹17,562
₹19,617 total
includes taxes & fees
20 Sept - 21 Sept
Old Mill Inn
Lake
Exterior
Lake
Lake

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.
₹12,048
₹13,458 total
includes taxes & fees
27 Sept - 28 Sept
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lobby
Standard Room, 1 King Bed, Non Smoking
Breakfast area
Lobby

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.
₹9,558
₹10,676 total
includes taxes & fees
27 Sept - 28 Sept
Quality Inn Lee - Lenox South
Lobby
Exterior
Property entrance
Pool

7. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Alpine retreat with ski adventures awaits at Berkshire Mountain Lodge in the snow-capped mountains.
₹7,522
₹10,513 total
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)
Lobby sitting area
Property amenity
Room

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.
₹8,496
₹9,490 total
includes taxes & fees
8 Sept - 9 Sept
Best Western Plus Berkshire Hills Inn & Suites
Pool
Property amenity
Reception
Exterior

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.
₹12,001
₹13,405 total
includes taxes & fees
10 Sept - 11 Sept
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Front of property
Room
Living area
In-room dining

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.
₹9,001
₹14,685 total
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

Front of property – evening/night
Room #10 Queen's Cottage | View from room
Room #4 - Roosevelt Suite, 1 King Bed, Fireplace, not pet friendly
Room #10 Queen's Cottage | Living room

Devonfield Inn B&B

Devonfield Inn B&B
Lee
₹37,704
₹42,115 total
includes taxes & fees
8 Sept - 9 Sept
Devonfield Inn B&B
Exterior
Living area
Exterior
Living area

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
₹9,355
₹10,449 total
includes taxes & fees
7 Sept - 8 Sept
The Central Downtown Inn & Suites
Restaurant
Interior
Thayer House, Room 201, 1 King bed, Jetted tub
Front of property

The Old Inn On The Green

The Old Inn On The Green
Great Barrington
₹31,183
₹37,629 total
includes taxes & fees
7 Sept - 8 Sept
The Old Inn On The Green
Suite, Private Bathroom (RedBird Suite) | View from room
Lobby sitting area
Suite, Private Bathroom (Parlour Suite)
Breakfast area

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
₹31,199
₹37,742 total
includes taxes & fees
28 Sept - 29 Sept
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Exterior detail
Fireplace
Lobby sitting area
Staircase

Hampton Terrace Inn

Hampton Terrace Inn
Lenox
₹21,101
₹23,570 total
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 8 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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