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Windsor hotel guide. Preferred hotel in Windsor, Massachusetts

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Check prices for these dates

Tonight
14 Sept - 15 Sept
Tomorrow
15 Sept - 16 Sept
This weekend
18 Sept - 20 Sept
Next weekend
25 Sept - 27 Sept

Our top choices for Windsor Preferred

1. The Orchards Hotel

The Orchards Hotel
Williamstown
United States
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The Orchards Hotel
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Top Windsor Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"The hotel is a perfect place to stay when attending a concert at Tanglewood. Its location is very convenient and our room was clean and comfortable. The on site restaurant (Mint) is lively and serves delicious Indian food."
William 1-night trip
Posted 7 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

10/10 Excellent
"The staff was very helpful"
Glenda 2-night trip
Posted 7 hours ago
Red Roof Inn PLUS+ South Deerfield – Amherst
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Very large room and really easy check in. (Great Staff). Excellent value for the price."
Albie 1-night trip
Posted 11 hours ago
Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Loved the pond trail! What a nice shift after a long day on the road."
Deborah 1-night trip
Posted 12 hours ago
The Yankee Inn
Berkshires Untold

Berkshires Untold

8/10 Good
"Location was great! We loved the new addition in the front, where the reception area was, as well as restaurant and bar area, and library. Also liked the fire pits and outdoor seating. Rooms themselves were very basic and motel-like, and rather dark, but they did have nice bath products (shampoo, conditioner and body lotion). We didn’t realize there was also a room darkening shade on the front window, so the first night we just closed the curtain, which was see-thru! Staff was pleasant, and coffee was ready bright and early."
Barbara A 2-night trip
Posted 12 hours ago
Berkshires Untold
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent
"All the staff I encountered were helpful and friendly. Room was modern and spacious. The free breakfast was very good. I loved the pool and the hot tub! I had an excellent 2-night stay!"
Victoria 2-night trip
Posted 1 day ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good
"Clean room, great location. Perfect base for a weekend in the Berkshires."
Alexandra 2-night trip
Posted 1 day ago
Hotel Downstreet, an Ascend Collection Hotel
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

8/10 Good
"Therooms were loud on the lower level."
Sheila 1-night trip
Posted 2 days ago
Quality Inn Lee - Lenox South
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good
"The temp was 67 degrees in our unit. I called the front desk and they sent someone immediately however who couldn’t get the heat to turn on. The thermostat was not set to turn on until later in the month. The owner must likely to blame for a lack of heat."
Michael 2-night trip
Posted 5 days ago
Holiday Inn Club Vacations Oak 'n Spruce Resort

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