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Find hotels near Chesterwood, South Lee from AED 456

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Check prices for these dates

Next weekend
10 Jul - 12 Jul
In two weeks
17 Jul - 19 Jul

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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, (112 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is AED 1,213
AED 1,467 total
includes taxes & fees
19 Jul - 20 Jul
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Individually decorated, individually furnished, desk, laptop workspace

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 AED 826
AED 923 total
includes taxes & fees
7 Jul - 8 Jul
Granville House
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)
"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 AED 1,465
AED 1,718 total
includes taxes & fees
19 Jul - 20 Jul
The Inn at Stockbridge
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, (138 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is AED 1,612
AED 1,801 total
includes taxes & fees
13 Jul - 14 Jul
Devonfield Inn B&B
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
5.8 km from Chesterwood
9.6 out of 10, Exceptional, (462 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is AED 575
AED 630 total
includes taxes & fees
6 Jul - 7 Jul
Shaker Mill Inn
Front of property

Chambery Inn

Chambery Inn
3.0 star property
8.7 km from Chesterwood
9.6 out of 10, Exceptional, (380 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 AED 992
AED 1,108 total
includes taxes & fees
6 Jul - 7 Jul
Chambery Inn
Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
3.3 km from Chesterwood
8.8 out of 10, Excellent, (1,004 reviews)
"Clean room and breakfast"
United States
Raphael
The price is AED 643
AED 882 total
includes taxes & fees
22 Jul - 23 Jul
The Red Lion 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
3.5 star property
6.6 km from Chesterwood
9.2 out of 10, Wonderful, (926 reviews)
"Wonderful stay for families."
United States
Kimberly
The price is AED 645
AED 792 total
includes taxes & fees
8 Jul - 9 Jul
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, (791 reviews)
"Dawn was super helpful in getting us checked in."
United States
Kristen
The price is AED 777
AED 868 total
includes taxes & fees
12 Jul - 13 Jul
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Front of property

Brook Farm Inn

Brook Farm Inn
3.5 star property
9.1 km from Chesterwood
9.4 out of 10, Exceptional, (167 reviews)
"Lovely stay!"
United States
Jiacheng
The price is AED 731
AED 846 total
includes taxes & fees
6 Jul - 7 Jul
Brook Farm Inn
Lobby lounge

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, (28 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is AED 746
AED 833 total
includes taxes & fees
19 Jul - 20 Jul
Element by Marriott Lenox Berkshires
Exterior

Prospect Berkshires

Prospect Berkshires
3.0 star property
12.8 km from Chesterwood
9.8 out of 10, Exceptional, (32 reviews)
"Great stay!"
United States
Conor
The price is AED 1,306
AED 1,582 total
includes taxes & fees
13 Jul - 14 Jul
Prospect Berkshires
Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

East Rock Inn

East Rock Inn
2.0 star property
10.1 km from Chesterwood
9.4 out of 10, Exceptional, (49 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 AED 532
AED 594 total
includes taxes & fees
21 Jul - 22 Jul
East Rock Inn
Exterior

The Little Lion

The Little Lion
3.0 star property
5.1 km from Chesterwood
8.6 out of 10, Excellent, (576 reviews)
"Such a peaceful and easy stay!"
United States
Mia
The price is AED 411
AED 460 total
includes taxes & fees
7 Jul - 8 Jul
The Little Lion
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
8.7 km from Chesterwood
9.0 out of 10, Wonderful, (876 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 AED 408
AED 456 total
includes taxes & fees
8 Jul - 9 Jul
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, (784 reviews)
"very responsive staff excellent check in and check out"
United States
Kathleen
The price is AED 606
AED 677 total
includes taxes & fees
27 Jul - 28 Jul
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Property amenity

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
12.1 km from Chesterwood
9.2 out of 10, Wonderful, (634 reviews)
"We arrived at the hotel and there was"
United States
Nancy
The price is AED 809
AED 903 total
includes taxes & fees
12 Jul - 13 Jul
Courtyard by Marriott Lenox Berkshires
Exterior

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
10.9 km from Chesterwood
9.0 out of 10, Wonderful, (9 reviews)
"The new owners have done a great job. The place is immaculate, the room was very comfortable and well appointed, the common areas charming. Highly recommended."
United States
Robert
The price is AED 972
AED 1,085 total
includes taxes & fees
15 Jul - 16 Jul
The Berkshire Mountain Inn
Aerial view

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
17.5 km from Chesterwood
9.8 out of 10, Exceptional, (111 reviews)
"Very nice hotel."
United States
Erdem
The price is AED 694
AED 778 total
includes taxes & fees
8 Jul - 9 Jul
Inn at Silver Maple Farm
Exterior

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, (1,003 reviews)
"Great place, nice amenities and convenient location, highly recommended."
United States
Arthur
The price is AED 476
AED 547 total
includes taxes & fees
6 Jul - 7 Jul
The Cornell Inn, Lenox & The 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
112 reviews
View
Individually decorated, individually furnished, desk, laptop workspace
Granville House
3.0 star property
10.0
Exceptional
102 reviews
View
Front of property
The Inn at Stockbridge
4.0 star property
9.8
Exceptional
99 reviews
View
Front of property - evening/night
Devonfield Inn B&B
4.0 star property
10.0
Exceptional
138 reviews
View
Garden
Shaker Mill Inn
2.5 star property
9.6
Exceptional
462 reviews
View

Top Chesterwood Hotel Reviews

Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10

Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10

10/10 Excellent
"The house and grounds are gorgeous and easy walking distance into Stockbridge to shop, dine and get drinks. There are also terrific hiking trails with walking distance called Laura‘s Tower and Ice Glenn. The house was very clean, spacious and equipped with everything we needed. The kitchen is enormous, making it a great space for everyone to gather and cooked together. We look forward to returning!"
Ann B. 3-night trip
Posted 3 hours ago
Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10

Hotels near other Chesterwood attractions

Norman Rockwell Museum

9.4/10 (347 reviews)
You can spend time studying the exhibits at Norman Rockwell Museum during your travels in 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, check out the 10 hotels and other accommodations you'll find within a mile.
What's the best hotel 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 traveler 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 are there close to Chesterwood?
Expedia has 10 hotels and other accommodations within a mile from Chesterwood.
If I need to cancel the hotel reservation for my stay near Chesterwood, will I receive a refund?
Yes, the majority of room reservations are fully refundable provided that you cancel before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you have a non-refundable reservation, you might be able to still cancel and be given a refund within 24 hours of booking. Enter dates in and click on "Search", then use the "fully refundable" filter to review the best options available near Chesterwood.
Where can I learn more about changing or cancelling my trip in the area near Chesterwood?
For more information about picking new dates or cancelling your stay near Chesterwood, head over to our customer service page.
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.

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