Windsor Holiday Rentals

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Holiday Rentals in Windsor

Station Chêne Rouge
2.5 star property
9.8 out of 10, Exceptional, 43 reviews
"my stay was so quiet and great for my dog. Getting back to nature was lovely. "
The price is NZ$280
includes taxes & fees
21 Jun - 22 Jun
Station Chêne Rouge
Sherby Prestige / King Bed / Central / Sleeps 6
9.2 out of 10, Wonderful, 7 reviews
"Nous avons apprécié la visite à Sherbrooke"
Sherby Prestige / King Bed / Central / Sleeps 6
Condos Hôtel Lion D'or
3.5 star property
7.6 out of 10, Good, 158 reviews
"Very good but they could have an elevator."
Condos Hôtel Lion D'or
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Dynamite 2-Bedroom House WiFi Garage Sleeps 6
9.4 out of 10, Exceptional, 22 reviews
"We had a fantastic time exploring Sherbrooke and Vlad's space was exactly as listed!"
Dynamite 2-Bedroom House WiFi Garage Sleeps 6
Near Mount Orford - Pool - Spa - Le Paruline
10.0 out of 10, Exceptional, 3 reviews
"Nous avons passé une magnifique fin de semaine. La montagne est tout près. Le chalet est accueillant."
Near Mount Orford - Pool - Spa - Le Paruline
Perfect for family vacation, golf or ski getaway!
10.0 out of 10, Exceptional, 3 reviews
"Nice location, clean apartment easy to check in and out. Thank you."
Perfect for family vacation, golf or ski getaway!
Access to the river - Spa - Inground pool - Domaine du Bassin 22
9.6 out of 10, Exceptional, 35 reviews
"Excellent! We were a group of 10 people (3 families) but could have easily handled 10 more people. Market, diner, fast food, brewery, park were all close by. Visited during the first week in April for the Total Solar Eclipse and location was excellent for it."
Access to the river - Spa - Inground pool - Domaine du Bassin 22
Private Cottage near Magog , Mont Orford & Lake Memphremagog
9.6 out of 10, Exceptional, 17 reviews
"Clean and cozy cottage, very private and well equipped for a short stay away from home. Right next to Mount Orford, it is ideal for those who enjoy hiking."
Private Cottage near Magog , Mont Orford & Lake Memphremagog
The Jackrabbit (Mount Orford)
9.4 out of 10, Exceptional, 3 reviews
"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."
The price is NZ$523
includes taxes & fees
1 Jul - 2 Jul
The Jackrabbit (Mount Orford)
Montagnard-SPA-Mont-Orford-SEPAQ-Wood fireplace
8.6 out of 10, Excellent, 9 reviews
"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...
The price is NZ$308
includes taxes & fees
9 Jun - 10 Jun
Montagnard-SPA-Mont-Orford-SEPAQ-Wood fireplace
À 5 minutes du Mont-Orford ! Avec accès au lac !
9.4 out of 10, Exceptional, 8 reviews
"We had a beautiful stay. The condo was 10 minutes to Mont Orford national park and 10 minutes to Magog. Very private back yard. Especially nice was the expresso machine. Would highly recommend staying at this condo."
À 5 minutes du Mont-Orford ! Avec accès au lac !
Hôtel à la maison - Chalet Les Saisons
9.4 out of 10, Exceptional, 3 reviews
"Everything was as stated"
Hôtel à la maison - Chalet Les Saisons
Hôtel à la maison - Le Fraser
10.0 out of 10, Exceptional, 4 reviews
"This was an amazing property. Excellent, clean, bright and spacious condo, with lots of storage space. Very well laid out!"
Hôtel à la maison - Le Fraser
Hôtel à la maison - La Cozy Casa
8.0 out of 10, Very good, 2 reviews
"The place was comfortable, clean, nicely decorated and in a beautiful location. "
Hôtel à la maison - La Cozy Casa
Hôtel à la maison - Chalet-Condo à la montagne (#5) avec spa
9.6 out of 10, Exceptional, 5 reviews
"The condo was stunning. Everything feels and looks like new!! Very clean and tidy!. We LOVED the patio. Really enjoyed our stay in the area!!"
Hôtel à la maison - Chalet-Condo à la montagne (#5) avec spa
Hotel à la maison - Chalet les Vacances, spa et foyer
10.0 out of 10, Exceptional, 4 reviews
"The cottage is functional and cute but a bit small for 5 adults. It's nice for 2/3 days."
Hotel à la maison - Chalet les Vacances, spa et foyer
A favorite chalet in Orford
9.8 out of 10, Exceptional, 13 reviews
"Notre fin de semaine entre amies s'est déroulé à merveille dans ce chalet propre et confortable."
The price is NZ$505
includes taxes & fees
25 Jun - 26 Jun
A favorite chalet in Orford
Hôtel à la maison - La Cima
10.0 out of 10, Exceptional, 5 reviews
"Beau condo très lumineux, tout neuf, je recommande fortement."
Hôtel à la maison - La Cima
Mont Orford - Spa - Grand-Duc
9.8 out of 10, Exceptional, 18 reviews
"Property was great. We enjoyed the stay!"
Mont Orford - Spa - Grand-Duc
Le Cocoon 5 minutes from Mont Orford and Magog
10.0 out of 10, Exceptional, 2 reviews
"Bel endroit. Bien situé. Confortable. Propre."
The price is NZ$506
includes taxes & fees
23 Jun - 24 Jun
Le Cocoon 5 minutes from Mont Orford and Magog
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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.

Other types of properties in Windsor you may be interested in

OTL Gouverneur Sherbrooke
5.0 star property
9.6 out of 10, Exceptional, 1,328 reviews
"Enjoyed my stay, will definitely come back again"
The price is NZ$293
includes taxes & fees
9 Jun - 10 Jun
OTL Gouverneur Sherbrooke
Hôtel Chéribourg
4.0 star property
8.0 out of 10, Very good, 1,249 reviews
"Very nice little place"
The price is NZ$184
includes taxes & fees
9 Jun - 10 Jun
Hôtel Chéribourg
Manoir des Sables Hôtel & Golf
4.0 star property
8.0 out of 10, Very good, 1,012 reviews
"Nice staff. They answered all my questions"
The price is NZ$200
includes taxes & fees
16 Jun - 17 Jun
Manoir des Sables Hôtel & Golf
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Windsor holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Windsor. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Windsor. Seeing all the best attractions is bound to make you fall in love with Windsor. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Windsor short-term rentals, that won’t be hard to do.

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?

Dynamite 2-Bedroom House WiFi Garage Sleeps 6: This holiday home rental outside of Windsor is located in the mountains, and has a balcony, a garden and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What’s there to see and do in Windsor?

While exploring the area, visit family-friendly sights like Multigolf Sherbrooke, 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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