Western Massachusetts Luxury Vacations

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Top Luxury Western Massachusetts Hotels

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

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

4.5 out of 5
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

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

Hotel Northampton

3.5 out of 5
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

Hotel Northampton
The Orchards Hotel

The Orchards Hotel

2.5 out of 5
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

The Orchards Hotel
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.