South Lee Chesterwood Hotels: 2026 Limited-Time Hotel Deals @Expedia

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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 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.

A motel with a parking lot and several cars parked.

1. Monument Mountain Motel

8.7 km from Chesterwood

Andrea

HK$470

HK$525 total

includes taxes & fees

8 Nov - 9 Nov

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

A coffee station with two coffee machines and a variety of coffee pods and cups.

A breakfast area with a counter, coffee machine, and a display of pastries.

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

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

8 km from Chesterwood

Maria Dulce

HK$651

HK$728 total

includes taxes & fees

10 Nov - 11 Nov

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.

3. Berkshire Mountain Lodge

15.9 km from Chesterwood

marilyn

HK$673

HK$927 total

includes taxes & fees

9 Nov - 10 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 view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

4. The Yankee Inn

14.9 km from Chesterwood

Basil

HK$832

HK$929 total

includes taxes & fees

1 Nov - 2 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 sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.

5. Quality Inn Lee - Lenox South

9.1 km from Chesterwood

Christine

HK$727

HK$812 total

includes taxes & fees

8 Nov - 9 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.

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

8.6 km from Chesterwood

Bruce

HK$1,127

HK$1,259 total

includes taxes & fees

2 Nov - 3 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 small, modern room with a desk, chair, and a flat-screen TV mounted on the wall.

A lakeside dock with chairs and a table, surrounded by greenery and a clear sky.

7. Berkshire Lake Lodge

16.2 km from Chesterwood

mike

HK$1,112

HK$1,243 total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a dining area featuring a table and chairs, a kitchenette with a coffee machine, and a television on the wall.

A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

A hotel room with a dining area, a sofa, a coffee station, and a TV mounted on the wall.

8. Howard Johnson by Wyndham Lenox

14.9 km from Chesterwood

Mark

HK$620

HK$693 total

includes taxes & fees

18 Oct - 19 Oct

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.

9. East Rock Inn

10.1 km from Chesterwood

ERIK

HK$1,036

HK$1,157 total

includes taxes & fees

10 Nov - 11 Nov

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.

10. Best Western Plus Berkshire Hills Inn & Suites

16.9 km from Chesterwood

James

HK$734

HK$819 total

includes taxes & fees

1 Nov - 2 Nov

A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

A covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.

A modern apartment with a living room, kitchenette, and dining area.

A compact living space with a kitchenette, a dining area, and a sofa.

11. The Central Downtown Inn & Suites

19.6 km from Chesterwood

Rena

HK$777

HK$868 total

includes taxes & fees

14 Oct - 15 Oct

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

A cozy room with a fireplace, a sofa, a table with a bottle and glasses, and a patterned pillow.

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

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

12. Chambery Inn

8.7 km from Chesterwood

Alexandra

HK$2,119

HK$2,367 total

includes taxes & fees

9 Nov - 10 Nov

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 covered corridor with a metal railing, white walls, and a view of a street with parked cars.

13. Sunset Inn

9.1 km from Chesterwood

Lauren

HK$699

HK$781 total

includes taxes & fees

26 Oct - 27 Oct

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 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.

14. Berkshires Untold

13 km from Chesterwood

Madhavi R

HK$1,022

HK$1,141 total

includes taxes & fees

5 Nov - 6 Nov

A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

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.

A hotel room with a bathroom, a bed, a desk, and a nightstand.

15. Quality Inn Great Barrington

10.3 km from Chesterwood

Joan

HK$594

HK$663 total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.

A hotel room with a sofa, a wooden table, a lamp, a telephone, and a painting on the wall.

A living room with a patterned carpet, two sofas, a dining table, and chairs.

A circular pool with a tiled edge, surrounded by a concrete deck and a grassy area with chairs and a small shed.

16. Travelodge by Wyndham Great Barrington Berkshires

6.2 km from Chesterwood

Mark

HK$620

HK$693 total

includes taxes & fees

12 Oct - 13 Oct

A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.

A hotel patio with outdoor seating and a fire pit.

A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.

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

HK$1,004

HK$1,121 total

includes taxes & fees

8 Nov - 9 Nov

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 reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

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

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

15.5 km from Chesterwood

Ginger

HK$777

HK$868 total

includes taxes & fees

9 Nov - 10 Nov

A red building with a sign reading "Shaker Mill Inn."

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

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

19. Shaker Mill Inn

5.8 km from Chesterwood

Steven

HK$1,020

HK$1,119 total

includes taxes & fees

10 Nov - 11 Nov

A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.

A residential street with a paved road, a lamp post, and flowering trees.

A motel with a parking lot, a swimming pool, and outdoor seating.

20. Berkshire Inn

19.1 km from Chesterwood

Kristina

HK$675

HK$754 total

includes taxes & fees

13 Oct - 14 Oct

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Compare popular hotels close to Chesterwood

Property	Property class	Guest rating
Monument Mountain Motel	9.0 Wonderful 920 reviews	View
Holiday Inn Express Hotel & Suites Great Barrington by IHG	8.8 Excellent 835 reviews	View
Berkshire Mountain Lodge	9.0 Wonderful 1,191 reviews	View
The Yankee Inn	9.2 Wonderful 1,001 reviews	View
Quality Inn Lee - Lenox South	8.6 Excellent 1,000 reviews	View

Top Chesterwood Hotel Reviews

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!"

The Red Lion Inn

8/10 Good

"Would go there again but would request to be in the main Inn, they have properties all over the town center that are considered the Inn. That was disappointing. A very unique property and super cute!"

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.

South Lee Chesterwood Hotels

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. Monument Mountain Motel

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

3. Berkshire Mountain Lodge

4. The Yankee Inn

5. Quality Inn Lee - Lenox South

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

7. Berkshire Lake Lodge

8. Howard Johnson by Wyndham Lenox

9. East Rock Inn

10. Best Western Plus Berkshire Hills Inn & Suites

11. The Central Downtown Inn & Suites

12. Chambery Inn

13. Sunset Inn

14. Berkshires Untold

15. Quality Inn Great Barrington

16. Travelodge by Wyndham Great Barrington Berkshires

17. Hilton Garden Inn Lenox Pittsfield

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

19. Shaker Mill Inn

20. Berkshire Inn

Compare popular hotels close to Chesterwood

Top Chesterwood Hotel Reviews

A Grand property in Historic Stockbridge

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

The Red Lion Inn

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