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Top Hotels Near Chesterwood in South Lee from NZ$162

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Tonight
24 Sept - 25 Sept
Tomorrow
25 Sept - 26 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct

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Our top choices for Chesterwood hotels

A building with a porch and multiple windows, surrounded by purple flowers.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
A café with a display case, a frozen food section, and a marketplace sign.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

1. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
6.7 km from Chesterwood
United States
Jared
NZ$265
includes taxes & fees
28 Sept - 29 Sept
Holiday Inn Club Vacations Oak 'n Spruce Resort
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 lodge with a large building and a dock by a lake, surrounded by forest.
A dining area with large windows, wooden furniture, and a view of a lake.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
8.6 km from Chesterwood
United States
Ann M
NZ$251
includes taxes & fees
1 Oct - 2 Oct
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A large house with a balcony and a grassy yard.
A two-story building with a gabled roof and a chimney.
A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.
A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.

3. The Little Lion

The Little Lion
5.1 km from Chesterwood
United States
Mary
NZ$204
includes taxes & fees
22 Oct - 23 Oct
The Little Lion
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.

4. Berkshire Lake Lodge

Berkshire Lake Lodge
16.2 km from Chesterwood
United States
mike
NZ$264
includes taxes & fees
28 Sept - 29 Sept
Berkshire Lake Lodge
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
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.

5. The Yankee Inn

The Yankee Inn
14.9 km from Chesterwood
United States
William
NZ$215
includes taxes & fees
25 Oct - 26 Oct
The Yankee Inn
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 hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

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

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
8.6 km from Chesterwood
United States
Bruce
NZ$333
includes taxes & fees
29 Sept - 30 Sept
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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 sign for East Rock Inn with a mountainous logo, surrounded by lush greenery and a gravel path leading to a building.
A grassy outdoor area with four blue Adirondack chairs arranged in a circle.

7. East Rock Inn

East Rock Inn
10.1 km from Chesterwood
United States
ERIK
NZ$251
includes taxes & fees
26 Oct - 27 Oct
East Rock Inn
A reception area with a fireplace, seating, and a doormat with the logo "Quality".
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.

8. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
9.1 km from Chesterwood
United States
Wendy
NZ$216
includes taxes & fees
19 Oct - 20 Oct
Quality Inn Lee - Lenox South
A clear blue swimming pool with a tiled edge and a few lounge chairs along the side.
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.
A swimming pool with a fenced area, lounge chairs, and a warning sign.

9. Sunset Inn

Sunset Inn
9.1 km from Chesterwood
United States
Lauren
NZ$162
includes taxes & fees
5 Oct - 6 Oct
Sunset Inn
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.

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

Holiday Inn Express Hotel & Suites Great Barrington by IHG
8 km from Chesterwood
United States
Maria Dulce
NZ$252
includes taxes & fees
19 Oct - 20 Oct
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.
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.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

11. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
12.5 km from Chesterwood
United States
Kirsty
NZ$333
includes taxes & fees
18 Oct - 19 Oct
Element by Marriott Lenox Berkshires
A two-story building with a sign reading "Chambéry Inn".
A hotel room with a TV displaying 'World of Dance', a fireplace, a bed, and a seating area with a remote control.
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.

12. Chambery Inn

Chambery Inn
8.7 km from Chesterwood
United States
Alexandra
NZ$517
includes taxes & fees
26 Oct - 27 Oct
Chambery Inn
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 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.

13. Shaker Mill Inn

Shaker Mill Inn
5.8 km from Chesterwood
United States
Mervin
NZ$350
includes taxes & fees
1 Oct - 2 Oct
Shaker Mill Inn
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 covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.

14. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
19.6 km from Chesterwood
United States
Rena
NZ$195
includes taxes & fees
27 Sept - 28 Sept
The Central Downtown Inn & Suites
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.
A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.
A reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.
A reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.

15. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
16.9 km from Chesterwood
United States
Joe
NZ$209
includes taxes & fees
18 Oct - 19 Oct
Best Western Plus Berkshire Hills Inn & Suites
A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.
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.
A house with a stone patio and wooden stools.
A wooden fire pit surrounded by six Adirondack chairs in a forested area.

16. Little Cat Lodge

Little Cat Lodge
16.3 km from Chesterwood
United States
Kees
NZ$354
includes taxes & fees
27 Sept - 28 Sept
Little Cat Lodge
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.
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.

17. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
12.1 km from Chesterwood
United States
Tracy
NZ$294
includes taxes & fees
29 Sept - 30 Sept
Courtyard by Marriott Lenox Berkshires
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.
A spacious living room with a large sofa, a coffee table, and a fireplace.
A hotel patio with outdoor seating and a fire pit.
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

18. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
15.5 km from Chesterwood
United States
James
NZ$288
includes taxes & fees
27 Sept - 28 Sept
Hilton Garden Inn Lenox Pittsfield
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.

19. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
14.7 km from Chesterwood
United States
Larry
NZ$247
includes taxes & fees
20 Oct - 21 Oct
Hampton Inn & Suites Berkshires-Lenox
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A snack bar with shelves of snacks and a refrigerated display.
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.

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
15.5 km from Chesterwood
United States
Susan
NZ$233
includes taxes & fees
20 Oct - 21 Oct
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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Top Chesterwood Hotel Reviews

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 12 days 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 2 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!
8 Mi to Tanglewood & Butternut Ski: Spacious Home!

8 Mi to Tanglewood & Butternut Ski: Spacious Home!

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
8 Mi to Tanglewood & Butternut Ski: Spacious Home!
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
Experienced Hosts. Quiet, Romantic, Spacious Apartment, Pet Friendly.

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

8/10 Good
"ok"
Stephanie Lieberman P. 2-night trip
Posted 2 months ago
Experienced Hosts. Quiet, Romantic, Spacious Apartment, Pet Friendly.
Stockbridge Retreat w/ Pool & Hot Tub!

Stockbridge Retreat w/ Pool & Hot Tub!

10/10 Excellent
"The house was amazing...exactly what we were hoping for. Tara (our host) was always available and super accommodating. The pool and hot tub were perfect! We rented for 2 weeks and invited our close friends to join us for the first weekend and our kids for the second weekend. Everyone loved it, enjoying the pool and hot tub. The inside was incredibly spacious and comfortable. We barbequed on the grill several nights, and truly felt as if we were living in the Berkshires and enjoying all that the region offers!"
Kenneth S. 14-night trip
Posted 2 months ago
Stockbridge Retreat w/ Pool & Hot Tub!
Secluded Family Home in Serene Stockbridge Woods

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."
Joe K. 4-night trip
Posted 2 months ago
Secluded Family Home in Serene Stockbridge Woods

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.