Book a hotel near Chesterwood, South Lee
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Top hotels close to Chesterwood
Classic Stockbridge Cottage
Stockbridge MA
0.26 mi from Chesterwood
This vacation home features a garden, laundry facilities, and barbecue grills.
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
26 Glendale Road, RR 183 Stockbridge MA
0.4 mi from Chesterwood
$414 nightly
The price is $462 total per night
$462 total
Jan 13 - Jan 14, 2026
Total with taxes and fees
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
Tranquil 3 BR Stockbridge House w/ Private Deck!
South Lee MA
0.85 mi from Chesterwood
Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.
Kitchen
Pet friendly
Secluded Family Home in Serene Stockbridge Woods
Stockbridge MA
1.11 mi from Chesterwood
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Modern Log Cabin with Saltwater Pool & Mountain Views By Evergreen Home
West Stockbridge MA
1.15 mi from Chesterwood
This vacation home features a gym and a hot tub. A garden and barbecue grills are also provided.
Prime Location and Charm – 5 Mins to Tanglewood & Best Berkshire Attractions
Stockbridge MA
1.45 mi from Chesterwood
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Glendale MA
1.54 mi from Chesterwood
Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.
Kitchen
Pet friendly
Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
Stockbridge MA
1.57 mi from Chesterwood
This farm stay features a garden, laundry facilities, and barbecue grills.
Free WiFi
Air conditioning
Spacious & Modern Berkshires Getaway
Stockbridge MA
1.61 mi from Chesterwood
A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.
Hot Tub
Kitchen
Secluded + Modern | Enclosed Patio, Forest Views | Woodland Zen by AvantStay
Stockbridge MA
1.65 mi from Chesterwood
This vacation home features a garden, laundry facilities, and concierge services. Barbecue grills are provided for your convenience.
Kitchen
Washer
Woodland Zen by Avantstay Modern Design + Patio
58 Glendale Rd Housatonic MA
1.65 mi from Chesterwood
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace and barbecue grills are also provided.
Kitchen
Washer
The Red Lion Inn
30 Main Street Stockbridge MA
Free Cancellation
Reserve now, pay when you stay
2.06 mi from Chesterwood
$176 nightly
The price is $197 total per night
$197 total
Jan 20 - Jan 21, 2026
Total with taxes and fees
This smoke-free hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.
Pool
Spa
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.
Chesterwood hotels essential information
Accommodation | 742 hotels |
|---|---|
Lowest Price | $197 |
Highest Price | $462 |
Popular hotels | The Red Lion Inn, The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood, Classic Stockbridge Cottage, Tranquil 3 BR Stockbridge House w/ Private Deck!, Secluded Family Home in Serene Stockbridge Woods, Modern Log Cabin with Saltwater Pool & Mountain Views By Evergreen Home, Prime Location and Charm – 5 Mins to Tanglewood & Best Berkshire Attractions, Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10, 1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge, Spacious & Modern Berkshires Getaway, Secluded + Modern | Enclosed Patio, Forest Views | Woodland Zen by AvantStay, Woodland Zen by Avantstay Modern Design + Patio |
Recent Chesterwood hotel reviews by fellow wanderers
The Red Lion Inn
5 out of 5
Posted 4 days ago
Travelocity Verified Review
"Wonderful stay in a winter wonderland that evening especially with use of the heated pool and hot tub being maintained! Loved it.
Shops inside were lovely as well, bars & restaurant on-site were fun with quirky decor. Whole hotel is quirky, which is fun!"
A verified traveler stayed at The Red Lion Inn
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