Find hotels near Chesterwood, South Lee from AED 410

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Check prices for these dates

Tonight
19 Feb - 20 Feb
Tomorrow
20 Feb - 21 Feb
This weekend
20 Feb - 22 Feb
Next weekend
27 Feb - 1 Mar

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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 AED 1,137
AED 1,375 total
includes taxes & fees
4 Mar - 5 Mar
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Room #10 Queen's Cottage | Living room | Flat-screen TV

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
7.5 km from Chesterwood
10.0 out of 10, Exceptional, (136 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
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, (446 reviews)
"Had everything we needed. Very thoughtful touches. "
United States
Mark
The price is AED 373
AED 410 total
includes taxes & fees
3 Mar - 4 Mar
Shaker Mill Inn
Exterior

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 AED 1,796
AED 2,006 total
includes taxes & fees
22 Feb - 23 Feb
33 Main
Front of property

Chambery Inn

Chambery Inn
3.0 star property
8.7 km from Chesterwood
9.6 out of 10, Exceptional, (375 reviews)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
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, (1,001 reviews)
"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."
United States
Gary
The price is AED 527
AED 753 total
includes taxes & fees
5 Mar - 6 Mar
The Red Lion Inn
Lobby

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
12.1 km from Chesterwood
10.0 out of 10, Exceptional, (27 reviews)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is AED 2,112
AED 2,317 total
includes taxes & fees
20 Feb - 21 Feb
Inn at Kenmore Hall
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, (767 reviews)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
The price is AED 591
AED 661 total
includes taxes & fees
25 Feb - 26 Feb
Fairfield Inn & Suites by Marriott Great Barrington Lenox/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
9.6 out of 10, Exceptional, (37 reviews)
"The room was clean and comfortable wi will back next year:) "
United States
Nadya
The price is AED 474
AED 529 total
includes taxes & fees
6 Mar - 7 Mar
East Rock Inn
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
Brook Farm 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
9.0 out of 10, Wonderful, (840 reviews)
"Great overnights stay, wish I was here longer "
United States
Thomas
The price is AED 367
AED 482 total
includes taxes & fees
22 Feb - 23 Feb
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Lobby lounge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
12.5 km from Chesterwood
9.8 out of 10, Exceptional, (19 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is AED 511
AED 570 total
includes taxes & fees
1 Mar - 2 Mar
Element Lenox Berkshires
Exterior

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 AED 404
AED 451 total
includes taxes & fees
22 Feb - 23 Feb
The Little Lion
Exterior

Prospect Berkshires

Prospect Berkshires
3.0 star property
12.8 km from Chesterwood
9.6 out of 10, Exceptional, (19 reviews)
"Excellent local stay - would recommend to all"
United States
Gentian
The price is AED 720
AED 927 total
includes taxes & fees
2 Mar - 3 Mar
Prospect Berkshires
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, (823 reviews)
"The room was clean, and the staff was friendly and helpful. "
United States
Damien
Monument Mountain Motel
Exterior detail

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
9.8 km from Chesterwood
9.0 out of 10, Wonderful, (43 reviews)
"Comfortable bed. Quiet location. Excellent breakfast. Friendly host."
United States
Kathleen
The price is AED 804
AED 898 total
includes taxes & fees
26 Feb - 27 Feb
Hampton Terrace Inn
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, (601 reviews)
"Our stay was great! "
United States
Gianna
The price is AED 463
AED 517 total
includes taxes & fees
15 Mar - 16 Mar
Courtyard by Marriott Lenox Berkshires
Lobby sitting area

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, (101 reviews)
"Great property, very comfortable, incredible staff, easy access to skiing in the area!"
United States
Dominick
The price is AED 511
AED 572 total
includes taxes & fees
3 Mar - 4 Mar
Inn at Silver Maple Farm
Exterior

The Whitlock

The Whitlock
2.0 star property
9.8 km from Chesterwood
8.6 out of 10, Excellent, (288 reviews)
"Super cute place and walking distance to a bunch of great shops and food! "
United States
Gina
The price is AED 514
AED 574 total
includes taxes & fees
9 Mar - 10 Mar
The Whitlock
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
10.7 km from Chesterwood
9.0 out of 10, Wonderful, (1,000 reviews)
"The Inn was very nice and the staff was super friendly and attentive."
United States
Steven
The price is AED 490
AED 564 total
includes taxes & fees
23 Feb - 24 Feb
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.
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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
Room #10 Queen's Cottage | Living room | Flat-screen TV
Devonfield Inn B&B
4.0 star property
10.0
Exceptional
136 reviews
View
Garden
Shaker Mill Inn
2.5 star property
9.6
Exceptional
446 reviews
View
Exterior
33 Main
4.0 star property
10.0
Exceptional
74 reviews
View
Front of property
Chambery Inn
3.0 star property
9.6
Exceptional
375 reviews
View

Top Chesterwood Hotel Reviews

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

10/10 Excellent
"Super clean spacious room! "
camille 2-night trip
Posted 4 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Hotels near other Chesterwood attractions

Norman Rockwell Museum

4.7/5 (252 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

Berkshire Botanical Garden

4.0/5 (1 review)
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, 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 Charles H. Baldwin & Sons while you're out sightseeing near Chesterwood.