Default HTG hotel image

Windsor Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Windsor holiday rentals

1. Fully equipped apartments with 1 bedroom, onsuite in our century-old residence.

Fully equipped apartments with 1 bedroom, onsuite in our century-old residence.
Richmond
10.0 out of 10, Exceptional, (2 reviews)
"Amazing host and comfortable space. "
Canada
Paul F.
The price is NZ$221
includes taxes & fees
14 Dec - 15 Dec
Fully equipped apartments with 1 bedroom, onsuite in our century-old residence.

2. Downtown Sherby: Central, Parking, King Bed, Sleeps 3

Downtown Sherby: Central, Parking, King Bed, Sleeps 3
Le Mont-Bellevue
8.4 out of 10, Very good, (11 reviews)
"Efficient apartment for a stay close to down town Sherbrooke, where hotels can be expensive. "
Canada
Jana
The price is NZ$341
includes taxes & fees
14 Dec - 15 Dec
Downtown Sherby: Central, Parking, King Bed, Sleeps 3

3. Entire unit with private Entrance in Sherbrooke

Entire unit with private Entrance in Sherbrooke
Fleurimont
8.0 out of 10, Very good, (4 reviews)
"Great location. Good connection with buses. Quiet. Nice appliances. Strong perfume fragrances which is difficult for me. Grateful to have had this apartment however. Enjoyed my stay."
United States
Dorothy Jo L.
The price is NZ$261
includes taxes & fees
3 Dec - 4 Dec
Entire unit with private Entrance in Sherbrooke

4. Fully equipped apartment with 2 bedrooms in our century-old residence.

Fully equipped apartment with 2 bedrooms in our century-old residence.
Richmond
10.0 out of 10, Exceptional, (2 reviews)
"The Gite Richmond Inn is absolutely wonderful! Krystal makes sure everything is ok with your stay & communication was excellent & easy. The house is clean, quiet & absolutely beautiful! If you love old houses definitely stay in Richmond here."
United States
Jill B.
The price is NZ$356
includes taxes & fees
20 Nov - 21 Nov
Fully equipped apartment with 2 bedrooms in our century-old residence.

5. Boutique Studio, Spa Bath & Parking, Sleeps 2

Boutique Studio, Spa Bath & Parking, Sleeps 2
Le Mont-Bellevue
10.0 out of 10, Exceptional, (3 reviews)
"This was a beautifully appointed studio apartment with a larger separate unit above it. It was perfect for two people and had everything we needed. The heated bathroom floor was a bonus as was the large bathtub! Vlad is a great host and was responsive to a couple of questions we had upon arrival. The unit is easy to access and there are many amenities within a mile including a grocery store and gas station. I highly recommend this studio if you need accommodations in the area. We never...
United States
Leslie M.
Boutique Studio, Spa Bath & Parking, Sleeps 2

6. Mi-Clos

Mi-Clos
2.0 star property
Orford
10.0 out of 10, Exceptional, (31 reviews)
"Amazing stay !"
Canada
Frederik
The price is NZ$492
includes taxes & fees
17 Nov - 18 Nov
Mi-Clos

7. Charming Apartment in a Historic Building

Charming Apartment in a Historic Building
Le Mont-Bellevue
9.6 out of 10, Exceptional, (5 reviews)
"La communication s’est très bien passé avec les hôtes. L’arrivée était surprenante. Il faut montrer deux étages d’escalier extérieurs. Les lumières automatiques ne sont pas bien réglées dans le sens où il faut déjà avoir les pieds sur les marches pour que ça s’allume. Une fois en haut, il est difficile de faire le code parce qu’il n’y a plus d’éclairage. Bel appartement quoique un peu cher. Cuisine fonctionnel, lits confortables et salon cosy. Les lieux étaient propres. Je recommande...
Canada
Lorraine
The price is NZ$341
includes taxes & fees
13 Dec - 14 Dec
Charming Apartment in a Historic Building

8. Dynamite 2-Bedroom House WiFi Garage Sleeps 6

Dynamite 2-Bedroom House WiFi Garage Sleeps 6
Le Mont-Bellevue
9.4 out of 10, Exceptional, (60 reviews)
"Clean, bright space with ample room in the bedrooms. Lovely, well-appointed bathroom. I'd definitely stay there again."
Canada
Kerry
The price is NZ$435
includes taxes & fees
19 Nov - 20 Nov
Dynamite 2-Bedroom House WiFi Garage Sleeps 6

9. Chalet BIA Foyer & Spa

Chalet BIA Foyer & Spa
Asbestos
9.6 out of 10, Exceptional, (14 reviews)
"Good overall stay, the outside area would benefit some upkeep,very comfortable beds, and main area, would go back,"
United States
Linda R.
The price is NZ$313
includes taxes & fees
15 Nov - 16 Nov
Chalet BIA Foyer & Spa

10. Sherby LUX: Central, Parking, Renovated, Sleeps 6

Sherby LUX: Central, Parking, Renovated, Sleeps 6
Le Mont-Bellevue
9.8 out of 10, Exceptional, (8 reviews)
"clean, good amenities, and parking"
Canada
Jeff
The price is NZ$374
includes taxes & fees
15 Nov - 16 Nov
Sherby LUX: Central, Parking, Renovated, Sleeps 6

11. Chalet BIA - Cap au Sud

Chalet BIA - Cap au Sud
Saint-Rémi-de-Tingwick
10.0 out of 10, Exceptional, (2 reviews)
"Endroit agréable et paisible."
Canada
François A.
The price is NZ$468
includes taxes & fees
8 Dec - 9 Dec
Chalet BIA - Cap au Sud

12. Aux Berges du Pont Suspendu - Grand Lac Brompton

Aux Berges du Pont Suspendu - Grand Lac Brompton
Saint-Denis-de-Brompton
9.8 out of 10, Exceptional, (8 reviews)
"This space is very cozy and was perfect for our little family getaway (3 of us). Thanks to the hosts!"
Canada
Beverly M.
The price is NZ$1,163
includes taxes & fees
22 Nov - 23 Nov
Aux Berges du Pont Suspendu - Grand Lac Brompton

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

Montagnard-SPA-Mont-Orford-SEPAQ-Wood fireplace
Orford
9.0 out of 10, Wonderful, (31 reviews)
"Lovely time with our dogs in a lovely, peaceful, and perfectly located chalet. Quiet, close to Magog, cute coffee places, i fully recommend !"
Canada
Priscilla G.
The price is NZ$324
includes taxes & fees
15 Nov - 16 Nov
Montagnard-SPA-Mont-Orford-SEPAQ-Wood fireplace

14. Sherby Prestige / King Bed / Central / Sleeps 6

Sherby Prestige / King Bed / Central / Sleeps 6
Le Mont-Bellevue
8.4 out of 10, Very good, (28 reviews)
"The place is really clean but the neighborhood is special, let say that people were screaming outside until 3-4am. There's also a constant water sound in the bedrooms coming from the water heating system. Bring earplugs."
Canada
Maxime
The price is NZ$454
includes taxes & fees
14 Dec - 15 Dec
Sherby Prestige / King Bed / Central / Sleeps 6

15. Spa et Accès au Lac Magog

Spa et Accès au Lac Magog
Sherbrooke
The price is NZ$814
includes taxes & fees
15 Nov - 16 Nov
Spa et Accès au Lac Magog

16. The Jackrabbit (Mount Orford)

The Jackrabbit (Mount Orford)
Orford
8.8 out of 10, Excellent, (12 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."
Canada
Zara M.
The price is NZ$401
includes taxes & fees
22 Nov - 23 Nov
The Jackrabbit (Mount Orford)

17. Magnificent Condo in Au Coeur d'Orford

Magnificent Condo in Au Coeur d'Orford
Orford
8.0 out of 10, Very good, (2 reviews)
"Très tranquille."
United States
Eugénie P.
The price is NZ$419
includes taxes & fees
15 Nov - 16 Nov
Magnificent Condo in Au Coeur d'Orford

18. Access to the river - Spa - Inground pool

Access to the river - Spa - Inground pool
Cookshire-Eaton
8.8 out of 10, Excellent, (5 reviews)
"Bel emplacement, mais route très passante à proximité et très proche d’un bâtiment de type industriel Aucune chaises longues au bord de la piscine Chaises autour de la table extérieure peu confortables Les problèmes de SPA et de branchement aux télévisions n’étaient toujours pas réglés au moment de notre départ"
United States
Claude J.
The price is NZ$888
includes taxes & fees
15 Nov - 16 Nov
Access to the river - Spa - Inground pool

19. Access to the river - Spa - Inground pool

Access to the river - Spa - Inground pool
Cookshire-Eaton
9.6 out of 10, Exceptional, (47 reviews)
"This place was absolutly awsom."
United States
Paulin T.
The price is NZ$1,805
includes taxes & fees
15 Nov - 16 Nov
Access to the river - Spa - Inground pool
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Windsor Hotel Reviews

Find out more about Windsor

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?

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 Multigolf Sherbrooke, or get outside and enjoy nature at Magog River Gorge. 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.