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Hotels near Chesterwood

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Check prices for these dates

Tonight
19 Oct - 20 Oct
Tomorrow
20 Oct - 21 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
RM1,559
RM1,886 total
includes taxes & fees
1 Nov - 2 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 corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.
A modern hotel lobby with a seating area, a sofa, and a large window with curtains.
A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

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
RM586
RM655 total
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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 coffee station with two coffee machines and a variety of coffee pods and cups.
A kitchenette with a microwave, coffee maker, and coffee cups.

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
RM339
RM378 total
includes taxes & fees
17 Nov - 18 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
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.

4. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
12.1 km from Chesterwood
United States
Vandhana
RM513
RM573 total
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Lenox Berkshires
A reception area with a fireplace, seating, and a doormat with the logo "Quality".
A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.
A hotel room with a bed, a desk, a television, a microwave, and a sofa.
A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.

5. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
9.1 km from Chesterwood
United States
Lucinda
RM378
RM422 total
includes taxes & fees
9 Nov - 10 Nov
Quality Inn Lee - Lenox South
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 dining area with large windows, wooden furniture, and a view of a lake.
A lakeside lodge with a dock, fishing rods, and outdoor seating.

6. 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
RM465
RM519 total
includes taxes & fees
15 Nov - 16 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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 motel with a parking lot and several cars parked.
A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.

7. Monument Mountain Motel

Monument Mountain Motel
8.7 km from Chesterwood
United States
Andrea
RM244
RM273 total
includes taxes & fees
1 Nov - 2 Nov
Monument Mountain Motel
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
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 hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.

8. The Yankee Inn

The Yankee Inn
14.9 km from Chesterwood
United States
Basil
RM433
RM483 total
includes taxes & fees
1 Nov - 2 Nov
The Yankee Inn
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 grocery store with shelves stocked with snacks and beverages, a refrigerated display case, and a wall with hexagonal patterns.
A hotel room with a bed, a nightstand with a lamp and phone, a chair, and framed pictures on the wall.

9. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
14.7 km from Chesterwood
United States
Thomas
RM448
RM500 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.
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.
An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".

10. Berkshires Untold

Berkshires Untold
13 km from Chesterwood
United States
Madhavi R
RM531
RM594 total
includes taxes & fees
1 Nov - 2 Nov
Berkshires Untold
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 Holiday Inn Club Vacations sign for Oak N'Spruce Resort.
A living room with a sofa, armchair, coffee table, and a patterned rug.

11. 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
RM478
RM613 total
includes taxes & fees
26 Oct - 27 Oct
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A red building with a sign reading "Shaker Mill Inn."
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.
A covered patio with a round glass table and metal chairs, a wooden deck, and a view of trees and hills.

12. Shaker Mill Inn

Shaker Mill Inn
5.8 km from Chesterwood
United States
Steven
RM506
RM555 total
includes taxes & fees
1 Nov - 2 Nov
Shaker Mill Inn
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 modern cafe with a counter, seating area, and large windows.

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
RM388
RM433 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.
An outdoor seating area with Adirondack chairs and a fire feature.
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.

14. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
12.5 km from Chesterwood
United States
Francis
RM551
RM615 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 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'.
A hotel room with a bathroom, a bed, a desk, and a nightstand.

15. Quality Inn Great Barrington

Quality Inn Great Barrington
10.3 km from Chesterwood
United States
Scott Patterson
RM309
RM345 total
includes taxes & fees
9 Nov - 10 Nov
Quality Inn Great Barrington
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 grassy outdoor area with four blue Adirondack chairs arranged in a circle.
A hotel room with two beds, a desk, a TV, and a window with curtains.

16. East Rock Inn

East Rock Inn
10.1 km from Chesterwood
United States
Sharon
RM542
RM605 total
includes taxes & fees
4 Nov - 5 Nov
East Rock Inn
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A bar with wooden floors and shelves filled with bottles.
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.

17. The Red Lion Inn

The Red Lion Inn
3.3 km from Chesterwood
United States
Stephan
RM643
RM921 total
includes taxes & fees
4 Nov - 5 Nov
The Red Lion Inn
A hotel patio with outdoor seating and a fire pit.
A modern reception area with a green textured wall, a reception desk, and a coffee machine.
A spacious living room with a large sofa, a coffee table, and a fireplace.
A modern kitchen with a marble countertop, stainless steel appliances, and a variety of food items displayed on the counter.

18. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
15.5 km from Chesterwood
United States
James
RM522
RM583 total
includes taxes & fees
1 Nov - 2 Nov
Hilton Garden Inn Lenox Pittsfield
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.
A spacious lobby with a fireplace, seating area, and a bar.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

19. Berkshire Mountain Lodge

Berkshire Mountain Lodge
15.9 km from Chesterwood
United States
Joel
RM353
RM486 total
includes taxes & fees
10 Nov - 11 Nov
Berkshire Mountain Lodge
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 grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.
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.

20. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
16.9 km from Chesterwood
United States
James
RM398
RM445 total
includes taxes & fees
15 Nov - 16 Nov
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 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
840 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
676 reviews
View
A reception area with a fireplace, seating, and a doormat with the logo "Quality".
Quality Inn Lee - Lenox South
8.6
Excellent
1,002 reviews
View

Top Chesterwood Hotel Reviews

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

10/10 Excellent
"O"
Joe 1-night trip
Posted 2 hours ago
Pleasant Valley Motel West Stockbridge
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good
"G"
Ryan 1-night trip
Posted 1 day ago
Holiday Inn Club Vacations Oak 'n Spruce Resort
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 3 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.
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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.
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.