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Top Romantic Western Massachusetts Hotels

D. Hotel Suites & Spa

1 Country Club Rd Holyoke MA

44 min drive from Jiminy Peak Mountain Resort

Rekindle the romance with your special someone. Consider booking a getaway at this hotel where you're sure to love the hot tub and spa. Other amenities to enjoy ...

9.2/10 Wonderful! (2,231 reviews)

Couples like: full-service spa, couples spa treatments, bar, hot tub

Travelers say...

Clean spacious room. Check in was easy, quick and friendly

Reviewed on Jan 18, 2026

Shaker Mill Inn

2 Oak Street West Stockbridge MA

37 min drive from Jiminy Peak Mountain Resort

Stay at this B&B in West Stockbridge. Enjoy free breakfast, free parking, and daily housekeeping. Popular attractions Ebenezer II Gifts and Antiques and Hotchkiss ...

9.6/10 Exceptional! (414 reviews)

Everything was great— the cleanliness, the plentiful breakfast, the character and coziness, and the proximity to Amici across the street (free dessert with your room key).

Reviewed on Jan 13, 2026

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

13 min walk from Jiminy Peak Mountain Resort

A garden and in-room fireplaces await at this romantic condo, which also offers a terrace and an outdoor pool.

8.6/10 Excellent! (2,208 reviews)

It is one of my favorite places to go but sometimes it is overcrowded and the people can be rude and rowdy. But the staff is fantastic they do a great job even with the crowds.

Reviewed on Jan 16, 2026

See all 1,464 properties in Western 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.