Search Hotels Near Chesterwood, South Lee

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

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)
"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 8.131.943 ₫
9.837.531 ₫ total
includes taxes & fees
15 Feb - 16 Feb
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, (1,001 reviews)
"Old time charm and hot tub under the stars"
United States
Lori
The price is 3.994.864 ₫
5.636.542 ₫ total
includes taxes & fees
21 Jan - 22 Jan
The Red Lion Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
5.8 km from Chesterwood
9.6 out of 10, Exceptional, (441 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 2.864.193 ₫
3.142.020 ₫ total
includes taxes & fees
21 Jan - 22 Jan
Shaker Mill Inn

Granville House

Granville House
3.0 star property
6.4 km from Chesterwood
10.0 out of 10, Exceptional, (92 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 4.572.198 ₫
5.107.198 ₫ total
includes taxes & fees
20 Jan - 21 Jan
Granville House

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 2.956.162 ₫
3.815.747 ₫ total
includes taxes & fees
22 Jan - 23 Jan
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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 3.547.395 ₫
3.962.440 ₫ total
includes taxes & fees
29 Jan - 30 Jan
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

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, (719 reviews)
"Nice warm pool and hot tub. Good little fitness center. "
United States
Fawn
The price is 2.811.639 ₫
3.140.602 ₫ total
includes taxes & fees
5 Feb - 6 Feb
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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 2.890.470 ₫
3.228.655 ₫ total
includes taxes & fees
18 Jan - 19 Jan
The Little Lion

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

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 2.568.577 ₫
2.869.099 ₫ total
includes taxes & fees
4 Feb - 5 Feb
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
8.7 km from Chesterwood
9.0 out of 10, Wonderful, (816 reviews)
"Unbelieveably clean for the price."
United States
Micah
Monument Mountain Motel

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 3.783.888 ₫
4.437.932 ₫ total
includes taxes & fees
22 Jan - 23 Jan
Lakehouse 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

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 1.970.775 ₫
2.201.487 ₫ total
includes taxes & fees
21 Jan - 22 Jan
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 2.031.861 ₫
2.269.589 ₫ total
includes taxes & fees
1 Feb - 2 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, (1,001 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is 1.537.204 ₫
1.686.313 ₫ total
includes taxes & fees
18 Jan - 19 Jan
Pleasant Valley Motel West Stockbridge

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, (16 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is 3.652.503 ₫
4.079.846 ₫ total
includes taxes & fees
21 Jan - 22 Jan
Element Lenox Berkshires

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 3.641.992 ₫
4.068.106 ₫ total
includes taxes & fees
26 Jan - 27 Jan
East Rock Inn

33 Main

33 Main
4.0 star property
9.8 km from Chesterwood
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is 10.519.371 ₫
11.750.137 ₫ total
includes taxes & fees
18 Jan - 19 Jan
33 Main
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.
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.