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

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

A multi-story building with a symmetrical facade, multiple balconies, and a central tower.

An indoor swimming pool with clear water, a lifeguard station, and a sign indicating no lifeguard on duty.

1. Holiday Inn Club Vacations Oak 'n Spruce Resort

4.2 mi from Chesterwood

Claudia

$135 nightly

$150 total

Sep 7 - Sep 8

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

2. Berkshire Lake Lodge

10 mi from Chesterwood

mike

$135 nightly

$151 total

Sep 29 - Sep 30

Total with taxes and fees

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

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

3. Hampton Inn & Suites Berkshires-Lenox

9.1 mi from Chesterwood

Nancy

$124 nightly

$139 total

Sep 9 - Sep 10

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

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

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

9.6 mi from Chesterwood

Ken

$118 nightly

$132 total

Sep 8 - Sep 9

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

A lodge with a large building and a dock by a lake, surrounded by forest.

A lakeside dock with kayaks and a covered boat ramp.

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

5.3 mi from Chesterwood

James

$128 nightly

$142 total

Sep 21 - Sep 22

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

6. Monument Mountain Motel

5.4 mi from Chesterwood

John

$95 nightly

$106 total

Sep 1 - Sep 2

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 wooden desk, a television, a mirror, and a bathroom visible through an open door.

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

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

7. Quality Inn Great Barrington

6.4 mi from Chesterwood

Sisile

$93 nightly

$103 total

Sep 20 - Sep 21

Total with taxes and fees

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

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

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.

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

5.3 mi from Chesterwood

Lisa

$161 nightly

$179 total

Sep 7 - Sep 8

Total with taxes and fees

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

A covered porch with wicker furniture and hanging flower baskets.

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.

9. The Red Lion Inn

2.1 mi from Chesterwood

Patricia

$191 nightly

$214 total

Sep 29 - Sep 30

Total with taxes and fees

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

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.

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

10. The Yankee Inn

9.3 mi from Chesterwood

Karen

$152 nightly

$170 total

Sep 27 - Sep 28

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.

11. Best Western Plus Berkshire Hills Inn & Suites

10.5 mi from Chesterwood

Jermaine

$115 nightly

$128 total

Sep 20 - Sep 21

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.

12. East Rock Inn

6.3 mi from Chesterwood

ERIK

$145 nightly

$161 total

Sep 22 - Sep 23

Total with taxes and fees

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

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

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.

13. Element by Marriott Lenox Berkshires

7.8 mi from Chesterwood

Lawrence

$178 nightly

$199 total

Sep 7 - Sep 8

Total with taxes and fees

A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.

An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.

A hotel reception area with a check-in counter, a Holiday Inn Express sign, and a beverage refrigerator.

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

5 mi from Chesterwood

BJORN

$115 nightly

$128 total

Sep 7 - Sep 8

Total with taxes and fees

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

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.

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

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.

15. Shaker Mill Inn

3.6 mi from Chesterwood

Mervin

$166 nightly

$182 total

Sep 8 - Sep 9

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

16. Hilton Garden Inn Lenox Pittsfield

9.6 mi from Chesterwood

James

$154 nightly

$172 total

Sep 13 - Sep 14

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

17. Quality Inn Lee - Lenox South

5.7 mi from Chesterwood

Christine

$110 nightly

$122 total

Sep 20 - Sep 21

Total with taxes and fees

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

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

A garden with wooden Adirondack chairs and a stone pathway.

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

18. Berkshire Mountain Lodge

9.9 mi from Chesterwood

Robert

$125 nightly

$139 total

Aug 31 - Sep 1

Total with taxes and fees

A stone fountain surrounded by trees in a park setting.

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

19. The Inn at Stockbridge

3.2 mi from Chesterwood

Michele

$396 nightly

$442 total

Sep 13 - Sep 14

Total with taxes and fees

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

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.

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

20. Courtyard by Marriott Lenox Berkshires

7.5 mi from Chesterwood

Laura

$178 nightly

$198 total

Sep 3 - Sep 4

Total with taxes and fees

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Top Chesterwood Hotel Reviews

The Red Lion Inn

10/10 Excellent

"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"

The Little Lion

8/10 Good

"Clean and comfortable room for reasonable price. Central area/lobby is nice place to sit and read, relax, and/or eat breakfast (coffee provided). Also red Adirondack chairs up on hill behind rooms and small tables/chairs in front of some rooms. Can use the outdoor pool and whirl pool a few miles away at the Red Lion Inn, which is desirable feature on summer days. A few negatives. While the building and rooms are set back from the road, it’s located off a busy road that goes between Stockbridge and Great Barrington. You will hear the cars during the day. It’s also not what I would consider an “Inn” as it’s really a motel. It used to be the Briarcliff Motel before the Red Lion Inn purchased it. Any questions, requests, or comments need to contact them as the Little Lion didn’t have any full time staff and no one at front desk in the lobby when we stayed. We received text with code for room door."

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"

Hearth House | Prime Location!

10/10 Excellent

"This property was better than expected! The photos don’t do it justice. It was ideal for my husband and me to share with our son and small granddaughter with them having their privacy upstairs, but ample room for us to all be together downstairs, and a wonderful bedroom suite for us. The yard and patio are lovely. We so appreciated the ample supplies provided (at some rentals we’ve had to run to a store to augment things that ran out) and the well appointed kitchen. We love the area and we’re only sorry our stay wasn’t long enough to take full advantage of everything on and off site. My only suggestion is that the information provided upon leaving would be helpful to have upfront, particularly because some things mentioned differed from information in the handbook on the property, and it would help to plan better for day of departure. Oh, and communication was terrific with Jayren being very responsive to any questions."

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."

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

10/10 Excellent

"The property was beautiful and perfectly located for our trip to hike the AT in Massachusetts."

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 $103 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 $103

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Our top choices for Chesterwood hotels

1. Holiday Inn Club Vacations Oak 'n Spruce Resort

2. Berkshire Lake Lodge

3. Hampton Inn & Suites Berkshires-Lenox

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

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

6. Monument Mountain Motel

7. Quality Inn Great Barrington

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

9. The Red Lion Inn

10. The Yankee Inn

11. Best Western Plus Berkshire Hills Inn & Suites

12. East Rock Inn

13. Element by Marriott Lenox Berkshires

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

15. Shaker Mill Inn

16. Hilton Garden Inn Lenox Pittsfield

17. Quality Inn Lee - Lenox South

18. Berkshire Mountain Lodge

19. The Inn at Stockbridge

20. Courtyard by Marriott Lenox Berkshires

Top Chesterwood Hotel Reviews

The Red Lion Inn

The Little Lion

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.

Hearth House | Prime Location!

Secluded Family Home in Serene Stockbridge Woods

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

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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