Stockbridge Holidays
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Top hotels in Stockbridge
The Red Lion Inn
30 Main Street Stockbridge MA
Fully refundableReserve now, pay when you stay
The price is S$294 per night from 20 Jul to 21 Jul
S$294
20 Jul - 21 Jul
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"Wonderful historic hotel. Beautiful property and absolutely lovely pool."
Reviewed on 26 Jun, 2026
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
26 Glendale Road, RR 183 Stockbridge MA
The price is S$517 per night from 27 Jul to 28 Jul
S$517
27 Jul - 28 Jul
includes taxes & fees
The Yankee Inn
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is S$184 per night from 6 Jul to 7 Jul
S$184
6 Jul - 7 Jul
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"The hot tub was welcomed after a long day of hiking the Berkshires!"
Reviewed on 26 Jun, 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.
Stay near popular Stockbridge attractions
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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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
