The Best Hotels Closest to Chesterwood in South Lee - 2026 Updated Prices

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Our top choices for Chesterwood hotels

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

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

1. Monument Mountain Motel

8.7 km from Chesterwood

Victor

1.554.544 ₫

1.736.362 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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.

A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.

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

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

8.6 km from Chesterwood

Bruce

3.731.165 ₫

4.167.711 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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

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

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

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

3. Berkshire Mountain Lodge

15.9 km from Chesterwood

Jay

2.226.619 ₫

3.067.392 ₫ total

includes taxes & fees

18 Oct - 19 Oct

A large, two-story house with a well-maintained lawn and a fence.

A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

A house with a fire pit in the yard, outdoor seating, and a large window overlooking the yard.

A bedroom with a large bed, a fireplace, a bathtub, and a window with a view of greenery.

4. Devonfield Inn B&B

7.5 km from Chesterwood

Sebastien

9.584.406 ₫

10.705.704 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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

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.

5. The Yankee Inn

14.9 km from Chesterwood

William

2.753.244 ₫

3.075.374 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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 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

Christine

2.848.049 ₫

3.181.271 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

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

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

A modern apartment with a living room, kitchenette, and dining area.

7. The Central Downtown Inn & Suites

19.6 km from Chesterwood

Rena

2.570.436 ₫

2.871.099 ₫ total

includes taxes & fees

15 Oct - 16 Oct

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

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

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.

8. Courtyard by Marriott Lenox Berkshires

12.1 km from Chesterwood

Tracy

3.262.594 ₫

3.644.317 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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

9. The Inn at Stockbridge

5.2 km from Chesterwood

Jodi

9.474.796 ₫

11.112.456 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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.

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

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

8 km from Chesterwood

Maria Dulce

2.467.530 ₫

2.756.231 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

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.

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.

11. Best Western Plus Berkshire Hills Inn & Suites

16.9 km from Chesterwood

Joe

2.428.050 ₫

2.712.132 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

12. Sunset Inn

9.1 km from Chesterwood

Lauren

2.184.871 ₫

2.440.501 ₫ total

includes taxes & fees

5 Oct - 6 Oct

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.

13. Hampton Inn & Suites Berkshires-Lenox

14.7 km from Chesterwood

Thomas

3.045.711 ₫

3.402.060 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.

A hotel patio with outdoor seating and a fire pit.

A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.

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

14. Hilton Garden Inn Lenox Pittsfield

15.5 km from Chesterwood

James

3.321.555 ₫

3.710.126 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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.

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

A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

15. Element by Marriott Lenox Berkshires

12.5 km from Chesterwood

Kirsty

3.922.074 ₫

4.380.957 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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.

16. Shaker Mill Inn

5.8 km from Chesterwood

Mervin

3.636.360 ₫

3.989.087 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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

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.

17. Chambery Inn

8.7 km from Chesterwood

Alexandra

7.010.046 ₫

7.830.221 ₫ total

includes taxes & fees

20 Oct - 21 Oct

A group of people performing yoga in an outdoor setting with grass and trees.

A hotel room with a flat-screen TV, a microwave, a refrigerator, a wooden dresser, a bedside lamp, and a framed picture on the wall.

A motel with a row of rooms, a parking lot, and a hilly backdrop.

A reception desk with a framed floral painting, a deer head, and a sign about pets.

18. Pleasant Valley Motel West Stockbridge

4.7 km from Chesterwood

James

1.599.382 ₫

1.754.523 ₫ total

includes taxes & fees

14 Oct - 15 Oct

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

A gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.

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.

19. Howard Johnson by Wyndham Lenox

14.9 km from Chesterwood

Mark

2.051.156 ₫

2.291.141 ₫ total

includes taxes & fees

5 Oct - 6 Oct

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 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.

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

15.5 km from Chesterwood

Sheldon

2.571.426 ₫

2.872.284 ₫ total

includes taxes & fees

1 Nov - 2 Nov

View all properties

Compare popular hotels close to Chesterwood

Property	Property class	Guest rating
Monument Mountain Motel	9.0 Wonderful 918 reviews	View
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires	9.4 Exceptional 813 reviews	View
Berkshire Mountain Lodge	9.0 Wonderful 1,168 reviews	View
Devonfield Inn B&B	10.0 Exceptional 141 reviews	View
The Yankee Inn	9.2 Wonderful 1,002 reviews	View

Top Chesterwood Hotel Reviews

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"Wonderful resort"

Pleasant Valley Motel West Stockbridge

8/10 Good

"The room was fairly clean, but the wallpaper is peeling away from the wall. The towel hanging on the towel rod had dark gray streaks like it had already been used."

Other attractions near Chesterwood

Norman Rockwell Museum

9.4/10 (347 reviews)

You can spend time browsing the exhibits at Norman Rockwell Museum during your trip to 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 studying the exhibits at 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 studying the exhibits at Naumkeag Museum 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 studying the exhibits at Schantz Galleries during your travels in 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 during your trip to 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 enjoy a show at Berkshire Theatre Festival during 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, take a look at the 11 hotels and other accommodation options you'll find within a mile.

How many hotels will I find near Chesterwood?

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

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

Yes! You'll find that most room reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you booked a non-refundable reservation, it might still be possible to cancel it and be given a refund within 24 hours of booking. Enter your dates, click on "Search", then you can filter by "fully refundable" to get the best options available near Chesterwood.

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.

Search Hotels Near Chesterwood, South Lee

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Our top choices for Chesterwood hotels

1. Monument Mountain Motel

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

3. Berkshire Mountain Lodge

4. Devonfield Inn B&B

5. The Yankee Inn

6. Quality Inn Lee - Lenox South

7. The Central Downtown Inn & Suites

8. Courtyard by Marriott Lenox Berkshires

9. The Inn at Stockbridge

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

11. Best Western Plus Berkshire Hills Inn & Suites

12. Sunset Inn

13. Hampton Inn & Suites Berkshires-Lenox

14. Hilton Garden Inn Lenox Pittsfield

15. Element by Marriott Lenox Berkshires

16. Shaker Mill Inn

17. Chambery Inn

18. Pleasant Valley Motel West Stockbridge

19. Howard Johnson by Wyndham Lenox

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

Compare popular hotels close to Chesterwood

Top Chesterwood Hotel Reviews

Holiday Inn Club Vacations Oak 'n Spruce Resort

Pleasant Valley Motel West 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