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Hotels in Windsor

Choose from 984 Windsor Hotel Deals

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
  • 10 min drive from Tanglewood Music Center
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! (961 reviews)
"Water pressure in shower overwhelmingly strong"

Reviewed on Jun 2, 2026

Berkshire Mountain Lodge
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
  • 35 min drive from Tanglewood Music Center
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 ...
8.8/10 Excellent! (2,388 reviews)
"While traveling in the area for summer we found Vacation Village. Great jump off point, great amenities, helpful staff, nice set up inside the condo, pots, pans, utensils, glassware, other cooking utensils in good shape. Private decks are a nice touch. Best bargain in the area by far!!! Will be ..."

Reviewed on Jun 1, 2026

Vacation Village in the Berkshires
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
  • 6 min drive from Tanglewood Music Center
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! (968 reviews)
"Very nice hotel. Highly recommend the restaurant."

Reviewed on Jun 2, 2026

Berkshires Untold
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
  • 8 min drive from Tanglewood Music Center
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 ...
9.2/10 Wonderful! (1,002 reviews)
"Beautiful and well maintained and close to shipping and food"

Reviewed on May 29, 2026

The Yankee Inn
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
  • 12 min drive from Tanglewood Music Center
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (1,001 reviews)
"We love the laid back shabby chic comfort of the Inn. It is our third visit in 2 years and a delightful getaway. The food is excellent. Breakfast has a good choice of menu options . We also love the pool"

Reviewed on May 29, 2026

The Red Lion Inn
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
  • 13 min drive from Tanglewood Music Center
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 ...
9.2/10 Wonderful! (904 reviews)
"Spacious well-equipped units. Staff was friendly and helpful. Activity center was very nice. Would definitely stay again"

Reviewed on May 28, 2026

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

2.5 out of 5
9 Greenfield Rd South Deerfield MA
  • 19 min drive from Tanglewood Music Center
Stay at this hotel in South Deerfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
7.2/10 Good! (1,000 reviews)
"Clean room, great staff, parking"

Reviewed on May 27, 2026

Red Roof Inn PLUS+ South Deerfield – Amherst
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
  • 5 min drive from Tanglewood Music Center
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! (1,001 reviews)
"Great breakfast and coffe is available 24 hours. Nice location to near by restaurants and great view by water."

Reviewed on May 24, 2026

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
  • 58 min drive from Tanglewood Music Center
Book a stay at this business-friendly hotel in North Adams. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,002 reviews)
"Check in was simple and quick. Staff was courteous and helpful. The room was clean and spacious. We had a pleasant stay and checkout was simple."

Reviewed on Jun 1, 2026

Hotel Downstreet, an Ascend Collection Hotel
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 out of 5
445 Pittsfield Rd Lenox MA
  • 8 min drive from Tanglewood Music Center
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 ...
9.2/10 Wonderful! (1,007 reviews)
"Spacious room with large walk-in shower, big bright breakfast room. Very pleasant."

Reviewed on Jun 1, 2026

Hampton Inn & Suites Berkshires-Lenox
Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
  • 17 min drive from Tanglewood Music Center
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 ...
9.6/10 Exceptional! (864 reviews)
"Hotels Amazing stay here"

Reviewed on May 29, 2026

Hotel On North
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
  • 1 hour drive from Tanglewood Music Center
Book a stay at this business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...
9.6/10 Exceptional! (631 reviews)
"Wonderful Inn with wonderful people in a wonderful town. One of my favorite places anywhere."

Reviewed on May 30, 2026

The Williams Inn
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 Windsor

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