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 sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.

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.

1. Quality Inn Lee - Lenox South

9.1 km from Chesterwood

Lucinda

NT$3,002

NT$3,353 total

includes taxes & fees

Nov 12 - Nov 13

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

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.

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

2. 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 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 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.

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

8.6 km from Chesterwood

NT$4,655

NT$5,200 total

includes taxes & fees

Nov 2 - Nov 3

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

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.

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

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

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

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

A coffee station with two coffee machines and a variety of coffee pods and cups.

5. 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 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

8.7 km from Chesterwood

Andrea

NT$1,939

NT$2,166 total

includes taxes & fees

Nov 15 - Nov 16

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

A room with a blue armchair, a wooden cabinet with a coffee maker, a television on the wall, and a small table with a cup.

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

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

7. Hampton Inn & Suites Berkshires-Lenox

14.7 km from Chesterwood

Thomas

NT$3,553

NT$3,968 total

includes taxes & fees

Nov 15 - Nov 16

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

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

8. 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 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.

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.

9. The Yankee Inn

14.9 km from Chesterwood

Basil

NT$3,435

NT$3,836 total

includes taxes & fees

Nov 1 - Nov 2

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 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.

10. Berkshire Lake Lodge

16.2 km from Chesterwood

mike

NT$4,593

NT$5,130 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 Quality Inn sign, a brick building, and a parking lot with cars.

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.

11. Quality Inn Great Barrington

10.3 km from Chesterwood

Scott Patterson

NT$2,451

NT$2,738 total

includes taxes & fees

Nov 12 - Nov 13

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

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

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

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

12. 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

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".

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

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

13. Berkshire Mountain Lodge

15.9 km from Chesterwood

Joel

NT$2,804

NT$3,856 total

includes taxes & fees

Nov 12 - Nov 13

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

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

14. 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

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

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.

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

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

16. The Little Lion

5.1 km from Chesterwood

Lidia

NT$3,354

NT$3,746 total

includes taxes & fees

Oct 19 - Oct 20

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

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

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

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

17. Berkshires Untold

13 km from Chesterwood

Madhavi R

NT$4,218

NT$4,712 total

includes taxes & fees

Nov 8 - Nov 9

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

A reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.

A hotel room with a patterned carpet, a sofa, a chair, a small table, a lamp, a television on a cabinet, and two framed pictures on the wall.

18. 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 hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

A hotel room with a dining area featuring a table and chairs, a kitchenette with a coffee machine, and a television on the wall.

A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

A hotel room with a dining area, a sofa, a coffee station, and a TV mounted on the wall.

19. Howard Johnson by Wyndham Lenox

14.9 km from Chesterwood

Aleksandr

NT$2,560

NT$2,859 total

includes taxes & fees

Oct 19 - Oct 20

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

20. East Rock Inn

10.1 km from Chesterwood

Sharon

NT$4,077

NT$4,554 total

includes taxes & fees

Nov 17 - Nov 18

View all properties

Compare popular hotels close to Chesterwood

Property	Property class	Guest rating
Quality Inn Lee - Lenox South	8.6 Excellent 1,001 reviews	View
The Black Swan Lee - Lenox, an Ascend Collection Hotel	9.2 Wonderful 1,005 reviews	View
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires	9.4 Exceptional 817 reviews	View
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires	9.2 Wonderful 1,003 reviews	View
Holiday Inn Express Hotel & Suites Great Barrington by IHG	8.8 Excellent 839 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%"

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"We were able to get rental as a last minute deal for a villa here and we're very pleased with the property. The two rooms were very spacious each with its own bathroom, one with jacuuzi. Was quiet and you don't see or hear neighbor next to you. The rooms were quite roomy. All amenities in kitchen and nice livingroom/dining area. Nice outdoor seating with table and nice view of mountains. Only issue encountered was figuring out how the showers worked, figured it out by pulling down a round lever on bottom of faucet. Very clean and spacious, nice experience."

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

Change your mind

Treat yourself

Be picky

Check prices for these dates

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Star rating

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Our top choices for Chesterwood hotels

1. Quality Inn Lee - Lenox South

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

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

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

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

6. Monument Mountain Motel

7. Hampton Inn & Suites Berkshires-Lenox

8. Courtyard by Marriott Lenox Berkshires

9. The Yankee Inn

10. Berkshire Lake Lodge

11. Quality Inn Great Barrington

12. Element by Marriott Lenox Berkshires

13. Berkshire Mountain Lodge

14. Hilton Garden Inn Lenox Pittsfield

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

16. The Little Lion

17. Berkshires Untold

18. Best Western Plus Berkshire Hills Inn & Suites

19. Howard Johnson by Wyndham Lenox

20. East Rock Inn

Compare popular hotels close to Chesterwood

Top Chesterwood Hotel Reviews

The Red Lion Inn

Holiday Inn Club Vacations Oak 'n Spruce Resort

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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