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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! (2,246 reviews)

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

Travelers say...

Stayed 3 nights, really great hotel and value.

Reviewed on Dec 11, 2025

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! (408 reviews)

Super friendly & the room is adorable! Simple check in. The room was spotlessly clean. We had a great stay. Thank you!

Reviewed on Dec 11, 2025

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! (2,169 reviews)

Your staff is very courteous and yes my room was spotless.

Reviewed on Dec 13, 2025

See all 1,481 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.