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, a garden, 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
$389 nightly
The price is $434 total per night
$434 total
Dec 12 - Dec 13
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 tours or tickets, 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

3-bedroom duplex in Stockbridge on the river
Stockbridge MA
0.43 mi from Chesterwood
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has a garden.
Kitchen
Washer

Secluded Family Home in Serene Stockbridge Woods
Stockbridge MA
1.11 mi from Chesterwood
$533 nightly
The price is $595 total per night
$595 total
Nov 16 - Nov 17
Total with taxes and fees
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

Refined Berkshires Haven. Between Stockbridge & Lenox. Nature, Arts & Wellness
Stockbridge MA
1.45 mi from Chesterwood
Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer

Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
Stockbridge MA
1.57 mi from Chesterwood
Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer

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, barbecue grills, and a garden. 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
$197 nightly
The price is $220 total per night
$220 total
Nov 29 - Nov 30
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 tours or tickets, luggage storage, and dry cleaning/laundry. 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 | 772 hotels |
|---|---|
Lowest Price | $220 |
Highest Price | $595 |
Popular hotels | Classic Stockbridge Cottage, The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood, The Red Lion Inn, 3-bedroom duplex in Stockbridge on the river, Secluded Family Home in Serene Stockbridge Woods, Refined Berkshires Haven. Between Stockbridge & Lenox. Nature, Arts & Wellness, Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10, Hearth House | Prime Location!, Forest Views, Enclosed Patio in Secluded Modern Home | Woodland Zen by AvantStay |
Recent Reviews

Classic Stockbridge Cottage
5/5 Excellent
"The house was very spacious and"
A verified traveler stayed at Classic Stockbridge Cottage
Posted 2 weeks ago


