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Hotels near Chesterwood

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Oct 5 - Oct 6
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Our top choices for Chesterwood hotels

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 cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.

1. The Yankee Inn

The Yankee Inn
14.9 km from Chesterwood
United States
William
P6,631
P7,406 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
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 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.

2. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
9.1 km from Chesterwood
United States
Christine
P6,859
P7,661 total
includes taxes & fees
Oct 26 - Oct 27
Quality Inn Lee - Lenox South
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 motel with a parking lot and several cars parked.

3. Monument Mountain Motel

Monument Mountain Motel
8.7 km from Chesterwood
United States
Victor
P3,744
P4,182 total
includes taxes & fees
Nov 1 - Nov 2
Monument Mountain Motel
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 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.

4. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
12.1 km from Chesterwood
United States
Tracy
P7,857
P8,776 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard by Marriott Lenox Berkshires
A modern hotel lobby with seating areas, tables, and a reception desk.
A kitchenette with a microwave, coffee maker, and coffee cups.
A breakfast area with a counter, coffee machine, and a display of pastries.
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

Holiday Inn Express Hotel & Suites Great Barrington by IHG
8 km from Chesterwood
United States
Maria Dulce
P5,942
P6,638 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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.
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.

6. 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
P8,986
P10,037 total
includes taxes & fees
Nov 2 - Nov 3
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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 dock with kayaks and a covered boat ramp.
A lodge with a large building and a dock by a lake, surrounded by forest.

7. 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
Bob
P7,231
P8,077 total
includes taxes & fees
Nov 1 - Nov 2
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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.
Exterior
Pool

8. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
14.7 km from Chesterwood
United States
Thomas
P7,181
P8,021 total
includes taxes & fees
Nov 4 - Nov 5
Hampton Inn & Suites Berkshires-Lenox
A building with a porch and multiple windows, surrounded by purple flowers.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.
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.

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

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
6.7 km from Chesterwood
United States
Jared
P6,981
P9,021 total
includes taxes & fees
Oct 8 - Oct 9
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
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".
A spacious lobby with a fireplace, seating area, and a bar.
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

10. Berkshire Mountain Lodge

Berkshire Mountain Lodge
15.9 km from Chesterwood
United States
marilyn
P5,362
P7,387 total
includes taxes & fees
Oct 18 - Oct 19
Berkshire Mountain 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
P9,445
P10,550 total
includes taxes & fees
Nov 1 - Nov 2
Element by Marriott Lenox Berkshires
A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.
A hotel reception area with framed artwork, a coffee machine, and a sign indicating 'Quality by Choice Hotels'.
A hotel room with a wooden desk, a television, a mirror, and a bathroom visible through an open door.
A Quality Inn sign, a brick building, and a parking lot with cars.

12. Quality Inn Great Barrington

Quality Inn Great Barrington
10.3 km from Chesterwood
United States
Joan
P4,775
P5,333 total
includes taxes & fees
Nov 1 - Nov 2
Quality Inn Great Barrington
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A bar with wooden floors and shelves filled with bottles.

13. The Red Lion Inn

The Red Lion Inn
3.3 km from Chesterwood
United States
Stephan
P9,853
P14,114 total
includes taxes & fees
Nov 3 - Nov 4
The Red Lion Inn
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 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.

14. Berkshire Lake Lodge

Berkshire Lake Lodge
16.2 km from Chesterwood
United States
mike
P7,980
P8,914 total
includes taxes & fees
Oct 6 - Oct 7
Berkshire Lake Lodge
An indoor swimming pool with clear water, tiled floors, and a blue wall.
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.
A modern cafe with a counter, seating area, and large windows.

15. 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
Sheldon
P6,443
P7,197 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.
A spacious living room with a large sofa, a coffee table, and a fireplace.
A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.

16. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
15.5 km from Chesterwood
United States
James
P7,999
P8,935 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Lenox Pittsfield
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 grassy outdoor area with four blue Adirondack chairs arranged in a circle.
A modern living room with a grey sofa, a wooden coffee table, and a dining area with a round table and chairs.

17. East Rock Inn

East Rock Inn
10.1 km from Chesterwood
United States
ERIK
P9,129
P10,197 total
includes taxes & fees
Nov 2 - Nov 3
East Rock Inn
A large house with a balcony and a grassy yard.
A two-story building with a gabled roof and a chimney.
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.

18. The Little Lion

The Little Lion
5.1 km from Chesterwood
United States
Lidia
P6,474
P7,232 total
includes taxes & fees
Oct 18 - Oct 19
The Little Lion
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 sofa, a coffee table, and a large window with a view of trees.

19. Berkshires Untold

Berkshires Untold
13 km from Chesterwood
United States
Madhavi R
P8,235
P9,199 total
includes taxes & fees
Nov 1 - Nov 2
Berkshires Untold
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.
A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.
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.

20. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
16.9 km from Chesterwood
United States
Joe
P5,847
P6,532 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Plus Berkshire Hills Inn & Suites
View all properties

Compare popular hotels close to Chesterwood

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
The Yankee Inn
9.2
Wonderful
1,007 reviews
View
A reception area with a fireplace, seating, and a doormat with the logo "Quality".
Quality Inn Lee - Lenox South
8.6
Excellent
1,004 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
918 reviews
View
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
Courtyard by Marriott Lenox Berkshires
9.2
Wonderful
662 reviews
View
A modern hotel lobby with seating areas, tables, and a reception desk.
Holiday Inn Express Hotel & Suites Great Barrington by IHG
9.0
Wonderful
831 reviews
View

Top Chesterwood Hotel Reviews

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 8 days ago
Pleasant Valley Motel West Stockbridge
The Inn at Stockbridge

The Inn at Stockbridge

8/10 Good
"Great property. Disappointed the pool wasn't clean despite having pool towels available."
Patrick 1-night trip
Posted 13 days ago
The Inn at 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.
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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.
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.
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.