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Kid-Friendly Hotels in Stockbridge

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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
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
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
Book a stay at this luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Chesterwood and Norman Rockwell Museum ...
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
See all 1,346 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 B&B in Lee. Enjoy free breakfast, free WiFi, and free parking. Popular attractions National Shrine of the Divine Mercy and Berkshire Theatre Festival ...
9.6/10 Exceptional! (99 reviews)
Great spot close to town. Cozy, tasteful, comfortable room. Nice breakfasts and pleasant interaction with the staff. We love the Berkshires and we’ll definitely stay here again.

Reviewed on Nov 24, 2025

The Inn at Stockbridge
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
8.8/10 Excellent! (1,002 reviews)
Quaint Inn located in the Berkshire. Dinner in the tavern was delish. The main inn lobby has plenty of seating to lounge around and people watch. We enjoyed our stay.

Reviewed on Nov 20, 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
Book a stay at this luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Chesterwood and Norman Rockwell Museum ...
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 Oct 27, 2025

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
See all 1,346 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
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
The Red Lion Inn
See all 1,346 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.