Hotels near Chesterwood

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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 S$391
includes taxes & fees
21 May - 22 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 S$242
includes taxes & fees
10 May - 11 May
Chambery Inn

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 S$97
includes taxes & fees
14 May - 15 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, (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 S$176
includes taxes & fees
27 May - 28 May
Holiday Inn Express Hotel & Suites Great Barrington 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, (779 reviews)
"Staff was lovely, everything was easy, clean and comfortable"
United States
Helena
The price is S$251
includes taxes & fees
14 May - 15 May
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
10.3 km from Chesterwood
8.4 out of 10, Very good, (1,008 reviews)
"Very friendly staff and conviently located"
United States
Dawn
The price is S$120
includes taxes & fees
13 May - 14 May
Quality Inn Great Barrington

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 S$106
includes taxes & fees
10 May - 11 May
Travelodge by Wyndham Great Barrington Berkshires

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 S$140
includes taxes & fees
20 May - 21 May
The Yankee Inn

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 S$220
includes taxes & fees
13 May - 14 May
The Cornell Inn, Lenox & The Berkshires

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 S$149
includes taxes & fees
31 May - 1 Jun
Sunset Inn

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
7.4 km from Chesterwood
6.4 out of 10, (663 reviews)
"Good to stay. "
United States
Ibinabo
The price is S$90
includes taxes & fees
25 May - 26 May
Econo Lodge Lee - Great Barrington

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 S$236
includes taxes & fees
27 May - 28 May
Element Lenox Berkshires

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
9.7 km from Chesterwood
5.4 out of 10, (466 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 S$93
includes taxes & fees
10 May - 11 May
Berkshire Travel 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 S$163
includes taxes & fees
11 May - 12 May
The Whitlock

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 S$591
includes taxes & fees
10 May - 11 May
Inn at Kenmore Hall

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 S$156
includes taxes & fees
19 May - 20 May
Quality Inn Lee - Lenox South

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 S$194
includes taxes & fees
17 May - 18 May
Hampton Inn & Suites Berkshires-Lenox

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 S$489
includes taxes & fees
10 May - 11 May
Prospect 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 S$362
includes taxes & fees
31 May - 1 Jun
Whistler's Inn Bed & Breakfast

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 S$167
includes taxes & fees
17 May - 18 May
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
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
Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi
Monument Mountain Motel
2.5 star property
9.0
Wonderful
849 reviews
View
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8.8
Excellent
760 reviews
View
Exterior
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
9.4
Exceptional
779 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.