The Best Hotels Closest to Chesterwood in South Lee for 2026

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Our top choices for Chesterwood hotels

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

A hotel room with a wooden dresser, a television, a microwave, and a mirror.

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

A motel with a parking lot and several cars parked.

1. Monument Mountain Motel

5.4 mi from Chesterwood

Victor

$76 nightly

$85 total

Oct 25 - Oct 26

Total with taxes and fees

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

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

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.

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

5.3 mi from Chesterwood

Bruce

$195 nightly

$217 total

Oct 4 - Oct 5

Total with taxes and fees

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

A two-story house with a covered porch, a driveway, and a lawn with outdoor seating.

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

$129 nightly

$144 total

Sep 29 - Sep 30

Total with taxes and fees

A large, two-story house with a well-maintained lawn and a fence.

A dining area with a table set for two, a view of a green landscape through large windows, and outdoor seating with a view.

A house with a fire pit in the yard, outdoor seating, and a large window overlooking the yard.

A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

4. Devonfield Inn B&B

4.7 mi from Chesterwood

Sebastien

$409 nightly

$457 total

Oct 25 - Oct 26

Total with taxes and fees

A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.

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

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

5. Quality Inn Lee - Lenox South

5.7 mi from Chesterwood

Wendy

$110 nightly

$122 total

Oct 19 - Oct 20

Total with taxes and fees

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

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.

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

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

9.6 mi from Chesterwood

Susan

$114 nightly

$127 total

Oct 20 - Oct 21

Total with taxes and fees

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

A spacious lobby with a fireplace, seating area, and a bar.

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

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

7. Berkshire Mountain Lodge

9.9 mi from Chesterwood

Jay

$109 nightly

$121 total

Oct 1 - Oct 2

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 hotel room with two beds, a desk, a TV, and a window with curtains.

8. East Rock Inn

6.3 mi from Chesterwood

ERIK

$141 nightly

$158 total

Oct 27 - Oct 28

Total with taxes and fees

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

An outdoor seating area with Adirondack chairs and a fire feature.

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.

9. Element by Marriott Lenox Berkshires

7.8 mi from Chesterwood

Kirsty

$169 nightly

$189 total

Oct 18 - Oct 19

Total with taxes and fees

A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.

A house with a stone patio and wooden stools.

A wooden fire pit surrounded by six Adirondack chairs in a forested area.

A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.

10. Little Cat Lodge

10.1 mi from Chesterwood

Kees

$199 nightly

$223 total

Sep 28 - Sep 29

Total with taxes and fees

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

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

A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.

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

11. Berkshires Untold

8.1 mi from Chesterwood

Drue

$143 nightly

$160 total

Sep 28 - Sep 29

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 hotel patio with outdoor seating and a fire pit.

A spacious living room with a large sofa, a coffee table, and a fireplace.

12. Hilton Garden Inn Lenox Pittsfield

9.6 mi from Chesterwood

James

$146 nightly

$163 total

Oct 25 - Oct 26

Total with taxes and fees

A red building with a sign reading "Shaker Mill Inn."

A stone fireplace with a television above it, a kitchen area to the left, and a wooden floor.

A covered patio with a round glass table and metal chairs, a wooden deck, and a view of trees and hills.

A cozy room with a bed, a sofa, a small table, and a desk. There are two lamps on the bed and a window with curtains.

13. Shaker Mill Inn

3.6 mi from Chesterwood

Mervin

$179 nightly

$196 total

Oct 1 - Oct 2

Total with taxes and fees

A large house with a balcony and a grassy yard.

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

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

14. The Little Lion

3.2 mi from Chesterwood

Mary

$115 nightly

$128 total

Oct 18 - Oct 19

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

A Quality Inn sign, a brick building, and a parking lot with cars.

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

15. Quality Inn Great Barrington

6.4 mi from Chesterwood

Joan

$101 nightly

$113 total

Oct 18 - Oct 19

Total with taxes and fees

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

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

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

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

5 mi from Chesterwood

Maria Dulce

$119 nightly

$133 total

Oct 19 - Oct 20

Total with taxes and fees

A hallway with wooden bookshelves, a door, and a bedroom with a bed and floral wallpaper.

A stone fountain surrounded by trees in a park setting.

A living room with a fireplace, leather sofas, and a dog.

17. The Inn at Stockbridge

3.2 mi from Chesterwood

Jodi

$460 nightly

$514 total

Sep 28 - Sep 29

Total with taxes and fees

A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

A modern apartment with a living room, kitchenette, and dining area.

A compact living space with a kitchenette, a dining area, and a sofa.

A covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.

18. The Central Downtown Inn & Suites

12.2 mi from Chesterwood

Rena

$99 nightly

$111 total

Sep 28 - Sep 29

Total with taxes and fees

A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

A bed with a white lace bedspread, a tray with cookies and a bottle, and two glasses of red wine.

A cozy living room with a fireplace, a blue sofa, a red armchair, and a coffee table with books and a teapot.

A loft bedroom with a sloped ceiling, a ceiling fan, a floor lamp, a bed with a patterned bedspread, a chair, and a small table.

19. Brook Farm Inn

5.7 mi from Chesterwood

Carrie

$237 nightly

$268 total

Oct 18 - Oct 19

Total with taxes and fees

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

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

A modern restaurant with wooden flooring, bar area, and seating arrangements.

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

20. Courtyard by Marriott Lenox Berkshires

7.5 mi from Chesterwood

Tracy

$141 nightly

$158 total

Oct 25 - Oct 26

Total with taxes and fees

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Top Chesterwood Hotel Reviews

The Red Lion Inn

10/10 Excellent

"If you want a perfect New England experience, this is the place. The hotel is amazing, it’s older so don’t think you’re going to walk into a modern place, but don’t let that deter you, the vibe is great! Will definitely stay here again."

Secluded Family Home in Serene Stockbridge Woods

10/10 Excellent

"Overall, lovely tidy house for family stays. Host is very accessible and friendly. Great location in quiet woods close to neighboring towns with lots of amenities. Best for casual folks who are comfortable dealing with forest critters should they come about. We didn't encounter any, but it would have been ok if we had. Only suggestion would be to have more hooks upstairs for hanging up damp towels and brighter lighting in the bedrooms. Loved the stars on the ceilings!"

A Grand property in Historic Stockbridge

10/10 Excellent

"The Taggart House exceeded our expectations. We were a group 5 women, grade school BFFs, celebrating a milestone birthday….. loved having our own bedrooms and bathrooms, more so because they were totally renovated. The sun porch was our favorite spot for everything - cozy, comfy and gorgeous. Our hosts happened to be nearby over the weekend and even set up our evening fire pit to ensure the required s’more-fest was a success. Highly recommend!"

Classic Stockbridge Cottage

10/10 Excellent

"The house was a lovely older home. Comfortable and clean inside. Kitchen and bathrooms were renovated making our stay very comfortable"

Hearth House | Prime Location!

10/10 Excellent

"Comfortable home in a great neighborhood."

Tranquil 3 BR Stockbridge House w/ Private Deck!

10/10 Excellent

"Another wonderful weekend at the Redway House … our 4th stay. And … we’ll be back in October! Our favorite things are hanging out on the deck, the comfy beds and being close to everything while being in a very quiet location! An awesome getaway!"

8 Mi to Tanglewood & Butternut Ski: Spacious Home!

10/10 Excellent

"We had an amazing stay and the area the house is in is perfect to visit all that the Berkshires has to offer! Loved our stay so much! Thank you!"

Vacation in a Berkshire Farmhouse

10/10 Excellent

"We had a wonderful stay at the farmhouse. I have been coming to the Berkshires for many years, and found this home to be the most perfect for our needs! The place was immaculate, comfortable beds, plenty of towels and linens. It was a great place for reunion of friends and family, a great place to gather and enjoy all that the Berkshires have to offer. I loved all of the spaces to hang out, the delightful screened porch in the mornings, the dining room was such a nice place to share meals, and the living room to hang out in the evenings. The property itself is so very beautiful, and a touch of whimsy with all of Elaine's garden sculptures in front of her studio. I forgot to mention that the location was also excellent I definitely will return! Thanks for everything Elaine!!"

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!"

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 $85 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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Things to do in Western Massachusetts

Find hotels near Chesterwood, South Lee from $85

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Our top choices for Chesterwood hotels

1. Monument Mountain Motel

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

3. Berkshire Lake Lodge

4. Devonfield Inn B&B

5. Quality Inn Lee - Lenox South

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

7. Berkshire Mountain Lodge

8. East Rock Inn

9. Element by Marriott Lenox Berkshires

10. Little Cat Lodge

11. Berkshires Untold

12. Hilton Garden Inn Lenox Pittsfield

13. Shaker Mill Inn

14. The Little Lion

15. Quality Inn Great Barrington

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

17. The Inn at Stockbridge

18. The Central Downtown Inn & Suites

19. Brook Farm Inn

20. Courtyard by Marriott Lenox Berkshires

Top Chesterwood Hotel Reviews

The Red Lion Inn

Secluded Family Home in Serene Stockbridge Woods

A Grand property in Historic Stockbridge

Classic Stockbridge Cottage

Hearth House | Prime Location!

Tranquil 3 BR Stockbridge House w/ Private Deck!

8 Mi to Tanglewood & Butternut Ski: Spacious Home!

Vacation in a Berkshire Farmhouse

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

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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