Stockbridge Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥109,000 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

Find the Best Stockbridge Vacation Packages

Stockbridge Hotel Deals

The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Fully refundableReserve now, pay when you stay
The price is ￥22,573 per night from May 19 to May 20
￥22,573
￥32,215 total
May 19 - May 20
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
Everything was great

Reviewed on May 9, 2026

The Red Lion Inn
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
The price is ￥48,488 per night from May 27 to May 28
￥48,488
￥58,658 total
May 27 - May 28
includes taxes & fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is ￥13,744 per night from May 24 to May 25
￥13,744
￥18,851 total
May 24 - May 25
includes taxes & fees
9/10 Wonderful! (926 reviews)
Room very spacious and clean. Full kitchen is a great bonus.

Reviewed on May 4, 2026

Berkshire Mountain Lodge
See all 1,382 properties in Stockbridge
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.

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.