Top Hotels Near Chesterwood in South Lee from NZ$106

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Our top choices for Chesterwood hotels

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 NZ$620
includes taxes & fees
17 Feb - 18 Feb
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
5.8 km from Chesterwood
9.6 out of 10, Exceptional, (444 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 NZ$208
includes taxes & fees
5 Feb - 6 Feb
Shaker Mill Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
3.3 km from Chesterwood
8.8 out of 10, Excellent, (1,001 reviews)
"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."
United States
Gary
The price is NZ$339
includes taxes & fees
5 Mar - 6 Mar
The Red Lion Inn

Granville House

Granville House
3.0 star property
6.4 km from Chesterwood
10.0 out of 10, Exceptional, (93 reviews)
"Absolutely magical at Christmas time! It was only for a quick overnight but felt like time stood still while we were there. The service was impeccable and Terry and Terri were a delight! I look forward to returning. "
United States
Jennifer
The price is NZ$322
includes taxes & fees
8 Feb - 9 Feb
Granville House

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 NZ$203
includes taxes & fees
8 Feb - 9 Feb
The Little Lion

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, (830 reviews)
"Great overnights stay, wish I was here longer "
United States
Thomas
The price is NZ$240
includes taxes & fees
9 Feb - 10 Feb
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
7.5 km from Chesterwood
10.0 out of 10, Exceptional, (135 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B

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)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is NZ$181
includes taxes & fees
24 Feb - 25 Feb
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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, (766 reviews)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
The price is NZ$279
includes taxes & fees
8 Feb - 9 Feb
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
8.7 km from Chesterwood
9.0 out of 10, Wonderful, (819 reviews)
"Unbelieveably clean for the price."
United States
Micah
Monument Mountain Motel

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, (730 reviews)
"Great property, very accommodating. "
United States
Shanice
The price is NZ$198
includes taxes & fees
10 Feb - 11 Feb
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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

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, (567 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is NZ$139
includes taxes & fees
5 Feb - 6 Feb
Travelodge by Wyndham Great Barrington Berkshires

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 NZ$156
includes taxes & fees
22 Feb - 23 Feb
Quality Inn Lee - Lenox South

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
4.7 km from Chesterwood
6.8 out of 10, (1,002 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is NZ$106
includes taxes & fees
12 Feb - 13 Feb
Pleasant Valley Motel West Stockbridge

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 NZ$228
includes taxes & fees
22 Feb - 23 Feb
East Rock 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

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 NZ$257
includes taxes & fees
22 Feb - 23 Feb
Element Lenox Berkshires

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
7.4 km from Chesterwood
6.4 out of 10, (656 reviews)
"The room was clean and the service adequate"
United States
David
The price is NZ$118
includes taxes & fees
18 Feb - 19 Feb
Econo Lodge Lee - Great Barrington

The Whitlock

The Whitlock
2.0 star property
9.8 km from Chesterwood
8.6 out of 10, Excellent, (286 reviews)
"Super cute place and walking distance to a bunch of great shops and food! "
United States
Gina
The price is NZ$224
includes taxes & fees
9 Feb - 10 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.

Top Chesterwood Hotel Reviews

Hotels near other Chesterwood attractions

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.