Hotels near Chesterwood
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
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 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
Deborah
The price is RM1,208
RM1,461 total
includes taxes & fees
23 Mar - 24 Mar
The Red Lion Inn
The Red Lion Inn3.3 km from Chesterwood
8.8 out of 10, Excellent, (1,001 reviews)
"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."
Gary
The price is RM604
RM849 total
includes taxes & fees
23 Feb - 24 Feb
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, (840 reviews)
"Great overnights stay, wish I was here longer "
Thomas
The price is RM366
RM485 total
includes taxes & fees
4 Mar - 5 Mar
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, (736 reviews)
"Great property, very accommodating. "
Shanice
The price is RM403
RM450 total
includes taxes & fees
15 Mar - 16 Mar
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, (1,000 reviews)
"Clean room, nice staff , decent breakfast. Overall a good stay . "
Anindita
The price is RM381
RM426 total
includes taxes & fees
18 Mar - 19 Mar
Monument Mountain Motel
Monument Mountain Motel8.7 km from Chesterwood
9.0 out of 10, Wonderful, (824 reviews)
"The room was clean, and the staff was friendly and helpful. "
Damien
Lakehouse Inn
Lakehouse Inn8.7 km from Chesterwood
9.6 out of 10, Exceptional, (292 reviews)
"A charming inn in the center of the Berkshires."
Danny
The price is RM562
RM659 total
includes taxes & fees
28 Feb - 1 Mar
The Little Lion
The Little Lion5.1 km from Chesterwood
8.6 out of 10, Excellent, (553 reviews)
"Great friendly staff"
Pablo
The price is RM429
RM480 total
includes taxes & fees
23 Feb - 24 Feb
Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South9.1 km from Chesterwood
8.4 out of 10, Very good, (1,004 reviews)
"Safe, clean rooms, decent breakfast "
Neil
The price is RM346
RM387 total
includes taxes & fees
9 Mar - 10 Mar
Brook Farm Inn
Brook Farm Inn9.1 km from Chesterwood
9.4 out of 10, Exceptional, (164 reviews)
"Everything was perfect - location and accommodation."
Christopher
Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington Berkshires6.2 km from Chesterwood
7.6 out of 10, Good, (570 reviews)
"Excellent location!!"
Abdul Samad
The price is RM293
RM327 total
includes taxes & fees
24 Feb - 25 Feb
The Inn at Stockbridge
The Inn at Stockbridge5.2 km from Chesterwood
9.8 out of 10, Exceptional, (99 reviews)
"Well-run and elegant property. "
Steven
The price is RM933
RM1,095 total
includes taxes & fees
22 Feb - 23 Feb
Chambery Inn
Chambery Inn8.7 km from Chesterwood
9.6 out of 10, Exceptional, (375 reviews)
"Amazing customer service! Location was very good to explore the area."
Sophia
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, (767 reviews)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
Dinh
The price is RM628
RM702 total
includes taxes & fees
25 Feb - 26 Feb
East Rock Inn
East Rock Inn10.1 km from Chesterwood
9.6 out of 10, Exceptional, (38 reviews)
"The room was clean and comfortable wi will back next year:) "
Nadya
The price is RM490
RM547 total
includes taxes & fees
6 Mar - 7 Mar
Element Lenox Berkshires
Element Lenox Berkshires12.5 km from Chesterwood
9.8 out of 10, Exceptional, (19 reviews)
"Spotless rooms and the friendliest service at the front desk! "
Mary
The price is RM542
RM606 total
includes taxes & fees
1 Mar - 2 Mar
Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West Stockbridge4.7 km from Chesterwood
6.8 out of 10, (1,001 reviews)
"Priced very reasonably and the room was clean and comfy!"
Wayne
The price is RM228
RM250 total
includes taxes & fees
3 Mar - 4 Mar
Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington7.4 km from Chesterwood
6.4 out of 10, (658 reviews)
"The room was clean and the service adequate"
David
The price is RM249
RM278 total
includes taxes & fees
6 Mar - 7 Mar
Quality Inn Great Barrington
Quality Inn Great Barrington10.3 km from Chesterwood
8.4 out of 10, Very good, (1,004 reviews)
"Clean room, great location"
Andrea
The price is RM259
RM289 total
includes taxes & fees
23 Mar - 24 Mar
Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires12.1 km from Chesterwood
9.2 out of 10, Wonderful, (601 reviews)
"Our stay was great! "
Gianna
The price is RM492
RM550 total
includes taxes & fees
15 Mar - 16 Mar
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.
Compare popular hotels close to Chesterwood
Property | Property class | Guest rating | Breakfast included | Pool | Spa | Pet-friendly | WiFi included | |
|---|---|---|---|---|---|---|---|---|
 The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood | 9.2 Wonderful 110 reviews | View | ||||||
 The Red Lion Inn | 8.8 Excellent 1,001 reviews | View | ||||||
 Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG | 9.0 Wonderful 840 reviews | View | ||||||
 Holiday Inn Express Hotel & Suites Great Barrington by IHG | 8.8 Excellent 736 reviews | View | ||||||
 The Black Swan Lee - Lenox, an Ascend Collection Hotel | 9.0 Wonderful 1,000 reviews | View |
Top Chesterwood Hotel Reviews
The Red Lion Inn
10/10 Excellent
