
Western Massachusetts Luxury Vacations
Book a Luxury Hotel + Flight or Car together to unlock savings
Photo by Groovy Trip
- Plan, book, travel with confidence
Better together
Save up to ₩234,741 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
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
Spoil yourself with classy accommodations at The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood, where you'll enjoy amenities ...
"Very expensive for a small room. My son and I could barely sleep in this remote quiet place. Staffs were very friendly."
Reviewed on Nov 2, 2024

Hotel Northampton
36 King Street, Northampton, MA
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! (1,001 reviews)
"Nice overall"
Reviewed on Aug 20, 2025

The Orchards Hotel
222 Adams Rd, Williamstown, MA
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 Mar 9, 2020
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.