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Sep 29 - Sep 30
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Sep 30 - Oct 1
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Our top choices for Chesterwood hotels

A building with a porch and multiple windows, surrounded by purple flowers.
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.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

1. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
6.7 km from Chesterwood
United States
Jared
₩158,426
₩203,435 total
includes taxes & fees
Oct 25 - Oct 26
Holiday Inn Club Vacations Oak 'n Spruce Resort
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 motel with a parking lot and several cars parked.

2. Monument Mountain Motel

Monument Mountain Motel
8.7 km from Chesterwood
United States
Victor
₩92,925
₩103,793 total
includes taxes & fees
Oct 25 - Oct 26
Monument Mountain Motel
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 swimming pool with a surrounding deck, a stone wall, and a building in the background.

3. The Yankee Inn

The Yankee Inn
14.9 km from Chesterwood
United States
William
₩146,240
₩163,355 total
includes taxes & fees
Oct 27 - Oct 28
The Yankee Inn
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 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.

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

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
8.6 km from Chesterwood
United States
Bruce
₩263,570
₩294,408 total
includes taxes & fees
Oct 4 - Oct 5
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A reception area with a fireplace, seating, and a doormat with the logo "Quality".
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.
A hotel room with a sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.

5. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
9.1 km from Chesterwood
United States
Christine
₩148,474
₩165,845 total
includes taxes & fees
Oct 19 - Oct 20
Quality Inn Lee - Lenox South
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.

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
15.5 km from Chesterwood
United States
Susan
₩144,006
₩160,854 total
includes taxes & fees
Oct 29 - Oct 30
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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 brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

7. The Red Lion Inn

The Red Lion Inn
3.3 km from Chesterwood
United States
Stephan
₩241,495
₩337,244 total
includes taxes & fees
Oct 19 - Oct 20
The Red Lion Inn
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

Courtyard by Marriott Lenox Berkshires
12.1 km from Chesterwood
United States
Tracy
₩192,113
₩214,589 total
includes taxes & fees
Oct 25 - Oct 26
Courtyard by Marriott Lenox Berkshires
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.
A spacious lobby with a fireplace, seating area, and a bar.
A garden with wooden Adirondack chairs and a stone pathway.

9. Berkshire Mountain Lodge

Berkshire Mountain Lodge
15.9 km from Chesterwood
United States
Jay
₩107,784
₩150,645 total
includes taxes & fees
Oct 1 - Oct 2
Berkshire Mountain Lodge
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 two-story house with a covered porch, a driveway, and a lawn with outdoor seating.

10. Berkshire Lake Lodge

Berkshire Lake Lodge
16.2 km from Chesterwood
United States
mike
₩172,745
₩192,956 total
includes taxes & fees
Oct 1 - Oct 2
Berkshire Lake Lodge
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.
A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.
An outdoor seating area with Adirondack chairs and a fire feature.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

11. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
12.5 km from Chesterwood
United States
Kirsty
₩228,838
₩255,613 total
includes taxes & fees
Oct 19 - Oct 20
Element by Marriott Lenox Berkshires
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 fireplace, and comfortable seating.

12. Berkshires Untold

Berkshires Untold
13 km from Chesterwood
United States
Drue
₩211,901
₩236,694 total
includes taxes & fees
Sep 30 - Oct 1
Berkshires Untold
A large house with a balcony and a grassy yard.
A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.
A two-story building with a gabled roof and a chimney.
A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.

13. The Little Lion

The Little Lion
5.1 km from Chesterwood
United States
Lidia
₩140,146
₩156,543 total
includes taxes & fees
Oct 18 - Oct 19
The Little Lion
A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A modern living room with a grey sofa, a wooden coffee table, and a dining area with a round table and chairs.
A sign for East Rock Inn with a mountainous logo, surrounded by lush greenery and a gravel path leading to a building.

14. East Rock Inn

East Rock Inn
10.1 km from Chesterwood
United States
ERIK
₩194,232
₩216,957 total
includes taxes & fees
Oct 12 - Oct 13
East Rock Inn
A snow-covered outdoor area with a patio, seating, and a covered dining area.
A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.
A modern living room with a fireplace, comfortable seating, and a large window with curtains.
A dining area with a glass table, red walls, and framed artwork.

15. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
10.7 km from Chesterwood
United States
Rosann
₩208,478
₩239,124 total
includes taxes & fees
Oct 27 - Oct 28
The Cornell Inn, Lenox & The Berkshires
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 breakfast area with a counter, coffee machine, and a display of pastries.

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

Holiday Inn Express Hotel & Suites Great Barrington by IHG
8 km from Chesterwood
United States
Maria Dulce
₩161,134
₩179,983 total
includes taxes & fees
Oct 19 - Oct 20
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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 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'.
A Quality Inn sign, a brick building, and a parking lot with cars.

17. Quality Inn Great Barrington

Quality Inn Great Barrington
10.3 km from Chesterwood
United States
Joan
₩136,964
₩152,989 total
includes taxes & fees
Oct 19 - Oct 20
Quality Inn Great Barrington
A large, two-story house with a well-maintained lawn and a fence.
A house with a fire pit in the yard, outdoor seating, and a large window overlooking the yard.
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 bedroom with a large bed, a fireplace, a bathtub, and a window with a view of greenery.

18. Devonfield Inn B&B

Devonfield Inn B&B
7.5 km from Chesterwood
United States
Sebastien
₩555,647
₩620,654 total
includes taxes & fees
Oct 25 - Oct 26
Devonfield Inn B&B
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 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 Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

19. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
16.9 km from Chesterwood
United States
Joe
₩143,234
₩159,992 total
includes taxes & fees
Oct 19 - Oct 20
Best Western Plus Berkshire Hills Inn & Suites
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 cozy room with a fireplace, a sofa, a table with a bottle and glasses, and a patterned pillow.
A large, historic building labeled "Chambéry Inn" with a vintage turquoise truck parked in front.

20. Chambery Inn

Chambery Inn
8.7 km from Chesterwood
United States
Alexandra
₩365,586
₩408,360 total
includes taxes & fees
Sep 30 - Oct 1
Chambery Inn
View all properties

Compare popular hotels close to Chesterwood

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet friendly
WiFi included
A building with a porch and multiple windows, surrounded by purple flowers.
Holiday Inn Club Vacations Oak 'n Spruce Resort
9.2
Wonderful
996 reviews
View
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.
Monument Mountain Motel
9.0
Wonderful
917 reviews
View
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
The Yankee Inn
9.2
Wonderful
1,016 reviews
View
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
9.4
Exceptional
812 reviews
View
A reception area with a fireplace, seating, and a doormat with the logo "Quality".
Quality Inn Lee - Lenox South
8.6
Excellent
1,010 reviews
View

Top Chesterwood Hotel Reviews

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent
"Wonderful resort"
Ofer 2-night trip
Posted 9 hours ago
Holiday Inn Club Vacations Oak 'n Spruce Resort
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"One of the most unique establishments in the US. It brings one back to time when life was much simpler. Highly recomended."
Michael 1-night trip
Posted 21 hours ago
The Red Lion Inn
Pleasant Valley Motel West Stockbridge

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."
Deborah 1-night trip
Posted 3 days ago
Pleasant Valley Motel West Stockbridge

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.
See properties

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.
See properties

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.
See properties

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.
See properties

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.