South Lee Hotel Guide - Chesterwood hotels in South Lee, United States of America.

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Check prices for these dates

Tonight
9 Jan - 10 Jan
Tomorrow
10 Jan - 11 Jan
This weekend
9 Jan - 11 Jan
Next weekend
16 Jan - 18 Jan

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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

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 €396
includes taxes & fees
22 Jan - 23 Jan
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
5.8 km from Chesterwood
9.6 out of 10, Exceptional, (440 reviews)
"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"
United States
Carin
The price is €103
includes taxes & fees
13 Jan - 14 Jan
Shaker Mill 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

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, (818 reviews)
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
United States
Stephanie
The price is €106
includes taxes & fees
15 Jan - 16 Jan
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Front of property
The Inn at Stockbridge

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 €240
includes taxes & fees
11 Jan - 12 Jan
The Inn at Stockbridge
Miscellaneous
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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, (1,003 reviews)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is €94
includes taxes & fees
1 Feb - 2 Feb
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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, (716 reviews)
"Nice warm pool and hot tub. Good little fitness center. "
United States
Fawn
The price is €94
includes taxes & fees
25 Jan - 26 Jan
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Room, 2 Queen Beds, Non Smoking
Monument Mountain Motel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
8.7 km from Chesterwood
9.0 out of 10, Wonderful, (814 reviews)
"Room was very well designed and clean. The woman who worked at the desk was wonderful!"
United States
Cynthia
Monument Mountain Motel
Exterior
The Little Lion

The Little Lion

The Little Lion
3.0 star property
5.1 km from Chesterwood
8.6 out of 10, Excellent, (548 reviews)
"Perfect for pets "
United States
Maria
The price is €105
includes taxes & fees
9 Feb - 10 Feb
The Little Lion
Front of property – evening/night
Devonfield Inn B&B

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
7.5 km from Chesterwood
10.0 out of 10, Exceptional, (134 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
Exterior
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

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, (761 reviews)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
The price is €129
includes taxes & fees
25 Jan - 26 Jan
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Porch
Lakehouse Inn

Lakehouse Inn

Lakehouse Inn
4.0 star property
8.7 km from Chesterwood
9.6 out of 10, Exceptional, (290 reviews)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is €145
includes taxes & fees
16 Jan - 17 Jan
Lakehouse Inn
In-room safe, desk, free cots/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires

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, (566 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is €72
includes taxes & fees
9 Feb - 10 Feb
Travelodge by Wyndham Great Barrington Berkshires
Front of property
Chambery Inn

Chambery Inn

Chambery Inn
3.0 star property
8.7 km from Chesterwood
9.6 out of 10, Exceptional, (374 reviews)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Lobby
Quality Inn Lee - Lenox South

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, (1,000 reviews)
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is €79
includes taxes & fees
1 Feb - 2 Feb
Quality Inn Lee - Lenox South
Desk, laptop workspace, blackout curtains, iron/ironing board
Pleasant Valley Motel West Stockbridge

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 €55
includes taxes & fees
22 Jan - 23 Jan
Pleasant Valley Motel West Stockbridge
Front of property
Brook Farm Inn

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
Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area
East Rock Inn

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 €125
includes taxes & fees
9 Feb - 10 Feb
East Rock Inn
In-room dining
Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
7.4 km from Chesterwood
6.4 out of 10, (653 reviews)
"The room was clean and the service adequate"
United States
David
The price is €68
includes taxes & fees
16 Jan - 17 Jan
Econo Lodge Lee - Great Barrington
Exterior
The Whitlock

The Whitlock

The Whitlock
2.0 star property
9.8 km from Chesterwood
8.6 out of 10, Excellent, (283 reviews)
"great location"
United States
Brian
The price is €118
includes taxes & fees
11 Jan - 12 Jan
The Whitlock
Lobby lounge
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
12.5 km from Chesterwood
9.6 out of 10, Exceptional, (15 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is €133
includes taxes & fees
21 Jan - 22 Jan
Element Lenox Berkshires
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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Absolutely fabulous!"
Lisa 1-night trip
Posted 4 days ago
The Red Lion 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. 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 Charles H. Baldwin & Sons while you're out sightseeing near Chesterwood.