Windsor Holiday Rentals from €122: 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

"All in all a lovely place. Quiet, private and cozy. Would definitely recommend to a friend!"

includes taxes & fees

5 Jan - 6 Jan

"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

15 Jan - 16 Jan

"This is our 2nd time this year and it did not disappoint us. It is clean, close to facilities and with a garage. Which fantastic before we were there during a snow storm. So we did not have to plow or shovel. It is also pet friendly and doggy recognized the place. So less stress on her. We will go back for sure. We highly recommend this place"

"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 . "

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

"Parfait!"

includes taxes & fees

5 Jan - 6 Jan

"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. "

includes taxes & fees

9 Jan - 10 Jan

"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

5 Jan - 6 Jan

"bel endroit! adoré mon séjour, endroit parfait"

includes taxes & fees

3 Feb - 4 Feb

"La propreté du chalet est excellente, la cuisine est très bien fournie. La laveuse et sècheuse est un atout. La vue du lac est superbe avec le quai pour en profiter au maximum."

"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."

"Bel environnement calme, propriété bien équipée avec les commodités nécessaire aux divers besoins. Le seul point négatif serait qu'une seule salle de toilette, c'est contraignant à 5 personnes. Mais nous demeurons très satisfaits de notre séjour au Paresseux Merci "

"I loved everything about the place was amazing."

"Faucet was clogged but used the other one which was fine , house had a little order but opened windows to air out which helped , felt like was constantly being watched constantly being messaged or she would walk out and talk to us wasn’t relaxing , also was sitting around the fire 2 men and she messaged and called multiple times about the noise when we were being super quiet was uncomfortable. Wouldn’t recommend if privacy is a priority on your get away ."

"We have stayed at this chalet several times now. It is always up to par. Very clean, love the trees and balcony. Will definitely visit again."

"We had a wonderful stay here. The cabin is just as described plus a few extra details you won’t find everywhere - the mattresses are extremely comfortable, the shower has great pressure, and there is an espresso machine! We all enjoyed our time at the cabin and in the area and would absolutely stay again. Thanks!"

"We spent Easter at the Jackrabbit and had a wonderful stay! We really enjoyed the area which was great for our multigenerational family and dog. The chalet is very nice and comfortable. It had everything we needed. We especially loved watching the neighbourhood from the dinning area (as did our dog). We talked about going back in a different season."

"I stayed through most of September and October. The chalet is comfortable and modern, including decent WIFI connection. Excellent, attentive contact from the owner. The community is near Mount Orford so there are lots of relatively small rolling hills that are fun for bicycling and running. Lovely forest trails in the park (only 2 km away), including some very challenging MTB trails. For the less active, there is a quiet park with a small waterfall, pond and forested area about 300 m. down...

"Notre séjour a été parfait. Par contre à notre arrivé, nous avions remarqué que l'eau du spa était jaune. Elle a été vidangé le lendemain. Nous n'avons donc pu l'utiliser cette journée. Le lendemain, (donc hier 4 dec) l eau est linpide mais nous avons pu remarqier que déjà des algues semblaient se former. Pour le reste très beau séjour, à recommander!"

includes taxes & fees

5 Jan - 6 Jan

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Other types of properties in Windsor you may be interested in

"Fantastic. Real 5 stars. Breakfast is incredible "

includes taxes & fees

19 Jan - 20 Jan

"Was quite loud at night but we were here in NYE. Would recommend the property "

includes taxes & fees

5 Jan - 6 Jan

Indoor pool, seasonal outdoor pool, pool umbrellas, pool loungers

"good"

includes taxes & fees

9 Jan - 10 Jan

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 €122 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

"Fantastic. Real 5 stars. Breakfast is incredible "

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 Richmond Art 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.

Members save 10% or more on over 100,000 hotels worldwide when you’re signed in

Holiday Rentals in Windsor

Plan, book, stay with confidence

Check Windsor holiday rental availability

Holiday Rentals in Windsor

Station Chêne Rouge

Station Chêne Rouge

Condo 2 Bedrooms Jardin des Sables

Condo 2 Bedrooms Jardin des Sables

Dynamite 2-Bedroom House WiFi Garage Sleeps 6

Dynamite 2-Bedroom House WiFi Garage Sleeps 6

Condos Hôtel Lion D'or

Condos Hôtel Lion D'or

Access to Lake Brompton - Spa - Pure Évasion

Access to Lake Brompton - Spa - Pure Évasion

Chalet BIA Foyer & Spa

Chalet BIA Foyer & Spa

Mont-Orford - Spa - Buck

Mont-Orford - Spa - Buck

A favorite chalet in Orford

A favorite chalet in Orford

Sherby Prestige / King Bed / Central / Sleeps 6

Sherby Prestige / King Bed / Central / Sleeps 6

Le Cocoon 5 minutes from Mont Orford and Magog

Le Cocoon 5 minutes from Mont Orford and Magog

Le P'tit St-François

Le P'tit St-François

The Rustic (Mont-Orford)

The Rustic (Mont-Orford)

Le Paresseux - 5 min to Mount Orford, 2 minutes away from Ski Orford, fully equipped cottage

Le Paresseux - 5 min to Mount Orford, 2 minutes away from Ski Orford, fully equipped cottage

Access to the river - Spa - Inground pool

Access to the river - Spa - Inground pool

Le Grand-Duc et Vicomte

Le Grand-Duc et Vicomte

Paradise 2, Gorgeous and cozy cottage, perfect for getaways. 2 minutes away from Mount Orford

Paradise 2, Gorgeous and cozy cottage, perfect for getaways. 2 minutes away from Mount Orford

Le Découverte Mont Orford SEPAQ

Le Découverte Mont Orford SEPAQ

The Jackrabbit (Mount Orford)

The Jackrabbit (Mount Orford)

Newly renovated 5 star Chalet only 5 min to Mt Orford! Come ski, hike & bike !

Newly renovated 5 star Chalet only 5 min to Mt Orford! Come ski, hike & bike !

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

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

Other types of properties in Windsor you may be interested in

OTL Gouverneur Sherbrooke

OTL Gouverneur Sherbrooke

Hôtel Chéribourg

Hôtel Chéribourg

Manoir des Sables Hôtel & Golf

Manoir des Sables Hôtel & Golf

Find out more about Windsor

Find out more about Windsor

Recent reviews of Windsor properties

Recent reviews of Windsor properties

OTL Gouverneur Sherbrooke

Frequently asked questions