Book a hotel near Chesterwood, West Stockbridge

Wander Wisely with the Travelocity Price Match Guarantee

Hotels near Chesterwood

Completely Renovated Historic Home in the Heart of the Berkshires

Stockbridge, MA

0.36 mi from Chesterwood

Get rates

This vacation home includes a garden and barbecue grills.

Stockbridge Country Inn

26 Glendale Road, RR 183, Stockbridge, MA

0.42 mi from Chesterwood

Get rates

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.

Tranquil 3BR Stockbridge House w/Private Deck

West Stockbridge, MA

0.85 mi from Chesterwood

Get rates

Situated in West Stockbridge, this vacation home is 0.9 mi (1.4 km) from Housatonic River and within 3 mi (5 km) of Norman Rockwell Museum and National Shrine of the Divine Mercy. Berkshire Botanical Garden and Chesterwood are also within 1 mi (2 km).

Gorgeous Home, Nature Lover's Delight in the Heart of the Berkshires

Housatonic, MA

1.52 mi from Chesterwood

Get rates

A gym is featured at this vacation home, along with a garden and barbecue grills. There's fun for all ages with a playground and an arcade/game room.

Tanglewood Suites

MA-102, Stockbridge, MA

Free Cancellation

Reserve now, pay when you stay

1.62 mi from Chesterwood

Get rates

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.

"Too Good" AKA 2 Goodrich St.

Stockbridge, MA

1.81 mi from Chesterwood

Get rates

This vacation home includes a garden and barbecue grills.

Beautifully Renovated Colonial Home

Housatonic, MA

1.89 mi from Chesterwood

Get rates

This vacation home includes a garden and barbecue grills.

A Grand Estate in Historic Stockbridge

Stockbridge, MA

1.89 mi from Chesterwood

Get rates

This vacation home includes a garden and barbecue grills.

The Red Lion Inn

30 Main Street, Stockbridge, MA

Free Cancellation

Reserve now, pay when you stay

2.06 mi from Chesterwood

Get rates

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.

Great house in Stockbridge

Stockbridge, MA

2.09 mi from Chesterwood

Get rates

Situated in Stockbridge, this vacation home is within 2 mi (3 km) of Housatonic River, National Shrine of the Divine Mercy, and Norman Rockwell Museum. Mission House and Naumkeag are also within 15 minutes.

One block from Main St Stockbridge

Stockbridge, MA

2.16 mi from Chesterwood

Get rates

Situated in Stockbridge, this vacation home is 0.4 mi (0.7 km) from Mission House and within 3 mi (5 km) of National Shrine of the Divine Mercy and Norman Rockwell Museum. Berkshire Theatre Festival and Naumkeag are also within 15 minutes.

Newly Renovated Home With All The Modern Amenities

Housatonic, MA

2.25 mi from Chesterwood

Get rates

Situated in Housatonic, this vacation home is 0.4 mi (0.6 km) from Housatonic River and 2.8 mi (4.5 km) from Chesterwood. Norman Rockwell Museum and National Shrine of the Divine Mercy are also within 6 mi (10 km).

Don't see what you're looking for?

See all available properties in Chesterwood

View all properties

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 Hotel & Travel Guide

Considering a trip to Chesterwood on your next vacation?

To reach it, make your way to Stockbridge, 110 miles (177 kilometers) from the state capital, Concord.

If you're just here to visit Chesterwood, it could be a good idea to get a room at the Stockbridge Country Inn. At 0.4 miles (0.6 kilometers) away, it's the closest hotel to the attraction.

The surrounding area's low-cost hotels offer an excellent standard of service while keeping their prices as low as can be. If you're not sure where to start, have a look at the Econo Lodge Lee - Great Barrington and the Travelodge Great Barrington Berkshires.

If you yearn for a touch of refinement, you are in luck. You will find a handful of high-end hotels that are a quick drive away. Great choices are the Hampton Terrace Inn and Devonfield Inn B&B.

Other Things to Do Near Chesterwood

You're here to experience Chesterwood, but you may well be just as pleased with what else the region has going on:

Responsible for the protection and display of valuable artworks, Norman Rockwell Museum is the ideal attraction for art lovers.
Berkshire Botanical Garden is a great place to spend a fine morning picnicking with your loved ones, tossing a ball around and admiring the plants and wildlife in the gardens.
Mission House is an excellent tourist attraction that's ideal for history fans.
Naumkeag is an outstanding local attraction that's tailor-made for history enthusiasts.
If you're looking to get in touch with your spirituality, plan a visit to National Shrine of the Divine Mercy, where you might want to join fellow worshipers and offer up prayers for happiness, health, good luck and more.