Search Hotels Near Chesterwood, South Lee

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Our top choices for Chesterwood hotels

1. 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, (904 reviews)
"Wonderful stay for families."
United States
Kimberly
The price is ₹12,732
₹16,078 total
includes taxes & fees
9 Jun - 10 Jun
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

2. Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
4.7 km from Chesterwood
6.8 out of 10, (1,002 reviews)
"The property is in terrible condition."
United States
Olga V
The price is ₹5,955
₹6,532 total
includes taxes & fees
18 Jun - 19 Jun
Pleasant Valley Motel West Stockbridge

3. 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, (784 reviews)
"Staff was lovely, everything was easy, clean and comfortable"
United States
Helena
The price is ₹18,481
₹20,643 total
includes taxes & fees
29 Jun - 30 Jun
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

4. 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, (582 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 ₹7,500
₹8,378 total
includes taxes & fees
7 Jun - 8 Jun
Travelodge by Wyndham Great Barrington Berkshires

5. 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, (769 reviews)
"Spotless, clean, comfortable, friendly staff."
United States
cynthia
The price is ₹13,387
₹14,953 total
includes taxes & fees
21 Jun - 22 Jun
Holiday Inn Express Hotel & Suites Great Barrington by IHG

6. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
7.4 km from Chesterwood
6.4 out of 10, (666 reviews)
"Decent place.friendly, quiet"
United States
William
The price is ₹6,750
₹7,540 total
includes taxes & fees
14 Jun - 15 Jun
Econo Lodge Lee - Great Barrington

7. 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, (1,003 reviews)
"It was a clean, friendly hotel."
United States
Cheri
The price is ₹11,635
₹12,997 total
includes taxes & fees
9 Jun - 10 Jun
Quality Inn Lee - Lenox South

8. Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
9.7 km from Chesterwood
5.4 out of 10, (468 reviews)
"The breakfast was not diabetic friendly. They stated pet friendly but no place for dog to go to the bathroom. Had to walk dog through garbage . Cigarette butts all over very the place. Beds were terrible. My towels had clumps of black hair on them. Lotion and shampoos left in room were used not new ones. Will not go back"
United States
Stacy
The price is ₹6,237
₹6,986 total
includes taxes & fees
7 Jun - 8 Jun
Berkshire Travel Lodge

9. Sunset Inn

Sunset Inn
2.0 star property
9.1 km from Chesterwood
7.6 out of 10, Good, (413 reviews)
"Nice place for a stay"
United States
Jay
The price is ₹9,922
₹11,082 total
includes taxes & fees
8 Jun - 9 Jun
Sunset Inn

10. 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, (1,001 reviews)
"Great place, nice amenities and convenient location, highly recommended."
United States
Arthur
The price is ₹14,466
₹16,643 total
includes taxes & fees
7 Jun - 8 Jun
The Cornell Inn, Lenox & The Berkshires

11. Chambery Inn

Chambery Inn
3.0 star property
8.7 km from Chesterwood
9.6 out of 10, Exceptional, (377 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 ₹16,234
₹18,134 total
includes taxes & fees
7 Jun - 8 Jun
Chambery Inn

12. The Whitlock

The Whitlock
2.0 star property
9.8 km from Chesterwood
8.6 out of 10, Excellent, (305 reviews)
"A beautiful old inn in the heart of a lovely old town."
United States
Linda
The price is ₹14,714
₹16,436 total
includes taxes & fees
21 Jun - 22 Jun
The Whitlock

13. 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, (629 reviews)
"I enjoyed relaxing by the firepit. The only thing that could of made it a better stay would be free breakfast or at least coffee and tea. They have a Starbucks and area where you can purchase items but it was more like self serve and pay at reception desk."
United States
Elizabeth
The price is ₹18,713
₹20,903 total
includes taxes & fees
11 Jun - 12 Jun
Courtyard by Marriott Lenox Berkshires

14. Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
9.6 km from Chesterwood
8.6 out of 10, Excellent, (4 reviews)
"Wonderful pet-friendly property in a fantastic location. Everything in the village is just a short walk away, making it easy to enjoy local shops, restaurants, and attractions."
United States
Leonardo
The price is ₹9,801
₹10,948 total
includes taxes & fees
7 Jun - 8 Jun
Hideaway Inn Lenox

15. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
15.5 km from Chesterwood
9.4 out of 10, Exceptional, (100 reviews)
"This is a great hotel-super clean, nice breakfast, staff very pleasant and helpful. Close to Pittsfield but quieter. Pool and hot tub were great. Highly recommend staying here if you’re in the area."
United States
Kathleen
The price is ₹12,817
₹14,317 total
includes taxes & fees
14 Jun - 15 Jun
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

16. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
15.5 km from Chesterwood
9.2 out of 10, Wonderful, (679 reviews)
"Five Star stay!"
United States
Adeline
The price is ₹13,888
₹15,514 total
includes taxes & fees
14 Jun - 15 Jun
Hilton Garden Inn Lenox Pittsfield

17. Little Cat Lodge

Little Cat Lodge
2.0 star property
16.3 km from Chesterwood
9.6 out of 10, Exceptional, (79 reviews)
"Very quiet setting with the ski mountain in view from the room. The heated pool was very nice."
United States
Zachary
The price is ₹14,441
₹16,174 total
includes taxes & fees
8 Jun - 9 Jun
Little Cat Lodge

18. 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)
"Breakfast was reasonable. We had issue with our room and the staff helpfully moved us to another room. Would stay again"
United States
Anandaraja
The price is ₹10,558
₹11,793 total
includes taxes & fees
10 Jun - 11 Jun
Best Western Plus Berkshire Hills Inn & Suites

19. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
14.9 km from Chesterwood
7.6 out of 10, Good, (863 reviews)
"Hotel was ok. Great for the price. But the bed was terrible. Old and soft. "
United States
robert
The price is ₹7,500
₹8,378 total
includes taxes & fees
8 Jun - 9 Jun
Howard Johnson by Wyndham Lenox

20. 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, (368 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 ₹10,823
₹12,090 total
includes taxes & fees
7 Jun - 8 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
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
9.2
Wonderful
904 reviews
View
Children’s activities
Pleasant Valley Motel West Stockbridge
2.0 star property
6.8
1,002 reviews
View
Exterior
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
9.4
Exceptional
784 reviews
View
In-room safe, desk, free cots/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
7.6
Good
582 reviews
View
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8.8
Excellent
769 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, 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.

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