Find hotels in Windsor, MA from AED 253

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Check Windsor hotel prices

Tonight
14 Nov - 15 Nov
Tomorrow night
15 Nov - 16 Nov
This weekend
15 Nov - 17 Nov
Next weekend
22 Nov - 24 Nov

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Compare 878 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

The Williams Inn
Front of property - evening/night
The Williams Inn
4.0 star property
9.6 out of 10, Exceptional, (370)
"Difficult to find. No signage Nice room "
The price is AED 724
AED 809 total
includes taxes & fees
1 Dec - 2 Dec
The Williams Inn
Vacation Village in the Berkshires
Lobby
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1746)
"Love staying here "
The price is AED 620
AED 717 total
includes taxes & fees
16 Nov - 17 Nov
Vacation Village in the Berkshires
Life House Berkshires
Lobby
Life House Berkshires
3.5 star property
9.0 out of 10, Wonderful, (437)
"Beautiful hotel close enough drive to multiple towns and hiking areas. Very comfortable beds. Beautiful restroom! TV has Apple compatibility if you are looking for that. The restaurant was absolutely amazing and they use all local business. Absolutely amazing!"
The price is AED 356
AED 398 total
includes taxes & fees
17 Nov - 18 Nov
Life House Berkshires
The Yankee, Trademark Collection by Wyndham
Exterior
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1000)
"Hot tub was great, good breakfast selection. Staff was courteous and very helpful. We would have liked the pool a bit warmer."
The price is AED 356
AED 398 total
includes taxes & fees
21 Nov - 22 Nov
The Yankee, Trademark Collection by Wyndham
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Exterior
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
3.0 star property
8.0 out of 10, Very Good, (676)
"The front desk staff went above and beyond to make sure that our stay went off without a hitch. Thank you kindly.!"
The price is AED 345
AED 386 total
includes taxes & fees
6 Dec - 7 Dec
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Jiminy Peak Mountain Resort
Exterior
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (919)
"Staff was friendly and helpful. The facility is a little run down, but it was clean. A lot was closed (ie. on site bar/restaurants) due to it being between seasons, which was disappointing. We used the hot tub, which was not very hot. We'd stay there again though. "
The price is AED 547
AED 600 total
includes taxes & fees
16 Nov - 17 Nov
Jiminy Peak Mountain Resort
Hotel Downstreet
Exterior
Hotel Downstreet
3.0 star property
8.6 out of 10, Excellent, (1002)
"It's place lies between the Manhattan Club and the St. Mark's Hotel, but in a sleepy ole' new england factory town. We love the Berkshires. This is where we now stay. We have been coming up for 27 years to these mountains."
The price is AED 426
AED 476 total
includes taxes & fees
1 Dec - 2 Dec
Hotel Downstreet
Hotel On North
Front of property - evening/night
Hotel On North
3.5 star property
9.6 out of 10, Exceptional, (647)
"Fantastic hotel! Beautiful restored building with loving attentive staff. I was pleasantly surprised by this stay and would highly recommend a stay here. Hope to return one day."
The price is AED 533
AED 595 total
includes taxes & fees
17 Nov - 18 Nov
Hotel On North
Berkshire Mountain Lodge
Exterior
Berkshire Mountain Lodge
3.0 star property
8.8 out of 10, Excellent, (410)
"My husband and I stayed here for 3 nights. It was a great location and the accommodations were exceptional. Loved having the separate bedroom and kitchen. It was quiet too. My husband watched football late into the evening and I went to bed... didn't hear his TV at all. Also we didn't hear any neighbors either... but I don't think the hotel was full. It was getting to be past peak on fall colors. Too bad they have only 1-bedroom rooms. Would have been fun to have more family members join in...
The price is AED 606
AED 750 total
includes taxes & fees
16 Nov - 17 Nov
Berkshire Mountain Lodge
Hampton Inn & Suites Berkshires-Lenox
Exterior
Hampton Inn & Suites Berkshires-Lenox
2.5 star property
9.2 out of 10, Wonderful, (1001)
"Staff was extremely friendly. The last morning we were there this sweet woman in the breakfast area told us that the kitchen was going to be closing and asked if I wanted anything else. It was about five of 10. I said eggs and she went into the kitchen and brought me out eggs, ketchup, salt, and pepper and a dish right to my table so super sweet, my husband and I will definitely be coming back "
The price is AED 434
AED 485 total
includes taxes & fees
1 Dec - 2 Dec
Hampton Inn & Suites Berkshires-Lenox
Berkshire Inn
Outdoor pool
Berkshire Inn
2.0 star property
7.6 out of 10, Good, (743)
"Very quiet!! And clean"
The price is AED 316
AED 353 total
includes taxes & fees
17 Nov - 18 Nov
Berkshire Inn
FairBridge Inn Express
Room
FairBridge Inn Express
2.5 star property
5.4 out of 10, (677)
"I don’t know so many complaints. Bed was good, clean. Plenty of park. Provided what we paid for and was expecting. "
The price is AED 290
AED 324 total
includes taxes & fees
17 Nov - 18 Nov
FairBridge Inn Express
Courtyard by Marriott Lenox Berkshires
Lobby lounge
Courtyard by Marriott Lenox Berkshires
3.0 star property
9.2 out of 10, Wonderful, (533)
"Nice, friendly staff. large lobby area with multiple seating areas. Coffee over priced. "
The price is AED 448
AED 501 total
includes taxes & fees
1 Dec - 2 Dec
Courtyard by Marriott Lenox Berkshires
Best Western Plus Berkshire Hills Inn & Suites
Exterior
Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
8.4 out of 10, Very Good, (1000)
"Room was clean, comfortable, and convenient. Dog Friendly! Will stay again!"
The price is AED 358
AED 400 total
includes taxes & fees
1 Dec - 2 Dec
Best Western Plus Berkshire Hills Inn & Suites
The Porches Inn at Mass MoCA
Outdoor pool
The Porches Inn at Mass MoCA
3.5 star property
9.4 out of 10, Exceptional, (367)
"Absolutely lovely. Bed was super comfortable, staff was friendly and helpful, lots of places to sit and relax. Easy walk to restaurants and across the street from the MOCA. Nice breakfast and you can even get a drink and a snack in the evening if you want. The sauna, whirlpool and heated pool at the end of October we a pleasant surprise. "
The price is AED 584
AED 714 total
includes taxes & fees
15 Dec - 16 Dec
The Porches Inn at Mass MoCA
Howard Johnson by Wyndham Lenox
Outdoor pool
Howard Johnson by Wyndham Lenox
2.0 star property
7.6 out of 10, Good, (700)
"It served our needs"
The price is AED 290
AED 324 total
includes taxes & fees
15 Nov - 16 Nov
Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham Williamstown
Exterior
Howard Johnson by Wyndham Williamstown
2.0 star property
6.4 out of 10, (820)
"Check in staff was friendly. Room was clean and comfy bed."
The price is AED 367
AED 410 total
includes taxes & fees
17 Nov - 18 Nov
Howard Johnson by Wyndham Williamstown
Hilton Garden Inn Lenox Pittsfield
Exterior
Hilton Garden Inn Lenox Pittsfield
3.0 star property
9.2 out of 10, Wonderful, (618)
"Check in and check out where quick and easy. The room was comfortable and clean. The staff were nice and accommodating. Central location to surrounding attractions. "
The price is AED 525
AED 586 total
includes taxes & fees
8 Dec - 9 Dec
Hilton Garden Inn Lenox Pittsfield
Wagon Wheel Inn
Exterior
Wagon Wheel Inn
2.0 star property
7.2 out of 10, Good, (597)
"Great location. Pleasant staff."
The price is AED 253
AED 283 total
includes taxes & fees
15 Nov - 16 Nov
Wagon Wheel Inn
Fairfield Inn & Suites by Marriott Williamstown
Exterior
Fairfield Inn & Suites by Marriott Williamstown
2.5 star property
8.8 out of 10, Excellent, (307)
"It was a wonderful stay, the staff was ready to help and it was a quiet clean place to do work and also go enjoy the beautiful town of Williamstown"
The price is AED 525
AED 587 total
includes taxes & fees
18 Nov - 19 Nov
Fairfield Inn & Suites by Marriott Williamstown
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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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 Yankee, Trademark Collection by Wyndham. See all available top hotels, or vacation rentals in Windsor.

What's the top vacation rental in Windsor?

Berkshire Village Carriage House - Super Private!!: This vacation home rental outside of Windsor is located in the mountains and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the books in this rental home to help you unwind. 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'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 Berkshire Museum 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.