"The property is so lovely and peaceful. I love the classic mid-century modern aesthetic. For visitors to the National Shrine of Divine Mercy, the Inn’s location couldn’t be more perfect with only a 5-minute walk to the Shrine. "
"We returned to the Chambery Inn to celebrate my wife's birthday and the Memorial Day weekend. We were very happy with our choice. We stayed in a beautiful room (203), which included a spacious sitting area and a well-appointed bath. The breakfast were nicely prepared and presented. The Inn provided timely information prior and during our stay. We will be back in the future. "
"Maureen and her lovely staff operate a first class B&B. Thoughtful amenities and conveniences, clean and comfortable. Amazing home cooked breakfast, both plentiful and delicious. Thank you"
"Nice , new , quiet and clean room. Bed was very comfortable . Missed the human touch of having a traditional office to call when lost and ideas where to eat, etc. "
"We greatly appreciate a pet friendly hotel with no extra pet fees! Hotel was dated but had charm and we loved using the pool at the beautiful Red Lion. "
"Breakfast each day was phenomenal, staff were all so friendly, hotel & room were beautifully decorated. We had a wonderful time & would stay here again!"
"What a wonderful one-night stay on the July 4th weekend. It’s a beautiful, comfortable inn with lovely hosts. Also in a great location, set back from a fairly busy country road with several good food options nearby, and charming villages and towns to tour. Highly recommend. "
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.
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.
Top Chesterwood Hotel Reviews
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
10/10 Excellent
"Loved the property, room was clean and had everything you needed!! We had an upgrade that was wonderful!! Only downfall was the outside little deck! No privacy all out In the open, side by side and facing the other units with a walkway in front of it!! Was looking forward to sitting out side but ended up not using it at all.
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Prime Location and Charm – 5 Mins to Tanglewood & Best Berkshire Attractions
10/10 Excellent
"Our group of 3 couples stayed at the Swell House for a trip to Tanglewood. This house is perfectly located for Tanglewood and other area attractions. We really enjoyed the screened in porch and peaceful backyard."
"Loved this house. Convenient to everything but comfortable enough just to hang out when it is raining. Kitchen well equipped. Even for us! We are the type of people who bring cutting boards, knives, salt and pepper mills and extra towels etc. None of that was needed. We spent time on the screened in porch watching the bunnies and bluebirds. Would be happy to stay again."
Secluded + Modern | Enclosed Patio, Forest Views | Woodland Zen by AvantStay
10/10 Excellent
"This property is appropriately named! From the moment we arrived a sense of relaxation overcame us. This was the best appointed vacation rental we have found. The owners truly thought of everything. I loved the soaking tub. My favorite moments were spent in the screened in room reading a book. Really enjoyed how the house felt like we were in a quiet sanctuary while we were just 6 miles from Stockbridge. We will definitely be back!"
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
10/10 Excellent
"Stayed for 3 nights over Presidents Day weekend, and we loved the spot! Recently refreshed with a new kitchen, floors and fixtures, it’s still felt warm and inviting. The electric fire / heater in the living room was well used, and we cooked our meals with the new appliances and well equipped kitchen. Proximity to Great Barrington, Stockbridge, Lenox, Lee, and all of the outdoor adventures (and shopping/restaurants) worked out perfectly, even given the snowy/ice weather. Plenty of space for the family and we even enjoyed a bit of sledding in the backyard. Definitely give this place a shot - we loved it! "
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
10/10 Excellent
"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"
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 9 hotels and other accommodations you'll find within a mile.
What's the best hotel to stay close to Chesterwood?
Expedia has 9 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.
