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4 Night Mountain vacations in Massachusetts

Price found within the past 48 hours. Click for updated prices.

The Yankee, Trademark Collection by Wyndham

￥135,580

per person

Feb 18 - Feb 22

found 3 hours ago

Roundtrip non-stop flight included

Tokyo (HND) to Albany (ALB)

9.2/10 Wonderful! (1,003 reviews)

The staff was very friendly upon arrival and check in was easy, the room was clean as well as the hot tub and pool I spent some time relaxing in after check-in. Complimentary breakfast was good and then spent my days after at the mountain that was a quick 5 minute drive away with great skiing and snowboarding.

Reviewed on Jan 3, 2026

Hampton Inn & Suites Berkshires-Lenox

￥155,954

per person

Feb 18 - Feb 22

found 3 hours ago

Roundtrip non-stop flight included

Tokyo (HND) to Albany (ALB)

9.2/10 Wonderful! (1,001 reviews)

The front desk lady was super nice and helpful. Checkin was quick and effortless :) My only complaints are we had a room near where they were doing construction, so that was kinda noisy. Also, when I reserved a room online I made sure I got one with the fridge and microwave. I didn't notcie4 until after we settled in and wanted to heat up leftovers that we didn't have a microwave :( :( At that point I was too tired from traveling to call down to the front desk.

Reviewed on Jan 2, 2026

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Top Mountain Massachusetts Hotels

Jiminy Peak Mountain Resort

37 Corey Rd Hancock MA

￥34,295

￥38,308 total

Jan 8 - Jan 9

includes taxes & fees

Book a stay at this ski condo in Hancock. Enjoy free parking, 2 restaurants, and 2 hot tubs. Our guests praise the property condition in our reviews. Popular ...

8.2/10 Very Good! (988 reviews)

This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the ...

Reviewed on Oct 5, 2025

Cavalier Cottage B&B

236 East Oxbow Road Shelburne Falls MA

35 min drive from Fenway Park

Stay at this 3-star business-friendly cottage in Shelburne Falls. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Catamount State Forest ...

Would return!

Perfect for a quiet, weekend getaway. We went to celebrate our 5 year anniversary and brought our dog, Ollie. Ollie's a very timid and nervous guy, but he felt very comfortable here. We went during the winter, but would be interested in returning in the summer because there seems to be a lot of outdoor ...

Reviewed on Apr 13, 2018

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Harbour House Inn

725 North State Road Cheshire MA

15 min drive from Fenway Park

￥33,669

￥35,588 total

Jan 7 - Jan 8

includes taxes & fees

Stay at this B&B in Cheshire. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Adams Theater and Mount Greylock State Reservation Visitor ...

9.6/10 Exceptional! (39 reviews)

Great place, great hosts, lovely experience. Would go back 100x.

Reviewed on Nov 14, 2025

See all 17,447 properties in Massachusetts

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.