Western Massachusetts Luxury Vacations
Book a Luxury Hotel + Flight or Car together to unlock savings
Photo by Photo courtesy of Berkshire Visitors Bureau
- 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 ...
"The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer ..."
Reviewed on Jul 27, 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! (1,002 reviews)
"Best place to stay in Northampton!!!"
Reviewed on Jun 21, 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.