Windsor Holiday Rentals from €148: Search Short-Term Rentals

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

Condo 2 Bedrooms Jardin des Sables : This holiday home rental outside of Windsor is located next to a golf course, and has a fireplace, a private balcony and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop.

Check Windsor holiday rental availability

Holiday Rentals in Windsor

"Rustic cabin. Hard to navigate in the dark and but pricey but overall great stay."

includes taxes & fees

10 Dec - 11 Dec

"There was a coffee machine but no coffee would have been nice to have a little coffee for the morning. The tv’s need to changed they are very old not smart tv’s and the picture on the tv is very poor. But as for the place was spacious clean and would stay again. Would be nice if they make the upgrades "

includes taxes & fees

2 Dec - 3 Dec

"This is the second time we’ve stayed here. It is clean, modern, and well equipped. We will stay here again if we can on our next trip to Sherbrooke. "

includes taxes & fees

27 Nov - 28 Nov

"Hiked, walked, shopped, even swam in a local lake. House was very clean and easy to get to. "

"Overall good . Some repairs needed in bathroom . The office was closed . We had to buy remotes for the tv we were told we would be reimbursed but that didn’t happen . However , the condo we rented overall was not bad . "

"Nice chalet next to a lot of local attractions. Memphrémagog lake was a 10 minutes drive. Chalet is cozy. My only downside would be the beds. I have a bad back and the beds were not as comfortable as I'm used to.. besides that great experience overall."

"Everything was good. We loved our stay and would definitely return if the opportunity presents itself"

"At first I was taken aback by the odd exterior (you need to go pretty far down the photos to see it, but the inside is very nice, nice kitchen extremely well stocked with pots, pans, tableware, espresso maker,drawer full of spices, lots of counter space. The living/dining room is nice too, as are the upstairs bedrooms. The area is peaceful, but we didn't use the yard which is small and hemmed in by woods and neighbors. Some of the "common area" photos are from elsewhere, like the dock with water...

"We recently stayed for three nights at this cabin (two adults, two teens and a dog) for a ski trip. As some others have indicated, the main area/first floor is small. The pictures show a sectional but when we visited there was only one couch and it is only big enough for 3 people so one of us had to sit on a chair to watch TV. The bedrooms (1 private room with a door, other bed is in loft area) are very good size. I would not recommend for families with small children or anyone with mobility...

includes taxes & fees

22 Dec - 23 Dec

"We had a great stay. This property was perfect for our family of 4 - two adults and two young boys. We had a blast with all to do in the area. It was so close to the ski hill and National park. We got a day of downhill as well as Nordic skiing in. So friendly and easy for kids/families to rent equipment and navigate the area. We will definitely stay again. Oh! And the hot tub was a plus!"

includes taxes & fees

25 Dec - 26 Dec

"Get condo , clean, very confortable beds, great kitchen."

"Cette établissement offre 3 chambres Fermées et une quatrième dans la mezzanine, ce qui a permis à chacun d’avoir de l’intimité. La cuisine avait plus que le nécessaire pour pouvoir y travailler. À noter qu’il y avait une machine Keurig et un nespresso dans les armoires. Le propriétaire répond rapidement lorsque nous le contactons! "

"Everything was perfect, although the living room furniture could be a little more comfortable. Maybe they were going for the look over the actual comfort?... Otherwise it was perfect."

"Tous ce qui était indiquer"

"Tout était impeccable. Comme ancien rénovateur je dirais que la porte de la salle de bain de la grande chambre aurait besoin d’un coup de rabot pour bien fermer."

"Tout était là comme l’annonce le décrivait. "

"The shack has all the needed comfort! My wife an myself have spent 2 weeks enjoying nature, trees and mountains! I was able to work during the day with a very good internet connection and we have been visiting Sherbrooke, Magog and Orford! The owners have been present whenever we had a question!"

"We enjoyed our time staying there. Just having a little struggle with the agent from property management as we decided to bring a 3 children(3,4 and 10 yrs old) along with us. But they strictly would not accommodate us. So if you would bring a 4-year old and up with you, he/she will be consider an adult. "

"Notre fin de semaine entre amies s'est déroulé à merveille dans ce chalet propre et confortable."

"Nous sommes restés 3 nuits. Lit confortable, pas vraiment profité du reste de l’appartement car nous avions de longues journées à l’extérieur. Logement au dessus d’un dépanneur mais n’est pas un problème. Généralement propre. Petit bémol, assez de poussière sur les moulures, spécialement dans la salle de bain ce qui n’est pas super."

includes taxes & fees

27 Nov - 28 Nov

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"This is our second time at the OTL and we absolutely loved it , very clean, friendly staff, enjoyed the morning breakfast it was very good. I would definitely recommend and definitely would return."

includes taxes & fees

15 Dec - 16 Dec

"Breakfast was perfect and have some choices. For the price with the breakfast, the room price is good. "

includes taxes & fees

25 Dec - 26 Dec

"Overall very good"

includes taxes & fees

28 Nov - 29 Nov

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as €148 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Recent reviews of Windsor properties

5/5 Excellent

"This is our second time at the OTL and we absolutely loved it , very clean, friendly staff, enjoyed the morning breakfast it was very good. I would definitely recommend and definitely would return."

A verified traveller stayed at OTL Gouverneur Sherbrooke

Posted 1 day ago

Frequently asked questions

Are there holiday rentals 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.

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

Condo 2 Bedrooms Jardin des Sables: This holiday home rental outside of Windsor is located next to a golf course, and has a fireplace, a private balcony and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop.

What’s there to see and do in Windsor?

While exploring the area, visit family-friendly sights like Musee de la Nature et des Sciences, or get outside and enjoy nature at Jacques-Cartier Park. In the wider area, you’ll find le Parc Historique de la Poudriere de Windsor and Sherbrooke Exhibition Center.

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 offer extras such as patios, hot tubs and fire pits to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for families.

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Holiday Rentals in Windsor

Check Windsor holiday rental availability

Holiday Rentals in Windsor

Station Chêne Rouge

Condo 2 Bedrooms Jardin des Sables

Dynamite 2-Bedroom House WiFi Garage Sleeps 6

Woodpecker, Spa,Foyer,Bike,Ski!

Condos Hôtel Lion D'or

The Rustic (Mont-Orford)

Access to Lake Brompton - Spa - Pure Évasion

Le Découverte Mont Orford SEPAQ

Montagnard-SPA-Mont-Orford-SEPAQ-Wood fireplace

Échappée Belle Spa Orford

Condo Neuf a Orford !

Near Mount Orford - Pool - Spa - Le Paruline

Hôtel à la maison - Le Bowker

Hôtel à la maison - Havre en montagne & spa privé

Perfect for family vacation, golf or ski getaway!

Hôtel à la maison - La Petite Échappée avec spa

Paradise, Spacious and Family friendly Cottage, fully equipped. Tons of activities

Mont-Orford - Spa - Buck

A favorite chalet in Orford

Sherby Prestige / King Bed / Central / Sleeps 6

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Find out more about Windsor

Recent reviews of Windsor properties

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Frequently asked questions