Find hotels near Chesterwood, South Lee from $74

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Our top choices for Chesterwood hotels

Tanglewood Suites

Tanglewood Suites
2.5 star property
1.6 mi from Chesterwood
6.4 out of 10, (22)
"NOT A REAL LOCATION. There was nothing there. Neighbors said this was a scam. Expedia ended up helping us find a local hotel room though the location was not as good. DO NOT BOOK THIS LOCATION -- it needs to be taken off the website."
United States
Elizabeth
$219 nightly
The price is $219
Dec 17 - Dec 18
Total with taxes and fees
Tanglewood Suites

Granville House

Granville House
3.0 star property
4 mi from Chesterwood
10.0 out of 10, Exceptional, (89)
"Outstanding all around!"
United States
Jonathan
$200 nightly
The price is $223
Jan 1 - Jan 2, 2026
Total with taxes and fees
Granville House

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
3.2 mi from Chesterwood
9.8 out of 10, Exceptional, (99)
"Well-run and elegant property. "
United States
Steven
$263 nightly
The price is $294
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Inn at Stockbridge

33 Main

33 Main
4.0 star property
6.1 mi from Chesterwood
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
$385 nightly
The price is $431
Jan 14 - Jan 15, 2026
Total with taxes and fees
33 Main

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
3.6 mi from Chesterwood
9.6 out of 10, Exceptional, (437)
"Nice place, easy check in"
United States
Robert
$101 nightly
The price is $111
Dec 18 - Dec 19
Total with taxes and fees
Shaker Mill Inn

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
7.8 mi from Chesterwood
9.8 out of 10, Exceptional, (12)
"New hotel very nice"
United States
joel
$131 nightly
The price is $146
Dec 22 - Dec 23
Total with taxes and fees
Element Lenox Berkshires

Chambery Inn

Chambery Inn
3.0 star property
5.4 mi from Chesterwood
9.6 out of 10, Exceptional, (373)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
$190 nightly
The price is $212
Dec 17 - Dec 18
Total with taxes and fees
Chambery Inn

Lakehouse Inn

Lakehouse Inn
4.0 star property
5.4 mi from Chesterwood
9.6 out of 10, Exceptional, (290)
"A charming inn in the center of the Berkshires."
United States
Danny
$184 nightly
The price is $206
Dec 19 - Dec 20
Total with taxes and fees
Lakehouse Inn

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
5.3 mi from Chesterwood
9.4 out of 10, Exceptional, (758)
"Clean room, very courteous staff "
United States
Thomas
$135 nightly
The price is $151
Dec 21 - Dec 22
Total with taxes and fees
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Brook Farm Inn

Brook Farm Inn
3.5 star property
5.7 mi from Chesterwood
9.4 out of 10, Exceptional, (164)
"Everything was perfect - location and accommodation."
United States
Christopher
$159 nightly
The price is $178
Dec 19 - Dec 20
Total with taxes and fees
Brook Farm Inn

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
10.8 mi from Chesterwood
9.8 out of 10, Exceptional, (98)
"Great stay, comfortable place"
United States
barry
$129 nightly
The price is $144
Dec 22 - Dec 23
Total with taxes and fees
Inn at Silver Maple Farm

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
7.5 mi from Chesterwood
10.0 out of 10, Exceptional, (27)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
$575 nightly
The price is $631
Dec 17 - Dec 18
Total with taxes and fees
Inn at Kenmore Hall

Prospect Berkshires

Prospect Berkshires
3.0 star property
7.9 mi from Chesterwood
9.6 out of 10, Exceptional, (15)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
$216 nightly
The price is $241
Jan 4 - Jan 5, 2026
Total with taxes and fees
Prospect Berkshires

East Rock Inn

East Rock Inn
2.0 star property
6.3 mi from Chesterwood
9.4 out of 10, Exceptional, (36)
"We had a great stay at East Rock Inn! Newly remodeled, clean room, comfortable bed, easy access to town. I will definitely stay there again."
United States
Laura
$129 nightly
The price is $145
Dec 22 - Dec 23
Total with taxes and fees
East Rock Inn

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
12.4 mi from Chesterwood
9.8 out of 10, Exceptional, (39)
"Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you! "
United States
Allison
$150 nightly
The price is $168
Dec 17 - Dec 18
Total with taxes and fees
Wilder House Berkshires

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
9.0 out of 10, Wonderful, (804)
"Convenient location, very roomy, well equipped kitchen. "
United States
Carolyn
$120 nightly
The price is $134
Dec 18 - Dec 19
Total with taxes and fees
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
5.3 mi from Chesterwood
9.0 out of 10, Wonderful, (1000)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
$100 nightly
The price is $112
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
5.4 mi from Chesterwood
9.0 out of 10, Wonderful, (805)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
$67 nightly
The price is $74
Dec 18 - Dec 19
Total with taxes and fees
Monument Mountain Motel

The Red Lion Inn

The Red Lion Inn
3.5 star property
2.1 mi from Chesterwood
8.8 out of 10, Excellent, (1004)
"The room was very clean. The bed, linens & towels were exceptional. All of the staff were wonderful. "
United States
Joyce
$180 nightly
The price is $202
Jan 6 - Jan 7, 2026
Total with taxes and fees
The Red Lion Inn

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, (590)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
$135 nightly
The price is $151
Dec 18 - Dec 19
Total with taxes and fees
Courtyard 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.

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 $74 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.
Can I find Expedia discounts for hotels near Chesterwood?
To look for discounts on hotels near Chesterwood, join One Key™—our free travel rewards program. One Key members always get our best prices and earn OneKeyCash™* on eligible bookings for every dollar spent. Another way to save is by bundling your hotel and flights together on Expedia.

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