The Best Hotels Closest to Chesterwood in South Lee for 2026

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Our top choices for Chesterwood hotels

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.

1. 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 living room with a sofa, armchair, coffee table, and a patterned rug.

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

2. 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 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 hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

3. The Yankee Inn

9.3 mi from Chesterwood

Karen

$116 nightly

$130 total

Sep 22 - Sep 23

Total with taxes and fees

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

A garden with wooden Adirondack chairs and a stone pathway.

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.

4. Berkshire Mountain Lodge

9.9 mi from Chesterwood

Robert

$113 nightly

$126 total

Oct 1 - Oct 2

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 a coffee machine, a water dispenser, and a sign indicating the fitness center.

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

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

5. Best Western Plus Berkshire Hills Inn & Suites

10.5 mi from Chesterwood

Prasanna

$90 nightly

$100 total

Sep 8 - Sep 9

Total with taxes and fees

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

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.

A cozy living room with a sofa, a small table, and a bookshelf. There is a window with curtains, and a painting on the wall.

6. Shaker Mill Inn

3.6 mi from Chesterwood

Mervin

$145 nightly

$159 total

Sep 9 - Sep 10

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.

7. Hampton Inn & Suites Berkshires-Lenox

9.1 mi from Chesterwood

Nancy

$122 nightly

$137 total

Sep 30 - Oct 1

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

8. 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 large house with a balcony and a grassy yard.

A two-story building with a gabled roof and a chimney.

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.

9. The Little Lion

3.2 mi from Chesterwood

Anne

$111 nightly

$124 total

Sep 8 - Sep 9

Total with taxes and fees

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

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.

10. 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 stone fountain surrounded by trees in a park setting.

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

11. The Inn at Stockbridge

3.2 mi from Chesterwood

Jodi

$396 nightly

$442 total

Sep 13 - Sep 14

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 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.

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

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

A cozy room with a wooden bench, a table with a pitcher, and a sofa with patterned cushions. Large windows with yellow blinds offer a view of greenery outside.

A house with a stone patio and wooden stools.

13. Little Cat Lodge

10.1 mi from Chesterwood

Kees

$199 nightly

$223 total

Sep 7 - Sep 8

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

A hotel room with two beds, a nightstand with a lamp, and a window with curtains.

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

14. The Central Downtown Inn & Suites

12.2 mi from Chesterwood

Rena

$89 nightly

$100 total

Sep 16 - Sep 17

Total with taxes and fees

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

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

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

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

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

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

A hotel patio with outdoor seating and a fire pit.

16. Hilton Garden Inn Lenox Pittsfield

9.6 mi from Chesterwood

James

$146 nightly

$163 total

Sep 10 - Sep 11

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 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.

A dining table set with a vase of flowers, a book, and cutlery.

17. Brook Farm Inn

5.7 mi from Chesterwood

Carrie

$265 nightly

$299 total

Sep 20 - Sep 21

Total with taxes and fees

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

A modern cafe with seating areas, a coffee station, and large windows offering a view of greenery.

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.

18. 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 two-story building with a sign reading "Chambéry Inn".

A hotel room with a TV displaying 'World of Dance', a fireplace, a bed, and a seating area with a remote control.

A hotel room with a large bed, a TV mounted above a fireplace, a desk, and a seating area with chairs.

A large, historic building labeled "Chambéry Inn" with a vintage turquoise truck parked in front.

19. Chambery Inn

5.4 mi from Chesterwood

Alexandra

$300 nightly

$335 total

Sep 7 - Sep 8

Total with taxes and fees

A clear blue swimming pool with a tiled edge and a few lounge chairs along the side.

A swimming pool with a fenced area, lounge chairs, and a warning sign.

A hotel room with two beds, a chair, and a bedside table with a phone.

A standard rectangular bathtub with a single faucet, tiled walls, and a geometric patterned floor.

20. Sunset Inn

5.7 mi from Chesterwood

Joann

$91 nightly

$101 total

Oct 6 - Oct 7

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."

Stockbridge Village in Summer

10/10 Excellent

"I had a delightful 3 weeks at Claudia’s little farmhouse. The location was perfect in all respects…walk to coffee and patisserie shops, minutes by car to Tanglewood, The Mount, Norman Rockwell’s museum, etc etc etc. (The sitting room baby grand and the back yard laden pear tree were the cherries on top!) I look forward to another stay!"

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"

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

Filter by

Star rating

Guest rating

Our top choices for Chesterwood hotels

1. Berkshire Lake Lodge

2. Holiday Inn Club Vacations Oak 'n Spruce Resort

3. The Yankee Inn

4. Berkshire Mountain Lodge

5. Best Western Plus Berkshire Hills Inn & Suites

6. Shaker Mill Inn

7. Hampton Inn & Suites Berkshires-Lenox

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

9. The Little Lion

10. Quality Inn Lee - Lenox South

11. The Inn at Stockbridge

12. Element by Marriott Lenox Berkshires

13. Little Cat Lodge

14. The Central Downtown Inn & Suites

15. Courtyard by Marriott Lenox Berkshires

16. Hilton Garden Inn Lenox Pittsfield

17. Brook Farm Inn

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

19. Chambery Inn

20. Sunset Inn

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!

Stockbridge Village in Summer

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.

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

Explore a world of travel with Expedia