10 Best Hotels & Accommodation Closest to Chesterwood in South Lee from AU$96

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Our top choices for Chesterwood hotels

A two-story house with a brick entrance and a white facade.

A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.

A dining area with tables set for a meal, surrounded by large windows offering a view of trees and a garden.

A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.

1. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

0.6 km from Chesterwood

Philippe

AU$556

includes taxes & fees

6 Nov - 7 Nov

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.

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.

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

8.6 km from Chesterwood

AU$230

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 hotel room with two beds, a desk, a TV, and a window with curtains.

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

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

8 km from Chesterwood

Cynthia

AU$133

includes taxes & fees

17 Nov - 18 Nov

A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

A motel with a parking lot and several cars parked.

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.

4. Monument Mountain Motel

8.7 km from Chesterwood

Andrea

AU$96

includes taxes & fees

8 Nov - 9 Nov

A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.

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.

5. Quality Inn Lee - Lenox South

9.1 km from Chesterwood

Lucinda

AU$148

includes taxes & fees

9 Nov - 10 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 dining area with large windows, wooden furniture, and a view of a lake.

A lodge with a large building and a dock by a lake, surrounded by forest.

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

8.6 km from Chesterwood

Gustavo

AU$180

includes taxes & fees

15 Nov - 16 Nov

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.

7. Courtyard by Marriott Lenox Berkshires

12.1 km from Chesterwood

Vandhana

AU$201

includes taxes & fees

8 Nov - 9 Nov

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 swimming pool with a surrounding deck, a stone wall, and a building in the background.

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.

8. The Yankee Inn

14.9 km from Chesterwood

Basil

AU$161

includes taxes & fees

1 Nov - 2 Nov

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 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.

9. Berkshires Untold

13 km from Chesterwood

Madhavi R

AU$208

includes taxes & fees

15 Nov - 16 Nov

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.

A gym with exercise equipment including treadmills, a stationary bike, and free weights.

A hotel room with a bed, a nightstand with a lamp and phone, a chair, and framed pictures on the wall.

10. Hampton Inn & Suites Berkshires-Lenox

14.7 km from Chesterwood

Thomas

AU$175

includes taxes & fees

3 Nov - 4 Nov

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 covered patio with a round glass table and metal chairs, a wooden deck, and a view of trees and hills.

A stone fireplace with a television above it, a kitchen area to the left, and a wooden floor.

11. Shaker Mill Inn

5.8 km from Chesterwood

Mahadeva

AU$195

includes taxes & fees

3 Nov - 4 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 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

6.7 km from Chesterwood

Michael

AU$215

includes taxes & fees

26 Oct - 27 Oct

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

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.

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

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

15.5 km from Chesterwood

Ginger

AU$152

includes taxes & fees

19 Nov - 20 Nov

A modern hotel room with a bed, a sofa, a desk, and a TV.

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.

A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.

14. Element by Marriott Lenox Berkshires

12.5 km from Chesterwood

Francis

AU$216

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 wooden desk, a television, a mirror, and a bathroom visible through an open door.

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'.

15. Quality Inn Great Barrington

10.3 km from Chesterwood

Scott Patterson

AU$121

includes taxes & fees

11 Nov - 12 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.

16. East Rock Inn

10.1 km from Chesterwood

Sharon

AU$217

includes taxes & fees

14 Nov - 15 Nov

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 large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

17. Hilton Garden Inn Lenox Pittsfield

15.5 km from Chesterwood

James

AU$205

includes taxes & fees

8 Nov - 9 Nov

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

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

A garden with wooden Adirondack chairs and a stone pathway.

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

18. Berkshire Mountain Lodge

15.9 km from Chesterwood

ulla

AU$170

includes taxes & fees

10 Nov - 11 Nov

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

A covered porch with wicker furniture and hanging flower baskets.

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.

19. The Red Lion Inn

3.3 km from Chesterwood

Mallory

AU$323

includes taxes & fees

8 Nov - 9 Nov

A two-story building with a sign reading "Chambéry Inn".

A hotel room with a large bed, a TV mounted above a fireplace, a desk, and a seating area with chairs.

A hotel room with a TV displaying 'World of Dance', a fireplace, a bed, and a seating area with a remote control.

A large, historic building labeled "Chambéry Inn" with a vintage turquoise truck parked in front.

20. Chambery Inn

8.7 km from Chesterwood

Alexandra

AU$372

includes taxes & fees

29 Oct - 30 Oct

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Compare popular hotels close to Chesterwood

Property	Property class	Guest rating
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood	9.2 Wonderful 120 reviews	View
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires	9.4 Exceptional 817 reviews	View
Holiday Inn Express Hotel & Suites Great Barrington by IHG	8.8 Excellent 841 reviews	View
Monument Mountain Motel	8.8 Excellent 928 reviews	View
Quality Inn Lee - Lenox South	8.6 Excellent 1,003 reviews	View

Top Chesterwood Hotel Reviews

Secluded Family Home in Serene Stockbridge Woods

10/10 Excellent

"The home is very spacious and was perfect for our family of 7 with two kids. We attend the local festivities at the botanical garden and about 5 minutes from Main Street and 12 to Lenox MA. Would come back to stay!"

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!"

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."

Hearth House | Prime Location!

10/10 Excellent

"Comfortable home in a great neighborhood."

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.

Top Hotels Near Chesterwood in South Lee from AU$96

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for Chesterwood hotels

1. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

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

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

4. Monument Mountain Motel

5. Quality Inn Lee - Lenox South

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

7. Courtyard by Marriott Lenox Berkshires

8. The Yankee Inn

9. Berkshires Untold

10. Hampton Inn & Suites Berkshires-Lenox

11. Shaker Mill Inn

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

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

14. Element by Marriott Lenox Berkshires

15. Quality Inn Great Barrington

16. East Rock Inn

17. Hilton Garden Inn Lenox Pittsfield

18. Berkshire Mountain Lodge

19. The Red Lion Inn

20. Chambery Inn

Compare popular hotels close to Chesterwood

Top Chesterwood Hotel Reviews

Secluded Family Home in Serene Stockbridge Woods

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

3-bedroom duplex in Stockbridge on the river

Classic Stockbridge Cottage

Spacious Retreat Near Tanglewood & Ski Resorts

Hearth House | Prime Location!

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