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Top Trending Hotels Near Chesterwood

Tanglewood Suites

2.5 star property
7.4 out of 10, Good, (18)
"Made a Friday night reservation for their 2BR suite in August. When we arrived at the location listed on Expedia, we found ourselves in a residential neighborhood with no "Tanglewood Suites" in sight. I had emailed in advance for clarification on the location but didn't get a reply. We called the place and the proprietor said there was no record of a reservation and that she never rents for one night only. We were left high and dry with no reasonably priced play to stay in the area. "
The price is £198
includes taxes & fees
25 Aug - 26 Aug
Tanglewood Suites

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (726)
"Was the perfect stop over for our way home. All the employees were extremely friendly. "
The price is £138
includes taxes & fees
25 Aug - 26 Aug
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
7.6 out of 10, Good, (540)
"Excellent location, friendly service, clean, comfortable room."
The price is £62
includes taxes & fees
1 Sept - 2 Sept
Travelodge by Wyndham Great Barrington Berkshires

East Rock Inn

2.0 star property
9.4 out of 10, Exceptional, (29)
"Quit eat and comfortable "
The price is £124
includes taxes & fees
15 Sept - 16 Sept
East Rock Inn

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (368)
"We returned to the Chambery Inn to celebrate my wife's birthday and the Memorial Day weekend. We were very happy with our choice. We stayed in a beautiful room (203), which included a spacious sitting area and a well-appointed bath. The breakfast were nicely prepared and presented. The Inn provided timely information prior and during our stay. We will be back in the future. "
Chambery Inn

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1001)
"Lovely place. Excellent staff, Wonderful breakfast."
The price is £134
includes taxes & fees
1 Sept - 2 Sept
The Cornell Inn, Lenox & The Berkshires

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (676)
"Fun place and very clean. Friendly staff and an amazing outdoor area to hang out."
The price is £132
includes taxes & fees
18 Aug - 19 Aug
Berkshires Untold

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1001)
"Best Quality- excellent location for dining - walk to restaurants. "
The price is £90
includes taxes & fees
1 Sept - 2 Sept
Quality Inn

The Whitlock

2.0 star property
8.6 out of 10, Excellent, (263)
"Wonderful ambience and people!"
The price is £146
includes taxes & fees
7 Sept - 8 Sept
The Whitlock

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (622)
"It was lovely!"
The price is £53
includes taxes & fees
1 Sept - 2 Sept
Econo Lodge Lee - Great Barrington

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (15)
"Really enjoyed my stay here, definitely need a car to get around"
The price is £111
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

The Dewey

3.5 star property
8.8 out of 10, Excellent, (321)
"excellent stay!! The Dewey is a cozy getaway location!"
The price is £145
includes taxes & fees
10 Sept - 11 Sept
The Dewey

Sunset Inn

2.0 star property
7.6 out of 10, Good, (400)
"No frills but it was a great stay!"
The price is £82
includes taxes & fees
2 Sept - 3 Sept
Sunset Inn

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (566)
"Amazing place to stay. Can’t wait to go again. "
Berkshire Mountain Lodge

Berkshire Travel Lodge

2.5 star property
5.4 out of 10, (432)
"Beautiful scenery. Room was not fancy but comfortable and clean. "
The price is £56
includes taxes & fees
19 Aug - 20 Aug
Berkshire Travel Lodge

Element Lenox Berkshires

3.0 star property
9.6 out of 10, Exceptional, (4)
"New hotel very nice"
The price is £125
includes taxes & fees
1 Sept - 2 Sept
Element Lenox Berkshires

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (639)
"It’s a three star hotel charging 5 star prices. They should include free breakfast."
The price is £124
includes taxes & fees
7 Sept - 8 Sept
Hilton Garden Inn Lenox Pittsfield

Little Cat Lodge

2.0 star property
9.4 out of 10, Exceptional, (55)
"Loved staying here. It was a beautiful room, clean and modern. Loved having a balcony to sit on at night. The breakfast was excellent and the service with a smile was great. Would love to come back again. "
The price is £148
includes taxes & fees
19 Aug - 20 Aug
Little Cat Lodge

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1001)
"Very clean rooms and excellent staff."
The price is £98
includes taxes & fees
1 Sept - 2 Sept
Best Western Plus Berkshire Hills Inn & Suites

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (785)
"My stay was perfect. I can't wait to stay there again. "
The price is £65
includes taxes & fees
1 Sept - 2 Sept
Howard Johnson by Wyndham Lenox
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

Destinations near South Lee

Tanglewood Music Center
Tanglewood Music Center

Tanglewood Music Center

You can make plans for a show at Tanglewood Music Center during your stay in Lenox. While you're in the area, stroll along the lakeside.

Animagic Museum of Animation

Animagic Museum of Animation

You can spend an afternoon browsing the exhibits at Animagic Museum of Animation during your travels in Lee. Amble around the area's gardens or attend a sporting event.

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 9 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. Other good choices within a few miles include The Red Lion Inn and Tanglewood Suites.

How many hotels will I find near Chesterwood?

Expedia has 9 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 Charles H. Baldwin & Sons while you're out sightseeing near Chesterwood.