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Check prices for these dates

Tonight
20 Oct - 21 Oct
Tomorrow
21 Oct - 22 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

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Our top choices for Chesterwood hotels

A two-story house with a brick entrance and a white facade.
A neatly arranged bedroom with a bed, bedside table, and a dresser.
A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.
A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.

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
₹31,179
₹37,717 total
includes taxes & fees
6 Nov - 7 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
8.6 km from Chesterwood
United States
Md
₹13,636
₹15,232 total
includes taxes & fees
3 Nov - 4 Nov
Fairfield Inn & Suites by Marriott Great Barrington 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 hotel room with two beds, a desk, a TV, and a window with curtains.

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

Holiday Inn Express Hotel & Suites Great Barrington by IHG
8 km from Chesterwood
United States
Cynthia
₹7,879
₹8,801 total
includes taxes & fees
17 Nov - 18 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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 motel with a parking lot and several cars parked.

4. Monument Mountain Motel

Monument Mountain Motel
8.7 km from Chesterwood
United States
Andrea
₹5,681
₹6,346 total
includes taxes & fees
1 Nov - 2 Nov
Monument Mountain Motel
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
Lucinda
₹8,795
₹9,824 total
includes taxes & fees
9 Nov - 10 Nov
Quality Inn Lee - Lenox South
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
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.

6. The Yankee Inn

The Yankee Inn
14.9 km from Chesterwood
United States
Basil
₹9,381
₹10,478 total
includes taxes & fees
26 Oct - 27 Oct
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 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
Gustavo
₹10,651
₹11,897 total
includes taxes & fees
15 Nov - 16 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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.
A covered outdoor area with stone pillars and a view of a road and green hills.

8. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
12.1 km from Chesterwood
United States
Vandhana
₹11,924
₹13,319 total
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Lenox Berkshires
A spacious hotel lobby with multiple seating areas, large windows, and a television.
A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.
A hotel room with a bed, a nightstand with a lamp and phone, a chair, and framed pictures on the wall.
A gym with exercise equipment including treadmills, a stationary bike, and free weights.

9. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
14.7 km from Chesterwood
United States
Thomas
₹10,409
₹11,626 total
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn & Suites Berkshires-Lenox
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.

10. Berkshires Untold

Berkshires Untold
13 km from Chesterwood
United States
Madhavi R
₹12,358
₹13,804 total
includes taxes & fees
1 Nov - 2 Nov
Berkshires Untold
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.

11. Shaker Mill Inn

Shaker Mill Inn
5.8 km from Chesterwood
United States
Mahadeva
₹11,771
₹12,913 total
includes taxes & fees
3 Nov - 4 Nov
Shaker Mill Inn
A building with a porch and multiple windows, surrounded by purple flowers.
A café with a display case, a frozen food section, and a marketplace sign.
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.

12. 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
Michael
₹11,106
₹14,262 total
includes taxes & fees
27 Oct - 28 Oct
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A snack bar with shelves of snacks and a refrigerated display.
A modern hotel with a large entrance, multiple floors, and a well-lit facade.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

13. 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
Ginger
₹9,021
₹10,076 total
includes taxes & fees
17 Nov - 18 Nov
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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.
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.

14. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
12.5 km from Chesterwood
United States
Francis
₹12,815
₹14,314 total
includes taxes & fees
8 Nov - 9 Nov
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 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.
A hotel reception area with framed artwork, a coffee machine, and a sign indicating 'Quality by Choice Hotels'.

15. Quality Inn Great Barrington

Quality Inn Great Barrington
10.3 km from Chesterwood
United States
Scott Patterson
₹7,181
₹8,021 total
includes taxes & fees
9 Nov - 10 Nov
Quality Inn Great Barrington
A hotel room with two beds, a small table, and a window.
A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.
A grassy outdoor area with four blue Adirondack chairs arranged in a circle.
A sign for East Rock Inn with a mountainous logo, surrounded by lush greenery and a gravel path leading to a building.

16. East Rock Inn

East Rock Inn
10.1 km from Chesterwood
United States
Sharon
₹12,826
₹14,327 total
includes taxes & fees
14 Nov - 15 Nov
East Rock Inn
A hotel patio with outdoor seating and a fire pit.
A modern kitchen with a marble countertop, stainless steel appliances, and a variety of food items displayed on the counter.
A spacious living room with a large sofa, a coffee table, and a fireplace.
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

17. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
15.5 km from Chesterwood
United States
James
₹12,139
₹13,559 total
includes taxes & fees
1 Nov - 2 Nov
Hilton Garden Inn Lenox Pittsfield
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 reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.

18. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
16.9 km from Chesterwood
United States
James
₹9,263
₹10,347 total
includes taxes & fees
15 Nov - 16 Nov
Best Western Plus Berkshire Hills Inn & Suites
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 covered porch with wicker furniture and hanging flower baskets.
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.

19. The Red Lion Inn

The Red Lion Inn
3.3 km from Chesterwood
United States
Mallory
₹14,953
₹21,418 total
includes taxes & fees
4 Nov - 5 Nov
The Red Lion Inn
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.
A garden with wooden Adirondack chairs and a stone pathway.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".
A spacious lobby with a fireplace, seating area, and a bar.

20. Berkshire Mountain Lodge

Berkshire Mountain Lodge
15.9 km from Chesterwood
United States
Joel
₹8,217
₹11,299 total
includes taxes & fees
10 Nov - 11 Nov
Berkshire Mountain Lodge
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
120 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
817 reviews
View
A modern hotel lobby with seating areas, tables, and a reception desk.
Holiday Inn Express Hotel & Suites Great Barrington by IHG
8.8
Excellent
841 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
8.8
Excellent
928 reviews
View
A reception area with a fireplace, seating, and a doormat with the logo "Quality".
Quality Inn Lee - Lenox South
8.6
Excellent
1,003 reviews
View

Top Chesterwood Hotel Reviews

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good
"The unit was clean and comfortable. Location was nice and quiet. Mini golf and hot tub were fun and appreciated. Unit was dated- cabinets were old. Kitchen was well- stocked. I would suggest having kitchen towels though. Blankets would have been nice ( as the weather was changing.)."
M S 3-night trip
Posted 12 hours ago
Holiday Inn Club Vacations Oak 'n Spruce Resort
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

10/10 Excellent
"O"
Joe 1-night trip
Posted 21 hours ago
Pleasant Valley Motel West Stockbridge
The Little Lion

The Little Lion

10/10 Excellent
"Quaint location that is loosely tied to the Historic Red Lion Inn at Stockbridge. There is no on site staff so everything is done through texting. You do get access to the Red Lion Inn which was a wonderful "amenity" without the cost of staying there. The Little Lion is a roadside motel with about 14 or 15 units. Very clean and obviously quiet. Was a great home base for a couple of days while we tooled around the Berkshires. Would definitely book again!"
Sean 2-night trip
Posted 4 days ago
The Little Lion
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 1 month ago
The Inn at Stockbridge

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.
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 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.
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, 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.

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