Hotels near Chesterwood

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Top 10 Hotels Near Chesterwood

Business centre
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)
"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 RM1,578
RM1,909 total
includes taxes & fees
1 Dec - 2 Dec
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
1 bedroom, premium bedding, iron/ironing board, free WiFi
Tanglewood Suites

Tanglewood Suites

2.5 star property
2.6 km from Chesterwood
6.4 out of 10, (22)
"NOT A REAL LOCATION. There was nothing there. Neighbors said this was a scam. Expedia ended up helping us find a local hotel room though the location was not as good. DO NOT BOOK THIS LOCATION -- it needs to be taken off the website."
United States
Elizabeth
The price is RM905
RM905 total
includes taxes & fees
1 Dec - 2 Dec
Tanglewood Suites
Outdoor pool, pool loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
3.3 km from Chesterwood
8.8 out of 10, Excellent, (1001)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is RM619
RM877 total
includes taxes & fees
15 Dec - 16 Dec
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, (435)
"Nice place, easy check in"
United States
Robert
The price is RM450
RM494 total
includes taxes & fees
19 Nov - 20 Nov
Shaker Mill Inn
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, (87)
"Outstanding all around!"
United States
Jonathan
The price is RM826
RM923 total
includes taxes & fees
25 Nov - 26 Nov
Granville House
Exterior
The Inn at Stockbridge

The Inn at Stockbridge

4.0 star property
5.2 km from Chesterwood
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
United States
Steven
The price is RM1,036
RM1,215 total
includes taxes & fees
20 Nov - 21 Nov
The Inn at Stockbridge
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, (695)
"Clean, comfortable facilty"
United States
Julie
The price is RM442
RM494 total
includes taxes & fees
24 Nov - 25 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Lobby
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
8.6 km from Chesterwood
9.4 out of 10, Exceptional, (754)
"Clean room, very courteous staff "
United States
Thomas
The price is RM591
RM660 total
includes taxes & fees
24 Nov - 25 Nov
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
6.6 km from Chesterwood
9.0 out of 10, Wonderful, (785)
"Place was great!"
United States
Benjamin
The price is RM530
RM650 total
includes taxes & fees
20 Nov - 21 Nov
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Exterior
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, (1002)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is RM455
RM509 total
includes taxes & fees
9 Dec - 10 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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, (791)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel
Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi
The Little Lion

The Little Lion

3.0 star property
5.1 km from Chesterwood
8.6 out of 10, Excellent, (544)
"The check-in was easy and the room was ready and clean. It was nice having our dogs with us. "
United States
Maria
The price is RM533
RM595 total
includes taxes & fees
24 Nov - 25 Nov
The Little Lion
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, (133)
"The inn has an excellent location and amenities."
United States
Christopher
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, (372)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
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
6.2 km from Chesterwood
7.6 out of 10, Good, (559)
"The staff were very friendly and accommodating "
United States
Tom
The price is RM310
RM346 total
includes taxes & fees
25 Nov - 26 Nov
Travelodge by Wyndham Great Barrington Berkshires
Lobby
Quality Inn

Quality Inn

2.5 star property
9.2 km from Chesterwood
8.4 out of 10, Very good, (1001)
"Clean room and good breakfast "
United States
Kelly
The price is RM383
RM428 total
includes taxes & fees
7 Dec - 8 Dec
Quality Inn
Exterior
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

2.0 star property
4.7 km from Chesterwood
6.8 out of 10, (1001)
"good average place to stay."
United States
Terry
The price is RM251
RM275 total
includes taxes & fees
22 Nov - 23 Nov
Pleasant Valley Motel West Stockbridge
1 bedroom, premium bedding, iron/ironing board, rollaway beds
Brook Farm Inn

Brook Farm Inn

3.5 star property
9.1 km from Chesterwood
9.4 out of 10, Exceptional, (162)
"Comfortable, quiet, convenient location, very friendly staff. "
United States
Susan
Brook Farm Inn
Desk, iron/ironing board, free cots/infant beds, rollaway beds
Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington

2.0 star property
7.4 km from Chesterwood
6.4 out of 10, (647)
"Great place. , good staff "
United States
ketul
The price is RM242
RM271 total
includes taxes & fees
1 Dec - 2 Dec
Econo Lodge Lee - Great Barrington
Private kitchen
East Rock Inn

East Rock Inn

2.0 star property
10.1 km from Chesterwood
9.4 out of 10, Exceptional, (36)
"We had a great stay at East Rock Inn! Newly remodeled, clean room, comfortable bed, easy access to town. I will definitely stay there again."
United States
Laura
The price is RM558
RM623 total
includes taxes & fees
4 Dec - 5 Dec
East Rock Inn
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.
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Top Chesterwood Hotel Reviews

Shaker Mill Inn

Shaker Mill Inn

10/10 Excellent
"Overall a unique cozy experience. "
Robert 5-night trip
Posted 10 days ago
Shaker Mill Inn

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. Other good choices within a few miles include The Red Lion Inn and Tanglewood Suites.
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 Charles H. Baldwin & Sons while you're out sightseeing near Chesterwood.