Find hotels near Chesterwood, South Lee from AED 281

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Our top choices for Chesterwood hotels

Granville House

Granville House
3.0 star property
6.4 km from Chesterwood
10.0 out of 10, Exceptional, (101 reviews)
"Beautiful home with warm and friendly hosts. The rooms were tastefully designed, the bed was very comfortable and the large bathroom was luxurious. The breakfast was absolutely delicious. We will definitely stay again next time we are in Great Barrington. "
United States
Nicole
The price is AED 1,010
AED 1,128 total
includes taxes & fees
1 Jun - 2 Jun
Granville House

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
5.2 km from Chesterwood
9.8 out of 10, Exceptional, (99 reviews)
"Well-run and elegant property. "
United States
Steven
The price is AED 965
AED 1,132 total
includes taxes & fees
25 May - 26 May
The Inn at Stockbridge

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
7.5 km from Chesterwood
10.0 out of 10, Exceptional, (138 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is AED 1,172
AED 1,309 total
includes taxes & fees
25 May - 26 May
Devonfield Inn B&B

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
5.8 km from Chesterwood
9.6 out of 10, Exceptional, (456 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is AED 375
AED 411 total
includes taxes & fees
26 May - 27 May
Shaker Mill Inn

33 Main

33 Main
4.0 star property
9.8 km from Chesterwood
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is AED 2,399
AED 2,679 total
includes taxes & fees
22 May - 23 May
33 Main

Chambery Inn

Chambery Inn
3.0 star property
8.7 km from Chesterwood
9.6 out of 10, Exceptional, (376 reviews)
"Yes the room was spotless and always the staff is ready to answer any questions that we might have. We have been enjoying the Chambery Inn for many years always had a great stay and again looking for our next visit. Vincent Farricielli and Roibert Modena. "
United States
robert
The price is AED 628
AED 702 total
includes taxes & fees
24 May - 25 May
Chambery Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
3.3 km from Chesterwood
8.8 out of 10, Excellent, (1,000 reviews)
"a delightful inn centrally located in charming Stockbridge"
United States
molly
The price is AED 564
AED 794 total
includes taxes & fees
28 May - 29 May
The Red Lion Inn

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
10.9 km from Chesterwood
9.8 out of 10, Exceptional, (6 reviews)
"The new owners have done a great job. The place is immaculate, the room was very comfortable and well appointed, the common areas charming. Highly recommended."
United States
Robert
The price is AED 908
AED 1,014 total
includes taxes & fees
25 May - 26 May
The Berkshire Mountain Inn

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
9.2 out of 10, Wonderful, (898 reviews)
"Family friendly resort with amenities the whole family can enjoy!"
United States
Justina
The price is AED 426
AED 548 total
includes taxes & fees
25 May - 26 May
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
8.6 km from Chesterwood
9.4 out of 10, Exceptional, (780 reviews)
"Staff was lovely, everything was easy, clean and comfortable"
United States
Helena
The price is AED 621
AED 694 total
includes taxes & fees
27 May - 28 May
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

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
The price is AED 674
AED 782 total
includes taxes & fees
2 Jun - 3 Jun
Brook Farm Inn

Prospect Berkshires

Prospect Berkshires
3.0 star property
12.8 km from Chesterwood
9.8 out of 10, Exceptional, (26 reviews)
"Excellent local stay - would recommend to all"
United States
Gentian
The price is AED 1,229
AED 1,496 total
includes taxes & fees
25 May - 26 May
Prospect Berkshires

East Rock Inn

East Rock Inn
2.0 star property
10.1 km from Chesterwood
9.4 out of 10, Exceptional, (45 reviews)
"The East Rock Inn is great. It's comfortable, clean and close to downtown Great Barrington. This was my second time staying here."
United States
Laura
The price is AED 497
AED 556 total
includes taxes & fees
4 Jun - 5 Jun
East Rock Inn

The Little Lion

The Little Lion
3.0 star property
5.1 km from Chesterwood
8.6 out of 10, Excellent, (561 reviews)
"Avoid this place."
United States
Carole
The price is AED 349
AED 390 total
includes taxes & fees
11 Jun - 12 Jun
The Little Lion

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
12.5 km from Chesterwood
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is AED 584
AED 652 total
includes taxes & fees
28 May - 29 May
Element by Marriott Lenox Berkshires

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, (1,001 reviews)
"We enjoyed our stay at the Black Swan and sitting on our balcony with a view of the lake. "
United States
Susan
The price is AED 446
AED 498 total
includes taxes & fees
1 Jun - 2 Jun
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
8.7 km from Chesterwood
9.0 out of 10, Wonderful, (856 reviews)
"Very clean and cozy in a great location! "
United States
Lidia
The price is AED 251
AED 281 total
includes taxes & fees
25 May - 26 May
Monument Mountain Motel

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, (766 reviews)
"Above average hotel breakfast. Very clean hotel."
United States
Helen
The price is AED 422
AED 472 total
includes taxes & fees
25 May - 26 May
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
9.8 km from Chesterwood
9.0 out of 10, Wonderful, (44 reviews)
"Comfortable bed. Quiet location. Excellent breakfast. Friendly host."
United States
Kathleen
The price is AED 1,006
AED 1,124 total
includes taxes & fees
25 May - 26 May
Hampton Terrace Inn

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
12.1 km from Chesterwood
9.2 out of 10, Wonderful, (625 reviews)
"Beautiful outdoor space. "
United States
Jairo
The price is AED 584
AED 653 total
includes taxes & fees
27 May - 28 May
Courtyard by Marriott Lenox Berkshires
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.

Compare popular hotels close to Chesterwood

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet friendly
WiFi included
Individually decorated, individually furnished, desk, laptop workspace
Granville House
3.0 star property
10.0
Exceptional
101 reviews
View
Front of property
The Inn at Stockbridge
4.0 star property
9.8
Exceptional
99 reviews
View
Front of property - evening/night
Devonfield Inn B&B
4.0 star property
10.0
Exceptional
138 reviews
View
Garden
Shaker Mill Inn
2.5 star property
9.6
Exceptional
456 reviews
View
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main
4.0 star property
10.0
Exceptional
74 reviews
View

Top Chesterwood Hotel Reviews

Hotels near other Chesterwood attractions

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, check out the 10 hotels and other accommodations you'll find within a mile.
What's the best hotel 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 traveler 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 are there close to Chesterwood?
Expedia has 10 hotels and other accommodations within a mile from Chesterwood.
If I need to cancel the hotel reservation for my stay near Chesterwood, will I receive a refund?
Yes, the majority of room reservations are fully refundable provided that you cancel before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you have a non-refundable reservation, you might be able to still cancel and be given a refund within 24 hours of booking. Enter dates in and click on "Search", then use the "fully refundable" filter to review the best options available near Chesterwood.
Where can I learn more about changing or cancelling my trip in the area near Chesterwood?
For more information about picking new dates or cancelling your stay near Chesterwood, head over to our customer service page.
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.