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Our top choices for Chesterwood hotels

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood0.6 km from Chesterwood
9.2 out of 10, Wonderful, (110)
The price is AED 1,403
AED 1,697 total
includes taxes & fees
22 Jan - 23 Jan

The Inn at Stockbridge
The Inn at Stockbridge5.2 km from Chesterwood
9.8 out of 10, Exceptional, (99)
The price is AED 877
AED 1,029 total
includes taxes & fees
11 Jan - 12 Jan


Shaker Mill Inn
Shaker Mill Inn5.8 km from Chesterwood
9.6 out of 10, Exceptional, (440)
The price is AED 392
AED 430 total
includes taxes & fees
13 Jan - 14 Jan


Lakehouse Inn
Lakehouse Inn8.7 km from Chesterwood
9.6 out of 10, Exceptional, (290)
The price is AED 529
AED 620 total
includes taxes & fees
16 Jan - 17 Jan

Inn at Kenmore Hall
Inn at Kenmore Hall12.1 km from Chesterwood
10.0 out of 10, Exceptional, (27)
The price is AED 1,561
AED 1,712 total
includes taxes & fees
20 Jan - 21 Jan

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires8.6 km from Chesterwood
9.4 out of 10, Exceptional, (761)
The price is AED 496
AED 554 total
includes taxes & fees
25 Jan - 26 Jan

East Rock Inn
East Rock Inn10.1 km from Chesterwood
9.6 out of 10, Exceptional, (37)
The price is AED 452
AED 505 total
includes taxes & fees
29 Jan - 30 Jan


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 IHG6.6 km from Chesterwood
9.0 out of 10, Wonderful, (818)
The price is AED 344
AED 456 total
includes taxes & fees
12 Jan - 13 Jan

The Little Lion
The Little Lion5.1 km from Chesterwood
8.6 out of 10, Excellent, (548)
The price is AED 404
AED 451 total
includes taxes & fees
11 Jan - 12 Jan

Element Lenox Berkshires
Element Lenox Berkshires12.5 km from Chesterwood
9.6 out of 10, Exceptional, (15)
The price is AED 511
AED 570 total
includes taxes & fees
19 Jan - 20 Jan

Prospect Berkshires
Prospect Berkshires12.8 km from Chesterwood
9.6 out of 10, Exceptional, (18)
The price is AED 779
AED 993 total
includes taxes & fees
26 Jan - 27 Jan

The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel8.6 km from Chesterwood
9.0 out of 10, Wonderful, (1003)
The price is AED 359
AED 401 total
includes taxes & fees
29 Jan - 30 Jan

Monument Mountain Motel
Monument Mountain Motel8.7 km from Chesterwood
9.0 out of 10, Wonderful, (814)

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG8 km from Chesterwood
8.8 out of 10, Excellent, (716)
The price is AED 360
AED 402 total
includes taxes & fees
25 Jan - 26 Jan

Hampton Terrace Inn
Hampton Terrace Inn9.8 km from Chesterwood
9.0 out of 10, Wonderful, (43)
The price is AED 804
AED 898 total
includes taxes & fees
13 Jan - 14 Jan

Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires12.1 km from Chesterwood
9.2 out of 10, Wonderful, (594)
The price is AED 544
AED 607 total
includes taxes & fees
21 Jan - 22 Jan

The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires10.7 km from Chesterwood
9.0 out of 10, Wonderful, (1000)
The price is AED 590
AED 678 total
includes taxes & fees
1 Feb - 2 Feb
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
10/10 Excellent
Hotels near other Chesterwood attractions
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Hotels near popular South Lee Attractions
- Hotels near Tanglewood Music Center
- Hotels near Ski Butternut
- Hotels near National Shrine of the Divine Mercy
- Hotels near Catamount Ski Area
- Hotels near Bousquet Ski Area
- Hotels near Lee Premium Outlets
- Hotels near Norman Rockwell Museum
- Hotels near Jacob's Pillow
- Hotels near The Mount
- Hotels near Taconic State Park
- Hotels near Catamount Aerial Adventure Park
- Hotels near Naumkeag Museum
- Hotels near Colonial Theater
- Hotels near Mahaiwe Performing Arts Center
- Hotels near Hancock Shaker Village
- Hotels near Berkshire Botanical Garden
- Hotels near Housatonic River Walk
- Hotels near Housatonic River
- Hotels near Wyndhurst Golf & Club
- Hotels near Goose Pond Reservation
Other Hotels near Chesterwood, South Lee
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