Massachusetts Ski Hotels from AED 316 - Fully Refundable Options

Top Cities in Massachusetts

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

A harbor with boats, waterfront houses, and an American flag.

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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.

AED 431 total

includes taxes & fees

23 Sep - 24 Sep

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.

AED 480 total

includes taxes & fees

28 Sep - 29 Sep

3. Berkshire Valley Inn

Williamstown

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

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.

AED 512 total

includes taxes & fees

19 Oct - 20 Oct

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.

AED 509 total

includes taxes & fees

29 Sep - 30 Sep

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.

AED 656 total

includes taxes & fees

4 Oct - 5 Oct

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.

AED 316 total

includes taxes & fees

23 Sep - 24 Sep

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Top Massachusetts Hotel Reviews

Harborside Inn Of Boston

10/10 Excellent

"I loved how conveniently located the hotel is. Everything is so close by, and it’s right in the middle of everything, so you really don’t need to rent a car to get around. What I liked most was the staff , everyone was so friendly and helpful. The hotel has an older, more historic feel inside, but I think that actually gives it a lot of character and makes it really charming."

Hyatt Regency Boston Harbor

10/10 Excellent

"We stayed for 7 nights and enjoyed our time there. We knew we selected a hotel that was across the water from downtown, but we really wanted a good view. It was a great decision! We took transportation to the Boston Waterfront, Boston Common and the Seaport district daily. This is a GREAT place for a “home base”. It was convenient to have a restaurant in our hotel. We had dinner there three times and the food is really good. They also give you free clam chowder daily if you stay there. it’s good chowder too. The view of Boston from the restaurant is the same as our room, amazing. Although I gave a five star rating there were a couple drawbacks: The hotel sits kind of alone out by the airport and we couldn’t get Uber Eats or Door Dash deliveries. The hotel store is very limited. The ice machine was broken on our floor the entire time. They don’t have a lot of ice in this hotel as it is and that was a bummer. My wife likes ice and taking the elevator to get it twice per day was not ideal. Like I mentioned previously, this was not enough to detract from our 5 star rating. The view was awesome and the location worked well, we just had to plan ahead. If you are visiting Boston this is a great option."

Room 1

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Top Cities in Massachusetts

Boston

Nantucket

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

Hyatt Regency Boston/Cambridge

The Dagny Boston

Copley Square Hotel, a FOUND Hotel

Omni Boston Hotel at the Seaport

Hyatt Regency Boston Harbor

The Revolution Hotel

citizenM Boston North Station

Explore a world of travel with Expedia

Ski Hotels in Massachusetts from AED 316

Change your mind

Treat yourself

Be picky

Top Cities in Massachusetts

Boston

Nantucket

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