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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
Book a stay at this family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in ...
9/10 Wonderful! (806 reviews)
very good stay my only recommendation would be to have more coffee supplies as their is only enough for one pot of coffee and we were staying two days other than that very peaceful and comfortable.

Reviewed on Dec 22, 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
Book a stay at this 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! (2,179 reviews)
My stay was great with no problems.

Reviewed on Dec 19, 2025

Vacation Village in the Berkshires
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! (1,006 reviews)
The room is so spotless, bathroom is so luxurious! The bed is so soft and sleep very quickly! The staffs are so great! Quick to answer to my questions and my needs. Definitely come back again to stay!

Reviewed on Dec 22, 2025

The Yankee, Trademark Collection by Wyndham
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
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (993 reviews)
N/a

Reviewed on Dec 20, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
  • 8 min walk from Chesterwood
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
8.6/10 Excellent! (1,002 reviews)
I had always wanted to stay at The Red Lion Inn and decided to treat myself to a one-night stay. Since it was in December I was especially excited to have a fireplace in the room. Sadly, I learned the fireplace didn’t work and that they are renovating some of the systems, but offered no partial refund ...

Reviewed on Dec 23, 2025

The Red Lion Inn
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
  • 21 min drive from Chesterwood
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (793 reviews)
Spacious room and loved pool and hot tub!

Reviewed on Dec 19, 2025

Berkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
  • 17 min drive from Chesterwood
Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
9/10 Wonderful! (820 reviews)
Staff is polite and extremely attentive. Made my stay a true pleasure and close to town. Highly recommend

Reviewed on Dec 23, 2025

Berkshires Untold
Huttopia Berkshires

Huttopia Berkshires

1 out of 5
312 Kittle Rd Williamstown MA
  • 48 min drive from Chesterwood
Stay at this campground in Williamstown. Enjoy free parking, breakfast (surcharge), and a picnic area. Popular attractions Jiminy Peak Mountain Resort and Mountain ...
10/10 Exceptional! (7 reviews)
Healthy food too!

Reviewed on Oct 20, 2025

Huttopia Berkshires
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! (1,001 reviews)
Very friendly and good Breakfast.

Reviewed on Dec 14, 2025

Best Western Plus Berkshire Hills Inn & Suites
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St Lee MA
  • 6 min drive from Chesterwood
Stay at this hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions ...
9/10 Wonderful! (1,000 reviews)
Very friendly and helpful woman at reception desk. Loved the Indian restaurant Mint right in the hotel.

Reviewed on Dec 22, 2025

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3 out of 5
70 Pittsfield Rd Lenox MA
  • 16 min drive from Chesterwood
Book a stay at this business-friendly hotel in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (592 reviews)
Clean room. Very nice staff. Quiet.

Reviewed on Nov 29, 2025

Courtyard by Marriott Lenox Berkshires
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)
From check in to the room itself to parking and breakfast everything was wonderful!!

Reviewed on Dec 15, 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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Frequently Asked Questions About South Lee hotels

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How many hotels are there in South Lee?

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Finding a cheap car rental deal in South Lee is as easy as scoring cheap hotels in South Lee. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.