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Our top choices for Chesterwood hotels

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, (110 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is Rp5.227.877
Rp6.324.368 total
includes taxes & fees
29 Mar - 30 Mar
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Red Lion Inn

The Red Lion Inn
3.5 star property
3.3 km 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 Rp2.526.742
Rp3.580.003 total
includes taxes & fees
7 Apr - 8 Apr
The Red Lion Inn

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, (744 reviews)
"Simple and clean hotel"
United States
Vitor
The price is Rp1.807.551
Rp2.019.035 total
includes taxes & fees
30 Mar - 31 Mar
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
5.8 km from Chesterwood
9.6 out of 10, Exceptional, (446 reviews)
"Had everything we needed. Very thoughtful touches. "
United States
Mark
The price is Rp1.925.802
Rp2.112.605 total
includes taxes & fees
22 Mar - 23 Mar
Shaker Mill Inn

Granville House

Granville House
3.0 star property
6.4 km 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 Rp2.939.382
Rp3.283.323 total
includes taxes & fees
15 Mar - 16 Mar
Granville House

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 Rp4.049.570
Rp4.749.597 total
includes taxes & fees
27 Mar - 28 Mar
The Inn at Stockbridge

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
9.2 out of 10, Wonderful, (1,001 reviews)
"Room was spotless, staff was very kind!"
United States
Ilia
The price is Rp1.550.777
Rp1.732.217 total
includes taxes & fees
6 Apr - 7 Apr
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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, (854 reviews)
"Room was awesome and very clean "
United States
Ryanashley
The price is Rp1.900.462
Rp2.453.074 total
includes taxes & fees
23 Mar - 24 Mar
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
8.7 km from Chesterwood
9.0 out of 10, Wonderful, (830 reviews)
"Nice place and very reasonable for great location "
United States
Raymond
Monument Mountain Motel

Lakehouse Inn

Lakehouse Inn
4.0 star property
8.7 km from Chesterwood
9.6 out of 10, Exceptional, (294 reviews)
"Friendly staff, great location, beautiful views, cozy room."
United States
Elizabeth
The price is Rp2.432.592
Rp2.853.066 total
includes taxes & fees
20 Mar - 21 Mar
Lakehouse Inn

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, (773 reviews)
"Staff was lovely, everything was easy, clean and comfortable"
United States
Helena
The price is Rp2.567.736
Rp2.868.161 total
includes taxes & fees
29 Mar - 30 Mar
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
7.5 km from Chesterwood
10.0 out of 10, Exceptional, (136 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B

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, (1,001 reviews)
"Our second time to stay overnight. Good for the price."
United States
Mercy
The price is Rp1.427.016
Rp1.593.977 total
includes taxes & fees
6 Apr - 7 Apr
Quality Inn Lee - Lenox South

The Little Lion

The Little Lion
3.0 star property
5.1 km from Chesterwood
8.6 out of 10, Excellent, (554 reviews)
"Great friendly staff"
United States
Pablo
The price is Rp1.858.230
Rp2.075.643 total
includes taxes & fees
16 Mar - 17 Mar
The Little Lion

Chambery Inn

Chambery Inn
3.0 star property
8.7 km from Chesterwood
9.6 out of 10, Exceptional, (376 reviews)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
12.5 km from Chesterwood
9.8 out of 10, Exceptional, (23 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is Rp2.348.127
Rp2.622.858 total
includes taxes & fees
26 Mar - 27 Mar
Element Lenox Berkshires

East Rock Inn

East Rock Inn
2.0 star property
10.1 km from Chesterwood
9.6 out of 10, Exceptional, (38 reviews)
"The room was clean and comfortable wi will back next year:) "
United States
Nadya
The price is Rp2.240.873
Rp2.503.054 total
includes taxes & fees
2 Apr - 3 Apr
East Rock Inn

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, (573 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is Rp1.266.975
Rp1.415.296 total
includes taxes & fees
15 Mar - 16 Mar
Travelodge by Wyndham Great Barrington Berkshires

Brook Farm Inn

Brook Farm Inn
3.5 star property
9.1 km from Chesterwood
9.4 out of 10, Exceptional, (164 reviews)
"Everything was perfect - location and accommodation."
United States
Christopher
Brook Farm Inn

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
4.7 km from Chesterwood
6.8 out of 10, (1,001 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is Rp988.240
Rp1.084.098 total
includes taxes & fees
24 Mar - 25 Mar
Pleasant Valley Motel West Stockbridge
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.

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.