The Best Hotels Closest to Chesterwood in South Lee for 2026

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Our top choices for Chesterwood hotels

A two-story house with a brick entrance and a white facade.

A neatly arranged bedroom with a bed, bedside table, and a dresser.

A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.

A dining area with tables set for a meal, surrounded by large windows offering a view of trees and a garden.

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

0.6 km from Chesterwood

Philippe

NT$12,375

NT$14,970 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

8 km from Chesterwood

Cynthia

NT$2,689

NT$3,004 total

includes taxes & fees

Nov 17 - Nov 18

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

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

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

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

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

8.6 km from Chesterwood

NT$4,654

NT$5,199 total

includes taxes & fees

Nov 2 - Nov 3

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.

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

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

4. Courtyard by Marriott Lenox Berkshires

12.1 km from Chesterwood

Vandhana

NT$4,070

NT$4,546 total

includes taxes & fees

Nov 1 - Nov 2

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 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.

5. The Yankee Inn

14.9 km from Chesterwood

Basil

NT$3,435

NT$3,836 total

includes taxes & fees

Nov 1 - Nov 2

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.

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

6. Quality Inn Lee - Lenox South

9.1 km from Chesterwood

Lucinda

NT$3,002

NT$3,353 total

includes taxes & fees

Nov 8 - Nov 9

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

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

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

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

7. Monument Mountain Motel

8.7 km from Chesterwood

Andrea

NT$1,939

NT$2,166 total

includes taxes & fees

Nov 1 - Nov 2

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

A lakeside dock with kayaks and a covered boat ramp.

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

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

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

8.6 km from Chesterwood

Gustavo

NT$3,690

NT$4,122 total

includes taxes & fees

Nov 15 - Nov 16

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

A gym with exercise equipment including treadmills, a stationary bike, and free weights.

A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.

A hotel room with a bed, a desk, a chair, and a carpeted floor.

9. Hampton Inn & Suites Berkshires-Lenox

14.7 km from Chesterwood

Thomas

NT$3,553

NT$3,968 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

10. Shaker Mill Inn

5.8 km from Chesterwood

Steven

NT$4,050

NT$4,443 total

includes taxes & fees

Nov 16 - Nov 17

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

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

11. Berkshires Untold

13 km from Chesterwood

Madhavi R

NT$4,218

NT$4,712 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

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

12. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

6.7 km from Chesterwood

Michael

NT$3,791

NT$4,868 total

includes taxes & fees

Oct 20 - Oct 21

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.

13. Element by Marriott Lenox Berkshires

12.5 km from Chesterwood

Kirsty

NT$4,374

NT$4,886 total

includes taxes & fees

Nov 8 - Nov 9

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

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

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

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

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

15.5 km from Chesterwood

Ginger

NT$3,078

NT$3,438 total

includes taxes & fees

Nov 17 - Nov 18

A hotel patio with outdoor seating and a fire pit.

A modern kitchen with a marble countertop, stainless steel appliances, and a variety of food items displayed on the counter.

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

A modern reception area with a green textured wall, a reception desk, and a coffee machine.

15. Hilton Garden Inn Lenox Pittsfield

15.5 km from Chesterwood

James

NT$4,143

NT$4,628 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

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

16. Quality Inn Great Barrington

10.3 km from Chesterwood

Scott Patterson

NT$2,451

NT$2,738 total

includes taxes & fees

Nov 8 - Nov 9

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.

17. East Rock Inn

10.1 km from Chesterwood

Sharon

NT$4,077

NT$4,554 total

includes taxes & fees

Nov 17 - Nov 18

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

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.

A covered porch with wicker furniture and hanging flower baskets.

A bar with wooden floors and shelves filled with bottles.

18. The Red Lion Inn

3.3 km from Chesterwood

Stephan

NT$5,104

NT$7,311 total

includes taxes & fees

Nov 4 - Nov 5

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.

19. Best Western Plus Berkshire Hills Inn & Suites

16.9 km from Chesterwood

James

NT$3,162

NT$3,532 total

includes taxes & fees

Nov 15 - Nov 16

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.

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

20. Berkshire Mountain Lodge

15.9 km from Chesterwood

Joel

NT$2,804

NT$3,856 total

includes taxes & fees

Nov 10 - Nov 11

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Compare popular hotels close to Chesterwood

Property	Property class	Guest rating
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood	9.2 Wonderful 120 reviews	View
Holiday Inn Express Hotel & Suites Great Barrington by IHG	8.8 Excellent 839 reviews	View
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires	9.4 Exceptional 817 reviews	View
Courtyard by Marriott Lenox Berkshires	9.2 Wonderful 675 reviews	View
The Yankee Inn	9.2 Wonderful 1,004 reviews	View

Top Chesterwood Hotel Reviews

The Red Lion Inn

10/10 Excellent

"This place is a must stay! We loved every bit of it and had a best time!!! Def recommend 100%"

The Little Lion

10/10 Excellent

"Quaint location that is loosely tied to the Historic Red Lion Inn at Stockbridge. There is no on site staff so everything is done through texting. You do get access to the Red Lion Inn which was a wonderful "amenity" without the cost of staying there. The Little Lion is a roadside motel with about 14 or 15 units. Very clean and obviously quiet. Was a great home base for a couple of days while we tooled around the Berkshires. Would definitely book again!"

Pleasant Valley Motel West Stockbridge

8/10 Good

"Older but well maintained, clean and had basic necessities. Very good for the price. Only problem was trying to adjust heat. Good hot shower. Would come again"

The Inn at Stockbridge

8/10 Good

"Great property. Disappointed the pool wasn't clean despite having pool towels available."

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's the area like around Chesterwood?

Chesterwood is located in a scenic area of South Lee known for its beautiful lakeside setting and hiking. If you're looking for a convenient place to stay, check out the 11 hotels and other accommodations you'll find within a mile.

What's the best hotel to stay close to Chesterwood?

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood is one of the top choices for your stay based on our traveler data, and this B&B offers free breakfast and free parking. It's located just a short 0.4 mi (0.6 km) from Chesterwood. Another good choice is The Red Lion Inn, located 2.1 mi (3.3 km) away.

How many hotels are there close to Chesterwood?

Expedia has 11 hotels and other accommodations within a mile from Chesterwood.

If I need to cancel the hotel reservation for my stay near Chesterwood, will I receive a refund?

Yes, the majority of room reservations are fully refundable provided that you cancel before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you have a non-refundable reservation, you might be able to still cancel and be given a refund within 24 hours of booking. Enter dates in and click on "Search", then use the "fully refundable" filter to review the best options available near Chesterwood.

Where can I learn more about changing or cancelling my trip in the area near Chesterwood?

For more information about picking new dates or cancelling your stay near Chesterwood, head over to our customer service page.

What can I see and do near Chesterwood?

You'll want to browse the exhibits at Norman Rockwell Museum and Mission House. Naumkeag Museum, The Mount, and Berkshire Theatre Festival are monuments to see when you're exploring the area around Chesterwood. Be sure to get some family photos at Berkshire Botanical Garden, Hoffman's Pottery, and Lenox Arts Center while you're out sightseeing near Chesterwood.

Find hotels near Chesterwood, South Lee from NT$2,166

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Our top choices for Chesterwood hotels

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

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

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

4. Courtyard by Marriott Lenox Berkshires

5. The Yankee Inn

6. Quality Inn Lee - Lenox South

7. Monument Mountain Motel

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

9. Hampton Inn & Suites Berkshires-Lenox

10. Shaker Mill Inn

11. Berkshires Untold

12. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

13. Element by Marriott Lenox Berkshires

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

15. Hilton Garden Inn Lenox Pittsfield

16. Quality Inn Great Barrington

17. East Rock Inn

18. The Red Lion Inn

19. Best Western Plus Berkshire Hills Inn & Suites

20. Berkshire Mountain Lodge

Compare popular hotels close to Chesterwood

Top Chesterwood Hotel Reviews

The Red Lion Inn

The Little Lion

Pleasant Valley Motel West Stockbridge

The Inn at Stockbridge

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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