The Best Hotels Closest to Chesterwood in South Lee for 2026

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Our top choices for Chesterwood hotels

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

A swimming pool with a surrounding deck, a stone wall, and a building in the background.

A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.

1. The Yankee Inn

9.3 mi from Chesterwood

Karen

$116 nightly

$130 total

Sep 22 - Sep 23

Total with taxes and fees

A modern hotel lobby with seating areas, tables, and a reception desk.

A kitchenette with a microwave, coffee maker, and coffee cups.

A coffee station with two coffee machines and a variety of coffee pods and cups.

A breakfast area with a counter, coffee machine, and a display of pastries.

2. Holiday Inn Express Hotel & Suites Great Barrington by IHG

5 mi from Chesterwood

BJORN

$132 nightly

$147 total

Sep 15 - Sep 16

Total with taxes and fees

A calm lake at dusk with a wooden dock and two chairs facing the water.

A small, modern room with a desk, chair, and a flat-screen TV mounted on the wall.

A lakeside dock with chairs and a table, surrounded by greenery and a clear sky.

A room with two beds, a round mirror, a red box, and a hanging light fixture.

3. Berkshire Lake Lodge

10 mi from Chesterwood

mike

$135 nightly

$151 total

Sep 15 - Sep 16

Total with taxes and fees

A building with a porch and multiple windows, surrounded by purple flowers.

A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

A café with a display case, a frozen food section, and a marketplace sign.

A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.

4. Holiday Inn Club Vacations Oak 'n Spruce Resort

4.2 mi from Chesterwood

Linda

$120 nightly

$134 total

Sep 14 - Sep 15

Total with taxes and fees

A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.

A hotel room with a bed, a desk, a television, a microwave, and a sofa.

A hotel room with a sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.

5. Quality Inn Lee - Lenox South

5.7 mi from Chesterwood

Christine

$101 nightly

$113 total

Sep 27 - Sep 28

Total with taxes and fees

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

A bar with wooden floors and shelves filled with bottles.

A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

A backyard with a swimming pool, lounge chairs, and a hot tub.

6. The Red Lion Inn

2.1 mi from Chesterwood

James

$209 nightly

$233 total

Sep 30 - Oct 1

Total with taxes and fees

A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

A row of white plastic chairs on a covered outdoor area with a white building in the background.

A motel with a parking lot and several cars parked.

A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.

7. Monument Mountain Motel

5.4 mi from Chesterwood

Charlie

$95 nightly

$106 total

Sep 7 - Sep 8

Total with taxes and fees

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.

8. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

5.3 mi from Chesterwood

Bruce

$189 nightly

$211 total

Sep 7 - Sep 8

Total with taxes and fees

A spacious hotel lobby with multiple seating areas, large windows, and a television.

A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.

A grocery store with shelves stocked with snacks and beverages, a refrigerated display case, and a wall with hexagonal patterns.

9. Hampton Inn & Suites Berkshires-Lenox

9.1 mi from Chesterwood

Nancy

$112 nightly

$125 total

Sep 30 - Oct 1

Total with taxes and fees

A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

A modern living room with a grey sofa, a wooden coffee table, and a dining area with a round table and chairs.

A grassy outdoor area with four blue Adirondack chairs arranged in a circle.

10. East Rock Inn

6.3 mi from Chesterwood

ERIK

$146 nightly

$163 total

Oct 6 - Oct 7

Total with taxes and fees

A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

A reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.

A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

A reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.

11. Best Western Plus Berkshire Hills Inn & Suites

10.5 mi from Chesterwood

Prasanna

$90 nightly

$100 total

Sep 9 - Sep 10

Total with taxes and fees

An indoor swimming pool with clear water, tiled floors, and a blue wall.

A modern hotel with a large entrance, multiple floors, and a well-lit facade.

A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

A snack bar with shelves of snacks and a refrigerated display.

12. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

9.6 mi from Chesterwood

Steve

$127 nightly

$142 total

Sep 10 - Sep 11

Total with taxes and fees

A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.

13. Element by Marriott Lenox Berkshires

7.8 mi from Chesterwood

Lawrence

$195 nightly

$218 total

Sep 13 - Sep 14

Total with taxes and fees

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.

A cozy library with bookshelves, a fireplace, and comfortable seating.

An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".

14. Berkshires Untold

8.1 mi from Chesterwood

David

$145 nightly

$162 total

Sep 28 - Sep 29

Total with taxes and fees

A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

A hotel reception area with framed artwork, a coffee machine, and a sign indicating 'Quality by Choice Hotels'.

A hotel room with a bathroom, a bed, a desk, and a nightstand.

A hotel room with a wooden desk, a television, a mirror, and a bathroom visible through an open door.

15. Quality Inn Great Barrington

6.4 mi from Chesterwood

Sisile

$104 nightly

$116 total

Sep 9 - Sep 10

Total with taxes and fees

A snow-covered outdoor area with a patio, seating, and a covered dining area.

A modern living room with a fireplace, comfortable seating, and a large window with curtains.

A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.

A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.

16. The Cornell Inn, Lenox & The Berkshires

6.7 mi from Chesterwood

Edward

$172 nightly

$191 total

Sep 7 - Sep 8

Total with taxes and fees

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

A garden with wooden Adirondack chairs and a stone pathway.

17. Berkshire Mountain Lodge

9.9 mi from Chesterwood

Robert

$113 nightly

$126 total

Oct 1 - Oct 2

Total with taxes and fees

A large house with a balcony and a grassy yard.

A room with a white desk, two floral chairs, a small round table with a plant, a hanging lamp, and two framed artworks on the wall.

A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.

A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.

18. The Little Lion

3.2 mi from Chesterwood

Anne

$105 nightly

$118 total

Sep 9 - Sep 10

Total with taxes and fees

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

A covered outdoor area with stone pillars and a view of a road and green hills.

An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.

A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

19. Courtyard by Marriott Lenox Berkshires

7.5 mi from Chesterwood

Tracy

$195 nightly

$217 total

Sep 13 - Sep 14

Total with taxes and fees

A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.

A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.

A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

A hotel patio with outdoor seating and a fire pit.

20. Hilton Garden Inn Lenox Pittsfield

9.6 mi from Chesterwood

James

$146 nightly

$163 total

Sep 10 - Sep 11

Total with taxes and fees

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Top Chesterwood Hotel Reviews

The Red Lion Inn

10/10 Excellent

"Charming, updated throughout. Extremely clean and well appointed. Extremely delightful stay."

Hearth House | Prime Location!

10/10 Excellent

"Comfortable home in a great neighborhood."

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

10/10 Excellent

"Our favorite place to rent in the Berkshires, with a perfect location, in Stockbridge. The owner responds to any message almost instantly. And she provides a cabinet of free candy! We will return next summer for our fourth year."

8 Mi to Tanglewood & Butternut Ski: Spacious Home!

10/10 Excellent

"Beautiful house, clean and sanitary. Enjoyed our stay immensely. Kudos to the house for putting together a fantastic environment."

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

10/10 Excellent

"My stay at Diane’s bed and breakfast was absolutely wonderful. Diane herself is incredibly warm, welcoming, and genuinely informative — she made the entire experience feel personal and cared for. The room was quaint, cozy, and charming in that classic New England way, with comfortable beds, plenty of towels, and a generous selection of bath amenities that made settling in effortless. Breakfast was a standout: a truly amazing cook‑to‑order meal that felt both homemade and high‑end. Every dish was fresh, delicious, and clearly prepared with pride. Parking was plentiful and convenient, making arrival and departure stress‑free. Overall, this B&B is a gem — comfortable, inviting, and thoughtfully run. I’d happily return and recommend it to anyone looking for a relaxing stay."

Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10

10/10 Excellent

"We love the beautiful Taggart River House! This was our second stay--eight of us really enjoyed our return visit to Stockbridge, Tanglewood and the Berkshires. The location is superb--walking distance to downtown Stockbridge can never be overrated. Short drives to everything else make this property ideal. Super responsive and helpful hosts! Very clean, well-appointed rooms and facilities, more than ample parking and easy-to-follow house rules and recommendations. Pictures are accurate. You will love it!"

Tranquil 3 BR Stockbridge House w/ Private Deck!

10/10 Excellent

"The house is lovely with a quirky charm. It is indeed a tranquil property surrounded by woods. Our hosts have thoughtfully overstocked the premises with towels, sheets, paper goods, and all sorts of kitchen tools and condiments. We had a lovely time."

Experienced Hosts. Quiet, Romantic, Spacious Apartment, Pet Friendly.

8/10 Good

"ok"

Secluded Family Home in Serene Stockbridge Woods

10/10 Excellent

"Tom was a great host. Easy to communicate and just a nice guy. The property was in a great location close to all the places we went to-Tanglewood, Norman Rockwell Museum, Botanical Gardens, Lenox, Stockbridge and more. Home was very spacious with a great outdoor deck. Nice grill that we used several times. Would definitely stay there again."

Other attractions near Chesterwood

Norman Rockwell Museum

9.4/10 (347 reviews)

You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area.

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Berkshire Botanical Garden

9.4/10 (14 reviews)

Explore the great outdoors at Berkshire Botanical Garden, a lovely green space in Stockbridge. While you're in the area, stroll along the lakeside.

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Mission House

9.6/10 (5 reviews)

You can spend time exploring the galleries in Mission House in Stockbridge. Wander the lakeside in this quaint area.

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Naumkeag Museum

9.4/10 (10 reviews)

You can spend time browsing the exhibits at Naumkeag Museum during your travels in Stockbridge. While you're in the area, stroll along the lakeside.

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National Shrine of the Divine Mercy

9.0/10 (83 reviews)

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.

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Schantz Galleries

7.2/10 (5 reviews)

You can spend an afternoon exploring the galleries in Schantz Galleries during your trip to Stockbridge. Wander the lakeside in this quaint area.

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Art et Industrie

8.0/10 (5 reviews)

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.

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Berkshire Theatre Festival

8.8/10 (3 reviews)

You can get tickets for a performance at Berkshire Theatre Festival on your trip to Stockbridge. Wander the lakeside in this quaint area.

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Frequently asked questions

What are the top-rated hotels near Chesterwood?

Discover the top-rated hotels near Chesterwood in South Lee that provide exceptional stays and stunning views for travelers seeking a memorable experience.Taggart Treehouse: Modern Luxury Meets Nature: Stunning river views, sleeps 10Taggart Treehouse offers a luxurious escape with breathtaking river views, just 2.0 miles from Chesterwood. Rated an impressive 10 by travelers, this modern retreat accommodates up to 10 travelers, perfect for larger groups. Guests can enjoy amenities such as a fully equipped kitchen with a dishwasher, oven, and coffee maker, along with a spacious patio and garden area for relaxation.Vacation in a Berkshire FarmhouseLocated 2.9 miles from Chesterwood, the Vacation in a Berkshire Farmhouse boasts a remarkable review rating of 9.8. This historic hotel combines charm with modern comforts, featuring a well-equipped kitchen, outdoor play areas, and nearby hiking trails. Guests can unwind on the patio or explore local attractions such as wineries and ski resorts, making it a versatile choice for all travelers.The Inn at StockbridgeThe Inn at Stockbridge is a 4-star gem just 4.1 miles from Chesterwood, rated 9.8 by travelers. Guests can indulge in complimentary cooked breakfasts and relax by the outdoor pool. With a variety of amenities, including a spa, fitness facilities, and beautifully designed rooms with premium bedding, this inn perfectly blends comfort and elegance, creating a peaceful retreat amidst the stunning Berkshire landscape.

What hotels are within walking distance to Chesterwood?

Discover cozy accommodations just a short stroll from Chesterwood, perfect for travelers seeking top-rated stays!The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and ChesterwoodThe Stockbridge Country Inn is a charming 4.5-star bed and breakfast located just a 12-minute walk from Chesterwood, with an excellent review rating of 9.2. Guests can enjoy delightful amenities such as complimentary breakfast options, an onsite art gallery, and a terrace for relaxation. Outdoor enthusiasts will appreciate the hiking and biking trails nearby, along with a golf course located just a short distance away. The inn boasts a luxurious historic design, complete with premium bedding and a fireplace, ensuring a comfortable and memorable stay.

How much is a hotel near Chesterwood?

Staying near Chesterwood is a treat, with plenty of hotels from $100 offering incredible amenities. If you're leaning toward a little luxury, prices can rise, especially in peak season. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a vacation during weekends or around public holidays.

What are the most popular family-friendly hotels near Chesterwood?

For families seeking a delightful stay near Chesterwood, these top-rated hotels offer family-friendly amenities ensuring a memorable getaway.Taggart Treehouse: Modern Luxury Meets Nature: Stunning river views, sleeps 10Taggart Treehouse: Modern Luxury Meets Nature is only 2.0 miles from Chesterwood and enjoys a perfect 10 travelers' rating. This unique hotel offers a cozy kitchen and a lovely patio, perfect for family gatherings. With a travel crib and stair gate for children, it ensures safety and comfort for younger travelers. The stunning river views and nearby nature trails make it an ideal retreat for families looking to connect and unwind.Vacation in a Berkshire FarmhouseVacation in a Berkshire Farmhouse is a fantastic option just 2.9 miles from Chesterwood, an impressive travelers' rating of 9.8. This inviting farmhouse features amenities tailored for families, including a spacious kitchen, outdoor play area for children, and a variety of toys to keep the little ones entertained. With a beautiful garden and patio, parents can relax while kids explore. Guests also enjoy nearby hiking, skiing, and antique shopping.Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHGHoliday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG, located 4.7 miles from Chesterwood, offers a family-friendly environment with a review rating of 9.0 and a 3.5-star rating. Families will appreciate the onsite playground, arcade game room, and spacious rooms equipped with kitchen facilities and a crib at no extra charge. Guests can also take advantage of the indoor and outdoor pools, hot tub, and nearby skiing activities for a fun-filled family vacation.

Which hotels near Chesterwood offer the best views?

For travelers seeking top-rated hotels with stunning views near Chesterwood, South Lee offers some delightful options.Vacation in a Berkshire FarmhouseLocated just 2.9 miles from Chesterwood, this charming farmhouse is rated an impressive 9.8 by travelers. Guests can relish breathtaking mountain views from the patio and enjoy outdoor adventures, including hiking and skiing nearby. The hotel features a fully equipped kitchen, a cozy garden, and ample parking, making it a perfect retreat for nature lovers who appreciate rustic charm.The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and ChesterwoodJust a short 12-minute walk from Chesterwood, this 4.5-star inn is rated 9.2 by travelers. Guests are treated to scenic mountain views from the terrace and can indulge in complimentary full breakfasts. With amenities like a pool, hiking options on-site, and a charming historic design, this inn provides a cozy and luxurious feel, making it an ideal spot for art and nature enthusiasts alike.Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHGThis 3.5-star resort is situated 4.7 miles from Chesterwood and boasts a review rating of 9.0. Guests can take advantage of the outdoor and indoor pools, hot tubs, and on-site tennis courts. The resort's balconies and patios offer lovely resort views, perfect for relaxation after a day of exploring. With family-friendly amenities and a variety of activities, it's a delightful choice for those looking to enjoy the Berkshires.

What are the best affordable hotels near Chesterwood?

For travelers seeking top-rated yet affordable hotels near Chesterwood, these charming properties offer the perfect blend of comfort and convenience without breaking the bank.Taggart Treehouse: Modern Luxury Meets Nature: Stunning river views, sleeps 10Taggart Treehouse is a spacious retreat just 2.0 miles from Chesterwood, rated an impressive 10 by travelers. This hotel features stunning river views and is perfect for families or groups, providing amenities like a fully equipped kitchen with a dishwasher and an oven, plus a cozy patio to enjoy the outdoors. Guests can also benefit from onsite parking and WiFi, ensuring a comfortable stay.Vacation in a Berkshire FarmhouseJust 2.9 miles from Chesterwood, Vacation in a Berkshire Farmhouse boasts a remarkable review rating of 9.8. This family-friendly farmhouse features an outdoor play area for children and is surrounded by opportunities for hiking, skiing, and winery tours. Guests can enjoy a kitchen equipped with modern appliances, a charming patio, and WiFi to stay connected during their stay.Shaker Mill InnLocated 4.9 miles from Chesterwood, Shaker Mill Inn is a cozy escape with a review rating of 9.6. This inn offers a free breakfast and self-parking, making it a convenient choice for travelers. Guests can relax in their rooms featuring a kitchenette and enjoy the beautiful garden or the private hot tub. With contactless check-in and a warm atmosphere, it's a delightful option for a restful stay.

Are there any hotels with pools close to Chesterwood?

For those seeking a refreshing stay near Chesterwood, these top-rated hotels with pools offer the perfect retreat for relaxation and fun.The Inn at StockbridgeThe Inn at Stockbridge, just 4.1 miles from Chesterwood, is a sophisticated 4-star retreat with an outstanding review rating of 9.8. This hotel features a serene outdoor pool surrounded by beautiful gardens, ideal for relaxation. Guests are treated to complimentary breakfast and access to a 24-hour fitness center, ensuring a comfortable and energizing stay.The Red Lion InnLocated only 2.3 miles from Chesterwood, The Red Lion Inn boasts a charming 3.5-star experience with a review rating of 8.8. Guests can unwind in the outdoor pool area, featuring comfortable sun loungers. This historic hotel offers a variety of amenities including a spa, 24-hour room service, and easy access to skiing and snowboarding activities, perfect for those looking to explore the nearby mountains.Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHGSituated just 4.7 miles from Chesterwood, the Holiday Inn Club Vacations Oak n' Spruce Resort is a family-friendly gem with an impressive review rating of 9.0. Guests can enjoy both indoor and outdoor pools, complete with sun loungers and a poolside bar for leisurely afternoons. Additional highlights include a hot tub, mini-golf, and on-site tennis facilities, making it an ideal choice for families and outdoor enthusiasts alike.

What are the best pet-friendly hotels near Chesterwood?

For travelers with pets visiting Chesterwood, finding a welcoming and comfortable hotel is a breeze with these top-rated options nearby.Vacation in a Berkshire FarmhouseJust 2.9 miles from Chesterwood, Vacation in a Berkshire Farmhouse is an idyllic retreat for pet owners, allowing pets in-room. With an outstanding review rating of 9.8, this farmhouse boasts a historic charm and offers a plethora of amenities that include a kitchen, outdoor play area for children, and nearby hiking opportunities. Guests can unwind on the patio or explore local attractions, making it an excellent choice for families and travelers with pets alike.The Inn at StockbridgeThe Inn at Stockbridge, located 4.1 miles from Chesterwood, is a charming 4-star hotel that welcomes dogs only. With a remarkable review rating of 9.8, this inn features an outdoor pool, spa services, and a lovely garden area, perfect for relaxing with pets. Guests can indulge in a complimentary cooked breakfast and enjoy comfortable accommodations with premium bedding and designer toiletries, ensuring a delightful stay for both you and your furry friend.Econo Lodge Lee - Great BarringtonEcono Lodge Lee - Great Barrington is just 5.0 miles from Chesterwood and offers a cozy stay for travelers with pets. This budget-friendly hotel allows pets in-room, making it a great choice for those traveling with furry companions. Guests can enjoy amenities like daily housekeeping, free continental breakfast, and access to a mini-golf course on-site. Rated by travelers at 6.4, it's a convenient option for families looking to explore the beautiful Berkshire region.

Can I book a fully refundable hotel close to Chesterwood?

Most bookings on Expedia are refundable if canceled within 24-48 hours of arrival, though this depends on the hotel's individual cancellation policy, which you should check in your booking confirmation. If free cancellation is available, you can cancel directly through your Expedia account by going to "My Trips" and selecting your reservation. To find fully refundable hotel options, simply enter "Chesterwood", set your travel dates, and use the "Fully refundable" filter under "Deals & Discounts" on the results page. Alternatively, explore deals with free cancellation options on Expedia.

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Stockbridge Vacation Rentals

Find hotels near Chesterwood, South Lee from $100

Upfront pricing

Treat yourself

Be picky

Check prices for these dates

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Star rating

Guest rating

Our top choices for Chesterwood hotels

1. The Yankee Inn

2. Holiday Inn Express Hotel & Suites Great Barrington by IHG

3. Berkshire Lake Lodge

4. Holiday Inn Club Vacations Oak 'n Spruce Resort

5. Quality Inn Lee - Lenox South

6. The Red Lion Inn

7. Monument Mountain Motel

8. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

9. Hampton Inn & Suites Berkshires-Lenox

10. East Rock Inn

11. Best Western Plus Berkshire Hills Inn & Suites

12. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

13. Element by Marriott Lenox Berkshires

14. Berkshires Untold

15. Quality Inn Great Barrington

16. The Cornell Inn, Lenox & The Berkshires

17. Berkshire Mountain Lodge

18. The Little Lion

19. Courtyard by Marriott Lenox Berkshires

20. Hilton Garden Inn Lenox Pittsfield

Top Chesterwood Hotel Reviews

The Red Lion Inn

Hearth House | Prime Location!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

8 Mi to Tanglewood & Butternut Ski: Spacious Home!

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

Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10

Tranquil 3 BR Stockbridge House w/ Private Deck!

Experienced Hosts. Quiet, Romantic, Spacious Apartment, Pet Friendly.

Secluded Family Home in Serene Stockbridge Woods

Other attractions near Chesterwood

Norman Rockwell Museum

Berkshire Botanical Garden

Mission House

Naumkeag Museum

National Shrine of the Divine Mercy

Schantz Galleries

Art et Industrie

Berkshire Theatre Festival

Frequently asked questions

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