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Check Windsor hotel prices

Tonight
May 24 - May 25
Tomorrow night
May 25 - May 26
This weekend
May 24 - May 26

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Top 10 Windsor hotels and places to stay

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 CA $159
CA $177 total
includes taxes & fees
Jun 11 - Jun 12
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 CA $203
CA $254 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 CA $136
CA $152 total
includes taxes & fees
May 28 - May 29
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 CA $231
CA $258 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 CA $216
CA $237 total
includes taxes & fees
Jun 13 - Jun 14
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 CA $220
CA $246 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 CA $369
CA $412 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 CA $205
CA $229 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 CA $205
CA $228 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 CA $144
CA $161 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 CA $157
CA $175 total
includes taxes & fees
May 30 - May 31
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 CA $220
CA $246 total
includes taxes & fees
Jun 5 - Jun 6
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 CA $299
CA $335 total
includes taxes & fees
May 27 - May 28
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 CA $123
CA $138 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 CA $225
CA $246 total
includes taxes & fees
May 28 - May 29
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 CA $108
CA $121 total
includes taxes & fees
May 27 - May 28
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 CA $95
CA $106 total
includes taxes & fees
May 30 - May 31
Wagon Wheel Inn
Exterior
Howard Johnson by Wyndham Lenox
2.0 star property
7.6 out of 10, Good, (610)
"Convenient "
The price is CA $108
CA $121 total
includes taxes & fees
May 28 - May 29
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 CA $219
CA $245 total
includes taxes & fees
May 27 - May 28
Stay Berkshires
Exterior
Willows Motel Williamstown
2.0 star property
8.8 out of 10, Excellent, (795)
"Personable "
The price is CA $108
CA $121 total
includes taxes & fees
May 28 - May 29
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

Quality Inn

Quality Inn

170 Housatonic Street, Lee, MA
The price is CA $136 per night from May 27 to May 28
CA $136
CA $151 total
includes taxes & fees
May 27 - May 28
8/10 Very Good! (898 reviews)

Windsor Travel Info

Number of hotels
851
Highest price
CA $369
Lowest price
CA $95
Known attractions
Tannery Falls

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.

What's the top vacation rental in Windsor?

Cozy apartment located in quiet Williamsburg: This vacation home rental outside of Windsor is in a rural location and equipped with air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. See all 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.

Recent Reviews in Windsor
Expedia verified reviews

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

5/5 Excellent
"Nice & quiet property. Will love the food at the restaurant, JAE. "
A verified traveller stayed at Hilton Garden Inn Lenox Pittsfield
Posted 1 day ago
Hilton Garden Inn Lenox Pittsfield