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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! (833 reviews)
The room was beautiful - great for our family. Plenty of room and we enjoyed the gurgling brook out back! The pool was great along with the hot tub. Although the hot tub was supposed to be adult only, it was not enforced unless we left to request someone to do it. The bar near the pool area was fun ...

Reviewed on Feb 8, 2026

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! (2,236 reviews)
Fairly clean and staff were friendly

Reviewed on Feb 13, 2026

Vacation Village in the Berkshires
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! (835 reviews)
We enjoyed our stay. Hotel is a little out dated but the rooms are a generous size at low prices. Pool was huge and as a lap swimmer this was fantastic. Checkout is early at 10:00. That is really the only complaint. Staff is very nice

Reviewed on Feb 8, 2026

Berkshire Mountain Lodge
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! (1,012 reviews)
Traveling during freezing temperatures was a challenge but once we arrived at the Yankee Inn, we felt welcome and comfortable. Pre check-in was easy and our room was clean and warm and cozy. We ordered in and were told there were tables on the 2nd floor outside the breakfast room where we could eat ...

Reviewed on Feb 9, 2026

The Yankee, Trademark Collection by Wyndham
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! (855 reviews)
This place was lovely. I travel a lot for my 2 college athletes and I wish I could have spent more time here. Great place!

Reviewed on Feb 10, 2026

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
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! (1,001 reviews)
Bathroom had somebody’s hair on the door and shower

Reviewed on Feb 9, 2026

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Quality Inn

Quality Inn

2.5 out of 5
372 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 ...
8.4/10 Very Good! (1,002 reviews)
Staff was very friendly, daily housekeeping, and very centrally located!

Reviewed on Feb 4, 2026

Quality Inn
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. ...
8.8/10 Excellent! (1,003 reviews)
Love the warmth and lobby’s wood-burning fireplace. Some of the amenities could be updated (EV chargers were broken, the fitness center was messy and missing weights) but there are few inns this charming in New England, and at this price level.

Reviewed on Feb 8, 2026

The Red Lion Inn
Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
  • 28 min drive from Chesterwood
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (823 reviews)
Room was spotless, staff was amazing! Loved the bathroom setup! Will recommend and stay again!

Reviewed on Feb 9, 2026

Hotel On North
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! (1,004 reviews)
Clean room, nice staff , decent breakfast. Overall a good stay .

Reviewed on Feb 8, 2026

The Black Swan Lee - Lenox, an Ascend Collection Hotel
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 ...
9.2/10 Wonderful! (8 reviews)
Healthy food too!

Reviewed on Oct 20, 2025

Huttopia Berkshires
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! (732 reviews)
Room was clean and breakfast was good

Reviewed on Feb 13, 2026

Holiday Inn Express Hotel & Suites Great Barrington by IHG
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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Choosing the right hotel in Massachusetts has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of South Lee’s 1,348 hotels. Choose the one that best catches your trip’s tourist drift.

If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $85. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great South Lee hotel deals at the last minute.

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Frequently Asked Questions About South Lee hotels

Where can I find the best last-minute travel deals?

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How many hotels are there in South Lee?

With over 1,348 hotels in South Lee, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $85.

How to find cheap car rentals in South Lee?

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.