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Sep 19 - Sep 20
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Sep 20 - Sep 21
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Sep 25 - Sep 27
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Our top choices for Chesterwood hotels

1. Quality Inn Great Barrington

Quality Inn Great Barrington
6.4 mi from Chesterwood
United States
Kimberly
$101 nightly
$113 total
Oct 18 - Oct 19
Total with taxes and fees
Quality Inn Great Barrington

2. Shaker Mill Inn

Shaker Mill Inn
3.6 mi from Chesterwood
United States
Mervin
$148 nightly
$162 total
Sep 21 - Sep 22
Total with taxes and fees
Shaker Mill Inn

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

Holiday Inn Express Hotel & Suites Great Barrington by IHG
5 mi from Chesterwood
United States
Maria Dulce
$119 nightly
$133 total
Oct 19 - Oct 20
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG

4. East Rock Inn

East Rock Inn
6.3 mi from Chesterwood
United States
ERIK
$143 nightly
$159 total
Oct 20 - Oct 21
Total with taxes and fees
East Rock Inn

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

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
5.3 mi from Chesterwood
United States
Bruce
$195 nightly
$217 total
Sep 24 - Sep 25
Total with taxes and fees
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

6. The Inn at Stockbridge

The Inn at Stockbridge
3.2 mi from Chesterwood
United States
Jodi
$447 nightly
$499 total
Sep 22 - Sep 23
Total with taxes and fees
The Inn at Stockbridge

7. The Yankee Inn

The Yankee Inn
9.3 mi from Chesterwood
United States
Robert
$116 nightly
$130 total
Sep 22 - Sep 23
Total with taxes and fees
The Yankee Inn

8. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
12.2 mi from Chesterwood
United States
Rena
$89 nightly
$100 total
Sep 27 - Sep 28
Total with taxes and fees
The Central Downtown Inn & Suites

9. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
7.8 mi from Chesterwood
United States
Kirsty
$169 nightly
$189 total
Oct 18 - Oct 19
Total with taxes and fees
Element by Marriott Lenox Berkshires

10. Sunset Inn

Sunset Inn
5.7 mi from Chesterwood
United States
Lauren
$94 nightly
$104 total
Oct 5 - Oct 6
Total with taxes and fees
Sunset Inn

11. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
10.5 mi from Chesterwood
United States
Joe
$106 nightly
$118 total
Oct 18 - Oct 19
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites

12. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
5.7 mi from Chesterwood
United States
Wendy
$110 nightly
$122 total
Oct 19 - Oct 20
Total with taxes and fees
Quality Inn Lee - Lenox South

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
9.6 mi from Chesterwood
United States
Susan
$114 nightly
$127 total
Oct 19 - Oct 20
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

14. Chambery Inn

Chambery Inn
5.4 mi from Chesterwood
United States
Alexandra
$294 nightly
$328 total
Sep 20 - Sep 21
Total with taxes and fees
Chambery Inn

15. Berkshires Untold

Berkshires Untold
8.1 mi from Chesterwood
United States
Drue
$143 nightly
$160 total
Sep 28 - Sep 29
Total with taxes and fees
Berkshires Untold

16. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
6.7 mi from Chesterwood
United States
Rosann
$212 nightly
$236 total
Sep 20 - Sep 21
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires

17. The Whitlock

The Whitlock
6.1 mi from Chesterwood
United States
Maeve
$139 nightly
$155 total
Sep 20 - Sep 21
Total with taxes and fees
The Whitlock

18. Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
3.8 mi from Chesterwood
United States
Kevin
$75 nightly
$84 total
Sep 20 - Sep 21
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires

19. Berkshire Inn

Berkshire Inn
11.9 mi from Chesterwood
United States
Kristina
$79 nightly
$88 total
Oct 20 - Oct 21
Total with taxes and fees
Berkshire Inn

20. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
9.3 mi from Chesterwood
United States
COLLEEN
$79 nightly
$88 total
Sep 20 - Sep 21
Total with taxes and fees
Howard Johnson by Wyndham Lenox
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Compare popular hotels close to Chesterwood

Property
Star rating
Guest rating
Breakfast included
Pool
Spa
Pet friendly
WiFi included
Lobby
Quality Inn Great Barrington
8.6
Excellent
1,001 reviews
View
Garden
Shaker Mill Inn
9.6
Exceptional
472 reviews
View
Lobby lounge
Holiday Inn Express Hotel & Suites Great Barrington by IHG
8.8
Excellent
825 reviews
View
Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu
East Rock Inn
9.6
Exceptional
54 reviews
View
Exterior
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
9.4
Exceptional
811 reviews
View

Top Chesterwood Hotel Reviews

The Red Lion Inn

The Red Lion Inn

8/10 Good
"Bedding and bed were lovely. excellent to have good lighting at sink as well as a magnified mirror! Often lacking in places we have stayed. AC had trouble cooling the room down until we turned it on full blast. too much ambient light from floodlight on property next door and from hall (I finally turned off hallway light which helped. ) Common areas and halls need some brightening up with fresh, lighter paint--seemed dingy. Was terribly frustrating trying to make the Nespresso machine work. We do not own one and there were NO INSTRUCTIONS. You should assume people do not know how to operate any appliances like that and should have a card with directions. We gave up and went to the Tavern where we had lovely coffee and breakfast. Also had a great dinner in Tavern after our arrival. The patch burrata salad was superb. As was our waitress."
Judith 1-night trip
Posted 4 days ago
The Red Lion Inn
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 7 days ago
A Grand property in Historic Stockbridge
Hearth House | Prime Location!

Hearth House | Prime Location!

10/10 Excellent
"Comfortable home in a great neighborhood."
lauren S. 3-night trip
Posted 2 weeks ago
Hearth House | Prime Location!
Classic Stockbridge Cottage

Classic Stockbridge Cottage

10/10 Excellent
"Beautifully decorated, charming and cozy. Many interesting books, games, artwork on the walls, a piano and ukulele. Fabulous bathrooms. All-around great place!"
Christina L. 2-night trip
Posted 3 weeks ago
Classic Stockbridge Cottage
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 3 weeks 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 1 month 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!

Other attractions near Chesterwood

Norman Rockwell Museum

9.4/10 (347 reviews)
You can spend time studying the exhibits at Norman Rockwell Museum during your travels in 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 exploring the galleries in 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 browsing the exhibits at Naumkeag Museum during your travels 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 exploring the galleries in Schantz Galleries during your trip to 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 in 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 get tickets for a performance at Berkshire Theatre Festival on your trip to Stockbridge. Wander the lakeside in this quaint area.
See properties

Frequently asked questions

What are the top-rated hotels near Chesterwood?
Discover the top-rated hotels near Chesterwood in South Lee that provide exceptional stays and stunning views for travelers seeking a memorable experience.Taggart Treehouse: Modern Luxury Meets Nature: Stunning river views, sleeps 10Taggart Treehouse offers a luxurious escape with breathtaking river views, just 2.0 miles from Chesterwood. Rated an impressive 10 by travelers, this modern retreat accommodates up to 10 travelers, perfect for larger groups. Guests can enjoy amenities such as a fully equipped kitchen with a dishwasher, oven, and coffee maker, along with a spacious patio and garden area for relaxation.Vacation in a Berkshire FarmhouseLocated 2.9 miles from Chesterwood, the Vacation in a Berkshire Farmhouse boasts a remarkable review rating of 9.8. This historic hotel combines charm with modern comforts, featuring a well-equipped kitchen, outdoor play areas, and nearby hiking trails. Guests can unwind on the patio or explore local attractions such as wineries and ski resorts, making it a versatile choice for all travelers.The Inn at StockbridgeThe Inn at Stockbridge is a 4-star gem just 4.1 miles from Chesterwood, rated 9.8 by travelers. Guests can indulge in complimentary cooked breakfasts and relax by the outdoor pool. With a variety of amenities, including a spa, fitness facilities, and beautifully designed rooms with premium bedding, this inn perfectly blends comfort and elegance, creating a peaceful retreat amidst the stunning Berkshire landscape.
What hotels are within walking distance to Chesterwood?
Discover cozy accommodations just a short stroll from Chesterwood, perfect for travelers seeking top-rated stays!The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and ChesterwoodThe Stockbridge Country Inn is a charming 4.5-star bed and breakfast located just a 12-minute walk from Chesterwood, with an excellent review rating of 9.2. Guests can enjoy delightful amenities such as complimentary breakfast options, an onsite art gallery, and a terrace for relaxation. Outdoor enthusiasts will appreciate the hiking and biking trails nearby, along with a golf course located just a short distance away. The inn boasts a luxurious historic design, complete with premium bedding and a fireplace, ensuring a comfortable and memorable stay.
How much is a hotel near Chesterwood?
Staying near Chesterwood is a treat, with plenty of hotels from $84 offering incredible amenities. If you're leaning toward a little luxury, prices can rise, especially in peak season. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a vacation during weekends or around public holidays.
What are the most popular family-friendly hotels near Chesterwood?
For families seeking a delightful stay near Chesterwood, these top-rated hotels offer family-friendly amenities ensuring a memorable getaway.Taggart Treehouse: Modern Luxury Meets Nature: Stunning river views, sleeps 10Taggart Treehouse: Modern Luxury Meets Nature is only 2.0 miles from Chesterwood and enjoys a perfect 10 travelers' rating. This unique hotel offers a cozy kitchen and a lovely patio, perfect for family gatherings. With a travel crib and stair gate for children, it ensures safety and comfort for younger travelers. The stunning river views and nearby nature trails make it an ideal retreat for families looking to connect and unwind.Vacation in a Berkshire FarmhouseVacation in a Berkshire Farmhouse is a fantastic option just 2.9 miles from Chesterwood, an impressive travelers' rating of 9.8. This inviting farmhouse features amenities tailored for families, including a spacious kitchen, outdoor play area for children, and a variety of toys to keep the little ones entertained. With a beautiful garden and patio, parents can relax while kids explore. Guests also enjoy nearby hiking, skiing, and antique shopping.Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHGHoliday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG, located 4.7 miles from Chesterwood, offers a family-friendly environment with a review rating of 9.0 and a 3.5-star rating. Families will appreciate the onsite playground, arcade game room, and spacious rooms equipped with kitchen facilities and a crib at no extra charge. Guests can also take advantage of the indoor and outdoor pools, hot tub, and nearby skiing activities for a fun-filled family vacation.
Which hotels near Chesterwood offer the best views?
For travelers seeking top-rated hotels with stunning views near Chesterwood, South Lee offers some delightful options.Vacation in a Berkshire FarmhouseLocated just 2.9 miles from Chesterwood, this charming farmhouse is rated an impressive 9.8 by travelers. Guests can relish breathtaking mountain views from the patio and enjoy outdoor adventures, including hiking and skiing nearby. The hotel features a fully equipped kitchen, a cozy garden, and ample parking, making it a perfect retreat for nature lovers who appreciate rustic charm.The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and ChesterwoodJust a short 12-minute walk from Chesterwood, this 4.5-star inn is rated 9.2 by travelers. Guests are treated to scenic mountain views from the terrace and can indulge in complimentary full breakfasts. With amenities like a pool, hiking options on-site, and a charming historic design, this inn provides a cozy and luxurious feel, making it an ideal spot for art and nature enthusiasts alike.Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHGThis 3.5-star resort is situated 4.7 miles from Chesterwood and boasts a review rating of 9.0. Guests can take advantage of the outdoor and indoor pools, hot tubs, and on-site tennis courts. The resort's balconies and patios offer lovely resort views, perfect for relaxation after a day of exploring. With family-friendly amenities and a variety of activities, it's a delightful choice for those looking to enjoy the Berkshires.
What are the best affordable hotels near Chesterwood?
For travelers seeking top-rated yet affordable hotels near Chesterwood, these charming properties offer the perfect blend of comfort and convenience without breaking the bank.Taggart Treehouse: Modern Luxury Meets Nature: Stunning river views, sleeps 10Taggart Treehouse is a spacious retreat just 2.0 miles from Chesterwood, rated an impressive 10 by travelers. This hotel features stunning river views and is perfect for families or groups, providing amenities like a fully equipped kitchen with a dishwasher and an oven, plus a cozy patio to enjoy the outdoors. Guests can also benefit from onsite parking and WiFi, ensuring a comfortable stay.Vacation in a Berkshire FarmhouseJust 2.9 miles from Chesterwood, Vacation in a Berkshire Farmhouse boasts a remarkable review rating of 9.8. This family-friendly farmhouse features an outdoor play area for children and is surrounded by opportunities for hiking, skiing, and winery tours. Guests can enjoy a kitchen equipped with modern appliances, a charming patio, and WiFi to stay connected during their stay.Shaker Mill InnLocated 4.9 miles from Chesterwood, Shaker Mill Inn is a cozy escape with a review rating of 9.6. This inn offers a free breakfast and self-parking, making it a convenient choice for travelers. Guests can relax in their rooms featuring a kitchenette and enjoy the beautiful garden or the private hot tub. With contactless check-in and a warm atmosphere, it's a delightful option for a restful stay.
Are there any hotels with pools close to Chesterwood?
For those seeking a refreshing stay near Chesterwood, these top-rated hotels with pools offer the perfect retreat for relaxation and fun.The Inn at StockbridgeThe Inn at Stockbridge, just 4.1 miles from Chesterwood, is a sophisticated 4-star retreat with an outstanding review rating of 9.8. This hotel features a serene outdoor pool surrounded by beautiful gardens, ideal for relaxation. Guests are treated to complimentary breakfast and access to a 24-hour fitness center, ensuring a comfortable and energizing stay.The Red Lion InnLocated only 2.3 miles from Chesterwood, The Red Lion Inn boasts a charming 3.5-star experience with a review rating of 8.8. Guests can unwind in the outdoor pool area, featuring comfortable sun loungers. This historic hotel offers a variety of amenities including a spa, 24-hour room service, and easy access to skiing and snowboarding activities, perfect for those looking to explore the nearby mountains.Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHGSituated just 4.7 miles from Chesterwood, the Holiday Inn Club Vacations Oak n' Spruce Resort is a family-friendly gem with an impressive review rating of 9.0. Guests can enjoy both indoor and outdoor pools, complete with sun loungers and a poolside bar for leisurely afternoons. Additional highlights include a hot tub, mini-golf, and on-site tennis facilities, making it an ideal choice for families and outdoor enthusiasts alike.
What are the best pet-friendly hotels near Chesterwood?
For travelers with pets visiting Chesterwood, finding a welcoming and comfortable hotel is a breeze with these top-rated options nearby.Vacation in a Berkshire FarmhouseJust 2.9 miles from Chesterwood, Vacation in a Berkshire Farmhouse is an idyllic retreat for pet owners, allowing pets in-room. With an outstanding review rating of 9.8, this farmhouse boasts a historic charm and offers a plethora of amenities that include a kitchen, outdoor play area for children, and nearby hiking opportunities. Guests can unwind on the patio or explore local attractions, making it an excellent choice for families and travelers with pets alike.The Inn at StockbridgeThe Inn at Stockbridge, located 4.1 miles from Chesterwood, is a charming 4-star hotel that welcomes dogs only. With a remarkable review rating of 9.8, this inn features an outdoor pool, spa services, and a lovely garden area, perfect for relaxing with pets. Guests can indulge in a complimentary cooked breakfast and enjoy comfortable accommodations with premium bedding and designer toiletries, ensuring a delightful stay for both you and your furry friend.Econo Lodge Lee - Great BarringtonEcono Lodge Lee - Great Barrington is just 5.0 miles from Chesterwood and offers a cozy stay for travelers with pets. This budget-friendly hotel allows pets in-room, making it a great choice for those traveling with furry companions. Guests can enjoy amenities like daily housekeeping, free continental breakfast, and access to a mini-golf course on-site. Rated by travelers at 6.4, it's a convenient option for families looking to explore the beautiful Berkshire region.
Can I book a fully refundable hotel close to Chesterwood?
Most bookings on Expedia are refundable if canceled within 24-48 hours of arrival, though this depends on the hotel's individual cancellation policy, which you should check in your booking confirmation. If free cancellation is available, you can cancel directly through your Expedia account by going to "My Trips" and selecting your reservation. To find fully refundable hotel options, simply enter "Chesterwood", set your travel dates, and use the "Fully refundable" filter under "Deals & Discounts" on the results page. Alternatively, explore deals with free cancellation options on Expedia.

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