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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! (812 reviews)
We had a great stay! Karaoke in the bar was a blast!! Great little condo!!

Reviewed on Dec 27, 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! (2,195 reviews)
No frills stay with a kitchen and dishwasher (make sure your room has one— some do not!!!). Location is across the street from Jiminy Peak, so skiing can be accomplished almost as easy as staying on their property. This is our fourth time staying and it always serves its purpose.

Reviewed on Dec 30, 2025

Vacation Village in the Berkshires
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! (1,004 reviews)
Staff was very pleasant and friendly. From front desk to valet.

Reviewed on Jan 1, 2026

Holiday Inn & Suites Pittsfield-Berkshires by IHG
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 stay was wonderful! The hotel is VERY clean, comfortable, and the staff are so lovely! I really enjoyed staying here. You're treated like family (in a good way). It is well situated for restaurants and skiing. I will definitely return.

Reviewed on Dec 29, 2025

The Yankee, Trademark Collection by Wyndham
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! (801 reviews)
The hotel was clean all over and the rooms were spacious and clean. Pool was nice. We loved the outdoor hot tub.

Reviewed on Jan 2, 2026

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! (823 reviews)
Staff and room were wonderful

Reviewed on Dec 30, 2025

Berkshires Untold
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)
Wonderful stay in a winter wonderland that evening especially with use of the heated pool and hot tub being maintained! Loved it. Shops inside were lovely as well, bars & restaurant on-site were fun with quirky decor. Whole hotel is quirky, which is fun!

Reviewed on Dec 26, 2025

The Red Lion Inn
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
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! (1,002 reviews)
Spotless room, helpful and friendly staff, five-star Indian food at in-house Mint restaurant:-)

Reviewed on Dec 29, 2025

The Black Swan Lee - Lenox, an Ascend Collection Hotel
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! (1,003 reviews)
Staff were very friendly and flexible. The rooms were comfortable, spacious and clean. Easy checking and checking out. Plenty of parking. Would definitely stay there again and again.

Reviewed on Dec 27, 2025

Hampton Inn & Suites Berkshires-Lenox
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 out of 5
415 Stockbridge Rd Great Barrington MA
  • 12 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 helpful staff and the ...
8.8/10 Excellent! (716 reviews)
Nice warm pool and hot tub. Good little fitness center.

Reviewed on Jan 2, 2026

Holiday Inn Express Hotel & Suites Great Barrington by IHG
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! (594 reviews)
clean room

Reviewed on Dec 28, 2025

Courtyard by Marriott Lenox Berkshires
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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