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Top hotels and accommodation in Windsor

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
9.0 out of 10, Wonderful, (1003)
"Great Indian restaurant in the hotel!"
The price is NZ$204
includes taxes & fees
2 Nov - 3 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (745)
"Great location and very clean. Beautifully decorated and the restaurant is amazing. Just wish it offered a free breakfast with the room. "
The price is NZ$168
includes taxes & fees
2 Nov - 3 Nov
Berkshires Untold

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1002)
"Nice area to visit "
The price is NZ$257
includes taxes & fees
2 Nov - 3 Nov
The Yankee, Trademark Collection by Wyndham

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (2039)
"Really nice place at a reasonable price"
The price is NZ$195
includes taxes & fees
2 Nov - 3 Nov
Vacation Village in the Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1003)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
The price is NZ$312
includes taxes & fees
28 Oct - 29 Oct
The Cornell Inn, Lenox & The Berkshires

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (892)
"Excellent customer service and great rooms"
The price is NZ$197
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (748)
"The lodging was convenient to all the area attractions."
The price is NZ$246
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Hotel Downstreet, an Ascend Collection Hotel

3.0 star property
8.8 out of 10, Excellent, (1000)
"Property was very clean and view of mountain from window was awesome beds very comfortable and loved the hot tub and pool"
The price is NZ$265
includes taxes & fees
4 Nov - 5 Nov
Hotel Downstreet, an Ascend Collection Hotel

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (676)
"Very convenient set up of both room and kitchen, resort very easy to navigate. "
The price is NZ$217
includes taxes & fees
2 Nov - 3 Nov
Berkshire Mountain Lodge

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1006)
"great place have stayed several times, and hope to return."
The price is NZ$339
includes taxes & fees
6 Nov - 7 Nov
The Red Lion Inn

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.4 out of 10, Exceptional, (51)
"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"
The price is NZ$275
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (4)
"Perfect place for a relaxing getaway! We loved everything! "
The price is NZ$188
includes taxes & fees
7 Oct - 8 Oct
Huttopia Berkshires

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (777)
"Great property! Very large clean room in a unique hotel! "
The price is NZ$236
includes taxes & fees
3 Nov - 4 Nov
Hotel On North

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (513)
"Great hotel, staff and restaurant!"
The price is NZ$381
includes taxes & fees
2 Nov - 3 Nov
The Williams Inn

The Constance by the Lenox Collection

3.5 star property
8.4 out of 10, Very good, (549)
"Staff was so friendly and helpful. The room was small and comfortable and the grounds were well kept. "
The price is NZ$182
includes taxes & fees
3 Nov - 4 Nov
The Constance by the Lenox Collection

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (303)
"The rooms are dated but very clean and neat. This family run motel is convenient to everything in Williamstown and the university. The check-in was easy and staff were knowledgeable and kind."
The price is NZ$145
includes taxes & fees
3 Nov - 4 Nov
Williamstown Motel

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1000)
"Great property would certainly stay again."
The price is NZ$195
includes taxes & fees
2 Nov - 3 Nov
Best Western Plus Berkshire Hills Inn & Suites

Howard Johnson by Wyndham Williamstown

2.0 star property
6.6 out of 10, (884)
"Great affordable place to stay while in the northern Berkshires."
The price is NZ$211
includes taxes & fees
7 Oct - 8 Oct
Howard Johnson by Wyndham Williamstown

Red Roof Inn PLUS+ South Deerfield – Amherst

2.5 star property
7.2 out of 10, Good, (1007)
"Great location"
The price is NZ$179
includes taxes & fees
2 Nov - 3 Nov
Red Roof Inn PLUS+ South Deerfield – Amherst

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (746)
"Perfect location for our passing through vacay."
The price is NZ$151
includes taxes & fees
2 Nov - 3 Nov
The Villager Motel
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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Top Windsor Hotel Reviews

More cheap accommodation in Windsor

More cheap accommodation in Windsor

Frequently asked questions

What's the best place to stay in Windsor?

Vacation Village in the Berkshires, located 13 mi (21 km) from the heart of Windsor, is a top choice for your stay, based on our traveller data. Other good options for your visit to the area are Berkshire Mountain Lodge and Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG. See all available top hotels, or vacation rentals in Windsor.

What are some of the best holiday rentals that Windsor has to offer?

Contemporary Berkshire Home with Views of Taconic Golf Course: This holiday home rental outside of Windsor offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. See all vacation rentals in Windsor.

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 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 Mount Greylock State Reservation Visitor Center, Mount Greylock and Barrington Stage Company. You'll also find Berkshire Museum and Colonial Theater 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, March, February and November, with each month seeing an average of 17 cm of snowfall.

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