Search Cottages in Windsor

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Cottages in Windsor

The NEST-an upscale beach cottage in Holiday Beach Conservation Area

9.8 out of 10, Exceptional, (147)
"Fantastic location. Felt like we had the entire park to ourselves. Gorgeous cottage inside and out. Very well stocked. Only 45 minutes from Windsor. "
The NEST-an upscale beach cottage in Holiday Beach Conservation Area

Lakefront 2 Bedroom Cottage For Rent

9.2 out of 10, Wonderful, (18)
"The cottage was VERY nice 🙂 great location - beautiful view of the water- will return for sure"
Lakefront 2 Bedroom Cottage For Rent

Beautiful, clean cottage, 4 min walk to the beach/playground. Many wineries!

9.8 out of 10, Exceptional, (127)
"Very modern, well taken care of, has everything you need, great location and views of lake"
Beautiful, clean cottage, 4 min walk to the beach/playground. Many wineries!

Unique Space - Beautiful home on 17th green of golf resort

10.0 out of 10, Exceptional, (1)
"I enjoyed my stay. Very quiet area, I loved it"
Unique Space - Beautiful home on 17th green of golf resort

Sippin' & Stylin' in Wine Country!

9.8 out of 10, Exceptional, (7)
"Beautiful cottage and excellent host! We had a great time visiting friends in the area and enjoyed staying here! Would definitely recommend!"
Sippin' & Stylin' in Wine Country!

Relaxing lakefront cottage near wineries and beach

10.0 out of 10, Exceptional, (24)
"This property is in a perfect location. The view was great. Loved the layered decking. The house was super clean. I would highly recommend staying at Heritage on the Rocks. "
Relaxing lakefront cottage near wineries and beach

The Hideaway- Lake view Cottage In Wine Country

10.0 out of 10, Exceptional, (62)
"There was absolutely nothing that this cottage didn't have Hosts thought of everything comfortable bed too"
The Hideaway- Lake view Cottage In Wine Country

Pelican Place ❤️ WALK EVERYWHERE! Your home away from home...

10.0 out of 10, Exceptional, (18)
"Booked for a short weekend trip in the area - solid location, very cute house, and pretty well represented by the pictures on the listing. Host was extremely pleasant and was very accommodating, would absolutely stay here again!"
Pelican Place ❤️ WALK EVERYWHERE! Your home away from home...

Cozy canal cottage on Cedar Island steps away from sandy Lake Erie beaches!!!!!!

9.8 out of 10, Exceptional, (14)
"The stay was amazing the area was great for kids. People on the island all seemed very nice . We will definitely be back 👍😁"
Cozy canal cottage on Cedar Island steps away from sandy Lake Erie beaches!!!!!!

Lake front escape - a quiet lake front cottage with easy access to the beach

9.6 out of 10, Exceptional, (103)
"House is clean, modern and well kept. Right next to beach which is very convenient. Coming in June was not prepared for the may flies. They do not bite but are annoying. BBQ in excellent shape. Hosts were great with communication. Rooms are great especially the master bedroom."
Lake front escape - a quiet lake front cottage with easy access to the beach

Colchester cottages a stones throw away from beaches, wineries, marina, parks.

9.8 out of 10, Exceptional, (18)
"We had a great stay. Excellent location! Friendly owner. The kids really enjoyed it. We will be back!"
Colchester cottages a stones throw away from beaches, wineries, marina, parks.

Drifted Inn - Riverfront Cabin

9.8 out of 10, Exceptional, (119)
"We had such a wonderful time at our stay in Amherstburg. It is a great location, cute little cottage."
Drifted Inn - Riverfront Cabin

Anchor down on your private Beachfront Cottage

10.0 out of 10, Exceptional, (11)
"Very comfortable, clean and well appointed. Supplied with all we needed. Tessa was always fast to respond to our needs. A perfect getaway for a few days."
The price is SAR 537
SAR 1,389 total
includes taxes & fees
5 Oct - 6 Oct
Anchor down on your private Beachfront Cottage

Spacious Cheerful home with 2 free parking

Spacious Cheerful home with 2 free parking

Colchester cottages a stones throw away from beaches, wineries, marina, parks.

9.4 out of 10, Exceptional, (3)
"Had a great time. Needed a couple items for the kitchen that were missing, but folks next door were able to grab the items for us from another cottage which was helpful. Cottage was clean and the chalk board was a nice touch. Disappointed there was construction so we could not bike to the wineries but in the end it all worked out anyway. thanks!"
Colchester cottages a stones throw away from beaches, wineries, marina, parks.

"That 70's Cottage" (on Lake Erie!) Free Firewood!

"That 70's Cottage" (on Lake Erie!) Free Firewood!

Special Jul 17-25, CD 200/Per night, Cedar Island Marina ,New HAVC & Renovated

8.6 out of 10, Excellent, (44)
"Our family had a wonderful vacation at this cottage on Cedar Island. The location is great! Dealing with the property manager Jamie was friendly and easy. All questions were answered promptly. Overall a fantastic time was had by all. Thank you so much Jamie!"
Special Jul 17-25, CD 200/Per night, Cedar Island Marina ,New HAVC & Renovated

Lake Erie & EPIC Wineries

10.0 out of 10, Exceptional, (25)
"Amazing get away very clean and close to everything "
Lake Erie & EPIC Wineries

Nature Oasis: Waterfront, pet friendly, kayaks, SUPs, dock, amenities galore

9.8 out of 10, Exceptional, (18)
"House was clean, comfortable, was in a great location for our needs and the owners were very accommodating. There were 6 of us that were in town for the weekend for a wedding and the 3 bedroom, 3 bath home was exactly what we needed. I would stay here again in a heartbeat. It seems like there is plenty to do related to the lake if you have the time for that. "
Nature Oasis: Waterfront, pet friendly, kayaks, SUPs, dock, amenities galore

Tranquil Kingsville Cottage - Private Beach & Pet-Friendly!

8.0 out of 10, Very Good, (4)
"With four bedrooms, two bathrooms, large kitchen, family room and lots of amenities, this was the perfect spot for a family vacation at the beach."
Tranquil Kingsville Cottage - Private Beach & Pet-Friendly!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Windsor Hotel Reviews

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 accommodations that are friendly on the wallet, refine your search by budget, star rating and amenities.