Find hotels near Chesterwood, South Lee from AED 244

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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 AED 1,685
AED 2,039 total
includes taxes & fees
22 Nov - 23 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 AED 804
AED 804 total
includes taxes & fees
22 Nov - 23 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 AED 735
AED 821 total
includes taxes & fees
24 Nov - 25 Nov
Granville House
Devonfield Inn B&B
Room
Devonfield Inn B&B
4.0 star property
10.0 out of 10, Exceptional, (117)
"The Inn is very nice, however the room received was too small and was very limited for comfort. Breakfasts were great and the concert on Saturday was especially special. Would stay again if another room was available . "
The price is AED 1,025
AED 1,145 total
includes taxes & fees
23 Nov - 24 Nov
Devonfield Inn B&B
Shaker Mill Inn
Garden
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (400)
"This place is so comfortable and roomy. Perfect place for a quiet getaway. "
The price is AED 533
AED 584 total
includes taxes & fees
24 Nov - 25 Nov
Shaker Mill Inn
33 Main
Room
33 Main
4.0 star property
10.0 out of 10, Exceptional, (69)
"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "
The price is AED 1,285
AED 1,436 total
includes taxes & fees
25 Nov - 26 Nov
33 Main
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 AED 698
AED 779 total
includes taxes & fees
24 Nov - 25 Nov
Chambery Inn
The Red Lion Inn
Front of property
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (1001)
"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 AED 632
AED 870 total
includes taxes & fees
2 Dec - 3 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 AED 713
AED 796 total
includes taxes & fees
25 Nov - 26 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 AED 373
AED 468 total
includes taxes & fees
26 Nov - 27 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)
"We stayed at the Little Lion for one night, this past weekend. We actually stayed at this motel years ago, when it was under different ownership. The price was reasonable for the area, as it is in-between seasons. As the website states, this is a contact-free motel, so there is no staff on-site. While this did not bother us, it may be concerning/confusing to some. Email communication prior to our arrival was great. We were sent a text before the 3:00 check-in time, with a code to get into...
The price is AED 261
AED 292 total
includes taxes & fees
9 Dec - 10 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 AED 558
AED 624 total
includes taxes & fees
24 Nov - 25 Nov
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, (1002)
"Need some upgrades "
The price is AED 350
AED 391 total
includes taxes & fees
5 Dec - 6 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 AED 404
AED 451 total
includes taxes & fees
22 Dec - 23 Dec
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 AED 433
AED 484 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 AED 244
AED 273 total
includes taxes & fees
24 Nov - 25 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 AED 433
AED 484 total
includes taxes & fees
11 Dec - 12 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 AED 584
AED 631 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, (1001)
"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 AED 448
AED 526 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 AED 389
AED 434 total
includes taxes & fees
24 Nov - 25 Nov
The Constance, The Whitlock, & The Dewey By The Lenox Collection
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.