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Compare 989 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
9.0 out of 10, Wonderful, (1006)
"Great Indian restaurant in the hotel!"
The price is ₩151,565
₩169,298 total
includes taxes & fees
Nov 2 - Nov 3
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Berkshires Untold
3.5 star property
9.0 out of 10, Wonderful, (755)
"Easy parking, great community spaces, beautiful decor! "
The price is ₩124,817
₩139,421 total
includes taxes & fees
Nov 2 - Nov 3
Berkshires Untold
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1006)
"Good breakfast King rooms are the best facing the mountains Recently remodeled "
The price is ₩191,292
₩213,674 total
includes taxes & fees
Nov 2 - Nov 3
The Yankee, Trademark Collection by Wyndham
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
8.0 out of 10, Very Good, (898)
"Excellent customer service and great rooms"
The price is ₩146,928
₩164,118 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (2059)
"Nice room clean and friendly staff"
The price is ₩130,849
₩161,808 total
includes taxes & fees
Nov 2 - Nov 3
Vacation Village in the Berkshires
The Cornell Inn, Lenox & The Berkshires
3.5 star property
9.0 out of 10, Wonderful, (1005)
"Very friendly staff. "
The price is ₩182,134
₩259,213 total
includes taxes & fees
Oct 27 - Oct 28
The Cornell Inn, Lenox & The Berkshires
Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
8.8 out of 10, Excellent, (1006)
"Super friendly staff, a free coffee bar in the lobby, loads of food and shopping options within walking distance, free on-site parking - what’s not to love! And the room was spotlessly clean and very very comfortable. We love this place!!!"
The price is ₩185,087
₩206,742 total
includes taxes & fees
Nov 11 - Nov 12
Hotel Downstreet, an Ascend Collection Hotel
Berkshire Mountain Lodge
3.0 star property
9.0 out of 10, Wonderful, (698)
"Great stay, perfect "
The price is ₩132,953
₩180,376 total
includes taxes & fees
Nov 2 - Nov 3
Berkshire Mountain Lodge
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
9.4 out of 10, Exceptional, (53)
"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"
The price is ₩170,038
₩189,923 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
9.0 out of 10, Wonderful, (754)
"Lovely spot, great accommodations, friendly staff, and great location."
The price is ₩165,615
₩204,906 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Huttopia Berkshires
1.0 star property
10.0 out of 10, Exceptional, (4)
"Perfect place for a relaxing getaway! We loved everything! "
The price is ₩139,796
₩156,152 total
includes taxes & fees
Oct 14 - Oct 15
Huttopia Berkshires
Hotel On North
3.5 star property
9.6 out of 10, Exceptional, (779)
"Great property! Very large clean room in a unique hotel! "
The price is ₩167,299
₩186,870 total
includes taxes & fees
Nov 11 - Nov 12
Hotel On North
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (1009)
"Picture perfect Inn"
The price is ₩212,547
₩301,147 total
includes taxes & fees
Nov 6 - Nov 7
The Red Lion Inn
The Williams Inn
4.0 star property
9.6 out of 10, Exceptional, (520)
"Nice place to stay for a wedding "
The price is ₩301,917
₩337,242 total
includes taxes & fees
Nov 2 - Nov 3
The Williams Inn
Williamstown Motel
2.0 star property
9.4 out of 10, Exceptional, (304)
"The rooms are dated but very clean and neat. This family run motel is convenient to everything in Williamstown and the university. The check-in was easy and staff were knowledgeable and kind."
The price is ₩112,693
₩125,877 total
includes taxes & fees
Nov 2 - Nov 3
Williamstown Motel
FairBridge Inn Express
2.5 star property
5.4 out of 10, (794)
"Good service and people"
The price is ₩96,288
₩107,557 total
includes taxes & fees
Oct 27 - Oct 28
FairBridge Inn Express
Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
8.6 out of 10, Excellent, (1011)
"Good breakfast; pleasant staff on duty 24/7; convenient location."
The price is ₩145,046
₩162,016 total
includes taxes & fees
Nov 2 - Nov 3
Best Western Plus Berkshire Hills Inn & Suites
Howard Johnson by Wyndham Williamstown
2.0 star property
6.6 out of 10, (887)
"Great affordable place to stay while in the northern Berkshires."
The price is ₩156,900
₩175,259 total
includes taxes & fees
Oct 14 - Oct 15
Howard Johnson by Wyndham Williamstown
The Central Downtown Inn & Suites
4.0 star property
8.8 out of 10, Excellent, (323)
"Nice place "
The price is ₩140,937
₩157,427 total
includes taxes & fees
Oct 31 - Nov 1
The Central Downtown Inn & Suites
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.
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Top Windsor Hotel Reviews

More cheap stays in Windsor

Frequently asked questions

What's the best place to stay in Windsor?
Vacation Village in the Berkshires, located 13 mi (21 km) from the heart of Windsor, is a top choice for your stay based on our traveler data. Other good options for your visit to the area are Berkshire Mountain Lodge and Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG. See all available top hotels, or vacation rentals in Windsor.
If I need to cancel my hotel reservation in Windsor, will I receive a refund?
Yes! Most hotel bookings are fully refundable provided that you cancel before the hotel's cancellation deadline, which often is within 24-48 hours of your arrival date. If your reservation is non-refundable, it might still be possible to cancel it and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Windsor.
Where can I learn more about changing or cancelling my trip to Windsor?
For more information about updating your trip to Windsor or cancelling it, click here.
What's the best hotel for staying near Albany International Airport (ALB)?
Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.
What is staying in Windsor like?
Visitors can enjoy all that Windsor has to offer including the restaurants and shopping. In Windsor, there are 2 hotels and other accommodations to choose from. Find out more about Windsor.
What should I do while I'm visiting Windsor?
Places to visit in the wider area include Mount Greylock State Reservation Visitor Center, Mount Greylock, and Barrington Stage Company. You'll also find Berkshire Museum and Colonial Theater in the area. Check out what more to see and do in Expedia's Windsor guide.
What's the seasonal weather like in Windsor?
The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Windsor are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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