Find hotels near Chesterwood, South Lee from AED 304

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21 Nov - 22 Nov
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Compare 743 hotels close to Chesterwood with room rates, reviews, and availability. Most hotels are fully refundable.

Business center
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)
"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 AED 1,403
AED 1,697 total
includes taxes & fees
4 Dec - 5 Dec
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
2 Bedrooms 1 Bath | 1 bedroom, premium bedding, iron/ironing board, free WiFi
Tanglewood Suites

Tanglewood Suites

2.5 star property
2.6 km from Chesterwood
6.4 out of 10, (22)
"NOT A REAL LOCATION. There was nothing there. Neighbors said this was a scam. Expedia ended up helping us find a local hotel room though the location was not as good. DO NOT BOOK THIS LOCATION -- it needs to be taken off the website."
United States
Elizabeth
The price is AED 804
AED 804 total
includes taxes & fees
1 Dec - 2 Dec
Tanglewood Suites
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, (87)
"Outstanding all around!"
United States
Jonathan
The price is AED 735
AED 821 total
includes taxes & fees
25 Nov - 26 Nov
Granville House
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, (133)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
12.5 km from Chesterwood
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
The price is AED 481
AED 537 total
includes taxes & fees
11 Dec - 12 Dec
Element Lenox Berkshires
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, (97)
"Great stay, comfortable place"
United States
barry
The price is AED 474
AED 531 total
includes taxes & fees
23 Nov - 24 Nov
Inn at Silver Maple Farm
Front of property
Chambery Inn

Chambery Inn

3.0 star property
8.7 km from Chesterwood
9.6 out of 10, Exceptional, (372)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Porch
Lakehouse Inn

Lakehouse Inn

4.0 star property
8.7 km from Chesterwood
9.6 out of 10, Exceptional, (289)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is AED 676
AED 793 total
includes taxes & fees
4 Dec - 5 Dec
Lakehouse Inn
Egyptian cotton sheets, premium bedding, down comforters, minibar
Prospect Berkshires

Prospect Berkshires

3.0 star property
12.8 km from Chesterwood
9.6 out of 10, Exceptional, (14)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is AED 955
AED 1,190 total
includes taxes & fees
23 Nov - 24 Nov
Prospect Berkshires
Lobby
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, (754)
"Clean room, very courteous staff "
United States
Thomas
The price is AED 555
AED 619 total
includes taxes & fees
26 Nov - 27 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds
Brook Farm Inn

Brook Farm Inn

3.5 star property
9.1 km from Chesterwood
9.4 out of 10, Exceptional, (162)
"Comfortable, quiet, convenient location, very friendly staff. "
United States
Susan
Brook Farm Inn
Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Private kitchen | Mini-fridge, microwave, electric kettle
East Rock Inn

East Rock Inn

2.0 star property
10.1 km from Chesterwood
9.4 out of 10, Exceptional, (36)
"We had a great stay at East Rock Inn! Newly remodeled, clean room, comfortable bed, easy access to town. I will definitely stay there again."
United States
Laura
The price is AED 477
AED 532 total
includes taxes & fees
11 Dec - 12 Dec
East Rock Inn
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
15.5 km from Chesterwood
9.4 out of 10, Exceptional, (60)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is AED 364
AED 407 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Seasonal outdoor pool
Little Cat Lodge

Little Cat Lodge

2.0 star property
16.3 km from Chesterwood
9.4 out of 10, Exceptional, (64)
"This is a very cute lodge, updated with a bit of vintage charm. Close to all the Berkshires must sees and nature hiking trails. "
United States
Kayla
Little Cat Lodge
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, (586)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is AED 419
AED 468 total
includes taxes & fees
21 Dec - 22 Dec
Courtyard by Marriott Lenox Berkshires
Exterior
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
14.7 km from Chesterwood
9.2 out of 10, Wonderful, (1000)
"Clean, pleasant staff and good breakfast. "
United States
Edward
The price is AED 408
AED 456 total
includes taxes & fees
30 Nov - 1 Dec
Hampton Inn & Suites Berkshires-Lenox
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
14.9 km from Chesterwood
9.2 out of 10, Wonderful, (1005)
"Great stay!"
United States
Ann
The price is AED 273
AED 304 total
includes taxes & fees
14 Dec - 15 Dec
The Yankee, Trademark Collection by Wyndham
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

3.0 star property
15.5 km from Chesterwood
9.2 out of 10, Wonderful, (657)
"Clean and convenient to Mt. Greylock. Kind staff. "
United States
Kristen
The price is AED 408
AED 456 total
includes taxes & fees
30 Nov - 1 Dec
Hilton Garden Inn Lenox Pittsfield
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, (787)
"Place was great!"
United States
Benjamin
The price is AED 391
AED 488 total
includes taxes & fees
24 Nov - 25 Nov
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Exterior
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, (1000)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is AED 390
AED 436 total
includes taxes & fees
11 Dec - 12 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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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Top Chesterwood Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"I love the ambience - historic and comfortable and excellent food. "
Nancy 1-night trip
Posted 2 weeks ago
The Red Lion Inn

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. Other good choices within a few miles include The Red Lion Inn and Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10.
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.

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