Stockbridge Vacations
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Find the Best Stockbridge Vacation Packages
Stockbridge Hotel Deals
The Red Lion Inn
30 Main Street Stockbridge MA
Fully refundableReserve now, pay when you stay
The price is ₩228,866 per night from May 18 to May 19
₩228,866
₩320,941 total
May 18 - May 19
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
Lovely and historic property. Friendly staff and very comfortable room. Dinner and breakfast were wonderful. We are repeat visitors.
Reviewed on May 11, 2026
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
26 Glendale Road, RR 183 Stockbridge MA
The price is ₩452,281 per night from May 25 to May 26
₩452,281
₩547,141 total
May 25 - May 26
includes taxes & fees
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
The price is ₩129,120 per night from May 24 to May 25
₩129,120
₩177,111 total
May 24 - May 25
includes taxes & fees
9/10 Wonderful! (931 reviews)
These are all 1 bedroom suites. There was plenty of room in kitchen cupboards for our groceries. The kitchen was well supplied with cooking utensils, dishes and glassware. The location is excellent with several grocery stores and restaurants close by. Everything was perfect except for the height ...
Reviewed on May 11, 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
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.
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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.
