Find hotels near Chesterwood, South Lee from ₩88,714

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Jul 21 - Jul 22
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Compare 745 hotels close to Chesterwood with room rates, reviews, and availability. Most hotels are fully refundable.

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

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 ₩606,525
₩733,722 total
includes taxes & fees
Jul 22 - Jul 23
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1001)
"I had excellent stay at the Red Lion Inn "
The price is ₩264,402
₩357,514 total
includes taxes & fees
Jul 22 - Jul 23
The Red Lion Inn
Shaker Mill Inn
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 ₩269,968
₩296,155 total
includes taxes & fees
Jul 30 - Jul 31
Shaker Mill Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

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 ₩230,046
₩276,388 total
includes taxes & fees
Jul 24 - Jul 25
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Granville House
Individually decorated, individually furnished, desk, laptop workspace

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 ₩346,506
₩387,043 total
includes taxes & fees
Jul 27 - Jul 28
Granville House
The Little Lion
Pet-friendly

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 ₩222,654
₩248,705 total
includes taxes & fees
Jul 22 - Jul 23
The Little Lion
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Lobby

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 ₩288,059
₩321,762 total
includes taxes & fees
Jul 24 - Jul 25
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Monument Mountain Motel
Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

2.5 star property
9.0 out of 10, Wonderful, (731)
"Helpful, friendly staff. Clean, convenient, quiet."
The price is ₩130,879
₩146,186 total
includes taxes & fees
Jul 22 - Jul 23
Monument Mountain Motel
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Standard Room | 1 bedroom, premium bedding, pillowtop beds, in-room safe

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 ₩228,221
₩254,922 total
includes taxes & fees
Jul 24 - Jul 25
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
The price is ₩562,342
₩628,136 total
includes taxes & fees
Jul 22 - Jul 23
Devonfield Inn B&B
Travelodge by Wyndham Great Barrington Berkshires
In-room safe, desk, free cribs/infant beds, free rollaway beds

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 ₩123,852
₩138,338 total
includes taxes & fees
Jul 24 - Jul 25
Travelodge by Wyndham Great Barrington Berkshires
Quality Inn
Lobby

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 ₩140,759
₩157,229 total
includes taxes & fees
Aug 4 - Aug 5
Quality Inn
East Rock Inn
Premium Apartment | Private kitchen | Electric kettle

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 ₩229,570
₩256,429 total
includes taxes & fees
Aug 5 - Aug 6
East Rock Inn
Econo Lodge Lee - Great Barrington
Standard Room, 1 King Bed | Desk, iron/ironing board, free cribs/infant beds, rollaway beds

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 ₩88,714
₩99,093 total
includes taxes & fees
Aug 4 - Aug 5
Econo Lodge Lee - Great Barrington
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1004)
"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 ₩247,814
₩331,213 total
includes taxes & fees
Jul 24 - Jul 25
The Cornell Inn, Lenox & The Berkshires
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very Good, (1003)
"Friendly staff, easy parking"
The price is ₩188,073
₩210,078 total
includes taxes & fees
Aug 4 - Aug 5
Quality Inn
Brook Farm Inn
Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds

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"
The price is ₩375,521
₩419,453 total
includes taxes & fees
Jul 22 - Jul 23
Brook Farm Inn
33 Main
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi

33 Main

4.0 star property
10.0 out of 10, Exceptional, (70)
"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "
The price is ₩680,501
₩760,120 total
includes taxes & fees
Jul 28 - Jul 29
33 Main
Apple Tree Inn
Seasonal outdoor pool

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 ₩230,447
₩257,416 total
includes taxes & fees
Aug 6 - Aug 7
Apple Tree Inn
The Constance by the Lenox Collection
Free WiFi, bed sheets

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (496)
"Had a fantastic stay, love this property. Cant wsit to go back"
The price is ₩246,478
₩275,316 total
includes taxes & fees
Jul 22 - Jul 23
The Constance by the Lenox Collection
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
"Terrific place. Spacious, clean, comfortable."
Carolyn 2-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.