A city skyline with a prominent casino building, a tall skyscraper, and several other high-rise buildings along a waterfront.

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Windsor cottages

Two blue Adirondack chairs on a wooden deck by a calm lake with trees in the background.

1. Creekside Cottage - Waterfront Retreat with Kayaks, Fishing & Game Room

Creekside Cottage - Waterfront Retreat with Kayaks, Fishing & Game Room
Kingsville
10.0 out of 10, Exceptional, (23 reviews)
"The perfect tiny oasis for us! This house has an incredible location and is perfect for a family getaway. We brought our dog and infant and had an incredible time. The hosts were also very prompt and communicative with any questions."
United States
Alli C.
The price is €256
includes taxes & fees
27 Oct - 28 Oct
Creekside Cottage - Waterfront Retreat with Kayaks, Fishing & Game Room
A patio with a view of the sea, featuring two red chairs and a stone pathway.

2. Anchor down on your private Beachfront Cottage

Anchor down on your private Beachfront Cottage
Essex
10.0 out of 10, Exceptional, (31 reviews)
"Amazing and beautiful place to visit. Perfect for a girls weekend "
United States
Julie D.
The price is €356
includes taxes & fees
4 Nov - 5 Nov
Anchor down on your private Beachfront Cottage
A deck with outdoor seating, including chairs and a table, overlooking a body of water.

3. Lake Erie & EPIC Wineries

Lake Erie & EPIC Wineries
Essex
10.0 out of 10, Exceptional, (35 reviews)
"Very clean fantastic view and close to everything"
United States
Peter and mary M.
The price is €267
includes taxes & fees
27 Oct - 28 Oct
Lake Erie & EPIC Wineries
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

Hampton Inn & Suites by Hilton Windsor

Hampton Inn & Suites by Hilton Windsor

8/10 Good
"We almost always stay at a Holiday Inn express. Everything was good. Good value, close to stuff, highly recommend"
Bobbie 1-night trip
Posted 1 hour ago
Hampton Inn & Suites by Hilton Windsor

Find out more about Windsor

Windsor Cottages information

Number of reviews
89
Accommodation
41 Cottages
Lowest Price
€256
Highest Price
€356

Frequently asked questions

Why book your cottage in Windsor with Expedia?
Booking a cottage in Windsor is as easy as deciding on your travel dates and selecting an ideal place for outdoor relaxation and recreation. From luxurious retreats to low-cost properties and cottages that offer amenities like a kitchenette, Expedia has something for all tastes and styles. As for epic deals? We've got them too!
How can I find cheap cottages in Windsor?
With Expedia's handy filter tool, comparing cheap cottages in Windsor is a snap. To discover accommodation that are friendly on the wallet, refine your search by budget, star rating and amenities.
What is there to do in Windsor near my cottage?
Windsor has enough experiences and sights to keep you on the go for weeks, beginning with Detroit Windsor Tunnel. Caesars Casino, Caesars Windsor and Adventure Bay Family Water Park are other awesome attractions. If you're lingering longer, Ambassador Bridge and Windsor Riverfront will round off your itinerary nicely.