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Our top choices for Chesterwood hotels

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

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
0.4 mi from Chesterwood
9.2 out of 10, Wonderful, (110 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
$335 nightly
The price is $374
Apr 26 - Apr 27
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Red Lion Inn

The Red Lion Inn
3.5 star property
2.1 mi from Chesterwood
8.8 out of 10, Excellent, (1,002 reviews)
"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."
United States
Gary
$189 nightly
The price is $211
Apr 21 - Apr 22
Total with taxes and fees
The Red Lion Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
3.6 mi from Chesterwood
9.6 out of 10, Exceptional, (447 reviews)
"Had everything we needed. Very thoughtful touches. "
United States
Mark
$108 nightly
The price is $118
Apr 14 - Apr 15
Total with taxes and fees
Shaker Mill Inn

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, (754 reviews)
"Staff was great! Clean room, parking was always available. Breakfast was great. Had a great time!"
United States
Brigid
$107 nightly
The price is $120
Apr 20 - Apr 21
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG

The Little Lion

The Little Lion
3.0 star property
3.2 mi from Chesterwood
8.6 out of 10, Excellent, (555 reviews)
"Clean … check in , good location for us .. we’ll be back in Maynn"
United States
Kathleen
$110 nightly
The price is $123
Apr 13 - Apr 14
Total with taxes and fees
The Little Lion

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, (864 reviews)
"Great place to enjoy with the whole family!!!"
United States
Elizabeth
$130 nightly
The price is $145
Apr 29 - Apr 30
Total with taxes and fees
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
5.3 mi from Chesterwood
9.4 out of 10, Exceptional, (777 reviews)
"Staff was lovely, everything was easy, clean and comfortable"
United States
Helena
$152 nightly
The price is $170
Apr 19 - Apr 20
Total with taxes and fees
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

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, (1,002 reviews)
"Room was spotless, staff was very kind!"
United States
Ilia
$100 nightly
The price is $112
Apr 19 - Apr 20
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, (839 reviews)
"Nice place and very reasonable for great location "
United States
Raymond
$67 nightly
The price is $74
Apr 14 - Apr 15
Total with taxes and fees
Monument Mountain Motel

Granville House

Granville House
3.0 star property
4 mi from Chesterwood
10.0 out of 10, Exceptional, (98 reviews)
"Very cosy and friendly "
United States
Dominic
$174 nightly
The price is $194
Apr 13 - Apr 14
Total with taxes and fees
Granville House

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
4.7 mi from Chesterwood
10.0 out of 10, Exceptional, (137 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
$299 nightly
The price is $334
Apr 14 - Apr 15
Total with taxes and fees
Devonfield Inn B&B

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, (1,000 reviews)
"Great visit all around. Centrally located to the skiing resorts, lots to do in town, decent breakfast spread, clean room, and for a short stay, housekeeping came when unexpected! "
United States
Amy
$93 nightly
The price is $104
Apr 26 - Apr 27
Total with taxes and fees
Quality Inn Lee - Lenox South

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
3.8 mi from Chesterwood
7.6 out of 10, Good, (576 reviews)
"Excellent location!!"
United States
Abdul Samad
$75 nightly
The price is $84
Apr 13 - Apr 14
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires

Chambery Inn

Chambery Inn
3.0 star property
5.4 mi 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
$190 nightly
The price is $212
Apr 13 - Apr 14
Total with taxes and fees
Chambery Inn

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
2.9 mi from Chesterwood
6.8 out of 10, (1,000 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
$71 nightly
The price is $78
Apr 14 - Apr 15
Total with taxes and fees
Pleasant Valley Motel West Stockbridge

Berkshires Untold

Berkshires Untold
3.5 star property
8.1 mi from Chesterwood
9.0 out of 10, Wonderful, (895 reviews)
"This was a great stay! The room and hotel itself were up to date and was overall a great location to check out the Berkshires. We ate one night at the hotel too and the dinner was really good! I recommend the mushroom ravioli, would stay again."
United States
Payton
$87 nightly
The price is $97
Apr 13 - Apr 14
Total with taxes and fees
Berkshires Untold

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
6.7 mi from Chesterwood
9.2 out of 10, Wonderful, (1,000 reviews)
"Beautiful Inn, hosts are most welcome and the breakfast was perfect. Heading back for certain!"
United States
Karen
$133 nightly
The price is $149
May 3 - May 4
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires

East Rock Inn

East Rock Inn
2.0 star property
6.3 mi from Chesterwood
9.4 out of 10, Exceptional, (44 reviews)
"The room was clean and comfortable wi will back next year:) "
United States
Nadya
$122 nightly
The price is $136
Apr 27 - Apr 28
Total with taxes and fees
East Rock Inn

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
7.8 mi from Chesterwood
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
$147 nightly
The price is $164
Apr 19 - Apr 20
Total with taxes and fees
Element Lenox Berkshires

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
4.6 mi from Chesterwood
6.4 out of 10, (661 reviews)
"Good to stay. "
United States
Ibinabo
$67 nightly
The price is $75
Apr 26 - Apr 27
Total with taxes and fees
Econo Lodge Lee - Great Barrington
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
Suite, Private Bathroom (RedBird Suite) | View from room
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
9.2
Wonderful
110 reviews
View
Exterior
The Red Lion Inn
3.5 star property
8.8
Excellent
1,002 reviews
View
Garden
Shaker Mill Inn
2.5 star property
9.6
Exceptional
447 reviews
View
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8.8
Excellent
754 reviews
View
Exterior
The Little Lion
3.0 star property
8.6
Excellent
555 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 $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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