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Check prices for these dates

Tonight
29 Mar - 30 Mar
Tomorrow
30 Mar - 31 Mar
Next weekend
3 Apr - 5 Apr
In two weeks
10 Apr - 12 Apr

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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
0.4 mi from Chesterwood
9.2 out of 10, Wonderful, (110 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is £282
includes taxes & fees
11 Apr - 12 Apr
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
2.1 mi from Chesterwood
8.8 out of 10, Excellent, (1,000 reviews)
"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."
United States
Gary
The price is £147
includes taxes & fees
7 Apr - 8 Apr
The Red Lion Inn
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
3.6 mi from Chesterwood
9.6 out of 10, Exceptional, (446 reviews)
"Had everything we needed. Very thoughtful touches. "
United States
Mark
The price is £83
includes taxes & fees
31 Mar - 1 Apr
Shaker Mill Inn
Individually decorated, individually furnished, desk, laptop workspace

Granville House

Granville House
3.0 star property
4 mi from Chesterwood
10.0 out of 10, Exceptional, (97 reviews)
"Everything about Granville House is delightful. The owners have paid attention to every detail, from the decor and the way the rooms are appointed to the comfortable bed and the delicious hot breakfast."
United States
Ann
The price is £147
includes taxes & fees
30 Mar - 31 Mar
Granville House
Exterior

The Little Lion

The Little Lion
3.0 star property
3.2 mi from Chesterwood
8.6 out of 10, Excellent, (555 reviews)
"Clean … check in , good location for us .. we’ll be back in Maynn"
United States
Kathleen
The price is £93
includes taxes & fees
31 Mar - 1 Apr
The Little Lion
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
5.4 mi from Chesterwood
9.0 out of 10, Wonderful, (836 reviews)
"Nice place and very reasonable for great location "
United States
Raymond
The price is £50
includes taxes & fees
5 Apr - 6 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
5.3 mi from Chesterwood
9.2 out of 10, Wonderful, (1,001 reviews)
"Room was spotless, staff was very kind!"
United States
Ilia
The price is £80
includes taxes & fees
19 Apr - 20 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
5.3 mi from Chesterwood
9.4 out of 10, Exceptional, (776 reviews)
"Staff was lovely, everything was easy, clean and comfortable"
United States
Helena
The price is £128
includes taxes & fees
15 Apr - 16 Apr
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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
4.1 mi from Chesterwood
9.0 out of 10, Wonderful, (858 reviews)
"Great place to enjoy with the whole family!!!"
United States
Elizabeth
The price is £110
includes taxes & fees
1 Apr - 2 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
5 mi from Chesterwood
8.8 out of 10, Excellent, (752 reviews)
"This is not my first stay. Great hotel to stay for ski trips "
United States
Michael
The price is £94
includes taxes & fees
13 Apr - 14 Apr
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Front of property

Chambery Inn

Chambery Inn
3.0 star property
5.4 mi 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 £144
includes taxes & fees
30 Mar - 31 Mar
Chambery Inn
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
3.8 mi from Chesterwood
7.6 out of 10, Good, (574 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is £63
includes taxes & fees
30 Mar - 31 Mar
Travelodge by Wyndham Great Barrington Berkshires
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
6.4 mi from Chesterwood
8.4 out of 10, Very good, (1,002 reviews)
"Great location, friendly staff"
United States
James
The price is £57
includes taxes & fees
13 Apr - 14 Apr
Quality Inn Great Barrington
Room #10 Queen's Cottage | Living room | Flat-screen TV

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
4.7 mi from Chesterwood
10.0 out of 10, Exceptional, (137 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
The price is £277
includes taxes & fees
30 Mar - 31 Mar
Devonfield Inn B&B
Desk, laptop workspace, blackout curtains, iron/ironing board

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
2.9 mi 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 £48
includes taxes & fees
31 Mar - 1 Apr
Pleasant Valley Motel West Stockbridge
Front of property

Brook Farm Inn

Brook Farm Inn
3.5 star property
5.7 mi from Chesterwood
9.4 out of 10, Exceptional, (164 reviews)
"Everything was perfect - location and accommodation."
United States
Christopher
The price is £150
includes taxes & fees
24 Apr - 25 Apr
Brook Farm Inn
Lobby lounge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
7.8 mi from Chesterwood
9.6 out of 10, Exceptional, (24 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is £117
includes taxes & fees
5 Apr - 6 Apr
Element Lenox Berkshires
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
6.3 mi from Chesterwood
9.4 out of 10, Exceptional, (41 reviews)
"The room was clean and comfortable wi will back next year:) "
United States
Nadya
The price is £102
includes taxes & fees
13 Apr - 14 Apr
East Rock Inn
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
8.1 mi from Chesterwood
9.0 out of 10, Wonderful, (882 reviews)
"This was a great stay! The room and hotel itself were up to date and was overall a great location to check out the Berkshires. We ate one night at the hotel too and the dinner was really good! I recommend the mushroom ravioli, would stay again."
United States
Payton
The price is £59
includes taxes & fees
31 Mar - 1 Apr
Berkshires Untold
Property amenity

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
7.5 mi from Chesterwood
9.2 out of 10, Wonderful, (611 reviews)
"Clean room, friendly and helpful staff. "
United States
Jennifer
The price is £124
includes taxes & fees
13 Apr - 14 Apr
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.
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
110 reviews
View
Exterior
The Red Lion Inn
3.5 star property
8.8
Excellent
1,000 reviews
View
Garden
Shaker Mill Inn
2.5 star property
9.6
Exceptional
446 reviews
View
Individually decorated, individually furnished, desk, laptop workspace
Granville House
3.0 star property
10.0
Exceptional
97 reviews
View
Exterior
The Little Lion
3.0 star property
8.6
Excellent
555 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
"Great place to enjoy with the whole family!!!"
Elizabeth 2-night trip
Posted 6 days 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 (252 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

4.0/5 (1 review)
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.