Massachusetts Ski Hotels from SAR 251 - Fully Refundable Options

Top Cities in Massachusetts

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

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

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.

SAR 378 total

includes taxes & fees

1 Nov - 2 Nov

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

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.

SAR 445 total

includes taxes & fees

1 Nov - 2 Nov

A dining table with plates of food, a coffee cup, and a plant.

3. Berkshire Valley Inn

Williamstown

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

A resort with multiple buildings, a parking area, and a mountainous backdrop.

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.

SAR 562 total

includes taxes & fees

19 Oct - 20 Oct

A spacious hotel lobby with multiple seating areas, large windows, and a television.

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.

SAR 460 total

includes taxes & fees

1 Nov - 2 Nov

A multi-story building with a covered entrance and a brick driveway.

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.

A bar area with a long counter, multiple bar stools, hanging pendant lights, and a bar stocked with bottles.

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.

SAR 564 total

includes taxes & fees

15 Nov - 16 Nov

A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

8. Monument Mountain Motel

Great Barrington

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

SAR 251 total

includes taxes & fees

1 Nov - 2 Nov

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Top Massachusetts Hotel Reviews

Harborside Inn Of Boston

10/10 Excellent

"Great location. Super short walk to the North End and Quincy Market. Bar & restaurant part of the hotel. Comfortable beds, modern room. Funky hotel layout. Would definitely stay here again."

The Midtown Hotel MOD Collection by Sonesta

8/10 Good

"I enjoyed the convenience and accessibility of the location. It had a beautiful view of the Christian Science Plaza. However, the continental breakfast was beyond sad. It was apples, packaged pastries, and not-so-good coffee. The morning staff, name was Abby was extremely rude and with a poor attitude that made us feel uncomfortable. Since check-in, she didn’t greet us or welcome us. She hardly made eye contact. I always waited to see if another staff could help in order to avoid her. Overall, due to convenience, pricing and room cleanliness, I’d stay again."

Hyatt Regency Boston

10/10 Excellent

"Location was great for walking the city. Parking was quite expensive but attached to hotel. The arrangement of the elevators and location of the lobby and pool/workout room was confusing. Room was clean and nice size. Great decor and modern design. Staff was friendly and extremely helpful on visiting the city. Ate at hotel restaurant—excellent."

citizenM Boston North Station

10/10 Excellent

"I love this hotel. I love the style of the rooms and the environment of the lounge area. My wife and I thoroughly enjoyed our stay. When we were checking out, one of the concierges working the check-in area asked us about our stay, if we had been before, etc. We hadn't purchased a breakfast plan, so she offered us to stay and eat the buffet style breakfast and have coffees on the hotel. The buffet was excellent and the cafe Americano the bartender made for us were perfect. Can't wait to stay at this neat hotel again."

Room 1

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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

Wyndham Boston Beacon Hill

The Godfrey Hotel Boston

Arcadian Hotel

Hyatt Regency Boston

citizenM Boston North Station

Ski Hotels in Massachusetts from SAR 251

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