Find hotels near Chesterwood, South Lee from AED 281

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Chesterwood hotels

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

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
10 May - 11 May
Chambery Inn

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
12.1 km from Chesterwood
10.0 out of 10, Exceptional, (28 reviews)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is AED 1,561
AED 1,713 total
includes taxes & fees
10 May - 11 May
Inn at Kenmore Hall

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, (779 reviews)
"Staff was lovely, everything was easy, clean and comfortable"
United States
Helena
The price is AED 653
AED 729 total
includes taxes & fees
20 May - 21 May
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Prospect Berkshires

Prospect Berkshires
3.0 star property
12.8 km from Chesterwood
9.8 out of 10, Exceptional, (25 reviews)
"Excellent local stay - would recommend to all"
United States
Gentian
The price is AED 1,463
AED 1,758 total
includes taxes & fees
17 May - 18 May
Prospect Berkshires

Element Lenox Berkshires

Element 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 613
AED 685 total
includes taxes & fees
20 May - 21 May
Element Lenox Berkshires

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
8.7 km from Chesterwood
9.0 out of 10, Wonderful, (849 reviews)
"Very clean and cozy in a great location! "
United States
Lidia
The price is AED 251
AED 281 total
includes taxes & fees
28 May - 29 May
Monument Mountain Motel

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)
"enjoy your vacation"
United States
lev
The price is AED 509
AED 586 total
includes taxes & fees
14 May - 15 May
The Cornell Inn, Lenox & The Berkshires

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, (760 reviews)
"Nice clean room, clean and well maintained breakfast was tasteful each day. Desk Clerk very helpful in giving out direction, Breaksfast person, very friendly. Hotel is centrally located, shop and restaurant nearby"
United States
Berdest
The price is AED 455
AED 509 total
includes taxes & fees
27 May - 28 May
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Little Cat Lodge

Little Cat Lodge
2.0 star property
16.3 km from Chesterwood
9.6 out of 10, Exceptional, (77 reviews)
"The room was very clean and was cleaned daily, staff was very friendly, breakfast buffet was excellent "
United States
John
The price is AED 559
AED 626 total
includes taxes & fees
11 May - 12 May
Little Cat Lodge

The Whitlock

The Whitlock
2.0 star property
9.8 km from Chesterwood
8.6 out of 10, Excellent, (295 reviews)
"Lovely historical hotel within walking distance to many great shops and restaurants. Staff members maintained good communication and were very helpful throughout our stay. Rooms were clean, quiet, and comfortable. Would definitely stay there again."
United States
Elaine
The price is AED 422
AED 471 total
includes taxes & fees
12 May - 13 May
The Whitlock

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
14.7 km from Chesterwood
9.2 out of 10, Wonderful, (1,008 reviews)
"Good location and great breakfast."
United States
Linda
The price is AED 504
AED 562 total
includes taxes & fees
17 May - 18 May
Hampton Inn & Suites Berkshires-Lenox

The Yankee Inn

The Yankee Inn
2.5 star property
14.9 km from Chesterwood
9.2 out of 10, Wonderful, (1,005 reviews)
"Great place to stay and close to shops and restaurants will be back!"
United States
Marie-Pascale
The price is AED 364
AED 406 total
includes taxes & fees
14 May - 15 May
The Yankee Inn

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, (1,004 reviews)
"Great location "
United States
Edith
The price is AED 404
AED 451 total
includes taxes & fees
19 May - 20 May
Quality Inn Lee - Lenox South

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, (578 reviews)
"The room was very clean but old and tired. Same with parking area. A decent value when travelling with a pet."
United States
Heather
The price is AED 275
AED 308 total
includes taxes & fees
10 May - 11 May
Travelodge by Wyndham Great Barrington Berkshires

Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
10.4 km from Chesterwood
8.0 out of 10, Very Good, (501 reviews)
"This family owned Inn is absolutely charming and the owners are so nice! I will definitely stay here again when I visit the Berkshires."
United States
Stacey
The price is AED 939
AED 1,049 total
includes taxes & fees
24 May - 25 May
Whistler's Inn Bed & Breakfast

Sunset Inn

Sunset Inn
2.0 star property
9.1 km from Chesterwood
7.6 out of 10, Good, (412 reviews)
"Decent clean quiet "
United States
William
The price is AED 388
AED 433 total
includes taxes & fees
26 May - 27 May
Sunset Inn

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
16.9 km from Chesterwood
8.6 out of 10, Excellent, (1,001 reviews)
"Room was clean. Breakfast was fresh and the area was pristine. All staff was pleasant. "
United States
Melinda
The price is AED 404
AED 451 total
includes taxes & fees
14 May - 15 May
Best Western Plus Berkshire Hills Inn & Suites

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
15.5 km from Chesterwood
9.2 out of 10, Wonderful, (92 reviews)
"Room was clean, bed was comfortable, pool was nice, breakfast and coffee were good!"
United States
Haley
The price is AED 433
AED 484 total
includes taxes & fees
17 May - 18 May
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
19.6 km from Chesterwood
8.6 out of 10, Excellent, (363 reviews)
"Easy access to parking, nearby everything and room was very clean. Definitely will come back here to stay again! "
United States
Aisha
The price is AED 389
AED 435 total
includes taxes & fees
31 May - 1 Jun
The Central Downtown Inn & Suites
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
Front of property
The Inn at Stockbridge
4.0 star property
9.8
Exceptional
99 reviews
View
Front of property
Chambery Inn
3.0 star property
9.6
Exceptional
376 reviews
View
Lobby
Inn at Kenmore Hall
3.0 star property
10.0
Exceptional
28 reviews
View
Exterior
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
9.4
Exceptional
779 reviews
View
Exterior
Prospect Berkshires
3.0 star property
9.8
Exceptional
25 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.