Find hotels near Chesterwood, South Lee from CA $97

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Our top choices for Chesterwood hotels

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
5.2 km from Chesterwood
9.8 out of 10, Exceptional, (99 reviews)
"Well-run and elegant property. "
United States
Steven
The price is CA $359
CA $421 total
includes taxes & fees
May 26 - May 27
The Inn at Stockbridge

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
8.7 km from Chesterwood
9.0 out of 10, Wonderful, (849 reviews)
"Very clean and cozy in a great location! "
United States
Lidia
The price is CA $93
CA $104 total
includes taxes & fees
May 17 - May 18
Monument Mountain Motel

Chambery Inn

Chambery Inn
3.0 star property
8.7 km from Chesterwood
9.6 out of 10, Exceptional, (376 reviews)
"Yes the room was spotless and always the staff is ready to answer any questions that we might have. We have been enjoying the Chambery Inn for many years always had a great stay and again looking for our next visit. Vincent Farricielli and Roibert Modena. "
United States
robert
The price is CA $234
CA $261 total
includes taxes & fees
May 10 - May 11
Chambery Inn

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, (760 reviews)
"Nice clean room, clean and well maintained breakfast was tasteful each day. Desk Clerk very helpful in giving out direction, Breaksfast person, very friendly. Hotel is centrally located, shop and restaurant nearby"
United States
Berdest
The price is CA $170
CA $189 total
includes taxes & fees
May 27 - May 28
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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, (779 reviews)
"Staff was lovely, everything was easy, clean and comfortable"
United States
Helena
The price is CA $243
CA $271 total
includes taxes & fees
May 20 - May 21
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
10.3 km from Chesterwood
8.4 out of 10, Very good, (1,008 reviews)
"Very friendly staff and conviently located"
United States
Dawn
The price is CA $116
CA $129 total
includes taxes & fees
May 12 - May 13
Quality Inn Great Barrington

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
6.2 km from Chesterwood
7.6 out of 10, Good, (578 reviews)
"The room was very clean but old and tired. Same with parking area. A decent value when travelling with a pet."
United States
Heather
The price is CA $102
CA $114 total
includes taxes & fees
May 11 - May 12
Travelodge by Wyndham Great Barrington Berkshires

The Yankee Inn

The Yankee Inn
2.5 star property
14.9 km from Chesterwood
9.2 out of 10, Wonderful, (1,005 reviews)
"Great place to stay and close to shops and restaurants will be back!"
United States
Marie-Pascale
The price is CA $135
CA $151 total
includes taxes & fees
May 17 - May 18
The Yankee Inn

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
10.7 km from Chesterwood
9.2 out of 10, Wonderful, (1,002 reviews)
"enjoy your vacation"
United States
lev
The price is CA $182
CA $210 total
includes taxes & fees
May 10 - May 11
The Cornell Inn, Lenox & The Berkshires

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
7.4 km from Chesterwood
6.4 out of 10, (663 reviews)
"Good to stay. "
United States
Ibinabo
The price is CA $87
CA $97 total
includes taxes & fees
May 25 - May 26
Econo Lodge Lee - Great Barrington

Sunset Inn

Sunset Inn
2.0 star property
9.1 km from Chesterwood
7.6 out of 10, Good, (412 reviews)
"Decent clean quiet "
United States
William
The price is CA $144
CA $161 total
includes taxes & fees
Jun 2 - Jun 3
Sunset Inn

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
9.7 km from Chesterwood
5.4 out of 10, (466 reviews)
"The breakfast was not diabetic friendly. They stated pet friendly but no place for dog to go to the bathroom. Had to walk dog through garbage . Cigarette butts all over very the place. Beds were terrible. My towels had clumps of black hair on them. Lotion and shampoos left in room were used not new ones. Will not go back"
United States
Stacy
The price is CA $90
CA $101 total
includes taxes & fees
May 11 - May 12
Berkshire Travel Lodge

The Whitlock

The Whitlock
2.0 star property
9.8 km from Chesterwood
8.6 out of 10, Excellent, (295 reviews)
"Lovely historical hotel within walking distance to many great shops and restaurants. Staff members maintained good communication and were very helpful throughout our stay. Rooms were clean, quiet, and comfortable. Would definitely stay there again."
United States
Elaine
The price is CA $157
CA $175 total
includes taxes & fees
May 12 - May 13
The Whitlock

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
12.5 km from Chesterwood
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is CA $228
CA $255 total
includes taxes & fees
May 25 - May 26
Element Lenox Berkshires

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
12.1 km from Chesterwood
10.0 out of 10, Exceptional, (28 reviews)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is CA $581
CA $638 total
includes taxes & fees
May 10 - May 11
Inn at Kenmore Hall

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
9.1 km from Chesterwood
8.4 out of 10, Very good, (1,004 reviews)
"Great location "
United States
Edith
The price is CA $150
CA $168 total
includes taxes & fees
May 19 - May 20
Quality Inn Lee - Lenox South

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
14.7 km from Chesterwood
9.2 out of 10, Wonderful, (1,008 reviews)
"Good location and great breakfast."
United States
Linda
The price is CA $187
CA $209 total
includes taxes & fees
May 17 - May 18
Hampton Inn & Suites Berkshires-Lenox

Prospect Berkshires

Prospect Berkshires
3.0 star property
12.8 km from Chesterwood
9.8 out of 10, Exceptional, (25 reviews)
"Excellent local stay - would recommend to all"
United States
Gentian
The price is CA $449
CA $548 total
includes taxes & fees
May 11 - May 12
Prospect Berkshires

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
16.9 km from Chesterwood
8.6 out of 10, Excellent, (1,001 reviews)
"Room was clean. Breakfast was fresh and the area was pristine. All staff was pleasant. "
United States
Melinda
The price is CA $150
CA $168 total
includes taxes & fees
May 14 - May 15
Best Western Plus Berkshire Hills Inn & Suites

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
15.5 km from Chesterwood
9.2 out of 10, Wonderful, (92 reviews)
"Room was clean, bed was comfortable, pool was nice, breakfast and coffee were good!"
United States
Haley
The price is CA $161
CA $180 total
includes taxes & fees
May 17 - May 18
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
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
Front of property
The Inn at Stockbridge
4.0 star property
9.8
Exceptional
99 reviews
View
Room, 2 Queen Beds, Non Smoking
Monument Mountain Motel
2.5 star property
9.0
Wonderful
849 reviews
View
Front of property
Chambery Inn
3.0 star property
9.6
Exceptional
376 reviews
View
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8.8
Excellent
760 reviews
View
Exterior
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
9.4
Exceptional
779 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 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 $97 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.
Can I find Expedia discounts for hotels near Chesterwood?
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