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$257 per night from 14 Jan to 15 Jan
S$257
14 Jan - 15 Jan, 2026
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
Old time charm and hot tub under the stars
Reviewed on 15 Dec, 2025
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
26 Glendale Road, RR 183 Stockbridge MA
The price is S$596 per night from 5 Jan to 6 Jan
S$596
5 Jan - 6 Jan, 2026
includes taxes & fees
9.2/10 Wonderful! (85 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
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
The price is S$164 per night from 4 Jan to 5 Jan
S$164
4 Jan - 5 Jan, 2026
includes taxes & fees
8.6/10 Excellent! (2,170 reviews)
Awesome for ski
Reviewed on 14 Dec, 2025
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.
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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.
