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Featured Stockbridge Family Hotels

The Red Lion Inn
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
The Red Lion Inn
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 out of 5
26 Glendale Road, RR 183, Stockbridge, MA
Stay at this 4.5-star luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Chesterwood ...
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
See all 1,307 properties in Stockbridge
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.

Hotels with Pools in Stockbridge

The Inn at Stockbridge
The Inn at Stockbridge
4 out of 5
30 East Street, Lee, MA
Stay at this 4-star B&B in Lee. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and National Shrine of the Divine ...
9.6/10 Exceptional! (98 reviews)
"We we were in the Out of Africa room, set apart in a complex of 4 suites in a unit apart from the Inn itself. The room was uniquely created to feel like an escape to Africa, and heated by a lovely gas fireplace. The breakfast both mornings, delicious. A perfect getaway!"

Reviewed on Feb 18, 2025

The Inn at Stockbridge
The Red Lion Inn
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
8.8/10 Excellent! (1,003 reviews)
"Love the history and ambiance. Service excellent. Restaurant dinner just fair. Clean rooms. Guests should not have to pay for music in the bar. Parking good. Very quiet."

Reviewed on Feb 22, 2025

The Red Lion Inn
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 out of 5
26 Glendale Road, RR 183, Stockbridge, MA
Stay at this 4.5-star luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Chesterwood ...
9.2/10 Wonderful! (80 reviews)
"The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer ..."

Reviewed on Jul 27, 2024

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
See all 1,307 properties in Stockbridge
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.

Hotels With Connecting Rooms in Stockbridge

The Red Lion Inn
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
The Red Lion Inn
See all 1,307 properties in Stockbridge
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.