Hotels near Chesterwood
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Featured Hotels near Chesterwood

Classic Stockbridge Cottage
Stockbridge MA
0.26 mi from Chesterwood
Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
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
$335 nightly
The price is $374 total per night
$374 total
May 27 - May 28
Total with taxes and fees
Guests of The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood enjoy access to free WiFi in public areas, conference space, and a seasonal outdoor pool. Free parking is included with your stay. Front-desk staff can help with concierge services, and provide local restaurant recommendations. Other amenities at this luxury bed & breakfast include coffee/tea in a common area, a computer station, and a library.
Pool
Breakfast included

Secluded Family Home in Serene Stockbridge Woods
Stockbridge MA
1.11 mi from Chesterwood
At this vacation home, guests have access to a gym, laundry facilities, and barbecue grills. This smoke-free vacation home also has a garden.
Kitchen
Washer

Experienced Hosts, 10 min to Tanglewood, Quaint Berkshires Getaway
West Stockbridge MA
1.53 mi from Chesterwood
Guests of this vacation home enjoy features like a gym, a hot tub, and laundry facilities. Additional amenities include barbecue grills and a garden.
Hot Tub
Kitchen

Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
Stockbridge MA
1.57 mi from Chesterwood
Guests staying at this farm stay have access to laundry facilities, barbecue grills, and a garden.
Free WiFi
Air conditioning

Spacious & Modern Berkshires Getaway
Stockbridge MA
1.61 mi from Chesterwood
Guests staying at this vacation home enjoy a hot tub, laundry facilities, and barbecue grills.
Hot Tub
Kitchen

Hearth House | Prime Location!
Stockbridge MA
1.64 mi from Chesterwood
This vacation home features a sauna and barbecue grills. This smoke-free vacation home also has a garden.
Kitchen
Washer

Forest Views, Enclosed Patio in Secluded Modern Home | Woodland Zen by AvantStay
Stockbridge MA
1.65 mi from Chesterwood
Guests staying at this vacation home have access to laundry facilities, a garden, and barbecue grills. Staff members can help with accommodation requests, and provide concierge services.
Kitchen
Washer

The Red Lion Inn
30 Main Street Stockbridge MA
Free Cancellation
Reserve now, pay when you stay
2.06 mi from Chesterwood
$188 nightly
The price is $210 total per night
$210 total
May 27 - May 28
Total with taxes and fees
Guests of The Red Lion Inn have access to an outdoor pool, a gym, and free WiFi in public areas. If you drive, take advantage of free parking. The 24-hour front desk has multilingual staff ready to assist with dry cleaning/laundry, securing valuables, and concierge services. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this golf hotel include meeting rooms, a 24-hour business center, and coffee/tea in a common area.
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 | 783 hotels |
|---|---|
Lowest Price | $210 |
Highest Price | $374 |
Popular hotels | Classic Stockbridge Cottage, The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood, The Red Lion Inn, Secluded Family Home in Serene Stockbridge Woods, Experienced Hosts, 10 min to Tanglewood, Quaint Berkshires Getaway, Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10, Spacious & Modern Berkshires Getaway, Forest Views, Enclosed Patio in Secluded Modern Home | Woodland Zen by AvantStay, Hearth House | Prime Location! |
Recent Reviews

The Red Lion Inn
5/5 Excellent
"Lovely and historic property. Friendly staff and very comfortable room. Dinner and breakfast were wonderful. We are repeat visitors. "
A verified traveler stayed at The Red Lion Inn
Posted 3 days ago


