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Compare 681 hotels close to Chesterwood with room rates, reviews, and availability. Most hotels are fully refundable.
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Black Swan Lee - Lenox, Ascend Hotel Collection
9.0 out of 10, Wonderful, (1004)
The price is AED 403
AED 450 total
includes taxes & fees
30 May - 31 May
The Red Lion Inn
The Red Lion Inn
8.8 out of 10, Excellent, (887)
The price is AED 584
AED 734 total
includes taxes & fees
27 May - 28 May
Life House Berkshires
Life House Berkshires
9.0 out of 10, Wonderful, (245)
The price is AED 404
AED 451 total
includes taxes & fees
28 May - 29 May
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Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
9.0 out of 10, Wonderful, (469)
The price is AED 511
AED 607 total
includes taxes & fees
28 May - 29 May
Seven Hills Inn
Seven Hills Inn
7.8 out of 10, Good, (467)
Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires
9.2 out of 10, Wonderful, (510)
The price is AED 558
AED 624 total
includes taxes & fees
30 May - 31 May
Lakehouse Inn
Lakehouse Inn
9.6 out of 10, Exceptional, (153)
The price is AED 496
AED 576 total
includes taxes & fees
27 May - 28 May
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
9.4 out of 10, Exceptional, (648)
The price is AED 558
AED 624 total
includes taxes & fees
27 May - 28 May
The Cornell Inn, Lenox
The Cornell Inn, Lenox
8.6 out of 10, Excellent, (1000)
The price is AED 444
AED 517 total
includes taxes & fees
4 Jun - 5 Jun
Monument Mountain Motel
Monument Mountain Motel
9.0 out of 10, Wonderful, (596)
The price is AED 257
AED 287 total
includes taxes & fees
27 May - 28 May
Apple Tree Inn
Apple Tree Inn
8.2 out of 10, Very Good, (213)
The price is AED 485
AED 603 total
includes taxes & fees
30 May - 31 May
Quality Inn
Quality Inn
8.0 out of 10, Very Good, (1001)
The price is AED 311
AED 347 total
includes taxes & fees
30 May - 31 May
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
8.8 out of 10, Excellent, (498)
The price is AED 484
AED 541 total
includes taxes & fees
27 May - 28 May
Chambery Inn
Chambery Inn
9.6 out of 10, Exceptional, (356)
The price is AED 915
AED 1,022 total
includes taxes & fees
27 May - 28 May
Blackberry River Inn
Blackberry River Inn
9.4 out of 10, Exceptional, (27)
The price is AED 667
AED 749 total
includes taxes & fees
26 May - 27 May
Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington Berkshires
7.6 out of 10, Good, (457)
The price is AED 253
AED 283 total
includes taxes & fees
27 May - 28 May
The Briarcliff Motel
The Briarcliff Motel
8.8 out of 10, Excellent, (385)
The price is AED 459
AED 513 total
includes taxes & fees
27 May - 28 May
The Ponds at Foxhollow by Capital Vacations
The Ponds at Foxhollow by Capital Vacations
8.6 out of 10, Excellent, (110)
Shaker Mill Inn
Shaker Mill Inn
9.6 out of 10, Exceptional, (383)
The price is AED 533
AED 584 total
includes taxes & fees
28 May - 29 May
Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington
6.4 out of 10, (506)
The price is AED 231
AED 258 total
includes taxes & fees
27 May - 28 May
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.
Hotels near Other West Stockbridge Attractions
Norman Rockwell Museum
4.5/5(193 reviews)
You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area.
Frequently asked questions
Recent reviews of Chesterwood hotelsExpedia verified reviews
5/5 Excellent
"👍"
A verified traveler stayed at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Posted 4 days ago
Hotels near popular West Stockbridge Attractions
- Hotels near Tanglewood Music Center
- Hotels near National Shrine of the Divine Mercy
- Hotels near Norman Rockwell Museum
- Hotels near Lee Premium Outlets
- Hotels near Jacob's Pillow
- Hotels near Ski Butternut
- Hotels near Catamount Ski Area
- Hotels near The Mount
- Hotels near Bousquet Ski Area
- Hotels near Hancock Shaker Village
- Hotels near Shakespeare and Company
- Hotels near Taconic State Park
- Hotels near Ventfort Hall Mansion and Gilded Age Museum
- Hotels near Housatonic River Walk
- Hotels near Catamount Aerial Adventure Park
- Hotels near Colonial Theater
- Hotels near Naumkeag Museum
- Hotels near October Mountain State Forest
- Hotels near Pittsfield State Forest
- Hotels near Wyndhurst Golf & Club
Other Hotels near Chesterwood, West Stockbridge
- Upstate New York Hotels
- Lenox Hotels
- Hudson Hotels
- The Berkshires Hotels
- Pittsfield Hotels
- Hudson Valley Hotels
- Great Barrington Hotels
- Williamstown Hotels
- Stockbridge Hotels
- Lee Hotels
- Appalachian Mountains Hotels
- Hancock Hotels
- Western Massachusetts Hotels
- West Stockbridge Hotels
- Otis Hotels
- Becket Hotels
- Salisbury Hotels
- Lanesborough Hotels
- Chatham Hotels
- Hillsdale Hotels
More Hotel Options in Chesterwood
- Adventure Hotels (1)
- Beach Hotels (1)
- Business Hotels (2)
- Cheap Hotels (1)
- Family Hotels (2)
- Golf Hotels (2)
- Historic Hotels (2)
- Hotel Wedding Venues (1)
- Hotel with a Concierge (1)
- Hotels with Bars (1)
- Hotels with Free Parking (2)
- Hotels with WiFi (2)
- Hotels with a Pool (1)
- Luxury Hotels (1)
- Pet-friendly Hotels (1)
- Resorts & Hotels with Spas (1)
- Romantic Hotels (1)
- Shopping Hotels (2)
- Ski Hotels (1)
- Winery Hotels (2)
Explore more hotels
- A Grand property in Historic Stockbridge
- Find your Sanctuary at The Rectory at Stockbridge
- Sweet Cozy Victorian in Housatonic. Close to everything.
- Walk into town, soak up sun on enclosed porch & steps away from nature trails!
- Pleasant Valley Motel West Stockbridge
- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
- Great Barrington/Housatonic Village Getaway—bring your dog!
- Heart of the Berkshires - Bright, Cozy, Near Lake
- Two Blocks from the Red Lion Inn & next to Berkshire Theater
- The Briarcliff Motel
- Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
- Lakeshore cabin with private beach and dock