Stockbridge Packages (Flight + Hotel)
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ฿4,531 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Stockbridge
The Red Lion Inn
30 Main Street Stockbridge MA
Fully refundableReserve now, pay when you stay
The price is ฿4,624 per night from 26 Jan to 27 Jan
฿4,624
฿6,552 total
26 Jan - 27 Jan 2026
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
I had always wanted to stay at The Red Lion Inn and decided to treat myself to a one-night stay. Since it was in December I was especially excited to have a fireplace in the room. Sadly, I learned the fireplace didn’t work and that they are renovating some of the systems, but offered no partial refund ...
Reviewed on 23 Dec 2025
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
26 Glendale Road, RR 183 Stockbridge MA
The price is ฿11,853 per night from 11 Jan to 12 Jan
฿11,853
฿14,339 total
11 Jan - 12 Jan 2026
includes taxes & fees
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 27 Oct 2025
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is ฿3,227 per night from 4 Jan to 5 Jan
฿3,227
฿3,945 total
4 Jan - 5 Jan 2026
includes taxes & fees
8.6/10 Excellent! (2,182 reviews)
A great place for our family to use as a base while skiing at Jiminy Peak! The pool was a huge hit.
Reviewed on 24 Dec 2025
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.
Popular places to visit
Berkshire Theatre Festival
You can enjoy a show at Berkshire Theatre Festival during your trip to Stockbridge. Wander the lakeside in this quaint area.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
