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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Windsor holiday rentals

Exterior
Brook Road Cabin

Brook Road Cabin

3.5 star property
Goshen
7.8 out of 10, Good, (9)
"In the aftermath of 30+” of snow we dug out and sought a new location with power and hot showers. How blessed we were to find this gem. A point of refuge and some much needed R&R. Cabin was quaint, warm, and comfortable, and the host was attentive and welcoming. Thank you for this port in the storm. 😊"
United States
Jill
Brook Road Cabin
Comfort Townhome | Private kitchen | Full-sized fridge, microwave, oven, stovetop
Brook Road Condo

Brook Road Condo

3.0 star property
Goshen
8.8 out of 10, Excellent, (3)
"Convenient location, quiet and rural. Accommodations were clean and neat. Nice to have full kitchen for meal prep and snacks."
United States
Margaret
The price is ฿5,474
฿9,115 total
includes taxes & fees
15 Dec - 16 Dec
Brook Road Condo
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

Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)

10/10 Excellent
"The room had extra amenities besides a Keurig, refrigerator, and microwave. These included make-up removal wipes, hand lotion, and seasonal decor plus a working desk and dining table. The owners of Riverhouse also equipped the lobby with coffee and tea, mini bagels with butter and cream cheese, granola bars, fresh fruit, and yogurt. Brochures of local attractions were on display. The friendly owners of Riverhouse made me feel right at home! Thank you!"
Amanda 2-night trip
Posted 22 hours ago
Riverhouse by Weekender (Formerly Jack Daniels Inn)

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

Frequently asked questions

Can I find a holiday rental in Windsor?

Yes, there are holiday rentals close to the most popular sights in Windsor, or you can select a more secluded option if you're looking for a relaxing stay.

How many holiday rentals will I find in Windsor?

Expedia has 5 holiday rentals for your stay in Windsor.

What’s there to see and do in Windsor?

Explore the area and family-friendly sights such as Eaton's Magic Morsel, or get out into nature at a spot like Black Pond. In the wider area, you’ll find Windsor Town Hall and Franklin Pierce Homestead.

What’s a holiday rental in Windsor like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Windsor. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a family trip.