Default HTG hotel image

Search Hotels Near Chesterwood, South Lee

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
27 Sept - 28 Sept
Tomorrow
28 Sept - 29 Sept
Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct

Filter by

Star rating

Guest rating

Our top choices for Chesterwood hotels

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 row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.

1. Monument Mountain Motel

Monument Mountain Motel
5.4 mi from Chesterwood
United States
Victor
£58
includes taxes & fees
25 Oct - 26 Oct
Monument Mountain Motel
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
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.
A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.

2. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
5.3 mi from Chesterwood
United States
Bruce
£143
includes taxes & fees
1 Oct - 2 Oct
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.

3. Devonfield Inn B&B

Devonfield Inn B&B
4.7 mi from Chesterwood
United States
Sebastien
£345
includes taxes & fees
25 Oct - 26 Oct
Devonfield Inn B&B
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 room with two beds, a round mirror, a red box, and a hanging light fixture.
A small, modern room with a desk, chair, and a flat-screen TV mounted on the wall.

4. Berkshire Lake Lodge

Berkshire Lake Lodge
10 mi from Chesterwood
United States
mike
£112
includes taxes & fees
6 Oct - 7 Oct
Berkshire Lake Lodge
A reception area with a fireplace, seating, and a doormat with the logo "Quality".
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.
A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.

5. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
5.7 mi from Chesterwood
United States
Christine
£92
includes taxes & fees
19 Oct - 20 Oct
Quality Inn Lee - Lenox South
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 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.

6. East Rock Inn

East Rock Inn
6.3 mi from Chesterwood
United States
ERIK
£120
includes taxes & fees
28 Oct - 29 Oct
East Rock Inn
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.
A spacious lobby with a fireplace, seating area, and a bar.
A garden with wooden Adirondack chairs and a stone pathway.
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

7. Berkshire Mountain Lodge

Berkshire Mountain Lodge
9.9 mi from Chesterwood
United States
Jay
£84
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge
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.
A cozy library with bookshelves, a fireplace, and comfortable seating.

8. Berkshires Untold

Berkshires Untold
8.1 mi from Chesterwood
United States
Drue
£118
includes taxes & fees
28 Sept - 29 Sept
Berkshires Untold
A modern hotel lobby with seating areas, tables, and a reception desk.
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.
A hotel room with two beds, a desk, a TV, and a window with curtains.

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

Holiday Inn Express Hotel & Suites Great Barrington by IHG
5 mi from Chesterwood
United States
Maria Dulce
£100
includes taxes & fees
19 Oct - 20 Oct
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.
A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.
A house with a stone patio and wooden stools.
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.

10. Little Cat Lodge

Little Cat Lodge
10.1 mi from Chesterwood
United States
Kees
£151
includes taxes & fees
28 Sept - 29 Sept
Little Cat Lodge
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 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.
A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.

11. The Little Lion

The Little Lion
3.2 mi from Chesterwood
United States
Mary
£87
includes taxes & fees
18 Oct - 19 Oct
The Little Lion
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.
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.

12. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
7.8 mi from Chesterwood
United States
Kirsty
£143
includes taxes & fees
18 Oct - 19 Oct
Element by Marriott Lenox Berkshires
A red building with a sign reading "Shaker Mill Inn."
A stone fireplace with a television above it, a kitchen area to the left, and a wooden floor.
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 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.

13. Shaker Mill Inn

Shaker Mill Inn
3.6 mi from Chesterwood
United States
Mervin
£148
includes taxes & fees
1 Oct - 2 Oct
Shaker Mill Inn
A clear blue swimming pool with a tiled edge and a few lounge chairs along the side.
A swimming pool with a fenced area, lounge chairs, and a warning sign.
A standard rectangular bathtub with a single faucet, tiled walls, and a geometric patterned floor.
A hotel room with two beds, a chair, and a bedside table with a phone.

14. Sunset Inn

Sunset Inn
5.7 mi from Chesterwood
United States
Lauren
£68
includes taxes & fees
27 Oct - 28 Oct
Sunset 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 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
6.4 mi from Chesterwood
United States
Joan
£85
includes taxes & fees
18 Oct - 19 Oct
Quality Inn Great Barrington
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 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.

16. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
10.5 mi from Chesterwood
United States
Joe
£89
includes taxes & fees
18 Oct - 19 Oct
Best Western Plus Berkshire Hills Inn & Suites
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.
A hotel room with two beds, a nightstand with a lamp, and a window with curtains.
A compact living space with a kitchenette, a dining area, and a sofa.
A modern apartment with a living room, kitchenette, and dining area.

17. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
12.2 mi from Chesterwood
United States
Rena
£83
includes taxes & fees
28 Sept - 29 Sept
The Central Downtown Inn & Suites
A hallway with wooden bookshelves, a door, and a bedroom with a bed and floral wallpaper.
A stone fountain surrounded by trees in a park setting.
A living room with a fireplace, leather sofas, and a dog.

18. The Inn at Stockbridge

The Inn at Stockbridge
3.2 mi from Chesterwood
United States
Jodi
£388
includes taxes & fees
28 Sept - 29 Sept
The Inn at Stockbridge
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.
A cozy living room with a fireplace, a blue sofa, a red armchair, and a coffee table with books and a teapot.
A loft bedroom with a sloped ceiling, a ceiling fan, a floor lamp, a bed with a patterned bedspread, a chair, and a small table.
A bed with a white lace bedspread, a tray with cookies and a bottle, and two glasses of red wine.

19. Brook Farm Inn

Brook Farm Inn
5.7 mi from Chesterwood
United States
Carrie
£193
includes taxes & fees
18 Oct - 19 Oct
Brook Farm Inn
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.

20. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
9.6 mi from Chesterwood
United States
James
£123
includes taxes & fees
25 Oct - 26 Oct
Hilton Garden Inn Lenox Pittsfield
View all properties

Top Chesterwood Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Another unforgettable experience at the Red Lion. My family has been coming up for 50 years, we’re happy to continue the tradition. Wether Fall, Spring, Summer or Winter, the 4 seasons at the Red Lion are always a favorite!"
Nelson 1-night trip
Posted 6 hours ago
The Red Lion Inn
Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods

10/10 Excellent
"Overall, lovely tidy house for family stays. Host is very accessible and friendly. Great location in quiet woods close to neighboring towns with lots of amenities. Best for casual folks who are comfortable dealing with forest critters should they come about. We didn't encounter any, but it would have been ok if we had. Only suggestion would be to have more hooks upstairs for hanging up damp towels and brighter lighting in the bedrooms. Loved the stars on the ceilings!"
Patrice J. 5-night trip
Posted 2 days ago
Secluded Family Home in Serene Stockbridge Woods
A Grand property in Historic Stockbridge

A Grand property in Historic Stockbridge

10/10 Excellent
"The Taggart House exceeded our expectations. We were a group 5 women, grade school BFFs, celebrating a milestone birthday….. loved having our own bedrooms and bathrooms, more so because they were totally renovated. The sun porch was our favorite spot for everything - cozy, comfy and gorgeous. Our hosts happened to be nearby over the weekend and even set up our evening fire pit to ensure the required s’more-fest was a success. Highly recommend!"
Margaret P. 4-night trip
Posted 2 weeks ago
A Grand property in Historic Stockbridge
Classic Stockbridge Cottage

Classic Stockbridge Cottage

10/10 Excellent
"The house was a lovely older home. Comfortable and clean inside. Kitchen and bathrooms were renovated making our stay very comfortable"
Denise M. 2-night trip
Posted 3 weeks ago
Classic Stockbridge Cottage
Hearth House | Prime Location!

Hearth House | Prime Location!

10/10 Excellent
"Comfortable home in a great neighborhood."
lauren S. 3-night trip
Posted 3 weeks ago
Hearth House | Prime Location!
Tranquil 3 BR Stockbridge House w/ Private Deck!

Tranquil 3 BR Stockbridge House w/ Private Deck!

10/10 Excellent
"Another wonderful weekend at the Redway House … our 4th stay. And … we’ll be back in October! Our favorite things are hanging out on the deck, the comfy beds and being close to everything while being in a very quiet location! An awesome getaway!"
Maureen M. 3-night trip
Posted 1 month ago
Tranquil 3 BR Stockbridge House w/ Private Deck!
Spacious Retreat near Tanglewood & Ski Resorts

Spacious Retreat near Tanglewood & Ski Resorts

10/10 Excellent
"We had an amazing stay and the area the house is in is perfect to visit all that the Berkshires has to offer! Loved our stay so much! Thank you!"
Ellen B. 4-night trip
Posted 1 month ago
Spacious Retreat near Tanglewood & Ski Resorts
Vacation in a Berkshire Farmhouse

Vacation in a Berkshire Farmhouse

10/10 Excellent
"We had a wonderful stay at the farmhouse. I have been coming to the Berkshires for many years, and found this home to be the most perfect for our needs! The place was immaculate, comfortable beds, plenty of towels and linens. It was a great place for reunion of friends and family, a great place to gather and enjoy all that the Berkshires have to offer. I loved all of the spaces to hang out, the delightful screened porch in the mornings, the dining room was such a nice place to share meals, and the living room to hang out in the evenings. The property itself is so very beautiful, and a touch of whimsy with all of Elaine's garden sculptures in front of her studio. I forgot to mention that the location was also excellent I definitely will return! Thanks for everything Elaine!!"
Cinde S. 7-night trip
Posted 1 month ago
Vacation in a Berkshire Farmhouse
Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10

Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10

10/10 Excellent
"We love the beautiful Taggart River House! This was our second stay--eight of us really enjoyed our return visit to Stockbridge, Tanglewood and the Berkshires. The location is superb--walking distance to downtown Stockbridge can never be overrated. Short drives to everything else make this property ideal. Super responsive and helpful hosts! Very clean, well-appointed rooms and facilities, more than ample parking and easy-to-follow house rules and recommendations. Pictures are accurate. You will love it!"
Susan K. 3-night trip
Posted 2 months ago
Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10

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.
See properties

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.
See properties

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.
See properties

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.
See properties

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.
See properties

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.
See properties

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.