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Check Windsor hotel prices

Tonight
May 23 - May 24
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May 24 - May 25
This weekend
May 24 - May 26
Next weekend
May 31 - Jun 2

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Compare 852 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Exterior
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1001)
"The omelette bar with the continental breakfast was killer."
The price is ₩158,155
₩176,668 total
includes taxes & fees
May 27 - May 28
The Yankee, Trademark Collection by Wyndham
Fridge, microwave, stovetop, coffee/tea maker
Berkshire Mountain Lodge
3.0 star property
8.8 out of 10, Excellent, (311)
"A good stay. Clean and quite. Nice pool and fun for the Kidspiration "
The price is ₩224,768
₩278,318 total
includes taxes & fees
May 27 - May 28
Berkshire Mountain Lodge
Lobby
Life House Berkshires
3.5 star property
9.0 out of 10, Wonderful, (245)
"Love the lobby (even smells great!) Love the decor and the outdoor patio. Happy with entire stay."
The price is ₩134,860
₩150,639 total
includes taxes & fees
May 30 - May 31
Life House Berkshires
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Front of property - evening/night
Hotel On North
3.5 star property
9.6 out of 10, Exceptional, (586)
"Very unique venue rooms were awesome staff was incredibly personable will certainly stay there again"
The price is ₩230,322
₩257,266 total
includes taxes & fees
May 27 - May 28
Hotel On North
Exterior
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (857)
"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"
The price is ₩216,595
₩237,605 total
includes taxes & fees
Jun 1 - Jun 2
Jiminy Peak Mountain Resort
Indoor pool
Courtyard by Marriott Lenox Berkshires
3.0 star property
9.2 out of 10, Wonderful, (510)
"Room was so nice. Bed was comfortable. Overall glad we stayed here. "
The price is ₩219,419
₩245,091 total
includes taxes & fees
May 27 - May 28
Courtyard by Marriott Lenox Berkshires
Front of property - evening/night
The Williams Inn
4.0 star property
9.6 out of 10, Exceptional, (294)
"Love the Williams Inn"
The price is ₩348,277
₩389,026 total
includes taxes & fees
May 27 - May 28
The Williams Inn
Exterior
Hampton Inn & Suites Berkshires-Lenox
2.5 star property
9.2 out of 10, Wonderful, (1000)
"No water for drinking on each floor, only in lobby. Some updates could be done. Lovely people."
The price is ₩203,599
₩227,420 total
includes taxes & fees
May 30 - May 31
Hampton Inn & Suites Berkshires-Lenox
Hypo-allergenic bedding, laptop workspace, blackout drapes
Hotel Downstreet
3.0 star property
8.6 out of 10, Excellent, (923)
"A great place to stay in North Adams. Clean, friendly and located just a couple of miles from an outstanding breakfast restaurant. "
The price is ₩202,972
₩226,716 total
includes taxes & fees
May 27 - May 28
Hotel Downstreet
Lobby
Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
8.4 out of 10, Very Good, (945)
"The hotel was farther off of the freeway than I thought it would be. But it was a nice quiet room with a good breakfast. The workout room had a decent treadmill. The stepper needed a battery and the Peloton needed help from the employee to connect to the internet so we didn't ask. The staff was super friendly and jumping to help with any issues. A very good experience."
The price is ₩155,294
₩173,464 total
includes taxes & fees
May 27 - May 28
Best Western Plus Berkshire Hills Inn & Suites
Indoor pool
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
3.0 star property
7.8 out of 10, Good, (580)
"loved how close to downtown the property is, we walked whwre we could. parking garage is closed for renovations but the staff was great and provided free valet and parked our car close or in front of the doors most days to help with us having a small child and my husband using a cane. loved the bar and pool as well. the hallways smelled strongly of weed but thankfully the smell stayed in the halls "
The price is ₩137,648
₩153,753 total
includes taxes & fees
May 29 - May 30
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Exterior
Fairfield Inn & Suites by Marriott Williamstown
2.5 star property
8.8 out of 10, Excellent, (270)
"Cleanliness. Conenience. Lobby decor. Friendly service. Late model hi def TV. Comfy bed."
The price is ₩219,319
₩244,979 total
includes taxes & fees
May 29 - May 30
Fairfield Inn & Suites by Marriott Williamstown
Terrace/patio
The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
8.8 out of 10, Excellent, (103)
"It was clean and quiet good Breakfast "
The price is ₩297,988
₩332,852 total
includes taxes & fees
Jun 24 - Jun 25
The Trail in Adams - Berkshires’ Art Hotel
Desk, iron/ironing board, free WiFi, bed sheets
Berkshire Inn
2.0 star property
7.6 out of 10, Good, (661)
"I liked how quiet it was. I liked the town"
The price is ₩122,587
₩136,931 total
includes taxes & fees
May 27 - May 28
Berkshire Inn
Exterior
Berkshire Valley Inn
2.5 star property
9.0 out of 10, Wonderful, (502)
"Very comfortable stay. Hotel as a lot of charm, staff was friendly and accommodating. Breakfast had healthy options. Also appreciated accommodations for pets, including the dog park and dog bowls/treats. Highly recommend!"
The price is ₩223,406
₩245,079 total
includes taxes & fees
Jun 2 - Jun 3
Berkshire Valley Inn
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express
2.5 star property
5.2 out of 10, (554)
"The staff."
The price is ₩107,616
₩120,203 total
includes taxes & fees
Jun 2 - Jun 3
FairBridge Inn Express
Property grounds
Wagon Wheel Inn
2.0 star property
7.2 out of 10, Good, (546)
"Deff stay again if in the area "
The price is ₩134,861
₩150,636 total
includes taxes & fees
Jun 24 - Jun 25
Wagon Wheel Inn
Exterior
Howard Johnson by Wyndham Lenox
2.0 star property
7.6 out of 10, Good, (610)
"Convenient "
The price is ₩107,616
₩120,203 total
includes taxes & fees
May 27 - May 28
Howard Johnson by Wyndham Lenox
Lake view
Stay Berkshires
2.0 star property
8.4 out of 10, Very Good, (336)
"The staff went to great lengths to solve a problem that arose with my reservation. I would strongly recommend Stay Berkshire for a visit to the Williamstown area. "
The price is ₩218,066
₩243,567 total
includes taxes & fees
May 29 - May 30
Stay Berkshires
Exterior
Willows Motel Williamstown
2.0 star property
8.8 out of 10, Excellent, (795)
"The breakfast was excellent, with a wide variety of fruits and baked items."
The price is ₩107,616
₩120,203 total
includes taxes & fees
May 27 - May 28
Willows Motel Williamstown
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See all available properties in Windsor
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.

More cheap stays in Windsor

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
The price is ₩107,616 per night from May 27 to May 28
₩107,616
per night
May 27 - May 28
7.6/10 Good! (609 reviews)

Windsor hotels information

Number of reviews
4,720
Accommodation
852 hotels
Lowest Price
₩107,616
Highest Price
₩348,277

Frequently asked questions

What's the best place to stay in Windsor?

The Red Lion Inn, located 20.7 mi (33.4 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 Life House Berkshires and The Black Swan Lee - Lenox, Ascend Hotel Collection. 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 are some hotels with pools in Windsor?

Vacation Village in the Berkshires: 3-star condo, 2-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool, and a health club. Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel and Hilton Garden Inn Lenox Pittsfield are two additional hotels with an onsite pool. View all hotels with pools in Windsor.

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 Savoy Mountain State Forest, Mount Greylock State Reservation Visitor Center, and Mohawk Trail State Forest. You'll also find Mount Greylock and Barrington Stage Company 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, April, March, and February, with each month seeing an average of 8 inches of snowfall.