Top Hotels Near Chesterwood in South Lee from AU$97

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Check prices for these dates

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4 Apr - 5 Apr
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5 Apr - 6 Apr
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10 Apr - 12 Apr
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17 Apr - 19 Apr

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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 AU$542
includes taxes & fees
22 Apr - 23 Apr
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, (1,001 reviews)
"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."
United States
Gary
The price is AU$281
includes taxes & fees
14 Apr - 15 Apr
The Red Lion Inn
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
9.2 out of 10, Wonderful, (1,002 reviews)
"Room was spotless, staff was very kind!"
United States
Ilia
The price is AU$168
includes taxes & fees
28 Apr - 29 Apr
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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 AU$386
includes taxes & fees
12 Apr - 13 Apr
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, (446 reviews)
"Had everything we needed. Very thoughtful touches. "
United States
Mark
The price is AU$158
includes taxes & fees
9 Apr - 10 Apr
Shaker Mill Inn
Room, 2 Queen Beds, Non Smoking

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
8.7 km from Chesterwood
9.0 out of 10, Wonderful, (837 reviews)
"Nice place and very reasonable for great location "
United States
Raymond
The price is AU$97
includes taxes & fees
8 Apr - 9 Apr
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, (754 reviews)
"Staff was great! Clean room, parking was always available. Breakfast was great. Had a great time!"
United States
Brigid
The price is AU$186
includes taxes & fees
20 Apr - 21 Apr
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, (861 reviews)
"Great place to enjoy with the whole family!!!"
United States
Elizabeth
The price is AU$224
includes taxes & fees
7 Apr - 8 Apr
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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, (776 reviews)
"Staff was lovely, everything was easy, clean and comfortable"
United States
Helena
The price is AU$246
includes taxes & fees
9 Apr - 10 Apr
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Porch

Lakehouse Inn

Lakehouse Inn
4.0 star property
8.7 km from Chesterwood
9.6 out of 10, Exceptional, (297 reviews)
"Friendly staff, great location, beautiful views, cozy room."
United States
Elizabeth
The price is AU$255
includes taxes & fees
18 Apr - 19 Apr
Lakehouse Inn
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, (1,000 reviews)
"Great visit all around. Centrally located to the skiing resorts, lots to do in town, decent breakfast spread, clean room, and for a short stay, housekeeping came when unexpected! "
United States
Amy
The price is AU$150
includes taxes & fees
19 Apr - 20 Apr
Quality Inn Lee - Lenox South
Exterior

The Little Lion

The Little Lion
3.0 star property
5.1 km from Chesterwood
8.6 out of 10, Excellent, (555 reviews)
"Clean … check in , good location for us .. we’ll be back in Maynn"
United States
Kathleen
The price is AU$178
includes taxes & fees
19 Apr - 20 Apr
The Little Lion
Front of property – evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
7.5 km from Chesterwood
10.0 out of 10, Exceptional, (137 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
The price is AU$484
includes taxes & fees
4 May - 5 May
Devonfield Inn B&B
Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area

East Rock Inn

East Rock Inn
2.0 star property
10.1 km from Chesterwood
9.4 out of 10, Exceptional, (43 reviews)
"The room was clean and comfortable wi will back next year:) "
United States
Nadya
The price is AU$195
includes taxes & fees
27 Apr - 28 Apr
East Rock Inn
Desk, laptop workspace, blackout curtains, 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, (1,002 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is AU$111
includes taxes & fees
24 Apr - 25 Apr
Pleasant Valley Motel West Stockbridge
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
The price is AU$287
includes taxes & fees
24 Apr - 25 Apr
Brook Farm Inn
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
13 km from Chesterwood
9.0 out of 10, Wonderful, (886 reviews)
"This was a great stay! The room and hotel itself were up to date and was overall a great location to check out the Berkshires. We ate one night at the hotel too and the dinner was really good! I recommend the mushroom ravioli, would stay again."
United States
Payton
The price is AU$149
includes taxes & fees
7 Apr - 8 Apr
Berkshires Untold
Lobby lounge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
12.5 km from Chesterwood
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is AU$232
includes taxes & fees
12 Apr - 13 Apr
Element Lenox Berkshires
Exterior

The Whitlock

The Whitlock
2.0 star property
9.8 km from Chesterwood
8.6 out of 10, Excellent, (292 reviews)
"Lovely historical hotel within walking distance to many great shops and restaurants. Staff members maintained good communication and were very helpful throughout our stay. Rooms were clean, quiet, and comfortable. Would definitely stay there again."
United States
Elaine
The price is AU$158
includes taxes & fees
5 Apr - 6 Apr
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, (661 reviews)
"Good to stay. "
United States
Ibinabo
The price is AU$109
includes taxes & fees
19 Apr - 20 Apr
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
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
Exterior
The Red Lion Inn
3.5 star property
8.8
Excellent
1,001 reviews
View
Lake
The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
9.2
Wonderful
1,002 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
446 reviews
View

Top Chesterwood Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"What a beautiful, unique building. Full of antiques and feels like going back in time. The ride up to my fourth floor room in the 19th century cage elevator was a wonderful touch. Can’t wait to go back again. "
Susan 1-night trip
Posted 1 day ago
The Red Lion Inn

Hotels near other Chesterwood attractions

Norman Rockwell Museum

4.7/5 (345 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

4.7/5 (14 reviews)
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 Lenox Arts Center while you're out sightseeing near Chesterwood.