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Compare 752 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 ₩437,649
₩529,441 total
includes taxes & fees
Oct 21 - Oct 22
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, (1007)
"great place have stayed several times, and hope to return."
The price is ₩210,714
₩298,549 total
includes taxes & fees
Nov 6 - Nov 7
The Red Lion 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, (750)
"The lodging was convenient to all the area attractions."
The price is ₩164,187
₩203,148 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (428)
"Very casual and easy check in and out; lovely and substantial breakfast"
The price is ₩189,501
₩207,882 total
includes taxes & fees
Nov 3 - Nov 4
Shaker Mill Inn
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, (742)
"The property is very nice and the staff was extremely friendly and helpful."
The price is ₩202,229
₩225,890 total
includes taxes & fees
Nov 2 - Nov 3
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Granville House
Individually decorated, individually furnished, desk, laptop workspace

Granville House

3.0 star property
10.0 out of 10, Exceptional, (85)
"Beautiful place! Terri and Terry are the best!"
The price is ₩309,708
₩345,940 total
includes taxes & fees
Oct 26 - Oct 27
Granville House
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
8.8 out of 10, Excellent, (669)
"Very comfortable and safe."
The price is ₩151,601
₩169,335 total
includes taxes & fees
Nov 3 - Nov 4
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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, (762)
"Excellent value. Owners are attentive. Rooms are clean and comfortable. "
The price is ₩84,639
₩94,538 total
includes taxes & fees
Nov 2 - Nov 3
Monument Mountain Motel
The Little Lion
Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi

The Little Lion

3.0 star property
8.6 out of 10, Excellent, (534)
"Comfy, quiet, and clean "
The price is ₩182,431
₩203,776 total
includes taxes & fees
Nov 2 - Nov 3
The Little Lion
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
9.0 out of 10, Wonderful, (1006)
"Great Indian restaurant in the hotel!"
The price is ₩150,258
₩167,837 total
includes taxes & fees
Nov 2 - Nov 3
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Inn at Stockbridge
Exterior

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
The price is ₩523,137
₩613,574 total
includes taxes & fees
Nov 2 - Nov 3
The Inn at Stockbridge
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (129)
"The inn has an excellent location and amenities."
The price is ₩482,380
₩538,820 total
includes taxes & fees
Nov 2 - Nov 3
Devonfield Inn B&B
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (369)
"ease of late check in. Super comfortable room."
The price is ₩318,180
₩355,407 total
includes taxes & fees
Oct 9 - Oct 10
Chambery Inn
Quality Inn
Lobby

Quality Inn

2.5 star property
8.4 out of 10, Very Good, (1004)
"Staff was very helpful - easy location - clean rooms!"
The price is ₩131,025
₩146,355 total
includes taxes & fees
Oct 26 - Oct 27
Quality Inn
Pleasant Valley Motel West Stockbridge
Exterior

Pleasant Valley Motel West Stockbridge

2.0 star property
6.8 out of 10, (1003)
"good average place to stay."
The price is ₩85,870
₩94,200 total
includes taxes & fees
Nov 1 - Nov 2
Pleasant Valley Motel West Stockbridge
Quality Inn
Lobby

Quality Inn

2.5 star property
8.4 out of 10, Very Good, (1004)
"Nice and clean would stay again."
The price is ₩119,004
₩132,927 total
includes taxes & fees
Nov 2 - Nov 3
Quality Inn
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, (550)
"Excellent location, friendly service, clean, comfortable room."
The price is ₩106,064
₩118,481 total
includes taxes & fees
Oct 15 - Oct 16
Travelodge by Wyndham Great Barrington Berkshires
Apple Tree Inn
Seasonal outdoor pool

Apple Tree Inn

3.0 star property
8.6 out of 10, Excellent, (309)
"Very clean room and comfortable bed. Friendly staff and restaurant/bar on site. "
The price is ₩234,190
₩261,590 total
includes taxes & fees
Oct 13 - Oct 14
Apple Tree Inn
East Rock Inn
Premium Apartment | Private kitchen | Electric kettle

East Rock Inn

2.0 star property
9.4 out of 10, Exceptional, (33)
"Room was really comfortable and clean. Beautiful views from the main court yard during the day and at night the sky was full of stars. Amazing. "
The price is ₩202,192
₩225,848 total
includes taxes & fees
Nov 2 - Nov 3
East Rock 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, (161)
"Inn was gorgeous and staff exceptional!"
The price is ₩221,674
₩247,610 total
includes taxes & fees
Oct 13 - Oct 14
Brook Farm 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.
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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
"This is a fun family resort... a great vacation place .. in a great location.. something for everyone. Perfect family reunion place.. All Ages happy.. "
Dave 2-night trip
Posted 2 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Hotels near other Chesterwood attractions

Norman Rockwell Museum

4.7/5 (252 reviews)
You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area.
See properties

Berkshire Botanical Garden

4.0/5 (1 review)
Explore the great outdoors at Berkshire Botanical Garden, a lovely green space in Stockbridge. While you're in the area, stroll along the lakeside.
See properties

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 10 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 10 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.