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Check prices for these dates

Tonight
21 Apr - 22 Apr
Tomorrow
22 Apr - 23 Apr
This weekend
24 Apr - 26 Apr
Next weekend
1 May - 3 May

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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, (111 reviews)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is ₹28,758
₹34,789 total
includes taxes & fees
4 May - 5 May
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, (1,001 reviews)
"All was great! The atmosphere, food, and rooms were very clean. "
United States
Brent
The price is ₹12,739
₹18,391 total
includes taxes & fees
30 Apr - 1 May
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, (447 reviews)
"Nice place, easy check in"
United States
Robert
The price is ₹9,873
₹10,831 total
includes taxes & fees
5 May - 6 May
Shaker Mill Inn
Exterior

The Little Lion

The Little Lion
3.0 star property
5.1 km from Chesterwood
8.6 out of 10, Excellent, (556 reviews)
"Clean … check in , good location for us .. we’ll be back in Maynn"
United States
Kathleen
The price is ₹10,243
₹11,442 total
includes taxes & fees
23 Apr - 24 Apr
The Little Lion
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, (100 reviews)
"Very cosy and friendly "
United States
Dominic
The price is ₹18,585
₹20,759 total
includes taxes & fees
3 May - 4 May
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, (881 reviews)
"Great place to enjoy with the whole family!!!"
United States
Elizabeth
The price is ₹10,476
₹13,523 total
includes taxes & fees
26 Apr - 27 Apr
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, (758 reviews)
"Simple and clean hotel"
United States
Vitor
The price is ₹9,499
₹10,609 total
includes taxes & fees
30 Apr - 1 May
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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, (842 reviews)
"Nice place and very reasonable for great location "
United States
Raymond
The price is ₹5,867
₹6,553 total
includes taxes & fees
28 Apr - 29 Apr
Monument Mountain Motel
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, (1,000 reviews)
"Room was spotless, staff was very kind!"
United States
Ilia
The price is ₹11,035
₹12,327 total
includes taxes & fees
27 Apr - 28 Apr
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior

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, (777 reviews)
"Nice stay. Friendly staff. Close to Butternut. We’ll be back"
United States
Reynaldo
The price is ₹14,155
₹15,811 total
includes taxes & fees
27 Apr - 28 Apr
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Front of property

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 ₹24,473
₹28,703 total
includes taxes & fees
5 May - 6 May
The Inn at Stockbridge
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, (137 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
The price is ₹27,785
₹31,035 total
includes taxes & fees
3 May - 4 May
Devonfield Inn B&B
Front of property

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 ₹15,889
₹17,748 total
includes taxes & fees
26 Apr - 27 Apr
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, (1,002 reviews)
"Great visit all around. Centrally located to the skiing resorts, lots to do in town, decent breakfast spread, clean room, and for a short stay, housekeeping came when unexpected! "
United States
Amy
The price is ₹10,129
₹11,314 total
includes taxes & fees
26 Apr - 27 Apr
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, (576 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is ₹6,969
₹7,785 total
includes taxes & fees
24 Apr - 25 Apr
Travelodge by Wyndham Great Barrington Berkshires
Exterior

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, (1,000 reviews)
"Great staff, great breakfast, clean facilities, quiet, good location"
United States
Chris
The price is ₹12,163
₹13,994 total
includes taxes & fees
7 May - 8 May
The Cornell Inn, Lenox & The Berkshires
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, (1,000 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is ₹6,607
₹7,248 total
includes taxes & fees
22 Apr - 23 Apr
Pleasant Valley Motel West Stockbridge
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
9.4 out of 10, Exceptional, (44 reviews)
"The room was clean and comfortable wi will back next year:) "
United States
Nadya
The price is ₹11,094
₹12,392 total
includes taxes & fees
4 May - 5 May
East Rock Inn
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
13 km from Chesterwood
9.0 out of 10, Wonderful, (907 reviews)
"Really helpful and nice staff, lovely and sophisticated decor/vibe, and great location. Loved the Le Labo bath products, too!"
United States
Aki
The price is ₹8,381
₹9,362 total
includes taxes & fees
10 May - 11 May
Berkshires Untold
Exterior

The Whitlock

The Whitlock
2.0 star property
9.8 km from Chesterwood
8.6 out of 10, Excellent, (293 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 ₹12,878
₹14,384 total
includes taxes & fees
4 May - 5 May
The Whitlock
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.
View all properties

Compare popular hotels close to Chesterwood

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
Suite, Private Bathroom (RedBird Suite) | View from room
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
9.2
Wonderful
111 reviews
View
Exterior
The Red Lion Inn
3.5 star property
8.8
Excellent
1,001 reviews
View
Garden
Shaker Mill Inn
2.5 star property
9.6
Exceptional
447 reviews
View
Exterior
The Little Lion
3.0 star property
8.6
Excellent
556 reviews
View
Individually decorated, individually furnished, desk, laptop workspace
Granville House
3.0 star property
10.0
Exceptional
100 reviews
View

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
"The kitchen was fully equipped, the staff was wonderful and there is plenty of active"
Kathleen 2-night trip
Posted 2 hours 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 (347 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

4.7/5 (14 reviews)
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 Lenox Arts Center while you're out sightseeing near Chesterwood.

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