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Top Hotels Near Chesterwood in South Lee from NZ$138

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Check prices for these dates

Next weekend
26 Jun - 28 Jun
In two weeks
3 Jul - 5 Jul

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Our top choices for Chesterwood hotels

Suite, Private Bathroom (RedBird Suite) | View from room

1. 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, (111 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is NZ$696
includes taxes & fees
5 July - 6 July
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Exterior

2. The Red Lion Inn

The Red Lion Inn
3.5 star property
3.3 km from Chesterwood
8.8 out of 10, Excellent, (1,004 reviews)
"Clean room and breakfast"
United States
Raphael
The price is NZ$366
includes taxes & fees
8 July - 9 July
The Red Lion Inn
Exterior

3. The Little Lion

The Little Lion
3.0 star property
5.1 km from Chesterwood
8.6 out of 10, Excellent, (569 reviews)
"Such a peaceful and easy stay!"
United States
Mia
The price is NZ$171
includes taxes & fees
23 June - 24 June
The Little Lion
Exterior

4. 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, (775 reviews)
"very responsive staff excellent check in and check out"
United States
Kathleen
The price is NZ$251
includes taxes & fees
25 June - 26 June
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Individually decorated, individually furnished, desk, laptop workspace

5. Granville House

Granville House
3.0 star property
6.4 km from Chesterwood
10.0 out of 10, Exceptional, (102 reviews)
"Beautiful home with warm and friendly hosts. The rooms were tastefully designed, the bed was very comfortable and the large bathroom was luxurious. The breakfast was absolutely delicious. We will definitely stay again next time we are in Great Barrington. "
United States
Nicole
The price is NZ$535
includes taxes & fees
22 June - 23 June
Granville House
Garden

6. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
5.8 km from Chesterwood
9.6 out of 10, Exceptional, (461 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is NZ$249
includes taxes & fees
22 June - 23 June
Shaker Mill Inn
Room, 2 Queen Beds, Non Smoking

7. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
8.7 km from Chesterwood
9.0 out of 10, Wonderful, (873 reviews)
"I was pleasantly surprised how clean,spacious,quiet and comfortable the room was ( two queens) Loved the place."
United States
Yekaterina
The price is NZ$216
includes taxes & fees
29 June - 30 June
Monument Mountain Motel
Exterior

8. 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, (787 reviews)
"Dawn was super helpful in getting us checked in."
United States
Kristen
The price is NZ$362
includes taxes & fees
30 June - 1 July
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Front of property

9. 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)
"Great spot close to town. Cozy, tasteful, comfortable room. Nice breakfasts and pleasant interaction with the staff. We love the Berkshires and we’ll definitely stay here again."
United States
Stephen
The price is NZ$738
includes taxes & fees
23 June - 24 June
The Inn at Stockbridge
Classic Double Room, 2 Queen Beds, Courtyard View | Bathroom

10. East Rock Inn

East Rock Inn
2.0 star property
10.1 km from Chesterwood
9.4 out of 10, Exceptional, (48 reviews)
"The East Rock Inn is great. It's comfortable, clean and close to downtown Great Barrington. This was my second time staying here."
United States
Laura
The price is NZ$248
includes taxes & fees
6 July - 7 July
East Rock Inn
Front of property – evening/night

11. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
7.5 km from Chesterwood
10.0 out of 10, Exceptional, (138 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is NZ$757
includes taxes & fees
24 June - 25 June
Devonfield Inn B&B
In-room safe, desk, free cots/infant beds, free rollaway beds

12. 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, (586 reviews)
"The room was very clean but old and tired. Same with parking area. A decent value when travelling with a pet."
United States
Heather
The price is NZ$154
includes taxes & fees
22 June - 23 June
Travelodge by Wyndham Great Barrington Berkshires
Front of property

13. Chambery Inn

Chambery Inn
3.0 star property
8.7 km from Chesterwood
9.6 out of 10, Exceptional, (379 reviews)
"Yes the room was spotless and always the staff is ready to answer any questions that we might have. We have been enjoying the Chambery Inn for many years always had a great stay and again looking for our next visit. Vincent Farricielli and Roibert Modena. "
United States
robert
The price is NZ$526
includes taxes & fees
29 June - 30 June
Chambery Inn
Lobby

14. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
10.3 km from Chesterwood
8.6 out of 10, Excellent, (1,011 reviews)
"Great staff breakfast was good location was close enough to walk but far enough from the noise "
United States
Braynd
The price is NZ$202
includes taxes & fees
25 June - 26 June
Quality Inn Great Barrington
Children’s activities

15. 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)
"The property is in terrible condition."
United States
Olga V
The price is NZ$138
includes taxes & fees
22 June - 23 June
Pleasant Valley Motel West Stockbridge
Exterior

16. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
10.7 km from Chesterwood
9.2 out of 10, Wonderful, (1,002 reviews)
"Great place, nice amenities and convenient location, highly recommended."
United States
Arthur
The price is NZ$391
includes taxes & fees
29 June - 30 June
The Cornell Inn, Lenox & The Berkshires
Superior Room, 1 King Bed, Jetted Tub | Jetted bathtub

17. The Yankee Inn

The Yankee Inn
2.5 star property
14.9 km from Chesterwood
9.2 out of 10, Wonderful, (1,004 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is NZ$248
includes taxes & fees
23 June - 24 June
The Yankee Inn
Exterior

18. The Whitlock

The Whitlock
2.0 star property
9.8 km from Chesterwood
8.6 out of 10, Excellent, (311 reviews)
"A beautiful old inn in the heart of a lovely old town."
United States
Linda
The price is NZ$302
includes taxes & fees
6 July - 7 July
The Whitlock
Lobby lounge

19. Berkshires Untold

Berkshires Untold
3.5 star property
13 km from Chesterwood
9.0 out of 10, Wonderful, (990 reviews)
"Great lobby and dining room atmosphere!"
United States
Carin
The price is NZ$321
includes taxes & fees
12 July - 13 July
Berkshires Untold
Lobby lounge

20. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
12.5 km from Chesterwood
9.8 out of 10, Exceptional, (26 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is NZ$407
includes taxes & fees
22 June - 23 June
Element by Marriott 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.
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
111 reviews
View
Exterior
The Red Lion Inn
3.5 star property
8.8
Excellent
1,004 reviews
View
Exterior
The Little Lion
3.0 star property
8.6
Excellent
569 reviews
View
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8.8
Excellent
775 reviews
View
Individually decorated, individually furnished, desk, laptop workspace
Granville House
3.0 star property
10.0
Exceptional
102 reviews
View

Top Chesterwood Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Our experience at the Red Lion Inn went beyond our expectations. The entire staff was most helpful, went above and beyond to make our stay enjoyable, and treated us as if we were the only guests staying there! The inn is magnificent and we felt we were staying in a museum! The accommodation was lovely and the dining room served gourmet food. We would love to go back. If you haven’t stayed there you are missing out on a great opportunity."
Marinus 2-night trip
Posted 2 days ago
The Red Lion Inn

Hotels near other Chesterwood attractions

Norman Rockwell Museum

9.4/5 (347 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

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.