Hotels near Chesterwood South Lee

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Top 5 hotels near Chesterwood at a glance

Holiday Inn Express Hotel & Suites Great Barrington by IHG — 2.5-star hotel in 8 km from Chesterwood. Guest rating: 8.8/10 — Excellent.
The Black Swan Lee - Lenox, an Ascend Collection Hotel — 3-star hotel in 8.6 km from Chesterwood. Guest rating: 9.0/10 — Wonderful.
Granville House — 3-star hotel in 6.4 km from Chesterwood. Guest rating: 10/10 — Exceptional.
The Little Lion — 3-star hotel in 5.1 km from Chesterwood. Guest rating: 8.6/10 — Excellent.
Quality Inn Lee - Lenox South — 2.5-star hotel in 9.1 km from Chesterwood. Guest rating: 8.4/10 — Very Good.

Where to stay near Chesterwood?

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

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.

Holiday Inn Express Hotel & Suites Great Barrington by IHG

8 km from Chesterwood

Christine

$115

$128 total

includes taxes & fees

Sep 7 - Sep 8

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

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8.6 km from Chesterwood

Diane

$128

$142 total

includes taxes & fees

Sep 21 - Sep 22

A dining table with pastries, a coffee pot, and a vase of sunflowers.

A small cabin with two Adirondack chairs in a grassy field, surrounded by trees and a mountain in the background.

A pool table in a room with a patterned rug, a shelf with decorative items, and a window with a view of greenery.

A bedroom with a wooden bed, bedside tables, a desk, and a chair.

Granville House

6.4 km from Chesterwood

Nicole

$275

$307 total

includes taxes & fees

Sep 3 - Sep 4

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.

The Little Lion

5.1 km from Chesterwood

Kathryn

$125

$140 total

includes taxes & fees

Sep 2 - Sep 3

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

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.

Quality Inn Lee - Lenox South

9.1 km from Chesterwood

"The hotel was very clean and well maintained. The lobby and stairs were very clean and looked as though everything was painted recently. The room was very clean and modern and bed was comfortable. The bathroom was also clean. We only stayed the one night for a concert at Tanglewood so we didn’t use any of the amenities or have the free breakfast. But if they were anything like the rest of the hotel, I’m sure they were above average. Would definitely stay again when in the area."

Bill

$110

$122 total

includes taxes & fees

Sep 21 - Sep 22

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

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

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 dining area with a table set for two, a view of a green landscape through large windows, and outdoor seating with a view.

Devonfield Inn B&B

7.5 km from Chesterwood

Christopher

$389

$435 total

includes taxes & fees

Sep 3 - Sep 4

A snow-covered outdoor area with a patio, seating, and a covered dining area.

A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.

A dining area with a glass table, red walls, and framed artwork.

A modern living room with a fireplace, comfortable seating, and a large window with curtains.

The Cornell Inn, Lenox & The Berkshires

10.7 km from Chesterwood

Arthur

$206

$236 total

includes taxes & fees

Sep 3 - Sep 4

A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.

A cozy room with a wooden bench, a table with a pitcher, and a sofa with patterned cushions. Large windows with yellow blinds offer a view of greenery outside.

A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.

A wooden fire pit surrounded by six Adirondack chairs in a forested area.

Little Cat Lodge

16.3 km from Chesterwood

Zachary

$199

$223 total

includes taxes & fees

Sep 2 - Sep 3

A large house with a covered patio area featuring outdoor seating and a fire pit.

A well-lit room with a large window, a clock, and a fireplace. There are several chairs and a table with a vase.

A cozy lounge area with plush seating, a fireplace, and large windows offering a view of the outdoors.

A sunlit room with large windows, a stone floor, and two rocking chairs.

The Whitlock

9.8 km from Chesterwood

William

$144

$160 total

includes taxes & fees

Sep 15 - Sep 16

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

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

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 sofa, a coffee table, and a large window with a view of trees.

Berkshires Untold

13 km from Chesterwood

Cornelia

$145

$162 total

includes taxes & fees

Sep 28 - Sep 29

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 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.

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

15.5 km from Chesterwood

Leonid

$118

$132 total

includes taxes & fees

Sep 8 - Sep 9

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.

Berkshire Lake Lodge

16.2 km from Chesterwood

"The phone number for the motel was disconnected. We could not contact the motel. The bathroom was so small even a slender person has to bend and twist to try to shut the door. There was no hairdryer. The sounds of the Thruway required earplugs. They knew we were coming, they could've turned on the AC so that it had fresh air. Although, obviously, great attempts were made to make it cozy and comfortable, it is not suitable for some people."

Laura

$146

$163 total

includes taxes & fees

Sep 6 - Sep 7

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

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

Courtyard by Marriott Lenox Berkshires

12.1 km from Chesterwood

Jairo

$178

$198 total

includes taxes & fees

Sep 7 - Sep 8

A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.

A hotel room with a sofa, a wooden table, a lamp, a telephone, and a painting on the wall.

A living room with a patterned carpet, two sofas, a dining table, and chairs.

A circular pool with a tiled edge, surrounded by a concrete deck and a grassy area with chairs and a small shed.

Travelodge by Wyndham Great Barrington Berkshires

6.2 km from Chesterwood

Abdul Samad

$85

$95 total

includes taxes & fees

Sep 7 - Sep 8

A white house with a balcony, green shutters, and a front door with a decorative glass panel. There are two large flower pots on the steps.

A room with a grand piano, a chessboard, a horse statue, and a blue armchair.

A grand staircase with red carpeted steps and a wooden handrail, leading to a landing with a vase of flowers and a framed picture.

A traditional living room with a fireplace, a grand piano, plush seating, and a bookshelf.

Hampton Terrace Inn

9.8 km from Chesterwood

Kathleen

$232

$259 total

includes taxes & fees

Sep 21 - Sep 22

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

A covered corridor with a metal railing, white walls, and a view of a street with parked cars.

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.

Sunset Inn

9.1 km from Chesterwood

Michael

$92

$103 total

includes taxes & fees

Sep 28 - Sep 29

A garden with a white gazebo, a brick pathway, and various plants and flowers.

A breakfast buffet with various dishes and beverages.

A house surrounded by trees with autumn foliage.

A spacious living room with a grand piano, a red armchair, and a chandelier.

Whistler's Inn Bed & Breakfast

10.4 km from Chesterwood

Stacey

$159

$178 total

includes taxes & fees

Sep 13 - Sep 14

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 backyard with a swimming pool, lounge chairs, and a hot tub.

A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

The Red Lion Inn

3.3 km from Chesterwood

Rita

$169

$239 total

includes taxes & fees

Sep 3 - Sep 4

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.

The Yankee Inn

14.9 km from Chesterwood

Francis

$85

$95 total

includes taxes & fees

Sep 28 - Sep 29

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 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.

Holiday Inn Club Vacations Oak 'n Spruce Resort

6.7 km from Chesterwood

Erika

$110

$142 total

includes taxes & fees

Sep 8 - Sep 9

View all properties

Compare popular hotels close to Chesterwood

Property	Property class	Guest rating
Holiday Inn Express Hotel & Suites Great Barrington by IHG	8.8 Excellent 815 reviews	View
The Black Swan Lee - Lenox, an Ascend Collection Hotel	9.0 Wonderful 1,003 reviews	View
Granville House	10.0 Exceptional 105 reviews	View
The Little Lion	8.6 Excellent 605 reviews	View
Quality Inn Lee - Lenox South	8.4 Very Good 1,006 reviews	View

Other landmarks near Chesterwood

Norman Rockwell Museum

9.4/10 (347 reviews)

Norman Rockwell Museum is 0.8 mi (1.2 km) from central Stockbridge, why not stop by during your stay. If you want to experience more of the culture Stockbridge has to offer, head to Berkshire Botanical Garden, Naumkeag Museum, and National Shrine of the Divine Mercy.

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Berkshire Botanical Garden

9.4/10 (14 reviews)

Ready for an education in local botany? Berkshire Botanical Garden should make your list of places to visit, located 1.2 mi (2 km) from central Stockbridge. Want to stretch your legs some more? Head to Naumkeag Museum and The Mount, both nearby.

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Mission House

9.6/10 (5 reviews)

If museums are on your list of things to see in Stockbridge, then you might want to head to Mission House. If you want to see more of the museums in Stockbridge, Norman Rockwell Museum and Animagic Museum of Animation aren't far.

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Naumkeag Museum

9.4/10 (10 reviews)

If museums are on your list of things to see, then you might want to head to Naumkeag Museum, located in the heart of Stockbridge.If you want to see more of the museums in Stockbridge, you can easily walk to Mission House.

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National Shrine of the Divine Mercy

9.0/10 (83 reviews)

If seeing the sights is on your list of things to do, head to National Shrine of the Divine Mercy— just one of the landmarks located 0.5 mi (0.8 km) from central Stockbridge.

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Schantz Galleries

7.2/10 (5 reviews)

Art fans might want to browse the collections at Schantz Galleries in Stockbridge. If you want to see more of the art galleries in Stockbridge, Norman Rockwell Museum and Art et Industrie aren't far.

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Art et Industrie

8.0/10 (5 reviews)

If you like art, you might want to check out the upcoming exhibitions at Art et Industrie in Great Barrington. If you want to see more of the art galleries in Great Barrington, Schantz Galleries and Norman Rockwell Museum aren't far.

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Berkshire Theatre Festival

8.8/10 (3 reviews)

Berkshire Theatre Festival is 0.9 mi (1.5 km) from central Stockbridge, why not stop by during your stay. If you enjoy the show and want to see another, Shakespeare and Company and Tanglewood Music Center are both not far.

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