Stockbridge Holidays
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Stockbridge Holiday
Our pick of the best Stockbridge Hotel Deals
The Red Lion Inn
30 Main Street Stockbridge MA
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,000 reviews)
great customer service
Reviewed on 18 Feb 2026
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
26 Glendale Road, RR 183 Stockbridge MA
The price is NZ$642 per night from 5 Apr to 6 Apr
NZ$642
5 Apr - 6 Apr
includes taxes & fees
9.2/10 Wonderful! (110 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
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is NZ$213 per night from 23 Mar to 24 Mar
NZ$213
23 Mar - 24 Mar
includes taxes & fees
9/10 Wonderful! (884 reviews)
This is our 3rd year staying here for my son’s birthday in March. Affordable and having the 2 rooms with a kitchen is so nice. My son’s favorite part is the pool which is always warm and clean, never smells too strong like some places. Hot tub feels amazing too. Will be back next year, or sooner ...
Reviewed on 22 Mar 2026
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.
Discover the most popular places to visit in Stockbridge
Norman Rockwell Museum
5/5(1 review)
You can spend time browsing the exhibits at Norman Rockwell Museum during your trip to 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
