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Hotels near Chesterwood

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Check prices for these dates

Tonight
4 Sept - 5 Sept
Tomorrow
5 Sept - 6 Sept
This weekend
4 Sept - 6 Sept
Next weekend
11 Sept - 13 Sept

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Our top choices for Chesterwood hotels

A two-story house with a brick entrance and a white facade.
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.
A neatly arranged bedroom with a bed, bedside table, and a dresser.

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

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
0.6 km from Chesterwood
United States
Philippe
RM1,335
RM1,615 total
includes taxes & fees
28 Sept - 29 Sept
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
A living room with a sofa, armchair, coffee table, and a patterned rug.
A café with a display case, a frozen food section, and a marketplace sign.
A multi-story building with a symmetrical facade, multiple balconies, and a central tower.

2. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
6.7 km from Chesterwood
United States
Linda
RM415
RM542 total
includes taxes & fees
7 Sept - 8 Sept
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 hotel room with a wooden dresser, a television, a microwave, and a mirror.
A row of white plastic chairs on a covered outdoor area with a white building in the background.
A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.

3. Monument Mountain Motel

Monument Mountain Motel
8.7 km from Chesterwood
United States
Charlie
RM346
RM386 total
includes taxes & fees
7 Sept - 8 Sept
Monument Mountain Motel
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 swimming pool with a surrounding deck, a stone wall, and a building in the background.
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.

4. The Yankee Inn

The Yankee Inn
14.9 km from Chesterwood
United States
Karen
RM424
RM474 total
includes taxes & fees
15 Sept - 16 Sept
The Yankee Inn
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
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.
A lakeside dock with kayaks and a covered boat ramp.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
8.6 km from Chesterwood
United States
James
RM515
RM576 total
includes taxes & fees
24 Sept - 25 Sept
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A calm lake at dusk with a wooden dock and two chairs facing the water.
A room with two beds, a round mirror, a red box, and a hanging light fixture.
A lakeside dock with chairs and a table, surrounded by greenery and a clear sky.
A two-story house with a covered porch, a driveway, and a lawn with outdoor seating.

6. Berkshire Lake Lodge

Berkshire Lake Lodge
16.2 km from Chesterwood
United States
mike
RM591
RM660 total
includes taxes & fees
6 Sept - 7 Sept
Berkshire Lake Lodge
A spacious hotel lobby with multiple seating areas, large windows, and a television.
A grocery store with shelves stocked with snacks and beverages, a refrigerated display case, and a wall with hexagonal patterns.

7. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
14.7 km from Chesterwood
United States
Nancy
RM487
RM544 total
includes taxes & fees
30 Sept - 1 Oct
Hampton Inn & Suites Berkshires-Lenox
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.
A garden with wooden Adirondack chairs and a stone pathway.
A spacious lobby with a fireplace, seating area, and a bar.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

8. Berkshire Mountain Lodge

Berkshire Mountain Lodge
15.9 km from Chesterwood
United States
Robert
RM322
RM450 total
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge
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 hotel room with two beds, a desk, a TV, and a window with curtains.
A sign for East Rock Inn with a mountainous logo, surrounded by lush greenery and a gravel path leading to a building.

9. East Rock Inn

East Rock Inn
10.1 km from Chesterwood
United States
ERIK
RM658
RM734 total
includes taxes & fees
17 Sept - 18 Sept
East Rock Inn
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 wooden desk, a television, a mirror, and a bathroom visible through an open door.
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.

10. Quality Inn Great Barrington

Quality Inn Great Barrington
10.3 km from Chesterwood
United States
Sisile
RM375
RM419 total
includes taxes & fees
24 Sept - 25 Sept
Quality Inn Great Barrington
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 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.

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

Holiday Inn Express Hotel & Suites Great Barrington by IHG
8 km from Chesterwood
United States
BJORN
RM485
RM542 total
includes taxes & fees
8 Sept - 9 Sept
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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 Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.
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.

12. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
16.9 km from Chesterwood
United States
Prasanna
RM363
RM406 total
includes taxes & fees
7 Sept - 8 Sept
Best Western Plus Berkshire Hills Inn & Suites
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.
A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

13. 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
RM649
RM725 total
includes taxes & fees
9 Sept - 10 Sept
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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 dining area with a table set for two, a view of a green landscape through large windows, and outdoor seating with a view.

14. Devonfield Inn B&B

Devonfield Inn B&B
7.5 km from Chesterwood
United States
Richard
RM1,613
RM1,802 total
includes taxes & fees
8 Sept - 9 Sept
Devonfield Inn B&B
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 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.

15. The Little Lion

The Little Lion
5.1 km from Chesterwood
United States
Anne
RM455
RM508 total
includes taxes & fees
7 Sept - 8 Sept
The Little Lion
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.
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.
A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

16. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
12.5 km from Chesterwood
United States
Lawrence
RM788
RM881 total
includes taxes & fees
14 Sept - 15 Sept
Element by Marriott Lenox Berkshires
A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.
A house with a stone patio and wooden stools.
A wooden fire pit surrounded by six Adirondack chairs in a forested area.
A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.

17. Little Cat Lodge

Little Cat Lodge
16.3 km from Chesterwood
United States
Kees
RM724
RM811 total
includes taxes & fees
7 Sept - 8 Sept
Little Cat Lodge
A red building with a sign reading "Shaker Mill Inn."
A covered patio with a round glass table and metal chairs, a wooden deck, and a view of trees and hills.
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 cozy living room with a sofa, a small table, and a bookshelf. There is a window with curtains, and a painting on the wall.

18. Shaker Mill Inn

Shaker Mill Inn
5.8 km from Chesterwood
United States
Mervin
RM619
RM679 total
includes taxes & fees
9 Sept - 10 Sept
Shaker Mill Inn
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.

19. Berkshires Untold

Berkshires Untold
13 km from Chesterwood
United States
David
RM532
RM594 total
includes taxes & fees
8 Sept - 9 Sept
Berkshires Untold
A reception area with a fireplace, seating, and a doormat with the logo "Quality".
A hotel room with a sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.
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.

20. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
9.1 km from Chesterwood
United States
Christine
RM409
RM457 total
includes taxes & fees
27 Sept - 28 Sept
Quality Inn Lee - Lenox South
View all properties

Compare popular hotels close to Chesterwood

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A two-story house with a brick entrance and a white facade.
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
9.2
Wonderful
116 reviews
View
A multi-story building with a symmetrical facade, multiple balconies, and a central tower.
Holiday Inn Club Vacations Oak 'n Spruce Resort
9.2
Wonderful
982 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
906 reviews
View
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
The Yankee Inn
9.2
Wonderful
1,009 reviews
View
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
The Black Swan Lee - Lenox, an Ascend Collection Hotel
9.0
Wonderful
1,001 reviews
View

Top Chesterwood Hotel Reviews

The Little Lion

The Little Lion

10/10 Excellent
"Easy check in. The rooms were clean. Beds comfy."
Jackie 1-night trip
Posted 2 days ago
The Little Lion
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"this grand old hotel is warm and welcoming — a real hub of Bershires life and history"
James 2-night trip
Posted 2 days ago
The Red Lion Inn
The Inn at Stockbridge

The Inn at Stockbridge

10/10 Excellent
"Lovely grounds, property.. room was lovely. Delicious breakfast friendly helpful owners and staff great location"
Jodi 1-night trip
Posted 5 days ago
The Inn at Stockbridge
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

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

10/10 Excellent
"My stay at Diane’s bed and breakfast was absolutely wonderful. Diane herself is incredibly warm, welcoming, and genuinely informative — she made the entire experience feel personal and cared for. The room was quaint, cozy, and charming in that classic New England way, with comfortable beds, plenty of towels, and a generous selection of bath amenities that made settling in effortless. Breakfast was a standout: a truly amazing cook‑to‑order meal that felt both homemade and high‑end. Every dish was fresh, delicious, and clearly prepared with pride. Parking was plentiful and convenient, making arrival and departure stress‑free. Overall, this B&B is a gem — comfortable, inviting, and thoughtfully run. I’d happily return and recommend it to anyone looking for a relaxing stay."
Lisa 1-night trip
Posted 2 weeks ago
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

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.
Where is the best place 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 traveller 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 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.