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$250 per night from 7 Apr to 8 Apr
S$250
7 Apr - 8 Apr
includes taxes & fees
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 S$481 per night from 14 Apr to 15 Apr
S$481
14 Apr - 15 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 S$153 per night from 27 Apr to 28 Apr
S$153
27 Apr - 28 Apr
includes taxes & fees
9/10 Wonderful! (888 reviews)
very clean and friendly staff
Reviewed on 24 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.
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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.
