Compare 755 hotels close to Chesterwood with room rates, reviews, and availability. Most hotels are fully refundable.
Chambery Inn
Chambery Inn
Chambery Inn
Chambery Inn
Chambery Inn
Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (368)
9.6/10
Exceptional
(368)
"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. "
"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. "
"Breakfast each day was phenomenal, staff were all so friendly, hotel & room were beautifully decorated. We had a wonderful time & would stay here again!"
"I like this place a lot and have stayed here many times over the years. Comfortable stay at a reasonable price at a convenient location in Pittsfield. "
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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"We stayed here with my parents and toddler son and it was great. The house was really wonderful, has everything you could possibly need in it. The location is amazing, on a large forested area with easy walking paths. The owners were super responsive and came to fix an issue when it popped up immediately. "
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."
"The house is just about perfect! We were able to get in quickly and many of the lights are intuitive - in logical places - so even though we didn't arrive till dusk, all was easy getting in.As we wandered and learned more about the house, we all marveled at the comfort. Chairs are comfortable, tables set in logical, easy reach, kitchen easily learnable. We enjoyed the art and the lack of sterility.We also enjoyed the nesting birds above the kitchen door. Mama was pretty cranky whenever we were in the dining area but I like to think that she got used to us and realized that we were all enchanted watching her come and go and feed her babies. We even saw one of them fledge! The second one was a bit later and we missed that one leaving but later that day, it was clear that the nest was empty. Thank you for the note on the door!I have two suggestions (?). One is that the master bedroom toilet has a loose rubber gasket which means that the toilet leaks slowly. Not a huge deal but pretty easily fixable, I believe.The other is that it might be a thought to put tall stakes as markers at the two large rocks on either side of the top of the driveway. By the time we left, we had them pretty much scoped out but still felt compelled to have someone outside the car to guide the driver. A couple of those thin orange rods might work well. We had three people in our party who have bum knees and so chose to use the upper entrance. Many thanks!!"
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!"
8 Mi to Tanglewood & Butternut Ski: Spacious Home!
10/10 Excellent
"This place truly has everything you could want in a vacation rental. It was exceptionally clean, spacious, and accommodating. From the moment we arrived, it felt like a home away from home. The host clearly puts a lot of care into maintaining the property and ensuring guests are comfortable. We had everything we needed for an enjoyable stay. Highly recommend and would definitely book again!"
"Great open kitchen/living room/dining with high ceilings; 3 large bedrroms and 2 full baths; great outdoor space. Also fun playspace fir kids in basement."
Learn about the local history of Stockbridge when you spend time at National Shrine of the Divine Mercy. While you're in the area, stroll along the lakeside.
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.
