Search for Cheap Deals on
Hotels in South Lee

Choose from 1376 South Lee Hotel Deals

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! (673 reviews)
"Wonderful SPACIOUS spotless unit with full kitchen, table and chair set, lovely forest view deck, two bathrooms, separate bedrooms and a comfortable sleep sofa!! Only problem was that there was no elevator to take our pieces of luggage to the third level. And we are Senior citizens! Otherwise, a ..."

Reviewed on Jul 14, 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! (1,874 reviews)
"Great stay with all plenty of things to do…"

Reviewed on Jul 14, 2025

Vacation Village in the 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! (1,012 reviews)
"Great"

Reviewed on Jul 13, 2025

Best Western Plus Berkshire Hills Inn & Suites
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! (633 reviews)
"It was ok for a one night"

Reviewed on Jul 15, 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! (821 reviews)
Comfy beds, chair, good closet, very clean
"Overnight stay while on a family visit. Comfortable room, good beds, great AC. Quiet as well."

Reviewed on Jul 13, 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 (741 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
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! (1,013 reviews)
"Dependable and well located."

Reviewed on Jul 13, 2025

The Yankee, Trademark Collection by Wyndham
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! (1,004 reviews)
"Live the front porch and dining room. We were first assigned a room in the Steven’s bldg. it was completely not up to standards. Musty smell , far from hotel and old dirty furniture. I complained to the front desk and was upgraded to a nicer building. Staff very cooperative. The pool was cloudy and ..."

Reviewed on Jul 13, 2025

The Red Lion Inn
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! (434 reviews)
"Really loved the Constance. Breakfast was very nice. Room was also very nice and clean. Comfy bed."

Reviewed on Jul 12, 2025

The Constance by the Lenox Collection
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! (513 reviews)
"Great area, very reasonable."

Reviewed on Jul 11, 2025

Berkshire Mountain Lodge
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)
Nice get away
"We had a very nice stay , the staff was friendly , everything was very clean and quiet. The breakfast was great , I’d stay again."

Reviewed on Jul 13, 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! (1,001 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

You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your South Lee hotel with Hotwire to complete your one-of-a-kind travel checklist.

For you, intrepid voyager, Hotwire has a large selection of the best hotels in South Lee.

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 1,376 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 $88. 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.

While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in South Lee. No matter your reason for visiting South Lee, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.

Frequently Asked Questions About South Lee hotels

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

If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can unlock great deals on your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in South Lee for as low as $88.

How many hotels are there in South Lee?

With over 1,376 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 $88.

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.