Windsor Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    Learn about One Key
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Windsor

Station Chêne Rouge
Terrace/patio
Station Chêne Rouge
2.5 star property
9.8 out of 10, Exceptional, (43)
"my stay was so quiet and great for my dog. Getting back to nature was lovely. "
The price is $94
$177 total
includes taxes & fees
Jun 17 - Jun 18
Station Chêne Rouge
Condos Hôtel Lion D'or
Front of property
Condos Hôtel Lion D'or
3.5 star property
7.6 out of 10, Good, (158)
"Very good but they could have an elevator."
Condos Hôtel Lion D'or
Sherby Prestige / King Bed / Central / Sleeps 6
Fridge, microwave, oven, stovetop
Sherby Prestige / King Bed / Central / Sleeps 6
9.2 out of 10, Wonderful, (7)
"Nous avons apprécié la visite à Sherbrooke"
Sherby Prestige / King Bed / Central / Sleeps 6
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Dynamite 2-Bedroom House WiFi Garage Sleeps 6
Fridge, microwave, oven, stovetop
Dynamite 2-Bedroom House WiFi Garage Sleeps 6
9.4 out of 10, Exceptional, (22)
"We had a fantastic time exploring Sherbrooke and Vlad's space was exactly as listed!"
The price is $109
$247 total
includes taxes & fees
Jun 16 - Jun 17
Dynamite 2-Bedroom House WiFi Garage Sleeps 6
Private Cottage near Magog , Mont Orford & Lake Memphremagog
Exterior
Private Cottage near Magog , Mont Orford & Lake Memphremagog
9.6 out of 10, Exceptional, (17)
"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
Montagnard-SPA-Mont-Orford-SEPAQ-Wood fireplace
Outdoor spa tub
Montagnard-SPA-Mont-Orford-SEPAQ-Wood fireplace
8.6 out of 10, Excellent, (9)
"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 $90
$202 total
includes taxes & fees
Jun 16 - Jun 17
Montagnard-SPA-Mont-Orford-SEPAQ-Wood fireplace
Near Mount Orford - Pool - Spa - Le Paruline
Interior
Near Mount Orford - Pool - Spa - Le Paruline
10.0 out of 10, Exceptional, (3)
"Nous avons passé une magnifique fin de semaine. La montagne est tout près. Le chalet est accueillant."
Near Mount Orford - Pool - Spa - Le Paruline
Hôtel à la maison - Chalet-Condo à la montagne (#5) avec spa
Outdoor dining
Hôtel à la maison - Chalet-Condo à la montagne (#5) avec spa
9.4 out of 10, Exceptional, (6)
"Tous ce qui était indiquer"
Hôtel à la maison - Chalet-Condo à la montagne (#5) avec spa
Perfect for family vacation, golf or ski getaway!
Exterior
Perfect for family vacation, golf or ski getaway!
10.0 out of 10, Exceptional, (3)
"Nice location, clean apartment easy to check in and out. Thank you."
Perfect for family vacation, golf or ski getaway!
Le Cocoon 5 minutes from Mont Orford and Magog
Property grounds
Le Cocoon 5 minutes from Mont Orford and Magog
10.0 out of 10, Exceptional, (2)
"Bel endroit. Bien situé. Confortable. Propre."
The price is $79
$218 total
includes taxes & fees
Jun 16 - Jun 17
Le Cocoon 5 minutes from Mont Orford and Magog
The Rustic (Mont-Orford)
3 bedrooms, WiFi, bed sheets
The Rustic (Mont-Orford)
10.0 out of 10, Exceptional, (1)
"This cute chalet was close to many outdoor activities (skiing, hiking, etc) as well as town. The house itself was very comfortable and worked well for us. I’d definitely stay again."
The price is $114
$260 total
includes taxes & fees
Jun 20 - Jun 21
The Rustic (Mont-Orford)
Access to the river - Spa - Inground pool - Domaine du Bassin 22
Fridge, microwave, oven, stovetop
Access to the river - Spa - Inground pool - Domaine du Bassin 22
9.6 out of 10, Exceptional, (35)
"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
The Jackrabbit (Mount Orford)
Property grounds
The Jackrabbit (Mount Orford)
9.4 out of 10, Exceptional, (3)
"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 $171
$336 total
includes taxes & fees
Jul 1 - Jul 2
The Jackrabbit (Mount Orford)
Hôtel à la maison - Chalet Les Saisons
Fridge, microwave, oven, stovetop
Hôtel à la maison - Chalet Les Saisons
9.4 out of 10, Exceptional, (3)
"Everything was as stated"
Hôtel à la maison - Chalet Les Saisons
A favorite chalet in Orford
Interior
A favorite chalet in Orford
9.6 out of 10, Exceptional, (14)
"Notre fin de semaine entre amies s'est déroulé à merveille dans ce chalet propre et confortable."
The price is $188
$324 total
includes taxes & fees
Jul 14 - Jul 15
A favorite chalet in Orford
Hôtel à la maison - La Cozy Casa
TV, fireplace
Hôtel à la maison - La Cozy Casa
8.0 out of 10, Very Good, (2)
"The place was comfortable, clean, nicely decorated and in a beautiful location. "
Hôtel à la maison - La Cozy Casa
Hotel à la maison - Chalet les Vacances, spa et foyer
Property grounds
Hotel à la maison - Chalet les Vacances, spa et foyer
10.0 out of 10, Exceptional, (4)
"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
Hôtel à la maison - La Cima
Fridge, microwave, oven, stovetop
Hôtel à la maison - La Cima
10.0 out of 10, Exceptional, (5)
"Beau condo très lumineux, tout neuf, je recommande fortement."
Hôtel à la maison - La Cima
Le P'tit St-François
Pool
Le P'tit St-François
10.0 out of 10, Exceptional, (13)
"Friendly owner, clean property"
Le P'tit St-François
Chalet Lac Magog
Property grounds
Chalet Lac Magog
10.0 out of 10, Exceptional, (2)
"Well located, the cottage offered everything we were hoping for. We all enjoy the peacefulness time. Highly recommended."
Chalet Lac Magog
Don't see what you're looking for?
See all available properties in Windsor
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
Reception
OTL Gouverneur Sherbrooke
5.0 star property
9.6 out of 10, Exceptional, (1341)
"Wonderful breakfast and very clean "
The price is $152
$181 total
includes taxes & fees
Jun 23 - Jun 24
OTL Gouverneur Sherbrooke
Hôtel Chéribourg
Exterior
Hôtel Chéribourg
4.0 star property
8.0 out of 10, Very Good, (1248)
"Classic 70's. Please check with the resort if accessability is a concern. Beautiful natural surroundings. 2 pools. Loved the outdoor pool and wonderful trees. I would return. "
The price is $93
$116 total
includes taxes & fees
Jun 24 - Jun 25
Hôtel Chéribourg
Manoir des Sables Hôtel & Golf
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers
Manoir des Sables Hôtel & Golf
4.0 star property
8.0 out of 10, Very Good, (1001)
"Nice stay, but the property needs a little TLC, especially in the back patio/hot tub area. The outdoor hot tub is in some disrepair, not “hot”, and unclean. "
The price is $100
$124 total
includes taxes & fees
Jun 30 - Jul 1
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.

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation 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 low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $79 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation 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 vacation.

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.

Frequently asked questions

Are there vacation rentals in Windsor?

Yes, we give you a choice of vacation rentals near popular local attractions in Windsor, or you can select a more remote option if you're looking for a relaxing stay.

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

Dynamite 2-Bedroom House WiFi Garage Sleeps 6: You might want to consider this vacation home rental near Windsor, which 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 larger area, you’ll find le Parc Historique de la Poudriere de Windsor and Sherbrooke Exhibition Center.

What’s a vacation rental in Windsor like?

Vacation rentals are privately owned properties you can book for a long or short time in Windsor. Vacation rentals offer extras like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can provide a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for a family trip.

Recent reviews of Windsor properties
Expedia verified reviews

Estrimont

Estrimont

5/5 Excellent
Beau séjour sauf souper décevant
"Chambre tres propre et lit confortable. Les bains sont vraiment un gros plus (sauna, spa, piscine ext. chauffée). Le seul point négatif pour nous a été le service au restaurant sur place pour le souper. Il y avait un grand groupe en même temps alors on a eu un service très médiocre et la nourriture(viande) n’était pas à la hauteur de nos attentes pour le prix payé. J’y retournerais certainement mais sans manger au restaurant sur place."
A verified traveler stayed at Estrimont
Posted 2 days ago
Estrimont