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Exclusive Chesterwood Vacation Deals
Frequently asked questions
Top Chesterwood hotel deals
![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/09e63194_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
The Red Lion Inn
30 Main Street, Stockbridge, MA
The price is $152 per night
$152
per night
Jun 26 - Jun 27
A full-service spa, 3 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. You'll appreciate the gym, bar/lounge, and concierge services.
Pool
Spa
![The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/a6ceeb05_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
26 Glendale Road, RR 183, Stockbridge, MA
The price is $479 per night
$479
per night
Jun 20 - Jun 21
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this bed & breakfast. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a lobby fireplace are also on offer.
Pool
Breakfast included
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.