Hotels closest to Chesterwood in South Lee

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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 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 view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

1. The Yankee Inn

14.9 km from Chesterwood

Basil

€106

includes taxes & fees

1 Nov - 2 Nov

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 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.

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

8.6 km from Chesterwood

Gustavo

€115

includes taxes & fees

8 Nov - 9 Nov

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

A hotel room with a wooden dresser, a television, a microwave, and a mirror.

3. Monument Mountain Motel

8.7 km from Chesterwood

Andrea

€60

includes taxes & fees

1 Nov - 2 Nov

A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.

A hotel room with a bed, a desk, a television, a microwave, and a sofa.

A hotel room with a sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.

4. Quality Inn Lee - Lenox South

9.1 km from Chesterwood

Christine

€92

includes taxes & fees

2 Nov - 3 Nov

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 kitchenette with a microwave, coffee maker, and coffee cups.

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

8 km from Chesterwood

Maria Dulce

€83

includes taxes & fees

12 Nov - 13 Nov

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.

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

8.6 km from Chesterwood

Kelly

€144

includes taxes & fees

2 Nov - 3 Nov

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

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.

A modern restaurant with wooden flooring, bar area, and seating arrangements.

7. Courtyard by Marriott Lenox Berkshires

12.1 km from Chesterwood

Tracy

€125

includes taxes & fees

1 Nov - 2 Nov

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

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.

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.

8. Berkshires Untold

13 km from Chesterwood

Madhavi R

€130

includes taxes & fees

12 Nov - 13 Nov

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 conference room with multiple tables and chairs, a flat-screen TV mounted on the wall, and a carpeted floor.

A room with a blue armchair, an orange armchair, a round table, a floor lamp, and a wardrobe.

9. Hampton Inn & Suites Berkshires-Lenox

14.7 km from Chesterwood

Thomas

€109

includes taxes & fees

12 Nov - 13 Nov

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 living room with a sofa, armchair, coffee table, and a patterned rug.

A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

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

6.7 km from Chesterwood

Jared

€135

includes taxes & fees

28 Oct - 29 Oct

A snow-covered outdoor area with a patio, seating, and a covered dining area.

A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.

A dining area with a glass table, red walls, and framed artwork.

A modern living room with a fireplace, comfortable seating, and a large window with curtains.

11. The Cornell Inn, Lenox & The Berkshires

10.7 km from Chesterwood

judith

€157

includes taxes & fees

28 Oct - 29 Oct

A large house with a balcony and a grassy yard.

A two-story building with a gabled roof and a chimney.

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 hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.

12. The Little Lion

5.1 km from Chesterwood

Lidia

€103

includes taxes & fees

19 Oct - 20 Oct

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 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.

13. Element by Marriott Lenox Berkshires

12.5 km from Chesterwood

Kirsty

€143

includes taxes & fees

8 Nov - 9 Nov

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 bathroom, a bed, a desk, and a nightstand.

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.

14. Quality Inn Great Barrington

10.3 km from Chesterwood

Joan

€77

includes taxes & fees

12 Nov - 13 Nov

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.

A hotel patio with outdoor seating and a fire pit.

15. Hilton Garden Inn Lenox Pittsfield

15.5 km from Chesterwood

James

€128

includes taxes & fees

1 Nov - 2 Nov

A calm lake at dusk with a wooden dock and two chairs facing the water.

A two-story house with a covered porch, a driveway, and a lawn with outdoor seating.

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.

16. Berkshire Lake Lodge

16.2 km from Chesterwood

mike

€142

includes taxes & fees

12 Nov - 13 Nov

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 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

10.1 km from Chesterwood

ERIK

€143

includes taxes & fees

13 Nov - 14 Nov

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

A spacious lobby with a fireplace, seating area, and a bar.

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

A garden with wooden Adirondack chairs and a stone pathway.

18. Berkshire Mountain Lodge

15.9 km from Chesterwood

Kathleen

€106

includes taxes & fees

9 Nov - 10 Nov

A wooden deck with a table and chairs, surrounded by a metal railing, overlooking a lush green landscape with trees.

A dining table set with placemats, candles, and a centerpiece of flowers.

A window view of a garden with rocks, bushes, and trees.

A red door with a wreath, number 5, and flower baskets on either side.

19. The Red Door B&B

9 km from Chesterwood

Anonymous traveller

€250

includes taxes & fees

26 Oct - 27 Oct

An indoor swimming pool with clear water, tiled floors, and a blue wall.

A modern cafe with a counter, seating area, and large windows.

A modern hotel with a large entrance, multiple floors, and a well-lit facade.

A snack bar with shelves of snacks and a refrigerated display.

20. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

15.5 km from Chesterwood

Ginger

€99

includes taxes & fees

10 Nov - 11 Nov

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Compare popular hotels close to Chesterwood

Property	Property class	Guest rating
The Yankee Inn	9.2 Wonderful 1,005 reviews	View
The Black Swan Lee - Lenox, an Ascend Collection Hotel	9.2 Wonderful 1,006 reviews	View
Monument Mountain Motel	8.8 Excellent 923 reviews	View
Quality Inn Lee - Lenox South	8.6 Excellent 1,003 reviews	View
Holiday Inn Express Hotel & Suites Great Barrington by IHG	8.8 Excellent 835 reviews	View

Top Chesterwood Hotel Reviews

The Red Lion Inn

8/10 Good

"We had a nice stay at the Red Lion Inn. Our room was clean and had a fireplace, but did not have a mini-refrigerator and the TV was placed to the side of the bed. The restaurant charged a lot ($65 for a filet mignon entree) and the food was not up to that price. The bread and salad were a la carte. The whole place seemed in need of a refresh."

A Grand property in Historic Stockbridge

10/10 Excellent

"My husband and his 5 sibs and their partners and I just spent 3 glorious days at the Taggart House. The house is spacious but cozy with the help of two strategically placed electric fireplaces AND new thermostats. There are many spaces to gather (or separate!), including a back patio we were able to utilize b/c the weather was so gorgeous. From the patio we had great views of the vast lawn leading down to the river. Beautiful! All of us appreciated the number of bedrooms and en suite baths given our age range—61-71. And every one of us appreciated the history of the house and the efforts to keep furnishings historically and stylistically appropriate. The house is comfortably appointed, not too precious, fun to move through once you learn the lay of the land, and in a perfect location on the edge of downtown Stockbridge. We’re already planning a return trip."

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

10/10 Excellent

"We found the Taggart House to be so convenient to the town of Stockbridge - it was a pleasure to be able to walk to the park with our kids, pick up a delicious local coffee or simply do some shopping in the interesting local shops. Even though it was close and on main street, it is set on the back part of the property overlooking the Housitonic River which was lovely, relaxing, very quiet and peaceful. We enjoyed the spaciousness of the home and the large kitchen, the rain showers in all of the bathrooms, two oversized soaking tubs and it was a real treat to have a laundry room on both floors! A big Thank You! to the owners for sharing their home for our family vacation!"

Forest Views, Enclosed Patio in Secluded Modern Home | Woodland Zen by AvantStay

10/10 Excellent

"The home was exactly as expected - So beautiful and accommodating. Communication with the host was excellent. We had a wonderful time in Woodland Zen. Can’t wait to return!"

Secluded Family Home in Serene Stockbridge Woods

10/10 Excellent

"The house is gorgeous and so cozy. Beautiful views of all the trees, secluded and quiet. It was perfect for our stay. Tom was very accommodating and communicative, it was such a delight I’ll never forget our stay here."

3-bedroom duplex in Stockbridge on the river

10/10 Excellent

"This is an absolutely beautiful spot. We did not stay long enough. Very clean and spacious. Beautiful river side yard. Tons of things to do in the cute nearby towns. Loved our stay and would recommend to others."

Classic Stockbridge Cottage

10/10 Excellent

"We thoroughly enjoyed our stay at this property. It was comfortable, clean and exactly liked the photos showed.Would definitely stay again."

Spacious Retreat Near Tanglewood & Ski Resorts

10/10 Excellent

"The house was excellent and had everything you could need plus! Very clean, many bedrooms. Kitchen well stocked with cooking utensils etc. large yards front and back which were great for yard games. The host was very responsive and helpful. Would definitely stay here again."

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!"

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.

South Lee Hotel Guide - Chesterwood hotels in South Lee, United States of America.

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Chesterwood hotels

1. The Yankee Inn

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

3. Monument Mountain Motel

4. Quality Inn Lee - Lenox South

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

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

7. Courtyard by Marriott Lenox Berkshires

8. Berkshires Untold

9. Hampton Inn & Suites Berkshires-Lenox

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

11. The Cornell Inn, Lenox & The Berkshires

12. The Little Lion

13. Element by Marriott Lenox Berkshires

14. Quality Inn Great Barrington

15. Hilton Garden Inn Lenox Pittsfield

16. Berkshire Lake Lodge

17. East Rock Inn

18. Berkshire Mountain Lodge

19. The Red Door B&B

20. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Compare popular hotels close to Chesterwood

Top Chesterwood Hotel Reviews

The Red Lion Inn

A Grand property in Historic Stockbridge

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

Forest Views, Enclosed Patio in Secluded Modern Home | Woodland Zen by AvantStay

Secluded Family Home in Serene Stockbridge Woods

3-bedroom duplex in Stockbridge on the river

Classic Stockbridge Cottage

Spacious Retreat Near Tanglewood & Ski Resorts

Tranquil 3 BR Stockbridge House w/ Private Deck!

Other attractions near Chesterwood

Norman Rockwell Museum

Berkshire Botanical Garden

Mission House

Naumkeag Museum

National Shrine of the Divine Mercy

Schantz Galleries

Art et Industrie

Berkshire Theatre Festival

Frequently asked questions