The Best Hotels Closest to Chesterwood in South Lee for 2026

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Our top choices for Chesterwood hotels

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

1. Holiday Inn Club Vacations Oak 'n Spruce Resort

4.2 mi from Chesterwood

Jared

$135 nightly

$150 total

Sep 27 - Sep 28

Total with taxes and fees

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

A lakeside lodge with a dock, fishing rods, and outdoor seating.

A lakeside dock with kayaks and a covered boat ramp.

A dining area with large windows, wooden furniture, and a view of a lake.

2. The Black Swan Lee - Lenox, an Ascend Collection Hotel

5.3 mi from Chesterwood

Ann M

$128 nightly

$143 total

Oct 1 - Oct 2

Total with taxes and fees

A large house with a balcony and a grassy yard.

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

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

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

3. The Little Lion

3.2 mi from Chesterwood

Mary

$115 nightly

$128 total

Oct 18 - Oct 19

Total with taxes and fees

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

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.

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

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

4. The Yankee Inn

9.3 mi from Chesterwood

William

$109 nightly

$122 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.

A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

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

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

5.3 mi from Chesterwood

Bruce

$169 nightly

$189 total

Sep 29 - Sep 30

Total with taxes and fees

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

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.

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

6. Berkshire Lake Lodge

10 mi from Chesterwood

mike

$129 nightly

$144 total

Sep 27 - Sep 28

Total with taxes and fees

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

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.

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

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

5 mi from Chesterwood

Maria Dulce

$128 nightly

$143 total

Oct 19 - Oct 20

Total with taxes and fees

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.

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

8. Quality Inn Lee - Lenox South

5.7 mi from Chesterwood

Wendy

$110 nightly

$122 total

Oct 19 - Oct 20

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

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

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

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

10. East Rock Inn

6.3 mi from Chesterwood

ERIK

$134 nightly

$150 total

Oct 26 - Oct 27

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

A covered corridor with a metal railing, white walls, and a view of a street with parked cars.

11. Sunset Inn

5.7 mi from Chesterwood

Lauren

$86 nightly

$96 total

Oct 6 - Oct 7

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.

12. Shaker Mill Inn

3.6 mi from Chesterwood

Mervin

$179 nightly

$196 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 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.

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

13. Best Western Plus Berkshire Hills Inn & Suites

10.5 mi from Chesterwood

Joe

$106 nightly

$118 total

Oct 18 - Oct 19

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

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

14. The Central Downtown Inn & Suites

12.2 mi from Chesterwood

Rena

$89 nightly

$100 total

Oct 19 - Oct 20

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

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

15. Chambery Inn

5.4 mi from Chesterwood

Alexandra

$273 nightly

$305 total

Oct 25 - Oct 26

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 hotel patio with outdoor seating and a fire pit.

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

16. Hilton Garden Inn Lenox Pittsfield

9.6 mi from Chesterwood

James

$146 nightly

$163 total

Sep 27 - Sep 28

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

A modern cafe with a counter, seating area, and large windows.

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

9.6 mi from Chesterwood

Susan

$118 nightly

$132 total

Oct 20 - Oct 21

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 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.

18. Courtyard by Marriott Lenox Berkshires

7.5 mi from Chesterwood

Tracy

$149 nightly

$167 total

Sep 29 - Sep 30

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.

19. Little Cat Lodge

10.1 mi from Chesterwood

Kees

$199 nightly

$223 total

Sep 27 - Sep 28

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.

20. Hampton Inn & Suites Berkshires-Lenox

9.1 mi from Chesterwood

Larry

$116 nightly

$130 total

Sep 30 - Oct 1

Total with taxes and fees

View all properties

Compare popular hotels close to Chesterwood

Property	Star rating	Guest rating
Holiday Inn Club Vacations Oak 'n Spruce Resort	9.2 Wonderful 990 reviews	View
The Black Swan Lee - Lenox, an Ascend Collection Hotel	9.2 Wonderful 1,000 reviews	View
The Little Lion	8.6 Excellent 614 reviews	View
The Yankee Inn	9.2 Wonderful 1,009 reviews	View
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires	9.4 Exceptional 811 reviews	View

Top Chesterwood Hotel Reviews

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!"

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!"

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

8/10 Good

"ok"

Stockbridge Retreat w/ Pool & Hot Tub!

10/10 Excellent

"The house was amazing...exactly what we were hoping for. Tara (our host) was always available and super accommodating. The pool and hot tub were perfect! We rented for 2 weeks and invited our close friends to join us for the first weekend and our kids for the second weekend. Everyone loved it, enjoying the pool and hot tub. The inside was incredibly spacious and comfortable. We barbequed on the grill several nights, and truly felt as if we were living in the Berkshires and enjoying all that the region offers!"

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 $96 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.

Explore a world of travel with Expedia

Things to do in Western Massachusetts

Find hotels near Chesterwood, South Lee from $96

Upfront pricing

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Chesterwood hotels

1. Holiday Inn Club Vacations Oak 'n Spruce Resort

2. The Black Swan Lee - Lenox, an Ascend Collection Hotel

3. The Little Lion

4. The Yankee Inn

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

6. Berkshire Lake Lodge

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

8. Quality Inn Lee - Lenox South

9. Element by Marriott Lenox Berkshires

10. East Rock Inn

11. Sunset Inn

12. Shaker Mill Inn

13. Best Western Plus Berkshire Hills Inn & Suites

14. The Central Downtown Inn & Suites

15. Chambery Inn

16. Hilton Garden Inn Lenox Pittsfield

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

18. Courtyard by Marriott Lenox Berkshires

19. Little Cat Lodge

20. Hampton Inn & Suites Berkshires-Lenox

Compare popular hotels close to Chesterwood

Top Chesterwood Hotel Reviews

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!

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

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

Stockbridge Retreat w/ Pool & Hot Tub!

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

Explore a world of travel with Expedia