Stockbridge Holidays
- Plan, book, travel with confidence
Better together
Save up to €185 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 hotels in Stockbridge
The Red Lion Inn
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is €226 per night from 30 Sept to 1 Oct
€226
30 Sept - 1 Oct
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"A great place if you appreciate and like history. The lobby is filled with antiques and the porch is great to rock in a chair and sip some wine. Parking is no issue and you can walk to local restaurants and shops."
Reviewed on 16 Sept 2025
Tanglewood Suites
MA-102, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is €228 per night from 21 Sept to 22 Sept
€228
21 Sept - 22 Sept
includes taxes & fees
6.4/10 (22 reviews)
"Bed was quite comfortable and the setting was in a beautiful neighborhood. Excellent proximity to Tanglewood. And host gave exceptional information regarding local eateries and things to do. I would have liked to have known at booking that the owner does not accept credit (as the hotels.com app allows ..."
Reviewed on 11 Aug 2025
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
26 Glendale Road, RR 183, Stockbridge, MA
The price is €318 per night from 6 Oct to 7 Oct
€318
6 Oct - 7 Oct
includes taxes & fees
"Very expensive for a small room. My son and I could barely sleep in this remote quiet place. Staffs were very friendly."
Reviewed on 2 Nov 2024
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
National Shrine of the Divine Mercy
3/5(1 review)
Learn about the local history of Stockbridge when you spend time at National Shrine of the Divine Mercy. While you're in the area, stroll along the lakeside.
Naumkeag Museum
You can spend time studying the exhibits at Naumkeag Museum in Stockbridge. While you're in the area, stroll along the lakeside.
Berkshire Botanical Garden
Explore the great outdoors at Berkshire Botanical Garden, a lovely green space in Stockbridge. While you're in the area, stroll along the lakeside.
More trip options
Expedia's Latest Trends
Hotels
Flights
Activities
Packages
Holiday Rentals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
