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Check prices for these dates

Tonight
14 Feb - 15 Feb
Tomorrow
15 Feb - 16 Feb
Next weekend
20 Feb - 22 Feb
In two weeks
27 Feb - 1 Mar

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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
0.6 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 SAR 1,161
SAR 1,404 total
includes taxes & fees
27 Feb - 28 Feb
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property

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 SAR 896
SAR 1,050 total
includes taxes & fees
22 Feb - 23 Feb
The Inn at Stockbridge
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
5.8 km from Chesterwood
9.6 out of 10, Exceptional, (445 reviews)
"Had everything we needed. Very thoughtful touches. "
United States
Mark
The price is SAR 388
SAR 426 total
includes taxes & fees
1 Mar - 2 Mar
Shaker Mill Inn
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
Porch

Lakehouse Inn

Lakehouse Inn
4.0 star property
8.7 km from Chesterwood
9.6 out of 10, Exceptional, (292 reviews)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is SAR 524
SAR 614 total
includes taxes & fees
15 Feb - 16 Feb
Lakehouse Inn
Lobby

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
12.1 km from Chesterwood
10.0 out of 10, Exceptional, (27 reviews)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is SAR 2,156
SAR 2,366 total
includes taxes & fees
16 Feb - 17 Feb
Inn at Kenmore Hall
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 SAR 566
SAR 633 total
includes taxes & fees
22 Feb - 23 Feb
Fairfield Inn & Suites by Marriott Great Barrington 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
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 SAR 484
SAR 540 total
includes taxes & fees
6 Mar - 7 Mar
East Rock 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
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, (834 reviews)
"Great overnights stay, wish I was here longer "
United States
Thomas
The price is SAR 422
SAR 545 total
includes taxes & fees
22 Feb - 23 Feb
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Lobby lounge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
12.5 km from Chesterwood
9.8 out of 10, Exceptional, (18 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is SAR 521
SAR 582 total
includes taxes & fees
22 Feb - 23 Feb
Element Lenox Berkshires
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 SAR 413
SAR 461 total
includes taxes & fees
15 Feb - 16 Feb
The Little Lion
Exterior

Prospect Berkshires

Prospect Berkshires
3.0 star property
12.8 km from Chesterwood
9.6 out of 10, Exceptional, (19 reviews)
"Excellent local stay - would recommend to all"
United States
Gentian
The price is SAR 720
SAR 930 total
includes taxes & fees
2 Mar - 3 Mar
Prospect 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 SAR 367
SAR 409 total
includes taxes & fees
6 Mar - 7 Mar
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Room, 2 Queen Beds, Non Smoking | 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, (822 reviews)
"The room was clean, and the staff was friendly and helpful. "
United States
Damien
Monument Mountain Motel
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, (732 reviews)
"Great property, very accommodating. "
United States
Shanice
The price is SAR 401
SAR 448 total
includes taxes & fees
22 Feb - 23 Feb
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior detail

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
9.8 km from Chesterwood
9.0 out of 10, Wonderful, (43 reviews)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
United States
Abby
The price is SAR 821
SAR 917 total
includes taxes & fees
18 Feb - 19 Feb
Hampton Terrace Inn
Lobby sitting area

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, (101 reviews)
"Great property, very comfortable, incredible staff, easy access to skiing in the area!"
United States
Dominick
The price is SAR 521
SAR 584 total
includes taxes & fees
3 Mar - 4 Mar
Inn at Silver Maple Farm
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
10.7 km from Chesterwood
9.0 out of 10, Wonderful, (1,001 reviews)
"The Inn was very nice and the staff was super friendly and attentive."
United States
Steven
The price is SAR 499
SAR 574 total
includes taxes & fees
22 Feb - 23 Feb
The Cornell Inn, Lenox & The Berkshires
Exterior

The Whitlock

The Whitlock
2.0 star property
9.8 km from Chesterwood
8.6 out of 10, Excellent, (287 reviews)
"Super cute place and walking distance to a bunch of great shops and food! "
United States
Gina
The price is SAR 446
SAR 499 total
includes taxes & fees
18 Feb - 19 Feb
The Whitlock
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
Front of property
The Inn at Stockbridge
4.0 star property
9.8
Exceptional
99 reviews
View
Garden
Shaker Mill Inn
2.5 star property
9.6
Exceptional
445 reviews
View
Front of property
Chambery Inn
3.0 star property
9.6
Exceptional
375 reviews
View
Porch
Lakehouse Inn
4.0 star property
9.6
Exceptional
292 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 overnights stay, wish I was here longer "
Thomas 1-night trip
Posted 1 month 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.
Where can I learn more about changing or cancelling my trip in the area near Chesterwood?
For more information about picking new dates or cancelling your stay near Chesterwood, head over to our customer service page.
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.