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Top Luxury Western Massachusetts Hotels

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

26 Glendale Road, RR 183 Stockbridge MA

46 min drive from Jiminy Peak Mountain Resort

Spoil yourself with classy accommodations at The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood, where you'll enjoy amenities ...

9.2/10 Wonderful! (85 reviews)

It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!

Reviewed on 2025/10/27

Hotel Northampton

36 King Street Northampton MA

37 min drive from Jiminy Peak Mountain Resort

Be treated to luxurious accommodations at Hotel Northampton, where you can enjoy amenities like designer toiletries, premium channels, and more. Notable amenities ...

9/10 Wonderful! (1,002 reviews)

We liked everything!

Reviewed on 2025/11/29

The Orchards Hotel

222 Adams Rd Williamstown MA

25 min drive from Jiminy Peak Mountain Resort

Treat yourself to a luxury stay at The Orchards Hotel, where you can enjoy amenities like massage services, pillowtop beds, and more. The outdoor pool, restaurant, ...

A little dated. Restaurant shut down for renovations, disappointing

Reviewed on 2020/3/9

See all 1,482 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.