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Check prices for these dates

Tonight
20 Jan - 21 Jan
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21 Jan - 22 Jan
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23 Jan - 25 Jan
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30 Jan - 1 Feb

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Our top choices for Chesterwood hotels

Suite, Private Bathroom (RedBird Suite) | View from room

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
0.6 km from Chesterwood
9.2 out of 10, Wonderful, (110 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is ₹28,121
₹34,019 total
includes taxes & fees
15 Feb - 16 Feb
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
3.3 km from Chesterwood
8.8 out of 10, Excellent, (1,003 reviews)
"All was great! The atmosphere, food, and rooms were very clean. "
United States
Brent
The price is ₹13,100
₹18,692 total
includes taxes & fees
25 Jan - 26 Jan
The Red Lion Inn
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
5.8 km from Chesterwood
9.6 out of 10, Exceptional, (443 reviews)
"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"
United States
Carin
The price is ₹9,112
₹9,996 total
includes taxes & fees
25 Jan - 26 Jan
Shaker Mill Inn
Individually decorated, individually furnished, desk, laptop workspace

Granville House

Granville House
3.0 star property
6.4 km from Chesterwood
10.0 out of 10, Exceptional, (92 reviews)
"Absolutely magical at Christmas time! It was only for a quick overnight but felt like time stood still while we were there. The service was impeccable and Terry and Terri were a delight! I look forward to returning. "
United States
Jennifer
The price is ₹15,811
₹17,661 total
includes taxes & fees
22 Jan - 23 Jan
Granville House
Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
6.6 km from Chesterwood
9.0 out of 10, Wonderful, (824 reviews)
"Great overnights stay, wish I was here longer "
United States
Thomas
The price is ₹10,223
₹13,195 total
includes taxes & fees
22 Jan - 23 Jan
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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, (723 reviews)
"Always love staying here. The staff is fantastic, amenities are great, and the breakfast is just lovely. Will be returning soon!"
United States
Domenic
The price is ₹7,815
₹8,729 total
includes taxes & fees
22 Jan - 23 Jan
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
8.6 km from Chesterwood
9.4 out of 10, Exceptional, (763 reviews)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
The price is ₹13,721
₹15,326 total
includes taxes & fees
25 Jan - 26 Jan
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Exterior

The Little Lion

The Little Lion
3.0 star property
5.1 km from Chesterwood
8.6 out of 10, Excellent, (549 reviews)
"Perfect for pets "
United States
Maria
The price is ₹9,995
₹11,165 total
includes taxes & fees
21 Jan - 22 Jan
The Little Lion
Lake

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
8.6 km from Chesterwood
9.0 out of 10, Wonderful, (1,003 reviews)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is ₹9,196
₹10,272 total
includes taxes & fees
29 Jan - 30 Jan
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Front of property – evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
7.5 km from Chesterwood
10.0 out of 10, Exceptional, (134 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
8.7 km from Chesterwood
9.0 out of 10, Wonderful, (817 reviews)
"Unbelieveably clean for the price."
United States
Micah
Monument Mountain Motel
Front of property

Chambery Inn

Chambery Inn
3.0 star property
8.7 km from Chesterwood
9.6 out of 10, Exceptional, (374 reviews)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
9.1 km from Chesterwood
8.4 out of 10, Very good, (1,001 reviews)
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is ₹7,260
₹8,110 total
includes taxes & fees
5 Feb - 6 Feb
Quality Inn Lee - Lenox South
In-room safe, desk, free cots/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
6.2 km from Chesterwood
7.6 out of 10, Good, (566 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is ₹6,815
₹7,613 total
includes taxes & fees
21 Jan - 22 Jan
Travelodge by Wyndham Great Barrington Berkshires
Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

East Rock Inn

East Rock Inn
2.0 star property
10.1 km from Chesterwood
9.6 out of 10, Exceptional, (37 reviews)
"The room was clean and comfortable wi will back next year:) "
United States
Nadya
The price is ₹11,336
₹12,662 total
includes taxes & fees
25 Jan - 26 Jan
East Rock Inn
Desk, laptop workspace, blackout curtains, iron/ironing board

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
4.7 km from Chesterwood
6.8 out of 10, (1,001 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is ₹5,316
₹5,831 total
includes taxes & fees
21 Jan - 22 Jan
Pleasant Valley Motel West Stockbridge
Lobby lounge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
12.5 km from Chesterwood
9.8 out of 10, Exceptional, (16 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is ₹12,631
₹14,108 total
includes taxes & fees
26 Jan - 27 Jan
Element Lenox Berkshires
Front of property

Brook Farm Inn

Brook Farm Inn
3.5 star property
9.1 km from Chesterwood
9.4 out of 10, Exceptional, (164 reviews)
"Everything was perfect - location and accommodation."
United States
Christopher
Brook Farm Inn
Exterior

The Whitlock

The Whitlock
2.0 star property
9.8 km from Chesterwood
8.6 out of 10, Excellent, (286 reviews)
"Super cute place and walking distance to a bunch of great shops and food! "
United States
Gina
The price is ₹11,722
₹13,093 total
includes taxes & fees
23 Jan - 24 Jan
The Whitlock
In-room dining

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
7.4 km from Chesterwood
6.4 out of 10, (654 reviews)
"The room was clean and the service adequate"
United States
David
The price is ₹6,134
₹6,851 total
includes taxes & fees
26 Jan - 27 Jan
Econo Lodge Lee - Great Barrington
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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"Very good "
Fernando 5-night trip
Posted 2 weeks ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Hotels near other Chesterwood attractions

Norman Rockwell Museum

4.7/5 (252 reviews)
You can spend time browsing the exhibits at Norman Rockwell Museum during your trip to Stockbridge. Wander the lakeside in this quaint area.
See properties

Berkshire Botanical Garden

4.0/5 (1 review)
Explore the great outdoors at Berkshire Botanical Garden, a lovely green space in Stockbridge. While you're in the area, stroll along the lakeside.
See properties

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

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