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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

3.5 out of 5
190 Meadow Street, South Lee, MA
  • 20 min walk from Chesterwood
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
9/10 Wonderful! (678 reviews)
"Terrific place. Spacious, clean, comfortable."

Reviewed on Jul 18, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
  • 47 min drive from Chesterwood
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,885 reviews)
"This is a great get away! Beautiful atmosphere and lots of variety of activities"

Reviewed on Jul 17, 2025

Vacation Village in the Berkshires
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
  • 17 min drive from Chesterwood
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (640 reviews)
"We enjoyed the unique character and flavor of the hotel!"

Reviewed on Jul 19, 2025

Berkshires Untold
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
  • 27 min drive from Chesterwood
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (823 reviews)
Very solid spot
"Great spot for exploring the area. Walking distance to downtown, and easy drive to nature, which is why I was in town w/ friends. Only complaint is that the hot water ran out really fast in the showers the days we were there"

Reviewed on Jul 16, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
  • 31 min drive from Chesterwood
Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking ...
5.2/10 (743 reviews)
"Rooms were much nicer than expected. Despite the somewhat dated exterior and overall first impression from the outside, the rooms were solidly good, clean, and comfortable. Good value for the price."

Reviewed on Jul 1, 2025

FairBridge Inn Express
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
  • 25 min drive from Chesterwood
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,008 reviews)
"Very friendly girl at the check-in who moved us (essentially upgraded us) to a suite after our initial room smelled of lingering cigarette smoke. She was very patient about my paranoia over the pilot light/flame in the room's fireplace. Great experience."

Reviewed on Jul 18, 2025

Best Western Plus Berkshire Hills Inn & Suites
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
  • 21 min drive from Chesterwood
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (519 reviews)
"Superb lodging and a nice reprieve. Not sure who invited the elephants to stay in the room above me but otherwise a great stopover!!"

Reviewed on Jul 18, 2025

Berkshire Mountain Lodge
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
  • 8 min walk from Chesterwood
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
8.8/10 Excellent! (1,001 reviews)
"We could use the pool and other amenities available prior to our room being available. It was great to sit outside have dinner whilst listening to live music."

Reviewed on Jul 17, 2025

The Red Lion Inn
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
  • 20 min drive from Chesterwood
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (1,002 reviews)
"The friendliness and excellent service received from the staff. While we stayed at the Yankee, we expected a delivery from UPS and the staff at the registration ensured that we would be informed as soon as it arrived at the Yankee. There was a delay from UPS and it caused us some stress. The Yankee ..."

Reviewed on Jul 18, 2025

The Yankee, Trademark Collection by Wyndham
The Constance by the Lenox Collection

The Constance by the Lenox Collection

3.5 out of 5
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
  • 12 min drive from Chesterwood
Stay at this 3.5-star hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.6/10 Excellent! (440 reviews)
A wonderfully elegant inn
"Lovely, charming inn. Very clean and comfortable. I especially appreciated the quiet air conditioning split. Logan, who checked us in, was very warm and helpful. Some suggestions: a safety bar in the shower would be helpful to older guests, as would a rubber mat on the shower floor; tile is slippery. ..."

Reviewed on Jul 17, 2025

The Constance by the Lenox Collection
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
  • 16 min drive from Chesterwood
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (1,006 reviews)
"Sheets were dirty, noisy AC system. Staff were polite and attentive. Breakfast was very good."

Reviewed on Jul 18, 2025

Quality Inn
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 out of 5
445 Pittsfield Rd, Lenox, MA
  • 20 min drive from Chesterwood
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (999 reviews)
"Ez drive to Lenox & Tanglewood....plenty of parking. Grabbed a room last minute & front desk was great about being sure it was ready. Husband happy to have a cookie at check-in! Always love having a coffee maker in room & nice little buffet breakfast included."

Reviewed on Jul 4, 2025

Hampton Inn & Suites Berkshires-Lenox
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.

Find cheap hotels in South Lee

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How many hotels are there in South Lee?

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