⭐ Top 10 Hotels Near Chesterwood for 2025

Top 10 Hotels Near Chesterwood

Enjoy meals in this inviting dining room with a large table, comfortable chairs, and ample natural light.

"Great breakfast, friendly helpful staff, pretty yard, good location "

includes taxes & fees

15 Jul - 16 Jul

Relax in this serene bedroom with a large bed, two chairs, and a small table, surrounded by lush views.

"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. "

includes taxes & fees

15 Jul - 16 Jul

Enjoy a leisurely meal in this beautifully set dining area with a long table, adorned with pastries and bread.

"Phenomenal hospitality, eclectic decor, luxurious sleep - we have been raving about our stay and will definitely be back!"

includes taxes & fees

28 Jul - 29 Jul

Stunning two-story house with a central entrance and beautifully manicured lawn.

"Very enjoyable comfortable stay"

Step into the charming Shaker Mill Inn, surrounded by lush greenery and a beautiful garden.

"Very cute and clean room. After driving all day we were so happy to see all muffins, scones, yogurt, cereal, oatmeal, strawberries, milk, OJ, hot chocolate and coffee already in the room for breakfast the next day. We had a great stay, thank you!"

includes taxes & fees

20 Jul - 21 Jul

Features a sleek glass-enclosed shower, vanity with sink and mirror, toilet, and bidet.

"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! "

includes taxes & fees

28 Jul - 29 Jul

Chambery Inn features a traditional two-story building with a pitched roof and multiple windows.

"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. "

Relax by the serene pool surrounded by lounge chairs and umbrellas.

"I had excellent stay at the Red Lion Inn "

includes taxes & fees

15 Jul - 16 Jul

Relax in a welcoming space with comfortable seating and a stunning chandelier.

"Nice outdoor seating areas, big pool, clean nicely appointed toom"

includes taxes & fees

16 Jul - 17 Jul

Relax in this inviting room with a comfortable bed, fireplace, and thoughtful amenities.

"This is a charming and very pleasant place to stay."

Play a round of golf amidst lush surroundings and scenic obstacles.

"We love this place. It's a wonderful location in the Berkshires, easy to get to all of the surrounding towns and attractions. The amenities are awesome, the units are spotless, and the service is friendly and prompt. Have stayed twice and cannot wait to return again!"

includes taxes & fees

16 Jul - 17 Jul

Guests can enjoy a serene outdoor setting with a tranquil lawn and a charming two-story building in the background.

"Hotel was clean and facilities were maintained. Best part was that you are permitted to use amenities at The Red Lion Inn down the road. "

includes taxes & fees

15 Jul - 16 Jul

Enjoy cooking in this well-equipped kitchen with a central island and bar stools, featuring a refrigerator, microwave, and oven.

"This was a return stay at Eden Rock. The room is modern, well-appointed, clean, with very comfortable beds. Access to an outside area is pleasant. Quiet location, convenient to Great Barrington and Berkshire attractions. While there is no front desk or reception area, instructions for accessing the room are easy to follow."

includes taxes & fees

28 Jul - 29 Jul

Comfortable retreat with a neatly made bed, wall-mounted lamps, and a convenient nightstand.

"Helpful, friendly staff. Clean, convenient, quiet."

Restful haven with a neatly made bed and a wooden headboard.

"Great place to stay. Excellent staff."

includes taxes & fees

20 Jul - 21 Jul

Welcome to this charming two-story house with a cozy front porch and balcony, featuring a wreath above the door and green shutters.

"Beautiful historic house in a great location. Responsive owner. Great visit!"

includes taxes & fees

16 Jul - 17 Jul

Relax by the fire pit in our outdoor seating area, surrounded by wicker furniture under a covered patio with a flat roof.

"After coming to Lenox for 15 years, I can easily say this is the best in town. "

includes taxes & fees

24 Jul - 25 Jul

Traditional two-story house with a welcoming porch and balcony, set amidst snow-covered trees.

"Breakfast each day was phenomenal, staff were all so friendly, hotel & room were beautifully decorated. We had a wonderful time & would stay here again!"

includes taxes & fees

21 Jul - 22 Jul

Relax in a stylish space with a bar area, seating area, and large windows offering views of the outdoors.

"Great place stay after an evening at Tanglewood!"

includes taxes & fees

25 Jul - 26 Jul

Set amidst lush greenery, this multi-story property features distinct buildings with gabled and flat roofs.

"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. "

includes taxes & fees

17 Jul - 18 Jul

Destinations near South Lee

Tanglewood Music Center

4/5(1 review)

You can make plans for a show at Tanglewood Music Center during your stay in Lenox. While you're in the area, stroll along the lakeside.

Recent Reviews in Chesterwood

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

5/5 Excellent

"We had an amazing stay! Rare gem in the berkshires. We had two two-bedroom units next to each other and it was more than enough space for our family of 10."

A verified traveller stayed at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Posted 1 day ago

5/5 Excellent

"Properly marketed and described. No particular amenities (aside from WiFi), but lots was apparently available at the mother ship, in town. But I wasn’t there for amenities, and I expect most guests weren’t. Clean room, easy parking, my dog was welcome. Busy road out front, but set back far night that I never heard any noise from there. Good place, would recommend "

A verified traveller stayed at The Little Lion

Posted 1 month ago

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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, take a look at the 8 hotels and other accommodation options you'll find within a mile.

Where is the best place 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 traveller 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 will I find near Chesterwood?

Expedia has 8 hotels and other accommodation options within a mile from Chesterwood.

If I need to cancel the hotel reservation for my stay near Chesterwood, will I receive a refund?

Yes! You'll find that most room reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you booked a non-refundable reservation, it might still be possible to cancel it and be given a refund within 24 hours of booking. Enter your dates, click on "Search", then you can filter by "fully refundable" to get the best options available near Chesterwood.

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.

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Top 10 Hotels Near Chesterwood

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

Tanglewood Suites

Granville House

Devonfield Inn B&B

Shaker Mill Inn

33 Main

Chambery Inn

The Red Lion Inn

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Brook Farm Inn

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

The Little Lion

East Rock Inn

Monument Mountain Motel

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Hampton Terrace Inn

Courtyard by Marriott Lenox Berkshires

The Cornell Inn, Lenox & The Berkshires

Berkshires Untold

Inn at Silver Maple Farm

Destinations near South Lee

Tanglewood Music Center

Recent Reviews in Chesterwood

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

The Red Lion Inn

The Little Lion

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Hotels near other Attractions

Hotels Near Chesterwood

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Frequently asked questions