Hotels closest to Chesterwood in South Lee

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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 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.

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

0.6 km from Chesterwood

Philippe

€343

includes taxes & fees

28 Sept - 29 Sept

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.

2. East Rock Inn

10.1 km from Chesterwood

ERIK

€139

includes taxes & fees

22 Sept - 23 Sept

A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.

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

A café with a display case, a frozen food section, and a marketplace sign.

A multi-story building with a symmetrical facade, multiple balconies, and a central tower.

3. Holiday Inn Club Vacations Oak 'n Spruce Resort

6.7 km from Chesterwood

Claudia

€129

includes taxes & fees

7 Sept - 8 Sept

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

John

€82

includes taxes & fees

1 Sept - 2 Sept

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

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

A lakeside lodge with a dock, fishing rods, and outdoor seating.

A dining area with large windows, wooden furniture, and a view of a lake.

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

8.6 km from Chesterwood

Rinat

€122

includes taxes & fees

17 Sept - 18 Sept

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 backyard with a swimming pool, lounge chairs, and a hot tub.

A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

6. The Red Lion Inn

3.3 km from Chesterwood

€195

includes taxes & fees

23 Sept - 24 Sept

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 Quality Inn sign, a brick building, and a parking lot with cars.

A hotel room with a wooden desk, a television, a mirror, and a bathroom visible through an open door.

7. Quality Inn Great Barrington

10.3 km from Chesterwood

Sisile

€89

includes taxes & fees

20 Sept - 21 Sept

A modern hotel lobby with seating areas, tables, and a reception desk.

A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.

An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.

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

8 km from Chesterwood

BJORN

€110

includes taxes & fees

7 Sept - 8 Sept

A spacious hotel lobby with multiple seating areas, large windows, and a television.

A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.

9. Hampton Inn & Suites Berkshires-Lenox

14.7 km from Chesterwood

Nancy

€126

includes taxes & fees

13 Sept - 14 Sept

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.

10. Berkshire Lake Lodge

16.2 km from Chesterwood

€144

includes taxes & fees

31 Aug - 1 Sept

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 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.

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

8.6 km from Chesterwood

Lisa

€154

includes taxes & fees

7 Sept - 8 Sept

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 reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.

A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

12. Best Western Plus Berkshire Hills Inn & Suites

16.9 km from Chesterwood

Jermaine

€110

includes taxes & fees

20 Sept - 21 Sept

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

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

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

13. The Yankee Inn

14.9 km from Chesterwood

Karen

€146

includes taxes & fees

27 Sept - 28 Sept

A large house with a covered patio area featuring outdoor seating and a fire pit.

A sunlit room with large windows, a stone floor, and two rocking chairs.

A corner dining area with a wooden table set for four, surrounded by upholstered chairs.

A well-lit room with a large window, a clock, and a fireplace. There are several chairs and a table with a vase.

14. The Whitlock

9.8 km from Chesterwood

Constance

€162

includes taxes & fees

9 Sept - 10 Sept

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.

15. Element by Marriott Lenox Berkshires

12.5 km from Chesterwood

Lawrence

€171

includes taxes & fees

7 Sept - 8 Sept

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 hotel lobby with a snow-covered entrance and a sign reading "Lobby".

16. Berkshire Mountain Lodge

15.9 km from Chesterwood

Robert

€110

includes taxes & fees

31 Aug - 1 Sept

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

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

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

17. Quality Inn Lee - Lenox South

9.1 km from Chesterwood

€105

includes taxes & fees

17 Sept - 18 Sept

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 seating areas, a coffee station, and large windows offering a view of greenery.

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

15.5 km from Chesterwood

Ken

€113

includes taxes & fees

8 Sept - 9 Sept

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 cozy living room with a sofa, a small table, and a bookshelf. There is a window with curtains, and a painting on the wall.

19. Shaker Mill Inn

5.8 km from Chesterwood

Mervin

€166

includes taxes & fees

9 Sept - 10 Sept

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 fireplace, and comfortable seating.

A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.

20. Berkshires Untold

13 km from Chesterwood

Christine

€134

includes taxes & fees

28 Sept - 29 Sept

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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 116 reviews	View
East Rock Inn	9.6 Exceptional 53 reviews	View
Holiday Inn Club Vacations Oak 'n Spruce Resort	9.2 Wonderful 973 reviews	View
Monument Mountain Motel	8.8 Excellent 900 reviews	View
The Black Swan Lee - Lenox, an Ascend Collection Hotel	9.0 Wonderful 1,002 reviews	View

Top Chesterwood Hotel Reviews

The Red Lion Inn

10/10 Excellent

"Great visit to Stockbridge. Can't think of a better place to stay than the iconic Red Lion Inn."

The Little Lion

8/10 Good

"Clean and comfortable room for reasonable price. Central area/lobby is nice place to sit and read, relax, and/or eat breakfast (coffee provided). Also red Adirondack chairs up on hill behind rooms and small tables/chairs in front of some rooms. Can use the outdoor pool and whirl pool a few miles away at the Red Lion Inn, which is desirable feature on summer days. A few negatives. While the building and rooms are set back from the road, it’s located off a busy road that goes between Stockbridge and Great Barrington. You will hear the cars during the day. It’s also not what I would consider an “Inn” as it’s really a motel. It used to be the Briarcliff Motel before the Red Lion Inn purchased it. Any questions, requests, or comments need to contact them as the Little Lion didn’t have any full time staff and no one at front desk in the lobby when we stayed. We received text with code for room door."

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

10/10 Excellent

"My stay at Diane’s bed and breakfast was absolutely wonderful. Diane herself is incredibly warm, welcoming, and genuinely informative — she made the entire experience feel personal and cared for. The room was quaint, cozy, and charming in that classic New England way, with comfortable beds, plenty of towels, and a generous selection of bath amenities that made settling in effortless. Breakfast was a standout: a truly amazing cook‑to‑order meal that felt both homemade and high‑end. Every dish was fresh, delicious, and clearly prepared with pride. Parking was plentiful and convenient, making arrival and departure stress‑free. Overall, this B&B is a gem — comfortable, inviting, and thoughtfully run. I’d happily return and recommend it to anyone looking for a relaxing stay."

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!"

Tranquil 3 BR Stockbridge House w/ Private Deck!

10/10 Excellent

"The house is lovely with a quirky charm. It is indeed a tranquil property surrounded by woods. Our hosts have thoughtfully overstocked the premises with towels, sheets, paper goods, and all sorts of kitchen tools and condiments. We had a lovely time."

Experienced Hosts. Quiet, Romantic, Spacious Apartment, Pet Friendly.

8/10 Good

"ok"

Hearth House | Prime Location!

10/10 Excellent

"This property was better than expected! The photos don’t do it justice. It was ideal for my husband and me to share with our son and small granddaughter with them having their privacy upstairs, but ample room for us to all be together downstairs, and a wonderful bedroom suite for us. The yard and patio are lovely. We so appreciated the ample supplies provided (at some rentals we’ve had to run to a store to augment things that ran out) and the well appointed kitchen. We love the area and we’re only sorry our stay wasn’t long enough to take full advantage of everything on and off site. My only suggestion is that the information provided upon leaving would be helpful to have upfront, particularly because some things mentioned differed from information in the handbook on the property, and it would help to plan better for day of departure. Oh, and communication was terrific with Jayren being very responsive to any questions."

Secluded Family Home in Serene Stockbridge Woods

10/10 Excellent

"Tom was a great host. Easy to communicate and just a nice guy. The property was in a great location close to all the places we went to-Tanglewood, Norman Rockwell Museum, Botanical Gardens, Lenox, Stockbridge and more. Home was very spacious with a great outdoor deck. Nice grill that we used several times. Would definitely stay there again."

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

10/10 Excellent

"The property was beautiful and perfectly located for our trip to hike the AT in Massachusetts."

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

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Our top choices for Chesterwood hotels

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

2. East Rock Inn

3. Holiday Inn Club Vacations Oak 'n Spruce Resort

4. Monument Mountain Motel

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

6. The Red Lion Inn

7. Quality Inn Great Barrington

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

9. Hampton Inn & Suites Berkshires-Lenox

10. Berkshire Lake Lodge

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

12. Best Western Plus Berkshire Hills Inn & Suites

13. The Yankee Inn

14. The Whitlock

15. Element by Marriott Lenox Berkshires

16. Berkshire Mountain Lodge

17. Quality Inn Lee - Lenox South

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

19. Shaker Mill Inn

20. Berkshires Untold

Compare popular hotels close to Chesterwood

Top Chesterwood Hotel Reviews

The Red Lion Inn

The Little Lion

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

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

Tranquil 3 BR Stockbridge House w/ Private Deck!

Experienced Hosts. Quiet, Romantic, Spacious Apartment, Pet Friendly.

Hearth House | Prime Location!

Secluded Family Home in Serene Stockbridge Woods

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

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