Search Hotels Near Chesterwood, South Lee

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
18 Jul - 19 Jul
Tomorrow
19 Jul - 20 Jul
This weekend
18 Jul - 20 Jul
Next weekend
25 Jul - 27 Jul

Filter by

Guest rating
Guest rating
Property class

Top Trending Hotels Near Chesterwood

Tanglewood Suites
Relax in this serene bedroom with a large bed, two chairs, and a small table, surrounded by lush views.

Tanglewood Suites

2.5 star property
8.0 out of 10, Very good, (15)
"The property is so lovely and peaceful. I love the classic mid-century modern aesthetic. For visitors to the National Shrine of Divine Mercy, the Inn’s location couldn’t be more perfect with only a 5-minute walk to the Shrine. "
The price is ₹23,119
₹23,119 total
includes taxes & fees
29 Jul - 30 Jul
Tanglewood Suites
Chambery Inn
Chambery Inn features a traditional two-story building with a pitched roof and multiple windows.

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (368)
"We returned to the Chambery Inn to celebrate my wife's birthday and the Memorial Day weekend. We were very happy with our choice. We stayed in a beautiful room (203), which included a spacious sitting area and a well-appointed bath. The breakfast were nicely prepared and presented. The Inn provided timely information prior and during our stay. We will be back in the future. "
Chambery Inn
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Relax in a welcoming space with comfortable seating and a stunning chandelier.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (715)
"Nice outdoor seating areas, big pool, clean nicely appointed toom"
The price is ₹17,790
₹19,872 total
includes taxes & fees
22 Jul - 23 Jul
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Monument Mountain Motel
Comfortable retreat with a neatly made bed, wall-mounted lamps, and a convenient nightstand.

Monument Mountain Motel

2.5 star property
9.0 out of 10, Wonderful, (730)
"Helpful, friendly staff. Clean, convenient, quiet."
Monument Mountain Motel
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Restful haven with a neatly made bed and a wooden headboard.

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
8.8 out of 10, Excellent, (638)
"Great place to stay. Excellent staff."
The price is ₹14,009
₹15,648 total
includes taxes & fees
31 Jul - 1 Aug
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Courtyard by Marriott Lenox Berkshires
Relax by the fire pit in our outdoor seating area, surrounded by wicker furniture under a covered patio with a flat roof.

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (566)
"After coming to Lenox for 15 years, I can easily say this is the best in town. "
The price is ₹18,248
₹20,383 total
includes taxes & fees
23 Jul - 24 Jul
Courtyard by Marriott Lenox Berkshires
The Cornell Inn, Lenox & The Berkshires
Traditional two-story house with a welcoming porch and balcony, set amidst snow-covered trees.

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1002)
"Breakfast each day was phenomenal, staff were all so friendly, hotel & room were beautifully decorated. We had a wonderful time & would stay here again!"
The price is ₹13,861
₹18,843 total
includes taxes & fees
22 Jul - 23 Jul
The Cornell Inn, Lenox & The Berkshires
Berkshires Untold
Relax in a stylish space with a bar area, seating area, and large windows offering views of the outdoors.

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (637)
"Great place stay after an evening at Tanglewood!"
The price is ₹37,050
₹41,385 total
includes taxes & fees
25 Jul - 26 Jul
Berkshires Untold
The Dewey
Exterior

The Dewey

3.5 star property
8.8 out of 10, Excellent, (315)
"excellent stay!! The Dewey is a cozy getaway location!"
The price is ₹17,646
₹19,711 total
includes taxes & fees
22 Jul - 23 Jul
The Dewey
Little Cat Lodge
Relax by the serene pool surrounded by lush greenery and shaded lounge chairs.

Little Cat Lodge

2.0 star property
9.4 out of 10, Exceptional, (52)
"Great place"
Little Cat Lodge
The Yankee, Trademark Collection by Wyndham
Classic hotel entrance with a covered walkway, surrounded by beautifully maintained gardens.

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1001)
"Loved the Yankee Inn!"
The price is ₹11,615
₹12,974 total
includes taxes & fees
30 Jul - 31 Jul
The Yankee, Trademark Collection by Wyndham
Hilton Garden Inn Lenox Pittsfield
Relax on the patio with wicker sofas and armchairs, surrounded by a fire feature and a beautiful garden view.

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (637)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is ₹16,911
₹18,890 total
includes taxes & fees
24 Jul - 25 Jul
Hilton Garden Inn Lenox Pittsfield
Quality Inn
Welcome to our reception area, featuring a comfortable seating space with a fireplace, flat-screen TV, and stunning views of the outside.

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1000)
"Friendly staff, easy parking"
The price is ₹11,615
₹12,974 total
includes taxes & fees
31 Jul - 1 Aug
Quality Inn
Quality Inn
Enjoy a spacious room with a modern kitchen, dining area, and comfortable seating space.

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1003)
"Good basic convenient accommodation in a heavily touristy area."
The price is ₹8,693
₹9,710 total
includes taxes & fees
31 Jul - 1 Aug
Quality Inn
Travelodge by Wyndham Great Barrington Berkshires
Relax in this inviting room with a large bed, flat-screen TV, and comfortable chair.

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
7.4 out of 10, Good, (533)
"Small Room. Terrible beds. Awful bathroom. Horrible shower. "
The price is ₹7,649
₹8,544 total
includes taxes & fees
31 Jul - 1 Aug
Travelodge by Wyndham Great Barrington Berkshires
Sunset Inn
Enjoy a refreshing swim in our pool surrounded by a tiled edge.

Sunset Inn

2.0 star property
7.6 out of 10, Good, (391)
"No frills but it was a great stay!"
The price is ₹9,090
₹10,154 total
includes taxes & fees
18 Aug - 19 Aug
Sunset Inn
Best Western Plus Berkshire Hills Inn & Suites
Welcome to our reception area, featuring a comfortable seating area, a reception desk, and a beautiful abstract art piece.

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1004)
"Very nice stay"
The price is ₹10,885
₹12,158 total
includes taxes & fees
28 Jul - 29 Jul
Best Western Plus Berkshire Hills Inn & Suites
Pleasant Valley Motel West Stockbridge
Orchids bloom in a serene, well-maintained setting.

Pleasant Valley Motel West Stockbridge

2.0 star property
6.8 out of 10, (983)
"Clean and convenient. Great value."
The price is ₹5,975
₹6,554 total
includes taxes & fees
22 Jul - 23 Jul
Pleasant Valley Motel West Stockbridge
The Central Downtown Inn & Suites
Compact kitchen with modern design, featuring white and wood cabinetry, refrigerator, coffee maker, and toaster.

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (298)
"Friendly staff, clean and perfect for a trip with the pups! "
The price is ₹11,087
₹12,384 total
includes taxes & fees
22 Jul - 23 Jul
The Central Downtown Inn & Suites
Holiday Inn Express & Suites Pittsfield - Berkshires
Enjoy a diverse selection of hot and cold dishes at our buffet.

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
10.0 out of 10, Exceptional, (3)
"Our stay was terrific, and we appreciated the staff's attentiveness, especially Anthony's."
The price is ₹15,998
₹17,870 total
includes taxes & fees
22 Jul - 23 Jul
Holiday Inn Express & Suites Pittsfield - 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

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

10/10 Excellent
"Had a great time"
Jennifer 2-night trip
Posted 3 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Frequently asked questions

What's the area like around Chesterwood?

Chesterwood is located in a scenic area of South Lee known for its beautiful lakeside setting and hiking. If you're looking for a convenient place to stay, take a look at the 8 hotels and other accommodation options you'll find within a mile.

Where is the best place to stay close to Chesterwood?

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood is one of the top choices for your stay based on our traveller data, and this B&B offers free breakfast and free parking. It's located just a short 0.4 mi (0.6 km) from Chesterwood. Other good choices within a few miles include The Red Lion Inn and Tanglewood Suites.

How many hotels will I find near Chesterwood?

Expedia has 8 hotels and other accommodation options within a mile from Chesterwood.

If I need to cancel the hotel reservation for my stay near Chesterwood, will I receive a refund?

Yes! You'll find that most room reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you booked a non-refundable reservation, it might still be possible to cancel it and be given a refund within 24 hours of booking. Enter your dates, click on "Search", then you can filter by "fully refundable" to get the best options available near Chesterwood.

What can I see and do near Chesterwood?

You'll want to browse the exhibits at Norman Rockwell Museum and Mission House. Naumkeag Museum, The Mount and Berkshire Theatre Festival are monuments to see when you're exploring the area around Chesterwood. Be sure to get some family photos at Berkshire Botanical Garden, Hoffman's Pottery and Charles H. Baldwin & Sons while you're out sightseeing near Chesterwood.