Hotels in Windsor
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Check prices for these dates
Tonight
Sep 11 - Sep 12Tomorrow
Sep 12 - Sep 13This weekend
Sep 11 - Sep 13Next weekend
Sep 18 - Sep 20Where to stay in Windsor?
1. The Yankee Inn
The Yankee InnLenox
$116
$130 total
includes taxes & fees
Sep 22 - Sep 23
2. FairBridge Inn Express
FairBridge Inn ExpressPittsfield
$62
$69 total
includes taxes & fees
Sep 13 - Sep 14
3. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
$110
$123 total
includes taxes & fees
Sep 14 - Sep 15
4. Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham LenoxLenox
$79
$88 total
includes taxes & fees
Sep 13 - Sep 14
5. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
$127
$141 total
includes taxes & fees
Sep 13 - Sep 14
6. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
$93
$126 total
includes taxes & fees
Oct 1 - Oct 2
7. Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
$115
$128 total
includes taxes & fees
Oct 13 - Oct 14
8. The Springs Motel
The Springs MotelNew Ashford
$114
$125 total
includes taxes & fees
Sep 13 - Sep 14
10. Vacation Village in the Berkshires
Vacation Village in the BerkshiresWilliamstown
$112
$136 total
includes taxes & fees
Sep 13 - Sep 14
11. Hotel On North
Hotel On NorthPittsfield
$152
$170 total
includes taxes & fees
Sep 13 - Sep 14
12. The Revival House
The Revival HouseAdams
$166
$185 total
includes taxes & fees
Sep 13 - Sep 14
13. Harbour House Inn
Harbour House InnCheshire
$254
$268 total
includes taxes & fees
Sep 14 - Sep 15
14. Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection HotelNorth Adams
$144
$160 total
includes taxes & fees
Sep 20 - Sep 21
15. Berkshire Inn
Berkshire InnPittsfield
$86
$96 total
includes taxes & fees
Sep 27 - Sep 28
16. The Trail in Adams - Berkshires’ Art Hotel
The Trail in Adams - Berkshires’ Art HotelAdams
$181
$202 total
includes taxes & fees
Sep 13 - Sep 14
17. Cozy Corner Motel
Cozy Corner MotelWilliamstown
$88
$104 total
includes taxes & fees
Sep 14 - Sep 15
18. Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-LenoxLenox
$134
$150 total
includes taxes & fees
Sep 23 - Sep 24
19. Williamstown Motel
Williamstown MotelWilliamstown
$99
$111 total
includes taxes & fees
Sep 13 - Sep 14
20. Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox PittsfieldPittsfield
$151
$169 total
includes taxes & fees
Sep 20 - Sep 21
Go beyond your typical stay in Windsor
Pet friendly
Cottage
Family friendly
Check out reviews of Windsor hotels guests love
Berkshires Untold
8/10 Good
"I didn’t like that you didn’t have a chair outside your room. It was very dark and confining once you were all the way upstairs with very little ease of access with no elevator to bring you back below, so it would’ve been nice to have some way of being outside without having to go back downstairs."
The Cornell Inn, Lenox & The Berkshires
10/10 Excellent
"Great and helpful staff. Delicious complimentary drinks and a free bottle of wine in your room!!"
The Whitlock
10/10 Excellent
"My husband and I enjoyed our two-night stay at The Whitlock. This historical inn was well located in town and very walkable. The bed was comfortable, bathroom updated, quiet and when we did encounter staff, Logan and Mary Ann, they were incredibly pleasant and helpful. Thank you for your hospitality."
Hotel Downstreet, an Ascend Collection Hotel
8/10 Good
"Great location for Mass Moca"
Berkshire Mountain Lodge
8/10 Good
"Loved having a full Kitchen, lots of space"
The Yankee Inn
10/10 Excellent
"Excellent in every way. Service, staff, amenities. Everything was perfect."
Willows Motel Williamstown
10/10 Excellent
"Awesome staff plus pet-friendly."
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."
Jiminy Peak Mountain Resort
10/10 Excellent
"My family had a wonderful time at Jiminy Peak Mountain Resort! The staff truly cared about making sure we had a great stay. When we had a last-minute change and needed to upgrade our room, they handled everything so seamlessly and were incredibly accommodating. The space we received was much larger than we expected, with four floors, three bedrooms, two bathrooms, and three pull-out sofas. There was more than enough room for our whole family to stay comfortably, and it was very affordable for the amount of space and amenities we received. They were also very generous with towels and blankets. Although we didn’t end up using everything, it was reassuring to know that plenty was available if we needed more. The view from the backyard was beautiful, and the resort attractions were only minutes away. We especially enjoyed the scenic chairlift ride and mountain coaster. Everyone in our family, from old to young, had a great time. Overall, it was a wonderful and very affordable family getaway. We really appreciated the hospitality, spacious accommodations, beautiful surroundings, and activities for all ages. We would definitely recommend Jiminy Peak Mountain Resort!"