Find hotels near Chesterwood, South Lee from SAR 250

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Compare 691 hotels close to Chesterwood with room rates, reviews, and availability. Most hotels are fully refundable.

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
View from room

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
9.2 out of 10, Wonderful, (105)
"The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer most questions"
The price is SAR 1,723
SAR 2,084 total
includes taxes & fees
25 Nov - 26 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Tanglewood Suites
Property grounds

Tanglewood Suites

2.5 star property
8.0 out of 10, Very Good, (15)
"Portion of hosts home, separate and available for rent. Heating system not efficient and took some work to sort out how to keep all areas of the unit comfortably heated. Beds clean and comfortable. Overall cleanliness was good. Bath facilities are an addition to existing structure and sufficient, but could use some TLC. Host is eager to please and pleasant to interact with. Listing indicates free breakfast for all guests. However, upon arrival, we were advised there is no winter offering of...
The price is SAR 822
SAR 822 total
includes taxes & fees
25 Nov - 26 Nov
Tanglewood Suites
Granville House
Room

Granville House

3.0 star property
10.0 out of 10, Exceptional, (76)
"The surroundings were quiet and peaceful. The hosts were welcoming and friendly. Wonderful people "
The price is SAR 751
SAR 839 total
includes taxes & fees
1 Dec - 2 Dec
Granville House
Devonfield Inn B&B
Room

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (117)
"Arrived Friday to see a Tanglewood concert. Inn provided lovely afternoon cocktails and appetizers with piano music. Saturday hosts sponsored garden concert with local artists - really nice after morning hike to water fall and early afternoon golf. Yummy Morning breakfast each day. Central to Stonebridge and Lenox. Hosts very knowledgeable "
The price is SAR 1,123
SAR 1,254 total
includes taxes & fees
5 Dec - 6 Dec
Devonfield Inn B&B
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (400)
"Quaint "
The price is SAR 544
SAR 597 total
includes taxes & fees
25 Nov - 26 Nov
Shaker Mill Inn
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (359)
"Lovely, unique property with huge rooms! Such a fun place to stay. "
The price is SAR 713
SAR 797 total
includes taxes & fees
25 Nov - 26 Nov
Chambery Inn
The Red Lion Inn
Front of property

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1020)
"Didn’t like that there are no trays in shower to hold any soaps or bottles while washing… nothing!!! Tub too high for elderly with slightest arthritis. No curtain on shower bathroom window. Took quite a while to get hot water to wash hands in sink. However, the inn is filled with amazing collectibles. The dinner was delicious. Plenty of seats but gave us a table facing wall (but near window) —why not more in middle of room area with more interesting view! And same table for breakfast and...
The price is SAR 544
SAR 776 total
includes taxes & fees
1 Dec - 2 Dec
The Red Lion Inn
Brook Farm Inn
Front of property

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (147)
"Very charming inn. The staff was very friendly and helpful."
The price is SAR 604
SAR 675 total
includes taxes & fees
27 Nov - 28 Nov
Brook Farm Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

3.5 star property
9.0 out of 10, Wonderful, (568)
"The unit was perfect in size, very good quality of towels. For the cribs, they provided new sheets and blanket that was important for us. "
The price is SAR 484
SAR 593 total
includes taxes & fees
25 Nov - 26 Nov
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
The Little Lion
Exterior

The Little Lion

3.0 star property
8.8 out of 10, Excellent, (435)
"this is a great little roadside motel that is perfect for road trips. clean and convenient. close to hoking if you like. minimal but totally fine. it’s what you want on a road trip"
The price is SAR 276
SAR 308 total
includes taxes & fees
8 Dec - 9 Dec
The Little Lion
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Pool

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.2 out of 10, Wonderful, (672)
"Great hotel with nice staff and facilities. Close to grocery, restaurants and Stockbridge tourist attractions."
The price is SAR 571
SAR 637 total
includes taxes & fees
1 Dec - 2 Dec
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1021)
"Great stay"
The price is SAR 357
SAR 399 total
includes taxes & fees
9 Dec - 10 Dec
The Black Swan Lee - Lenox, Ascend Hotel Collection
East Rock Inn
Front of property

East Rock Inn

2.0 star property
9.2 out of 10, Wonderful, (12)
"Love this motel. Visit the area monthly, this was my 5th visit at East Rock, every time has been perfect."
The price is SAR 416
SAR 464 total
includes taxes & fees
25 Nov - 26 Nov
East Rock Inn
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Exterior

Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel

2.5 star property
8.8 out of 10, Excellent, (564)
"Look clean, great staffs."
The price is SAR 443
SAR 495 total
includes taxes & fees
3 Dec - 4 Dec
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Monument Mountain Motel
Room

Monument Mountain Motel

2.5 star property
8.8 out of 10, Excellent, (678)
"Nice people operating a very clean, comfortable motel. A bargain."
The price is SAR 250
SAR 279 total
includes taxes & fees
25 Nov - 26 Nov
Monument Mountain Motel
Courtyard by Marriott Lenox Berkshires
Lobby lounge

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (533)
"Nice, friendly staff. large lobby area with multiple seating areas. Coffee over priced. "
The price is SAR 458
SAR 512 total
includes taxes & fees
5 Dec - 6 Dec
Courtyard by Marriott Lenox Berkshires
Inn at Silver Maple Farm
Front of property

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (79)
"Everything "
The price is SAR 597
SAR 645 total
includes taxes & fees
25 Nov - 26 Nov
Inn at Silver Maple Farm
The Cornell Inn, Lenox
Exterior

The Cornell Inn, Lenox

3.0 star property
8.8 out of 10, Excellent, (1035)
"We were greeted warmly upon arrival with hot beverages and brownies. There were bakery items available all during our stay, and the property features a quaint little bar with many offerings. The breakfast was served in a bright and very well-appointed room with a fireplace and the staff were very friendly and attentive. The food was very nicely presented and delicious. This is a wonderful bed and breakfast at a very affordable price. Will definitely return. "
The price is SAR 458
SAR 537 total
includes taxes & fees
25 Nov - 26 Nov
The Cornell Inn, Lenox
The Constance, The Whitlock, & The Dewey By The Lenox Collection
Terrace/patio

The Constance, The Whitlock, & The Dewey By The Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (404)
"This was a comfortable, clean room in a great little shopping and dining neighborhood. The staff was very friendly and helpful. I look forward to staying here again! "
The price is SAR 336
SAR 375 total
includes taxes & fees
25 Nov - 26 Nov
The Constance, The Whitlock, & The Dewey By The Lenox Collection
Life House Berkshires
Lobby

Life House Berkshires

3.5 star property
9.0 out of 10, Wonderful, (442)
"Beautiful room and very comfy and convenient location."
The price is SAR 449
SAR 502 total
includes taxes & fees
25 Nov - 26 Nov
Life House 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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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 8 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 Tanglewood Suites.

How many hotels are there close to Chesterwood?

Expedia has 8 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.