Massachusetts Ski Hotels from ￥15,193 - Fully Refundable Options

A coastal village with houses, a lighthouse, and boats on the water.

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A historic building with "QUINCY MARKET" sign, surrounded by modern buildings and a clock tower.

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Our top choices for Massachusetts ski hotels

1. Vacation Village in the Berkshires

Williamstown

Explore ski paradise at Jiminy Peak with mountainside hot tubs and slope-view relaxation at this Williamstown family retreat.

￥17,192 total

includes taxes & fees

Aug 31 - Sep 1

Superior Room, 1 King Bed, Jetted Tub | Jetted tub

2. The Yankee Inn

Lenox

Embrace winter magic at this mountainside retreat offering an indoor pool, hot tub, and direct access to Bousquet Ski Area.

￥27,207 total

includes taxes & fees

Sep 13 - Sep 14

3. Berkshire Valley Inn

Williamstown

Ski dreams come alive at this mountain-adjacent retreat with a seasonal outdoor pool and nearby cross-country trails.

￥29,588 total

includes taxes & fees

Sep 24 - Sep 25

4. Jiminy Peak Mountain Resort

Hancock

Escape to a ski lover's paradise at Jiminy Peak with slope-side access and two inviting hot tubs.

￥24,192 total

includes taxes & fees

Sep 2 - Sep 3

5. 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.

￥22,029 total

includes taxes & fees

Sep 9 - Sep 10

6. Westford Regency Inn & Conference Center

Westford

Ski-lovers will discover alpine adventure at Nashoba Valley Ski Area, just minutes from this welcoming Westford retreat with slope storage.

7. Doubletree by Hilton Hotel Leominster

Leominster

Ski into winter magic with slope access and cozy lodgings near Wachusett Mountain Ski Area, just moments from your indoor pool retreat.

￥28,289 total

includes taxes & fees

Sep 6 - Sep 7

Room, 2 Queen Beds, Non Smoking | Iron/ironing board, cribs (free), rollaway beds (surcharge), WiFi (free)

8. Monument Mountain Motel

Great Barrington

Scenic Berkshires ski retreat offers winter thrills just minutes from Butternut Mountain and Great Barrington's charm.

￥15,193 total

includes taxes & fees

Sep 21 - Sep 22

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Top Massachusetts Hotel Reviews

Harborside Inn Of Boston

10/10 Excellent

"Fantastic location… close to seaport attractions and Quincy Hall Market place"

The Dagny Boston

8/10 Good

"Pretty hotel, very clean. Excellent location. Our room was very large and very clean with comfortable beds. The city view was of some roofs on one side then street on the other. The coffee machine only had cups for espresso size, very small. The coffee shop was great. The staff was nice, typical of a regular check in, asked our name here is your key. Did not ask why we were in town or if we needed any recommendations or tell us a lot about the hotel itself. The gentleman that brought up our bags I think his name was Joe, was very friendly and asked questions of how he could help. Overall, we had a great stay, just missing that little bit of extra personal experience to make it exceptional. We would recommend."

Hilton Boston Park Plaza

10/10 Excellent

"My girlfriend and I were on a two week East Coast vacation from Las Vegas to get away from the heat and to celebrate my birthday and visit family. We had dropped off our rental car which just happened to be near the Hilton Park Plaza. We had no intention of staying there we were just going to ask them to hold our luggage give them $20 or so and see if they would do it. And they did. We sat down at their bar, which is very well staffed and loved the area so much that we had a drink and basically a late lunch. The prices were a lot cheaper than we expected and definitely a lot less expensive than a Las Vegas hotel. So we decided that we didn’t have to go home yet, and we extended the trip for three more days based on our experience at the Hilton Park Plaza in Boston. I then looked on Expedia and booked a room that had a beautiful view of the city and we were pretty high up as far as the floors I believe we were on the seventh or eighth floor and they have a total of 15. We had a wonderful experience and ended up booking yet the next night and having two nights in Boston and then going to see a Boston Red Sox game was definitely the pinnacle of our Boston excursion. Not to mention it’s a very walkable city where we were staying. The weather was wonderful. We wanted to have some drizzle and we got it because we’re so used to the hot desert temperature that the East Coast is such a complete opposite that it made us yearn to move back east to experience this more often."

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Change your mind

Treat yourself

Be picky

Top Cities in Massachusetts

Boston

Check availability on Massachusetts Ski Hotels

Our top choices for Massachusetts ski hotels

1. Vacation Village in the Berkshires

2. The Yankee Inn

3. Berkshire Valley Inn

4. Jiminy Peak Mountain Resort

5. Hampton Inn & Suites Berkshires-Lenox

6. Westford Regency Inn & Conference Center

7. Doubletree by Hilton Hotel Leominster

8. Monument Mountain Motel

9. Shaker Mill Inn

10. The Colonial Hotel

Top Massachusetts Hotel Reviews

Harborside Inn Of Boston

The Midtown Hotel MOD Collection by Sonesta

The Dagny Boston

The Revolution Hotel

Hyatt Regency Boston/Cambridge

Doubletree By Hilton Boston Logan Airport Chelsea

Hilton Boston Park Plaza

The Godfrey Hotel Boston

Arcadian Hotel

Explore a world of travel with Expedia

Ski Hotels in Massachusetts from ￥15,193

Change your mind

Treat yourself

Be picky

Top Cities in Massachusetts

Boston

Check availability on Massachusetts Ski Hotels

Our top choices for Massachusetts ski hotels

1. Vacation Village in the Berkshires

2. The Yankee Inn

3. Berkshire Valley Inn

4. Jiminy Peak Mountain Resort

5. Hampton Inn & Suites Berkshires-Lenox

6. Westford Regency Inn & Conference Center

7. Doubletree by Hilton Hotel Leominster

8. Monument Mountain Motel

9. Shaker Mill Inn

10. The Colonial Hotel

Top Massachusetts Hotel Reviews

Harborside Inn Of Boston

Explore a world of travel with Expedia