Customized for your search:

Chesterwood Hotels in The Berkshires, MA

The Berkshires hotels
The Berkshires

Top Trending Hotels Near Chesterwood

Stockbridge Country Inn - Stockbridge Hotels
Rating: 3.5 Stars
Check availability

Stockbridge Country Inn

26 Glendale Road, Stockbridge 01262 - Map
 
 
4.7 out of 5 (18 reviews)
Situated in Stockbridge, this bed & breakfast is within 1 mi (2 km) of Chesterwood and Norman Rockwell Museum. Berkshire …More
The Red Lion Inn - Stockbridge Hotels
Rating: 3.0 Stars
Check availability

The Red Lion Inn

30 Main Street, Stockbridge 01262 - Map
 
 
4.7 out of 5 (30 reviews)
Situated in the historical district, this historic hotel is within a 15-minute walk of Mission House, Berkshire Theatre …More
1862 Seasons on Main Bed and Breakfast - Stockbridge Hotels
Rating: 4.5 Stars
Check availability

1862 Seasons on Main Bed and Breakfast

47 Main Street, Stockbridge 01262 - Map
 
 
Situated in Stockbridge, this romantic bed & breakfast is within 1 mi (2 km) of Mission House, Berkshire Theatre Festival …More
Pleasant Valley Motel West Stockbridge - West Stockbridge Hotels
Rating: 2.0 Stars
Check availability

Pleasant Valley Motel West Stockbridge

42 Stockbridge Rd, West Stockbridge 01266 - Map
 
 
3.6 out of 5 (376 reviews)
Situated in West Stockbridge, this motel is 2.4 mi (3.8 km) from Berkshire Botanical Garden and within 6 mi (10 km) of Norman …More
The Briarcliff Motel - Great Barrington Hotels
Rating: 2.0 Stars
$140
Check availability

The Briarcliff Motel

506 Stockbridge Road, Great Barrington 01230 - Map
 
 
4.7 out of 5 (30 reviews)
Situated in Great Barrington, this motel is within 6 mi (10 km) of Mission House, Berkshire Theatre Festival, and Naumkeag …More
Federal House Inn - Lee Hotels
Rating: 3.5 Stars
Check availability

Federal House Inn

1560 Pleasant Street, Lee 01260 - Map
 
 
4.7 out of 5 (59 reviews)
Situated in Lee, this bed & breakfast is 1.2 mi (2 km) from Berkshire Theatre Festival and within 3 mi (5 km) of Mission …More
Shaker Mill Inn - West Stockbridge Hotels
Rating: 2.5 Stars
Check availability

Shaker Mill Inn

7 Albany Road, West Stockbridge 01266 - Map
 
 
4.7 out of 5 (71 reviews)
Located in the heart of West Stockbridge, this bed & breakfast is within 6 mi (10 km) of Berkshire Botanical Garden, Norman …More
Holiday Inn Express Hotel & Suites Great Barrington - Great Barrington Hotels
Rating: 2.5 Stars
Check availability

Holiday Inn Express Hotel & Suites Great Barrington

415 Stockbridge Rd, Great Barrington 01230 - Map
 
 
4.2 out of 5 (143 reviews)
Situated in Great Barrington, this hotel is within 6 mi (10 km) of Mahaiwe Performing Arts Center, Lake Mansfield Park, and …More
Travelodge Great Barrington Berkshires - Great Barrington Hotels
Rating: 2.0 Stars
Check availability

Travelodge Great Barrington Berkshires

400 Stockbridge Rd, Great Barrington 01230 - Map
 
 
3.2 out of 5 (154 reviews)
Situated in Great Barrington, this motel is within 6 mi (10 km) of Mahaiwe Performing Arts Center, Lake Mansfield Park, and …More
Thornewood Inn - Great Barrington Hotels
Rating: 3.5 Stars
Check availability

Thornewood Inn

453 Stockbridge Road, Great Barrington 01230 - Map
 
 
4.0 out of 5 (2 reviews)
Situated in a rural location, this inn is 2.7 mi (4.4 km) from Mahaiwe Performing Arts Center and 3 mi (4.8 km) from Lake …More

Search from 74 Hotels Near Chesterwood, The Berkshires


    Need help booking?

    Call 1-800-551-2409
    Visit Customer Support »

    Why book with Expedia ?

    • 510,000+ hotels worldwide
    • No Expedia Cancellation Fee
    • Best price guarantee
    • 91% customer satisfaction

    Chesterwood, The Berkshires Hotel Guide

    Marvel at the sights, revel in the sounds, and soak up the local atmosphere: When you book a room at the best The Berkshires hotels near Chesterwood, you’ll be in the top spot to do it all. Chesterwood hotels are known for their unbeatable locations and tourist-friendly amenities, and the range of must-stay hotels lets you customize your vacation to suit your unique needs.

    Read More

    Browse Expedia’s selection and check out the best hotels close to Chesterwood for the world-class spas and restaurants, or snatch up one of the cheap hotel deals near Chesterwood, if you’re searching for an inexpensive retreat. You might even find some seasonal rates and discounts on the most highly rated accommodations right here on Expedia. Whether you’re jetting off for business or are traveling for pleasure, scoring a cheap deal on Chesterwood hotels in The Berkshires provides an incredible opportunity to discover the city with cash to spare.

    Hide
    Customers Rate Expedia
    Powered by feefo
    91% recommended
    4.5
    From 29,939 Reviews