Find hotels in Windsor, MA from AED 284

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Check Windsor hotel prices

Tonight
24 Nov - 25 Nov
Tomorrow night
25 Nov - 26 Nov
Next weekend
29 Nov - 1 Dec

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Compare 883 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, (371)
"A lovely hotel in close proximity to the Clark. Highly recommended!"
The price is AED 748
AED 836 total
includes taxes & fees
8 Dec - 9 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)
"Property was beautiful, great staff "
The price is AED 620
AED 717 total
includes taxes & fees
26 Nov - 27 Nov
Vacation Village in the Berkshires
Life House Berkshires
Lobby

Life House Berkshires

3.5 star property
9.0 out of 10, Wonderful, (442)
"Beautiful room and very comfy and convenient location."
The price is AED 440
AED 491 total
includes taxes & fees
26 Nov - 27 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, (1008)
"Staff was very nice, friendly and accommodating. The room was nice, clean, comfortable and spacious. "
The price is AED 343
AED 384 total
includes taxes & fees
1 Dec - 2 Dec
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, (682)
"We stayed for two weeks and couldn’t have been happier with the service. Such nice people, and so understanding. Six stars if I could!"
The price is AED 348
AED 388 total
includes taxes & fees
13 Dec - 14 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, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is AED 547
AED 600 total
includes taxes & fees
26 Nov - 27 Nov
Jiminy Peak Mountain Resort
Hotel On North
Front of property - evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (650)
"Very nice!"
The price is AED 533
AED 595 total
includes taxes & fees
26 Nov - 27 Nov
Hotel On North
Hotel Downstreet
Exterior

Hotel Downstreet

3.0 star property
8.6 out of 10, Excellent, (1043)
"Great location, wonderful staff, fun pool and cool art. Would definitely stay again! "
The price is AED 426
AED 476 total
includes taxes & fees
8 Dec - 9 Dec
Hotel Downstreet
Berkshire Mountain Lodge
Exterior

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (411)
"Loved our room. Very clean"
The price is AED 606
AED 750 total
includes taxes & fees
26 Nov - 27 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, (1030)
"The stay was ok but the key to our door was broken and the receptionist promised to change it but she didnt so we have no key to properly enter the room.I also told another receptionist and still the same. "
The price is AED 434
AED 485 total
includes taxes & fees
1 Dec - 2 Dec
Hampton Inn & Suites Berkshires-Lenox
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, (1010)
"Room was clean, comfortable, and convenient. Dog Friendly! Will stay again!"
The price is AED 331
AED 370 total
includes taxes & fees
1 Dec - 2 Dec
Best Western Plus Berkshire Hills Inn & Suites
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
11 Dec - 12 Dec
Courtyard by Marriott Lenox Berkshires
Berkshire Inn
Outdoor pool

Berkshire Inn

2.0 star property
7.6 out of 10, Good, (747)
"Nice area "
The price is AED 316
AED 353 total
includes taxes & fees
26 Nov - 27 Nov
Berkshire Inn
The Porches Inn at Mass MoCA
Outdoor pool

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (369)
"We had an excellent time and loved all the beautiful details. Will definitely stay here again."
The price is AED 590
AED 721 total
includes taxes & fees
24 Dec - 25 Dec
The Porches Inn at Mass MoCA
FairBridge Inn Express
Room

FairBridge Inn Express

2.5 star property
5.4 out of 10, (678)
"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
26 Nov - 27 Nov
FairBridge Inn Express
Howard Johnson by Wyndham Lenox
Outdoor pool

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (701)
"It served our needs"
The price is AED 290
AED 324 total
includes taxes & fees
26 Nov - 27 Nov
Howard Johnson by Wyndham Lenox
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 501
AED 559 total
includes taxes & fees
22 Dec - 23 Dec
Hilton Garden Inn Lenox Pittsfield
Howard Johnson by Wyndham Williamstown
Exterior

Howard Johnson by Wyndham Williamstown

2.0 star property
6.4 out of 10, (824)
"Very nice, very convenient."
The price is AED 367
AED 410 total
includes taxes & fees
26 Nov - 27 Nov
Howard Johnson by Wyndham Williamstown
Fairfield Inn & Suites by Marriott Williamstown
Exterior

Fairfield Inn & Suites by Marriott Williamstown

2.5 star property
8.8 out of 10, Excellent, (308)
"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 492
AED 550 total
includes taxes & fees
15 Dec - 16 Dec
Fairfield Inn & Suites by Marriott Williamstown
1896 House Country Inn & Motels
Exterior

1896 House Country Inn & Motels

2.5 star property
6.6 out of 10, (404)
"Excellent experience for the price. Lovely area next to creek. Helpful staff"
The price is AED 284
AED 318 total
includes taxes & fees
28 Nov - 29 Nov
1896 House Country Inn & Motels
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.