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Our top choices for Chesterwood hotels

1. The Red Lion Inn

The Red Lion Inn
3.5 star property
2.1 mi from Chesterwood
8.8 out of 10, Excellent, (1,008 reviews)
"Fantastic pool to top off the great location and fun historic hotel!"
United States
Antoinette G.
$223 nightly
The price is $249
Jul 27 - Jul 28
Total with taxes and fees
The Red Lion Inn

2. 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
3.5 star property
4.1 mi from Chesterwood
9.2 out of 10, Wonderful, (941 reviews)
"Wonderful stay for families."
United States
Kimberly
$156 nightly
The price is $174
Aug 23 - Aug 24
Total with taxes and fees
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
5.4 mi from Chesterwood
9.0 out of 10, Wonderful, (885 reviews)
"I was pleasantly surprised how clean,spacious,quiet and comfortable the room was ( two queens) Loved the place."
United States
Yekaterina
$124 nightly
The price is $138
Jul 26 - Jul 27
Total with taxes and fees
Monument Mountain Motel

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
9.6 mi from Chesterwood
9.4 out of 10, Exceptional, (140 reviews)
"Breakfast was good, good location, friendly staff."
United States
Courtney
$147 nightly
The price is $165
Jul 27 - Jul 28
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

5. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
10.5 mi from Chesterwood
8.6 out of 10, Excellent, (1,004 reviews)
"Hotel was clean and staff helpful and courteous. Hotel is a little tired (showing it's age) but I would certainly not hesitate to book a future stay."
United States
Andrew
$106 nightly
The price is $119
Jul 30 - Jul 31
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites

6. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
6.4 mi from Chesterwood
8.6 out of 10, Excellent, (1,002 reviews)
"Comfortable rooms within walking distance to Great Barrington."
United States
Lynn
$118 nightly
The price is $132
Aug 13 - Aug 14
Total with taxes and fees
Quality Inn Great Barrington

7. Berkshire Lake Lodge

Berkshire Lake Lodge
10 mi from Chesterwood
9.6 out of 10, Exceptional, (7 reviews)
"Everything was perfect!!"
United States
Grzegorz
$184 nightly
The price is $206
Aug 3 - Aug 4
Total with taxes and fees
Berkshire Lake Lodge

8. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
9.9 mi from Chesterwood
9.0 out of 10, Wonderful, (1,021 reviews)
"Clean room, friendly staff, nice property"
United States
Joseph
$142 nightly
The price is $158
Aug 23 - Aug 24
Total with taxes and fees
Berkshire Mountain Lodge

9. The Yankee Inn

The Yankee Inn
2.5 star property
9.3 mi from Chesterwood
9.2 out of 10, Wonderful, (1,013 reviews)
"A comfortable, clean place with good breakfast, good amenities, and a good hot tub."
United States
Michael
$145 nightly
The price is $162
Aug 5 - Aug 6
Total with taxes and fees
The Yankee Inn

10. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
9.1 mi from Chesterwood
9.2 out of 10, Wonderful, (1,000 reviews)
"Perfect place to stay if going to Tanglewood or Stockbridge."
United States
Barry
$180 nightly
The price is $201
Aug 23 - Aug 24
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox

11. Wilder House Berkshires

Wilder House Berkshires
2.0 star property
12.4 mi from Chesterwood
9.8 out of 10, Exceptional, (58 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
$195 nightly
The price is $218
Jul 27 - Jul 28
Total with taxes and fees
Wilder House Berkshires

12. Berkshires Untold

Berkshires Untold
3.5 star property
8.1 mi from Chesterwood
9.0 out of 10, Wonderful, (1,010 reviews)
"Nice place to stay."
United States
Debra
$152 nightly
The price is $170
Aug 23 - Aug 24
Total with taxes and fees
Berkshires Untold

13. Chambery Inn

Chambery Inn
3.0 star property
5.4 mi from Chesterwood
9.6 out of 10, Exceptional, (382 reviews)
"Location is convenient to walk through downtown Lee and to get to a show at Tanglewood."
United States
Joseph
$300 nightly
The price is $335
Jul 26 - Jul 27
Total with taxes and fees
Chambery Inn

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

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
5 mi from Chesterwood
8.8 out of 10, Excellent, (793 reviews)
"very responsive staff excellent check in and check out"
United States
Kathleen
$140 nightly
The price is $156
Aug 23 - Aug 24
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG

15. The Little Lion

The Little Lion
3.0 star property
3.2 mi from Chesterwood
8.6 out of 10, Excellent, (590 reviews)
"Such a peaceful and easy stay!"
United States
Mia
$125 nightly
The price is $139
Aug 3 - Aug 4
Total with taxes and fees
The Little Lion

16. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
5.7 mi from Chesterwood
8.4 out of 10, Very Good, (1,004 reviews)
"Great place"
United States
Michelle
$135 nightly
The price is $151
Aug 17 - Aug 18
Total with taxes and fees
Quality Inn Lee - Lenox South

17. East Rock Inn

East Rock Inn
2.0 star property
6.3 mi from Chesterwood
9.6 out of 10, Exceptional, (51 reviews)
"Virtual check in. I prefer real staff."
United States
Eleanor
$156 nightly
The price is $174
Aug 19 - Aug 20
Total with taxes and fees
East Rock Inn

18. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
3.2 mi from Chesterwood
9.8 out of 10, Exceptional, (99 reviews)
"Great spot close to town. Cozy, tasteful, comfortable room. Nice breakfasts and pleasant interaction with the staff. We love the Berkshires and we’ll definitely stay here again."
United States
Stephen
$389 nightly
The price is $435
Jul 26 - Jul 27
Total with taxes and fees
The Inn at Stockbridge

19. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
7.5 mi from Chesterwood
9.2 out of 10, Wonderful, (640 reviews)
"I usually stay here when I'm going to a concert at Tanglewood, it's comfortable, quiet, and convenient. The staff are really friendly. There's a Tesla EV charging station directly across Route 20 from the hotel."
United States
Michael
$220 nightly
The price is $246
Jul 29 - Jul 30
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires

20. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
7.8 mi from Chesterwood
9.8 out of 10, Exceptional, (28 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
$212 nightly
The price is $237
Aug 13 - Aug 14
Total with taxes and fees
Element by Marriott Lenox Berkshires
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
Property grounds
The Red Lion Inn
3.5 star property
8.8
Excellent
1,008 reviews
View
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
9.2
Wonderful
941 reviews
View
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, cribs (free), rollaway beds (surcharge), WiFi (free)
Monument Mountain Motel
2.5 star property
9.0
Wonderful
885 reviews
View
Indoor pool
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
9.4
Exceptional
140 reviews
View
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, desk, laptop workspace, blackout drapes
Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
8.6
Excellent
1,004 reviews
View

Top Chesterwood Hotel Reviews

Hotels near other Chesterwood attractions

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 10

Taggart 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 Farmhouse

Located 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 Stockbridge

The 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 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 $119 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 10

Taggart 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 Farmhouse

Vacation 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 IHG

Holiday 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 Farmhouse

Located 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 Chesterwood

Just 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 IHG

This 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 10

Taggart 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 Farmhouse

Just 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 Inn

Located 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 Stockbridge

The 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 Inn

Located 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 IHG

Situated 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 Farmhouse

Just 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 Stockbridge

The 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 Barrington

Econo 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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