Stockbridge Packages (Flight + Hotel)
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Top hotels in Stockbridge
The Red Lion Inn
30 Main Street Stockbridge MA
The price is ฿5,119 per night from 28 May to 29 May
฿5,119
฿7,179 total
28 May - 29 May
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"The staff is wonderful!"
Reviewed on 17 May 2026
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
26 Glendale Road, RR 183 Stockbridge MA
The price is ฿10,793 per night from 2 Jun to 3 Jun
฿10,793
฿13,057 total
2 Jun - 3 Jun
includes taxes & fees
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is ฿2,852 per night from 31 May to 1 Jun
฿2,852
฿3,912 total
31 May - 1 Jun
includes taxes & fees
9/10 Wonderful! (942 reviews)
"the Kitchen appeared to be fully equiped. The only cpmplaint I have was there were no avaiable plugs for mt CPAP machine nect to the bed> Easy fix is to offit the room with a multi plug on the night table.or lamp with plugs. Also there were no USB charging ports. Otherwise the facility was great"
Reviewed on 19 May 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.
Popular places to visit
Berkshire Theatre Festival
You can enjoy a show at Berkshire Theatre Festival during your trip to Stockbridge. Wander the lakeside in this quaint area.
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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.
