Search Hotels Near Chesterwood, South Lee
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)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
Robert
The price is ฿11,932
฿14,434 total
includes taxes & fees
3 Feb - 4 Feb
The Red Lion Inn
The Red Lion Inn3.3 km from Chesterwood
8.8 out of 10, Excellent, (1,001 reviews)
"Old time charm and hot tub under the stars"
Lori
The price is ฿4,769
฿6,728 total
includes taxes & fees
21 Jan - 22 Jan
Shaker Mill Inn
Shaker Mill Inn5.8 km from Chesterwood
9.6 out of 10, Exceptional, (440 reviews)
"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"
Carin
The price is ฿3,437
฿3,770 total
includes taxes & fees
14 Jan - 15 Jan
Granville House
Granville House6.4 km from Chesterwood
10.0 out of 10, Exceptional, (92 reviews)
"Absolutely magical at Christmas time! It was only for a quick overnight but felt like time stood still while we were there. The service was impeccable and Terry and Terri were a delight! I look forward to returning. "
Jennifer
The price is ฿5,436
฿6,072 total
includes taxes & fees
14 Jan - 15 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 reviews)
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
Stephanie
The price is ฿3,319
฿4,319 total
includes taxes & fees
15 Jan - 16 Jan
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 ฿7,461
฿8,750 total
includes taxes & fees
29 Jan - 30 Jan
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, (719 reviews)
"Nice warm pool and hot tub. Good little fitness center. "
Fawn
The price is ฿3,074
฿3,434 total
includes taxes & fees
25 Jan - 26 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 reviews)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
Dinh
The price is ฿4,468
฿4,990 total
includes taxes & fees
29 Jan - 30 Jan
The Little Lion
The Little Lion5.1 km from Chesterwood
8.6 out of 10, Excellent, (548 reviews)
"Perfect for pets "
Maria
The price is ฿3,437
฿3,839 total
includes taxes & fees
14 Jan - 15 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, (1,004 reviews)
"Room was clean and the staff was super friendly and helpful!"
Ethan
The price is ฿3,054
฿3,411 total
includes taxes & fees
2 Feb - 3 Feb
Devonfield Inn B&B
Devonfield Inn B&B7.5 km from Chesterwood
10.0 out of 10, Exceptional, (134 reviews)
"The inn has an excellent location and amenities."
Christopher
Monument Mountain Motel
Monument Mountain Motel8.7 km from Chesterwood
9.0 out of 10, Wonderful, (815 reviews)
"Room was very well designed and clean. The woman who worked at the desk was wonderful!"
Cynthia
Chambery Inn
Chambery Inn8.7 km from Chesterwood
9.6 out of 10, Exceptional, (374 reviews)
"Amazing customer service! Location was very good to explore the area."
Sophia
Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South9.1 km from Chesterwood
8.4 out of 10, Very good, (1,001 reviews)
"Safe, clean rooms, decent breakfast "
Neil
The price is ฿2,515
฿2,809 total
includes taxes & fees
1 Feb - 2 Feb
Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington Berkshires6.2 km from Chesterwood
7.6 out of 10, Good, (566 reviews)
"Excellent location!!"
Abdul Samad
The price is ฿2,343
฿2,617 total
includes taxes & fees
14 Jan - 15 Jan
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 ฿1,828
฿2,005 total
includes taxes & fees
14 Jan - 15 Jan
Element Lenox Berkshires
Element Lenox Berkshires12.5 km from Chesterwood
9.8 out of 10, Exceptional, (16 reviews)
"Spotless rooms and the friendliest service at the front desk! "
Mary
The price is ฿4,343
฿4,851 total
includes taxes & fees
19 Jan - 20 Jan
East Rock Inn
East Rock Inn10.1 km from Chesterwood
9.6 out of 10, Exceptional, (37 reviews)
"The room was clean and comfortable wi will back next year:) "
Nadya
The price is ฿4,330
฿4,837 total
includes taxes & fees
14 Jan - 15 Jan
Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington7.4 km from Chesterwood
6.4 out of 10, (653 reviews)
"The room was clean and the service adequate"
David
The price is ฿2,337
฿2,610 total
includes taxes & fees
1 Feb - 2 Feb
The Whitlock
The Whitlock9.8 km from Chesterwood
8.6 out of 10, Excellent, (283 reviews)
"great location"
Brian
The price is ฿4,093
฿4,572 total
includes taxes & fees
14 Jan - 15 Jan
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
The Red Lion Inn
10/10 Excellent