Hotels near Chesterwood

    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
Jul 27 - Jul 28
Tomorrow
Jul 28 - Jul 29
Next weekend
Aug 1 - Aug 3
In two weeks
Aug 8 - Aug 10

Filter by

Guest rating
Guest rating
Star rating

Top Trending Hotels Near Chesterwood

The Red Lion Inn
Relax by the serene pool surrounded by lounge chairs and umbrellas.

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1009)
"I had excellent stay at the Red Lion Inn "
The price is P10,798
P14,613 total
includes taxes & fees
Aug 13 - Aug 14
The Red Lion Inn
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Enjoy meals in this inviting dining room with a large table, comfortable chairs, and ample natural light.

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

4.5 star property
9.2 out of 10, Wonderful, (105)
"Great breakfast, friendly helpful staff, pretty yard, good location "
The price is P24,900
P30,122 total
includes taxes & fees
Jul 30 - Jul 31
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and 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 P15,368
P15,368 total
includes taxes & fees
Jul 28 - Jul 29
Tanglewood Suites
Granville House
Enjoy a leisurely meal in this beautifully set dining area with a long table, adorned with pastries and bread.

Granville House

3.0 star property
10.0 out of 10, Exceptional, (82)
"Phenomenal hospitality, eclectic decor, luxurious sleep - we have been raving about our stay and will definitely be back!"
The price is P14,225
P15,890 total
includes taxes & fees
Jul 28 - Jul 29
Granville House
Shaker Mill Inn
Step into the charming Shaker Mill Inn, surrounded by lush greenery and a beautiful garden.

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (416)
"Very cute and clean room. After driving all day we were so happy to see all muffins, scones, yogurt, cereal, oatmeal, strawberries, milk, OJ, hot chocolate and coffee already in the room for breakfast the next day. We had a great stay, thank you!"
The price is P10,798
P11,845 total
includes taxes & fees
Jul 28 - Jul 29
Shaker Mill Inn
The Little Lion
Guests can enjoy a serene outdoor setting with a tranquil lawn and a charming two-story building in the background.

The Little Lion

3.0 star property
8.6 out of 10, Excellent, (517)
"We greatly appreciate a pet friendly hotel with no extra pet fees! Hotel was dated but had charm and we loved using the pool at the beautiful Red Lion. "
The price is P9,141
P10,210 total
includes taxes & fees
Jul 28 - Jul 29
The Little Lion
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, (732)
"Helpful, friendly staff. Clean, convenient, quiet."
Monument Mountain Motel
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, (719)
"No complaints at all. Great place to stay!"
The price is P8,627
P9,636 total
includes taxes & fees
Aug 14 - Aug 15
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Play a round of golf amidst lush surroundings and scenic obstacles.

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (681)
"Terrific place. Spacious, clean, comfortable."
The price is P9,084
P10,944 total
includes taxes & fees
Jul 30 - Jul 31
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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, (640)
"Great place to stay. Excellent staff."
The price is P9,941
P11,104 total
includes taxes & fees
Aug 3 - Aug 4
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Brook Farm Inn
Relax in this inviting room with a comfortable bed, fireplace, and thoughtful amenities.

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (155)
"Maureen and her lovely staff operate a first class B&B. Thoughtful amenities and conveniences, clean and comfortable. Amazing home cooked breakfast, both plentiful and delicious. Thank you"
Brook Farm Inn
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, (987)
"Clean and convenient. Great value."
The price is P3,972
P4,357 total
includes taxes & fees
Aug 3 - Aug 4
Pleasant Valley Motel West Stockbridge
East Rock Inn
Enjoy cooking in this well-equipped kitchen with a central island and bar stools, featuring a refrigerator, microwave, and oven.

East Rock Inn

2.0 star property
9.4 out of 10, Exceptional, (28)
"Nice , new , quiet and clean room. Bed was very comfortable . Missed the human touch of having a traditional office to call when lost and ideas where to eat, etc. "
The price is P9,425
P10,527 total
includes taxes & fees
Aug 10 - Aug 11
East Rock Inn
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 P11,597
P12,954 total
includes taxes & fees
Aug 24 - Aug 25
Courtyard by Marriott Lenox Berkshires
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
7.6 out of 10, Good, (534)
"Small Room. Terrible beds. Awful bathroom. Horrible shower. "
The price is P5,085
P5,679 total
includes taxes & fees
Jul 31 - Aug 1
Travelodge by Wyndham Great Barrington Berkshires
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, (1008)
"Good basic convenient accommodation in a heavily touristy area."
The price is P5,779
P6,455 total
includes taxes & fees
Aug 10 - Aug 11
Quality Inn
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, (1006)
"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 P7,614
P10,739 total
includes taxes & fees
Aug 27 - Aug 28
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, (643)
"We enjoyed the unique character and flavor of the hotel!"
The price is P25,657
P28,659 total
includes taxes & fees
Aug 1 - Aug 2
Berkshires Untold
Econo Lodge Lee - Great Barrington
Relax in comfort with a large bed, two bedside tables, and a balcony with a view.

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (614)
"It was a clean, well-run, low cost option. "
The price is P3,642
P4,068 total
includes taxes & fees
Aug 10 - Aug 11
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.

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
"Loved the property, room was clean and had everything you needed!! We had an upgrade that was wonderful!! Only downfall was the outside little deck! No privacy all out In the open, side by side and facing the other units with a walkway in front of it!! Was looking forward to sitting out side but ended up not using it at all. "
Cheryl 1-night trip
Posted 4 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, check out the 9 hotels and other accommodations you'll find within a mile.

What's the best hotel 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 traveler 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 are there close to Chesterwood?

Expedia has 9 hotels and other accommodations within a mile from Chesterwood.

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

Yes, the majority of room reservations are fully refundable provided that you cancel before the hotel’s cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you have a non-refundable reservation, you might be able to still cancel and be given a refund within 24 hours of booking. Enter dates in and click on "Search", then use the "fully refundable" filter to review the best options available near Chesterwood.

Where can I learn more about changing or cancelling my trip in the area near Chesterwood?

For more information about picking new dates or cancelling your stay near Chesterwood, head over to our customer service page.

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.