Stockbridge Holidays
Book a Hotel + Flight or Car together to unlock savings
Top hotels in Stockbridge
The Red Lion Inn
30 Main Street Stockbridge MA
Fully refundableReserve now, pay when you stay
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 8.153.916 ₫ per night from 8 Apr to 9 Apr
8.153.916 ₫
9.864.112 ₫ total
8 Apr - 9 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 2.465.312 ₫ per night from 29 Mar to 30 Mar
2.465.312 ₫
3.342.367 ₫ total
29 Mar - 30 Mar
includes taxes & fees
9/10 Wonderful! (885 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.
Popular places to visit
Norman Rockwell Museum
You can spend time browsing the exhibits at Norman Rockwell Museum during your trip to Stockbridge. Wander the lakeside in this quaint area.
Berkshire Botanical Garden
Explore the great outdoors at Berkshire Botanical Garden, a lovely green space in Stockbridge. While you're in the area, stroll along the lakeside.
Berkshire Theatre Festival
You can enjoy a show at Berkshire Theatre Festival during your trip to Stockbridge. Wander the lakeside in this quaint area.
