Hotels near Chesterwood

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Check prices for these dates

Tonight
Feb 17 - Feb 18
Tomorrow
Feb 18 - Feb 19
This weekend
Feb 20 - Feb 22
Next weekend
Feb 27 - Mar 1

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Our top choices for Chesterwood hotels

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, (110 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is P17,937
P21,699 total
includes taxes & fees
Mar 9 - Mar 10
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, (1,000 reviews)
"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."
United States
Gary
The price is P8,698
P12,306 total
includes taxes & fees
Mar 17 - Mar 18
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, (446 reviews)
"Had everything we needed. Very thoughtful touches. "
United States
Mark
The price is P6,147
P6,743 total
includes taxes & fees
Mar 4 - Mar 5
Shaker Mill Inn
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, (734 reviews)
"Great property, very accommodating. "
United States
Shanice
The price is P5,981
P6,681 total
includes taxes & fees
Mar 16 - Mar 17
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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, (840 reviews)
"Great overnights stay, wish I was here longer "
United States
Thomas
The price is P5,796
P7,607 total
includes taxes & fees
Feb 22 - Feb 23
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Exterior

The Little Lion

The Little Lion
3.0 star property
5.1 km from Chesterwood
8.6 out of 10, Excellent, (553 reviews)
"Great friendly staff"
United States
Pablo
The price is P6,376
P7,122 total
includes taxes & fees
Feb 22 - Feb 23
The Little Lion
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, (767 reviews)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
The price is P8,756
P9,780 total
includes taxes & fees
Feb 25 - Feb 26
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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)
"Clean room, nice staff , decent breakfast. Overall a good stay . "
United States
Anindita
The price is P5,666
P6,328 total
includes taxes & fees
Mar 17 - Mar 18
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Iron/ironing board, free cribs/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, (823 reviews)
"The room was clean, and the staff was friendly and helpful. "
United States
Damien
Monument Mountain Motel
Living room

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
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, (1,004 reviews)
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is P5,005
P5,591 total
includes taxes & fees
Mar 8 - Mar 9
Quality Inn Lee - Lenox South
Front of property

Chambery Inn

Chambery Inn
3.0 star property
8.7 km from Chesterwood
9.6 out of 10, Exceptional, (375 reviews)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Front of property

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
Lobby lounge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
12.5 km from Chesterwood
9.8 out of 10, Exceptional, (19 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is P8,060
P9,003 total
includes taxes & fees
Mar 1 - Mar 2
Element Lenox Berkshires
In-room safe, desk, free cribs/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, (570 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is P4,347
P4,856 total
includes taxes & fees
Feb 19 - Feb 20
Travelodge by Wyndham Great Barrington Berkshires
Living area

East Rock Inn

East Rock Inn
2.0 star property
10.1 km from Chesterwood
9.6 out of 10, Exceptional, (37 reviews)
"The room was clean and comfortable wi will back next year:) "
United States
Nadya
The price is P7,826
P8,741 total
includes taxes & fees
Mar 20 - Mar 21
East Rock Inn
Desk, laptop workspace, blackout drapes, 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, (1,001 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is P3,391
P3,720 total
includes taxes & fees
Feb 19 - Feb 20
Pleasant Valley Motel West Stockbridge
Property amenity

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
12.1 km from Chesterwood
9.2 out of 10, Wonderful, (601 reviews)
"Our stay was great! "
United States
Gianna
The price is P7,306
P8,161 total
includes taxes & fees
Mar 15 - Mar 16
Courtyard by Marriott Lenox Berkshires
Exterior

The Whitlock

The Whitlock
2.0 star property
9.8 km from Chesterwood
8.6 out of 10, Excellent, (288 reviews)
"Super cute place and walking distance to a bunch of great shops and food! "
United States
Gina
The price is P7,480
P8,355 total
includes taxes & fees
Feb 24 - Feb 25
The Whitlock
In-room dining

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
7.4 km from Chesterwood
6.4 out of 10, (658 reviews)
"The room was clean and the service adequate"
United States
David
The price is P3,695
P4,127 total
includes taxes & fees
Mar 4 - Mar 5
Econo Lodge Lee - Great Barrington
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
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
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8.8
Excellent
734 reviews
View
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
9.0
Wonderful
840 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
"Super clean spacious room! "
camille 2-night trip
Posted 2 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 studying the exhibits at Norman Rockwell Museum during your travels in 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, check out the 10 hotels and other accommodations you'll find within a mile.
What's the best hotel 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 traveler 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 are there close to Chesterwood?
Expedia has 10 hotels and other accommodations within a mile from Chesterwood.
If I need to cancel the hotel reservation for my stay near Chesterwood, will I receive a refund?
Yes, the majority of room reservations are fully refundable provided that you cancel before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you have a non-refundable reservation, you might be able to still cancel and be given a refund within 24 hours of booking. Enter dates in and click on "Search", then use the "fully refundable" filter to review 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.