"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. "
"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. "
"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....
"
"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....
"
"Good sized room with a comfortable bed. Friendly staff and breakfast was nice. The area was rather odd. Far too expensive for what I got but prices were really high the night I stayed. "
"Good sized room with a comfortable bed. Friendly staff and breakfast was nice. The area was rather odd. Far too expensive for what I got but prices were really high the night I stayed. "
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.
Secluded + Modern | Enclosed Patio, Forest Views | Woodland Zen by AvantStay
10/10 Excellent
"We loved our stay here. The layout was perfect for two couples (or a couple and a small family) with bedrooms and living areas on both ends of the house. Would highly recommend to anyone!"
"We were in Stockbridge for the first time for our annual family Thanksgiving and orienteering event. Most stayed at the inn, but some rented the Taggert House as a place where family could easily be together It was perfect and so conveniently located a short and beautiful walk to town. The house is huge, the kitchen is roomy and well-stocked, the beds were comfortable and each bedroom had its own bathroom. The pool table was a big hit. Parking was easy. The owners couldn’t have been nicer or more responsive. I highly recommend the Taggert House and, if your group is extra large, also rent their River House just behind it. Five stars plus. We will be back! "
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
10/10 Excellent
"It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!"
"Our stay at the Stockbridge Home was fabulous! Lovely home! Clean, well stocked kitchen and beautiful comfortable bedrooms. The bathrooms were spotless and spacious. We loved the private backyard in the quiet neighborhood. We were able to walk into town on safe walkways. Short drive to hiking trails. We would highly recommend this home for your visit to the Berkshires! Thank you Lucas and Drew! Excellent hosts. "
"The house was clean and cozy but large enough for a big family. We brought our dog and there were no problems doing so. The hosts responded to all of our inquiries very quickly. The house was on a hill so kids and dogs would need outside supervision. The kids rooms indoors were wonderful! The deck was the perfect place to read and unwind. "
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.
You can spend an afternoon exploring the galleries in Art et Industrie in Great Barrington. Amble around this quaint area's gardens, or seek out the hiking trails.
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?
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.