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.
Kitchen
Washer
Completely Renovated Historic Home in the Heart of the Berkshires
Glendale MA
0.36 mi from Chesterwood
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
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 5 - Jan 6, 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
Lofted Hideaway on Pixley Hill
West Stockbridge MA
1.1 mi from Chesterwood
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
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.
Pool
Hot Tub
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
Tanglewood Suites
MA-102 Stockbridge MA
Free Cancellation
Reserve now, pay when you stay
1.62 mi from Chesterwood
$219 nightly
The price is $219 total per night
$219 total
Dec 16 - Dec 17
Total with taxes and fees
A steam room, free self parking, and barbecue grills are featured at this bed & breakfast. Enjoy the free continental breakfast each morning. A garden and a picnic area are also provided.
Breakfast included
Parking included
The Red Lion Inn
30 Main Street Stockbridge MA
Free Cancellation
Reserve now, pay when you stay
2.06 mi from Chesterwood
$180 nightly
The price is $202 total per night
$202 total
Jan 6 - Jan 7, 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 | 744 hotels |
|---|---|
Lowest Price | $202 |
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, Completely Renovated Historic Home in the Heart of the Berkshires, Tranquil 3 BR Stockbridge House w/ Private Deck!, Secluded Family Home in Serene Stockbridge Woods, Lofted Hideaway on Pixley Hill, 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, Tanglewood Suites, 1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge |
Recent Chesterwood hotel reviews by fellow wanderers
The Red Lion Inn
5 out of 5
Posted 3 days ago
Travelocity Verified Review
"We had a very nice experience staying at the Red Lion Inn. Our room was upgraded when checking in which was a nice surprise. The hotel was beautifully decorated for the season. We loved the cozy feel of the fireplace in the lobby especially on such a cold day. "
A verified traveler stayed at The Red Lion Inn
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