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May 10 - May 11
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May 11 - May 12
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May 10 - May 12

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Top hotels and accommodation in Windsor

The Yankee, Trademark Collection by Wyndham
Exterior
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1001)
"Friendly place, better than expected breakfast"
The price is AU$156
per night
22 May - 23 May
The Yankee, Trademark Collection by Wyndham
Berkshire Mountain Lodge
Fridge, microwave, stovetop, coffee/tea maker
Berkshire Mountain Lodge
3.0 star property
8.8 out of 10, Excellent, (310)
"A good stay. Clean and quite. Nice pool and fun for the Kidspiration "
The price is AU$278
per night
14 May - 15 May
Berkshire Mountain Lodge
Life House Berkshires
Lobby
Life House Berkshires
3.5 star property
9.2 out of 10, Wonderful, (233)
"It’s the perfect place to go for a weekend or weeklong stay and be as isolated as social as you want. The towns nearby are fantastic. Will definitely be back a lot "
The price is AU$167
per night
12 May - 13 May
Life House Berkshires
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Hotel On North
Front of property - evening/night
Hotel On North
3.5 star property
9.6 out of 10, Exceptional, (585)
"Comfortable "
The price is AU$260
per night
12 May - 13 May
Hotel On North
Jiminy Peak Mountain Resort
Outdoor pool, pool umbrellas, pool loungers
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 AU$247
per night
12 May - 13 May
Jiminy Peak Mountain Resort
Courtyard by Marriott Lenox Berkshires
Indoor pool
Courtyard by Marriott Lenox Berkshires
3.0 star property
9.2 out of 10, Wonderful, (507)
"Beautiful location, property in very good condition, clean. "
The price is AU$272
per night
27 May - 28 May
Courtyard by Marriott Lenox Berkshires
The Williams Inn
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 AU$413
per night
22 May - 23 May
The Williams Inn
Hampton Inn & Suites Berkshires-Lenox
Exterior
Hampton Inn & Suites Berkshires-Lenox
2.5 star property
9.2 out of 10, Wonderful, (1001)
"The hotel is in a quiet location with plenty of parking. Outside area average..would be nice to have an actual patio area instead of tables on the grass. The pool room could be warmer. The staff is pleasant. Breakfast is average, nice to have the waffle maker. Enjoyed our stay well enough..but I would say that nothing stands out about it. It wasnt a bad place, or a great place..its just average!"
The price is AU$235
per night
27 May - 28 May
Hampton Inn & Suites Berkshires-Lenox
Hotel Downstreet
Hypo-allergenic bedding, laptop workspace, blackout curtains
Hotel Downstreet
3.0 star property
8.6 out of 10, Excellent, (916)
"Near Mass MoCA, friendly staff, great view from my room"
The price is AU$251
per night
12 May - 13 May
Hotel Downstreet
Best Western Plus Berkshire Hills Inn & Suites
Lobby
Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
8.4 out of 10, Very good, (939)
"People at desk are very helpful and friendly. Fitness center is dirty and smelly. Room is fine. We like the fridge and microwave. "
The price is AU$177
per night
13 May - 14 May
Best Western Plus Berkshire Hills Inn & Suites
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Indoor pool
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
3.0 star property
7.8 out of 10, Good, (577)
"Staff, friendly and accommodating"
The price is AU$191
per night
28 May - 29 May
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Fairfield Inn & Suites by Marriott Williamstown
Exterior
Fairfield Inn & Suites by Marriott Williamstown
2.5 star property
8.8 out of 10, Excellent, (265)
"The rooms were nicely laid out and well designed. The property was very clean and quiet. It looked brand new."
The price is AU$256
per night
19 May - 20 May
Fairfield Inn & Suites by Marriott Williamstown
The Trail in Adams - Berkshires’ Art Hotel
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 AU$369
per night
13 May - 14 May
The Trail in Adams - Berkshires’ Art Hotel
Berkshire Inn
Desk, iron/ironing board, free WiFi, bed sheets
Berkshire Inn
2.0 star property
7.6 out of 10, Good, (658)
"This location is so convenient to the Berkshire Museum and downtown Pittsfield! There are plenty of great restaurants a short distance away. The price is right and we used the savings to eat at local spots for breakfast, too. They have done some nice updates, so it doesn't feel like the motels that I went to when I was a kid with my parents. "
The price is AU$135
per night
12 May - 13 May
Berkshire Inn
Berkshire Valley Inn
Exterior
Berkshire Valley Inn
2.5 star property
9.0 out of 10, Wonderful, (500)
"Very pretty and super clean. "
The price is AU$205
per night
14 May - 15 May
Berkshire Valley Inn
Wagon Wheel Inn
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 AU$116
per night
12 May - 13 May
Wagon Wheel Inn
Howard Johnson by Wyndham Lenox
Exterior
Howard Johnson by Wyndham Lenox
2.0 star property
7.6 out of 10, Good, (609)
"Convenient "
The price is AU$133
per night
12 May - 13 May
Howard Johnson by Wyndham Lenox
Stay Berkshires
Lake view
Stay Berkshires
2.0 star property
8.4 out of 10, Very good, (335)
"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 AU$270
per night
13 May - 14 May
Stay Berkshires
Willows Motel Williamstown
Exterior
Willows Motel Williamstown
2.0 star property
8.8 out of 10, Excellent, (789)
"Comfortable, clean, friendly helpful people. Walkable to attractions -Clark, College, Restaurants. Homey. "
The price is AU$127
per night
27 May - 28 May
Willows Motel Williamstown
The Porches Inn at Mass MoCA
Exterior
The Porches Inn at Mass MoCA
3.5 star property
9.4 out of 10, Exceptional, (340)
"Pool!!!"
The price is AU$312
per night
30 May - 31 May
The Porches Inn at Mass MoCA
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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.

Frequently asked questions

If I need to cancel my hotel reservation in Windsor, will I receive a refund?

Yes! The majority of room reservations are fully refundable if cancelled before the hotel’s cancellation deadline, which in most cases is within 24 or 48 hours of check in. If you have a reservation that's non-refundable, it may still be possible to cancel it and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Windsor.

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 that feature an on-site pool. View all hotels with pools in Windsor.

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 accommodation options 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. Take a look at what more there is to see and do in Expedia's Windsor guide.

What's the weather like in Windsor?

The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Windsor are January, April, March and February, with each month seeing an average of 20 cm of snowfall.