Hotels near Chesterwood South Lee

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

This weekend
Next weekend

Where to stay near Chesterwood?

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 $330
$399 total
includes taxes & fees
Jul 5 - Jul 6
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, (1,004 reviews)
"Ideal location if one is looking to stay in Stockbridge. The guest house we stayed in was quiet and comfortable. But our room was looking a little worn and in need of some updates, such as the carpet. The property has an excellent restaurant. The property was undergoing a renovation during our stay, so the parking situation was at first confusing, but we got the hang of it quickly,"
United States
Paul
The price is $151
$214 total
includes taxes & fees
Jul 1 - Jul 2
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, (776 reviews)
"Great location, amenities, pool and hot tub for the kids, friendly staff, comfortable room."
United States
Jennifer
The price is $129
$144 total
includes taxes & fees
Jun 25 - Jun 26
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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
9.2 out of 10, Wonderful, (914 reviews)
"Rooms are large, beds are comfortable, everything clean. Plenty to do on the property and beautiful nearby towns to visit. Style and amenities are a bit dated, but that hardly matters,considering the value. Ideal for families."
United States
Lloyd
The price is $134
$169 total
includes taxes & fees
Jun 23 - Jun 24
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
5.8 km from Chesterwood
9.6 out of 10, Exceptional, (461 reviews)
The price is $149
$163 total
includes taxes & fees
Jun 23 - Jun 24
Shaker Mill Inn

The Little Lion

The Little Lion
3.0 star property
5.1 km from Chesterwood
8.6 out of 10, Excellent, (569 reviews)
"Repeat visitor / love it 😍. EZ to check in. Grat location : comfortable beds. Very Cleam. . Consistent. Pretty grounds"
United States
Elise
The price is $88
$98 total
includes taxes & fees
Jun 23 - Jun 24
The Little Lion

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
8.7 km from Chesterwood
9.0 out of 10, Wonderful, (873 reviews)
"Room was clean and cozy, bed comfy, pillows comfy, bathroom nice and clean, plenty of towels, AC worked, and plenty of parking for two cars since we usually travel with 2 vehicles. "
United States
Dom
The price is $86
$96 total
includes taxes & fees
Jun 23 - Jun 24
Monument Mountain Motel

Granville House

Granville House
3.0 star property
6.4 km from Chesterwood
10.0 out of 10, Exceptional, (102 reviews)
"Very cosy and friendly "
United States
Dominic
The price is $275
$307 total
includes taxes & fees
Jun 23 - Jun 24
Granville House

East Rock Inn

East Rock Inn
2.0 star property
10.1 km from Chesterwood
9.4 out of 10, Exceptional, (48 reviews)
"This hotel is fantastic! Absolutely beautiful location. Convenient to Great Barrington stores, laundromat, etc. Very pleasant, helpful, and responsive Management and staff. I totally enjoyed my stay at the East Rock Inn, and I will stay there again. Highly recommend!"
United States
Edward
The price is $145
$162 total
includes taxes & fees
Jul 6 - Jul 7
East Rock Inn

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
10.3 km from Chesterwood
8.6 out of 10, Excellent, (1,012 reviews)
"Very nice staff. Clean and comfortable rooms."
United States
SHANNON
The price is $104
$116 total
includes taxes & fees
Jun 24 - Jun 25
Quality Inn Great Barrington

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, (1,003 reviews)
"Very clean, quiet, pleasant staff and a good breakfast."
United States
Lynne
The price is $135
$151 total
includes taxes & fees
Jun 29 - Jun 30
Hampton Inn & Suites Berkshires-Lenox

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
7.5 km from Chesterwood
10.0 out of 10, Exceptional, (138 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
The price is $429
$479 total
includes taxes & fees
Jul 15 - Jul 16
Devonfield Inn B&B

The Whitlock

The Whitlock
2.0 star property
9.8 km from Chesterwood
8.6 out of 10, Excellent, (312 reviews)
"Nice rooms, great location."
United States
Rick
The price is $155
$173 total
includes taxes & fees
Jul 6 - Jul 7
The Whitlock

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
15.9 km from Chesterwood
9.0 out of 10, Wonderful, (997 reviews)
"Very spacious and a good spot if you like to cook for yourself. Decor is dated but it's clean and good value."
United States
Barbara
The price is $135
$173 total
includes taxes & fees
Jun 23 - Jun 24
Berkshire Mountain Lodge

Little Cat Lodge

Little Cat Lodge
2.0 star property
16.3 km from Chesterwood
9.6 out of 10, Exceptional, (85 reviews)
"The room is clean and thoughtfully appointed. Staff is pleasant and helpful."
United States
Joshua
The price is $169
$189 total
includes taxes & fees
Jun 23 - Jun 24
Little Cat Lodge

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, (587 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is $79
$88 total
includes taxes & fees
Jun 23 - Jun 24
Travelodge by Wyndham Great Barrington Berkshires

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
17.5 km from Chesterwood
9.8 out of 10, Exceptional, (108 reviews)
"This is a charming, friendly, comfortable inn that goes out of its way to be helpful. This was our second time here. We will surely book it again when we come back to this area."
United States
Margaret S
The price is $159
$178 total
includes taxes & fees
Jun 23 - Jun 24
Inn at Silver Maple Farm

Sunset Inn

Sunset Inn
2.0 star property
9.1 km from Chesterwood
7.6 out of 10, Good, (416 reviews)
"Very comfortable bed and good hot shower. A good value for your money. Nice staff at front desk."
United States
Kathleen
The price is $110
$123 total
includes taxes & fees
Jul 6 - Jul 7
Sunset 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 $80
$88 total
includes taxes & fees
Jun 25 - Jun 26
Pleasant Valley Motel West Stockbridge

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, (1,003 reviews)
"Good clean accommodation, simple, no frills."
United States
Scott
The price is $132
$148 total
includes taxes & fees
Jun 24 - Jun 25
Quality Inn Lee - Lenox South
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
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
1,004 reviews
View
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8.8
Excellent
776 reviews
View
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
9.2
Wonderful
914 reviews
View
Garden
Shaker Mill Inn
2.5 star property
9.6
Exceptional
461 reviews
View

Other landmarks near Chesterwood