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Our top choices for Chesterwood hotels

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

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8 km from Chesterwood
8.8 out of 10, Excellent, (853 reviews)
"Always a pleasurable stay. The rooms are clean, the amenities are appreciated, and the staff very attentive. Great location and as a single traveler I always feel safe staying here."
United States
Cynthia
The price is CA $116
CA $130 total
includes taxes & fees
Dec 2 - Dec 3
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
8.6 km from Chesterwood
9.4 out of 10, Exceptional, (820 reviews)
"Nice view and location for fall color."
United States
Md
The price is CA $224
CA $251 total
includes taxes & fees
Nov 8 - Nov 9
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

3. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
10.3 km from Chesterwood
8.6 out of 10, Excellent, (1,003 reviews)
"Our room was spotless and the staff was helpful and welcoming!"
United States
Lynne
The price is CA $106
CA $118 total
includes taxes & fees
Nov 25 - Nov 26
Quality Inn Great Barrington

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
8.6 km from Chesterwood
9.2 out of 10, Wonderful, (1,005 reviews)
"Amazing place, clean, staff is awesome , amazing location , amazing views! Free breakfast, free coffee bar , free gym and the best it’s pet friendly !"
United States
Gustavo
The price is CA $152
CA $170 total
includes taxes & fees
Nov 15 - Nov 16
The Black Swan Lee - Lenox, an Ascend Collection Hotel

5. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
8.7 km from Chesterwood
8.8 out of 10, Excellent, (938 reviews)
"Super clean and cozy and safe"
United States
Andrea
The price is CA $84
CA $93 total
includes taxes & fees
Nov 4 - Nov 5
Monument Mountain Motel

6. The Yankee Inn

The Yankee Inn
2.5 star property
14.9 km from Chesterwood
9.2 out of 10, Wonderful, (1,010 reviews)
"The location was good for our trip."
United States
Basil
The price is CA $145
CA $161 total
includes taxes & fees
Nov 20 - Nov 21
The Yankee Inn

7. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
12.1 km from Chesterwood
9.2 out of 10, Wonderful, (683 reviews)
"Great stay!"
United States
Vandhana
The price is CA $159
CA $178 total
includes taxes & fees
Nov 29 - Nov 30
Courtyard by Marriott Lenox Berkshires

8. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
5.8 km from Chesterwood
9.6 out of 10, Exceptional, (483 reviews)
"Loved the location, fireplace and vibe"
United States
Mahadeva
The price is CA $203
CA $222 total
includes taxes & fees
Nov 4 - Nov 5
Shaker Mill Inn

9. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
14.7 km from Chesterwood
9.0 out of 10, Wonderful, (1,001 reviews)
"Breakfast was great"
United States
Thomas
The price is CA $153
CA $171 total
includes taxes & fees
Nov 9 - Nov 10
Hampton Inn & Suites Berkshires-Lenox

10. East Rock Inn

East Rock Inn
2.0 star property
10.1 km from Chesterwood
9.6 out of 10, Exceptional, (58 reviews)
"East Rock was a nice, clean, and comfortable place to stay. Everything was great, and I enjoyed my stay."
United States
Sharon
The price is CA $179
CA $199 total
includes taxes & fees
Dec 4 - Dec 5
East Rock Inn

11. The Red Lion Inn

The Red Lion Inn
3.5 star property
3.3 km from Chesterwood
8.8 out of 10, Excellent, (1,004 reviews)
"Enjoyed staying in the old hotel and loved the large porch with the bar to relax on."
United States
Mallory
The price is CA $220
CA $315 total
includes taxes & fees
Nov 8 - Nov 9
The Red Lion Inn

12. Berkshires Untold

Berkshires Untold
3.5 star property
13 km from Chesterwood
9.0 out of 10, Wonderful, (1,063 reviews)
"A very good place to stay"
United States
Madhavi R
The price is CA $170
CA $190 total
includes taxes & fees
Nov 29 - Nov 30
Berkshires Untold

13. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
9.1 km from Chesterwood
8.6 out of 10, Excellent, (1,002 reviews)
"Perfect for a travel stop-over."
United States
James
The price is CA $118
CA $132 total
includes taxes & fees
Dec 2 - Dec 3
Quality Inn Lee - Lenox South

14. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
15.5 km from Chesterwood
9.2 out of 10, Wonderful, (716 reviews)
"Great place to stay. Great staff and convenient location. Nice restaurant as well."
United States
James
The price is CA $166
CA $185 total
includes taxes & fees
Nov 22 - Nov 23
Hilton Garden Inn Lenox Pittsfield

15. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
16.9 km from Chesterwood
8.4 out of 10, Very good, (1,000 reviews)
"Room was spacious and clean"
United States
James
The price is CA $131
CA $146 total
includes taxes & fees
Dec 2 - Dec 3
Best Western Plus Berkshire Hills Inn & Suites

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

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
3.5 star property
6.7 km from Chesterwood
9.2 out of 10, Wonderful, (1,002 reviews)
"Nice place to stay"
United States
Michael
The price is CA $155
CA $200 total
includes taxes & fees
Nov 5 - Nov 6
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

17. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
12.5 km from Chesterwood
9.6 out of 10, Exceptional, (51 reviews)
"Clean, spacious room Accommodating staff especially Shawn and Jennifer at the front desk. Very nice pool and gym Definitely coming back"
United States
Francis
The price is CA $189
CA $211 total
includes taxes & fees
Nov 9 - Nov 10
Element by Marriott Lenox Berkshires

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
15.5 km from Chesterwood
9.2 out of 10, Wonderful, (254 reviews)
"This a much better Holiday Inn than the one at Saugerties that we went one day before."
United States
Yuguo
The price is CA $144
CA $161 total
includes taxes & fees
Dec 2 - Dec 3
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

19. The Little Lion

The Little Lion
3.0 star property
5.1 km from Chesterwood
8.6 out of 10, Excellent, (637 reviews)
"A fine place for a quick overnight trip to the Berkshires."
United States
David
The price is CA $116
CA $129 total
includes taxes & fees
Nov 9 - Nov 10
The Little Lion

20. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
15.9 km from Chesterwood
9.0 out of 10, Wonderful, (1,253 reviews)
"Comfortable stay, well stocked kitchen and room."
United States
Charline
The price is CA $116
CA $160 total
includes taxes & fees
Nov 8 - Nov 9
Berkshire Mountain Lodge
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Compare popular hotels close to Chesterwood

Property
Star rating
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8.8
Excellent
853 reviews
View
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
9.4
Exceptional
820 reviews
View
A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.
Quality Inn Great Barrington
2.5 star property
8.6
Excellent
1,003 reviews
View
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
9.2
Wonderful
1,005 reviews
View
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.
Monument Mountain Motel
2.5 star property
8.8
Excellent
938 reviews
View

Hotels recommended for families near Chesterwood

Top Chesterwood Hotel Reviews

Other attractions near Chesterwood

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 travellers seeking a memorable experience.

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

Taggart Treehouse offers a luxurious escape with breathtaking river views, just 3.2 km from Chesterwood. Rated an impressive 10 by travellers, this modern retreat accommodates up to 10 travellers, 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 Farmhouse

Located 4.7 km 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 travellers.

The Inn at Stockbridge

The Inn at Stockbridge is a 4-star gem just 6.6 km from Chesterwood, rated 9.8 by travellers. 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 travellers seeking top-rated stays!

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

The 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 CA $93 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 trip 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 10

Taggart Treehouse: Modern Luxury Meets Nature is only 3.2 km from Chesterwood and enjoys a perfect 10 travellers' 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 travellers. The stunning river views and nearby nature trails make it an ideal retreat for families looking to connect and unwind.

Vacation in a Berkshire Farmhouse

Vacation in a Berkshire Farmhouse is a fantastic option just 4.7 km from Chesterwood, an impressive travellers' 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 IHG

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG, located 7.6 km 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 holidays.
Which hotels near Chesterwood offer the best views?
For travellers seeking top-rated hotels with stunning views near Chesterwood, South Lee offers some delightful options.

Vacation in a Berkshire Farmhouse

Located just 4.7 km from Chesterwood, this charming farmhouse is rated an impressive 9.8 by travellers. 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 Chesterwood

Just a short 12-minute walk from Chesterwood, this 4.5-star inn is rated 9.2 by travellers. 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 IHG

This 3.5-star resort is situated 7.6 km 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 travellers 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 10

Taggart Treehouse is a spacious retreat just 3.2 km from Chesterwood, rated an impressive 10 by travellers. 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 Farmhouse

Just 4.7 km 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 Inn

Located 7.9 km 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 travellers. 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 Stockbridge

The Inn at Stockbridge, just 6.6 km 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 centre, ensuring a comfortable and energizing stay.

The Red Lion Inn

Located only 3.7 km 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 IHG

Situated just 7.6 km 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 travellers with pets visiting Chesterwood, finding a welcoming and comfortable hotel is a breeze with these top-rated options nearby.

Vacation in a Berkshire Farmhouse

Just 4.7 km 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 travellers with pets alike.

The Inn at Stockbridge

The Inn at Stockbridge, located 6.6 km 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 Barrington

Econo Lodge Lee - Great Barrington is just 8.0 km from Chesterwood and offers a cozy stay for travellers 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 travellers 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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