Stockbridge Vacation Packages
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Your Stockbridge Vacation
With a Stockbridge vacation package, say goodbye to endless planning and hello to hassle-free adventure. Every detail of your escape has been taken care of before departing, so you can make the most of your time experiencing this lively city. Eager to venture out and explore? Tanglewood Music Center, National Shrine of the Divine Mercy and Lee Premium Outlets are three of the best places to visit during your trip to Stockbridge. Your perfect Stockbridge vacation is a couple of clicks away. Browse hotels, airfares and more on Expedia for a getaway that's tailored just for you.
Stockbridge Hotel Deals
The Red Lion Inn
Great stay. The only thing I would say - and I’ve been staying at the hotel since the 80s - it might be time for a few updates here and there. It runs the risk of going from rustic charm to grandma’s house in the not tooooo distant future.
Reviewed on Jan 29, 2026
Vacation Village in the Berkshires
Spacious 2 bed 2 bath!
Reviewed on Feb 3, 2026
Berkshire Mountain Lodge
The doors wouldn’t stay locked
Reviewed on Feb 6, 2026
Discover the most popular places to visit in Stockbridge
Norman Rockwell Museum
You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area.
National Shrine of the Divine Mercy
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 browsing the exhibits at Naumkeag Museum during your travels in Stockbridge. While you're in the area, stroll along the lakeside.
