Hotels near Chesterwood

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22 Jul - 23 Jul
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25 Jul - 27 Jul
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Top 10 Hotels Near Chesterwood

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 S$668
includes taxes & fees
29 Jul - 30 Jul
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and 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, (1002)
"I had excellent stay at the Red Lion Inn "
The price is S$322
includes taxes & fees
6 Aug - 7 Aug
The Red Lion Inn
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 S$252
includes taxes & fees
30 Jul - 31 Jul
Shaker Mill Inn
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, (678)
"Terrific place. Spacious, clean, comfortable."
The price is S$216
includes taxes & fees
30 Jul - 31 Jul
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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, (516)
"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 S$229
includes taxes & fees
29 Jul - 30 Jul
The Little Lion
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, (716)
"Nice outdoor seating areas, big pool, clean nicely appointed toom"
The price is S$296
includes taxes & fees
24 Jul - 25 Jul
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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 S$358
includes taxes & fees
27 Jul - 28 Jul
Granville House
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, (731)
"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, (639)
"Great place to stay. Excellent staff."
The price is S$235
includes taxes & fees
24 Jul - 25 Jul
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Devonfield Inn B&B
Stunning two-story house with a central entrance and beautifully manicured lawn.

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
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, (985)
"Clean and convenient. Great value."
The price is S$98
includes taxes & fees
27 Jul - 28 Jul
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, (27)
"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 S$197
includes taxes & fees
5 Aug - 6 Aug
East Rock 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 S$127
includes taxes & fees
31 Jul - 1 Aug
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, (1007)
"Good basic convenient accommodation in a heavily touristy area."
The price is S$145
includes taxes & fees
4 Aug - 5 Aug
Quality Inn
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, (611)
"It is clean and reasonably priced. We were comfortable and close to Tanglewood. "
The price is S$91
includes taxes & fees
4 Aug - 5 Aug
Econo Lodge Lee - Great Barrington
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
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
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, (640)
"We enjoyed the unique character and flavor of the hotel!"
The price is S$617
includes taxes & fees
25 Jul - 26 Jul
Berkshires Untold
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, (1003)
"Friendly staff, easy parking"
The price is S$193
includes taxes & fees
4 Aug - 5 Aug
Quality Inn
Apple Tree Inn
Relax by the serene pool surrounded by lush greenery and a picturesque view.

Apple Tree Inn

3.0 star property
8.4 out of 10, Very good, (288)
"I loved the pool and the wonderful view from the pool. I felt very safe here and there was an overall sense of being welcomed."
The price is S$228
includes taxes & fees
6 Aug - 7 Aug
Apple Tree Inn
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

The Little Lion

The Little Lion

10/10 Excellent
"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. "
Lisa 3-night trip
Posted 1 day ago
The Little Lion

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 9 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 9 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.