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South Lee Chesterwood Hotels

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Check prices for these dates

This weekend
19 Jun - 21 Jun
Next weekend
26 Jun - 28 Jun

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Star rating

Our top choices for Chesterwood hotels

Exterior

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8 km from Chesterwood
8.8 out of 10, Excellent, (773 reviews)
"very responsive staff excellent check in and check out"
United States
Kathleen
The price is HK$1,168
HK$1,304 total
includes taxes & fees
29 Jun - 30 Jun
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
10.7 km from Chesterwood
9.2 out of 10, Wonderful, (1,002 reviews)
"Great place, nice amenities and convenient location, highly recommended."
United States
Arthur
The price is HK$1,308
HK$1,505 total
includes taxes & fees
22 Jun - 23 Jun
The Cornell Inn, Lenox & The Berkshires
Restaurant

Little Cat Lodge

Little Cat Lodge
2.0 star property
16.3 km from Chesterwood
9.6 out of 10, Exceptional, (83 reviews)
"Excellent lodge, recommend."
United States
Jason
The price is HK$1,728
HK$1,935 total
includes taxes & fees
2 Jul - 3 Jul
Little Cat Lodge
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
19.8 km from Chesterwood
8.0 out of 10, Very good, (1,002 reviews)
"Quiet room. Comfortable bed linens"
United States
Margo
The price is HK$995
HK$1,112 total
includes taxes & fees
29 Jun - 30 Jun
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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.
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Top Chesterwood Hotel Reviews

The Red Lion Inn

The Red Lion Inn

8/10 Good
"We thought we were booking a room at the Inn and expected to eat in the restaurant after a long day of travel. Our room was actually around the corner in an old house. ?We were underdressed for the restaurant (jeans, sneakers, decent shirts) and ate in the pub in the basement."
Doug 1-night trip
Posted 3 days ago
The Red Lion Inn

Hotels near other Chesterwood attractions

Norman Rockwell Museum

9.4/5 (347 reviews)
You can spend time browsing the exhibits at Norman Rockwell Museum during your trip to Stockbridge. Wander the lakeside in this quaint area.
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Frequently asked questions

What's the area like around Chesterwood?
Chesterwood is located in a scenic area of South Lee known for its beautiful lakeside setting and hiking. If you're looking for a convenient place to stay, take a look at the 10 hotels and other accommodation options you'll find within a mile.
Where is the best place to stay close to Chesterwood?
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood is one of the top choices for your stay based on our traveller data, and this B&B offers free breakfast and free parking. It's located just a short 0.4 mi (0.6 km) from Chesterwood. Another good choice is The Red Lion Inn, located 2.1 mi (3.3 km) away.
How many hotels will I find near Chesterwood?
Expedia has 10 hotels and other accommodation options within a mile from Chesterwood.
If I need to cancel the hotel reservation for my stay near Chesterwood, will I receive a refund?
Yes! You'll find that most room reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you booked a non-refundable reservation, it might still be possible to cancel it and be given a refund within 24 hours of booking. Enter your dates, click on "Search", then you can filter by "fully refundable" to get the best options available near Chesterwood.
What can I see and do near Chesterwood?
You'll want to browse the exhibits at Norman Rockwell Museum and Mission House. Naumkeag Museum, The Mount and Berkshire Theatre Festival are monuments to see when you're exploring the area around Chesterwood. Be sure to get some family photos at Berkshire Botanical Garden, Hoffman's Pottery and Lenox Arts Center while you're out sightseeing near Chesterwood.