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Windsor Holiday Rentals

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Our top choices for Windsor holiday rentals

1. Station Chêne Rouge

Station Chêne Rouge
2.5 star property
Hatley
9.6 out of 10, Exceptional, (106 reviews)
"Great staff , well kept and clean property , exactly as advertised ! Loved being able to have our dog with us as well :) would definitely return ! So quiet and relaxing"
Canada
Kevin
The price is NZ$255
includes taxes & fees
30 Sept - 1 Oct
Station Chêne Rouge

2. 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$233
includes taxes & fees
18 Oct - 19 Oct
Fully equipped apartments with 1 bedroom, onsuite in our century-old residence.

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

Downtown Sherby: Central, Parking, King Bed, Sleeps 3
Le Mont-Bellevue
8.2 out of 10, Very good, (10 reviews)
"Efficient apartment for a stay close to down town Sherbrooke, where hotels can be expensive. "
Canada
Jana
The price is NZ$325
includes taxes & fees
1 Oct - 2 Oct
Downtown Sherby: Central, Parking, King Bed, Sleeps 3

4. 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$448
includes taxes & fees
30 Sept - 1 Oct
Dynamite 2-Bedroom House WiFi Garage Sleeps 6

5. Entire unit with private Entrance in Sherbrooke

Entire unit with private Entrance in Sherbrooke
Fleurimont
8.8 out of 10, Excellent, (3 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$250
includes taxes & fees
1 Oct - 2 Oct
Entire unit with private Entrance in Sherbrooke

6. Chalet BIA Foyer & Spa

Chalet BIA Foyer & Spa
Asbestos
9.6 out of 10, Exceptional, (13 reviews)
"Très bien et très convivial. Très propre "
Canada
Patrick
The price is NZ$345
includes taxes & fees
1 Oct - 2 Oct
Chalet BIA Foyer & Spa

7. Le Cleveland, Bord de l`eau, Foyer, Spa

Le Cleveland, Bord de l`eau, Foyer, Spa
Cleveland
10.0 out of 10, Exceptional, (1 review)
"We've spent 2 days in paradise. It was a splendid location, extremely quiet, and the cabin had everything you need to make your journey very special. If you like nature, that's the best place to stay in the region. The description was fairly accurate, except for a couple of things. There is only 1 bathroom, not 2 as it says on the Expedia website. When we made the reservation, the website also said 3 bedrooms (has there been an error which was then corrected ?), but there was two bedrooms, which...
Canada
Claire
Le Cleveland, Bord de l`eau, Foyer, Spa

8. Charming apartment in heritage home

Charming apartment in heritage home
Le Mont-Bellevue
10.0 out of 10, Exceptional, (4 reviews)
"Cute place. Did not love the location."
United States
Nikki H.
The price is NZ$309
includes taxes & fees
12 Oct - 13 Oct
Charming apartment in heritage home

9. 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$405
includes taxes & fees
30 Sept - 1 Oct
Chalet BIA - Cap au Sud

10. 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$366
includes taxes & fees
14 Oct - 15 Oct
Fully equipped apartment with 2 bedrooms in our century-old residence.

11. Mi-Clos

Mi-Clos
2.0 star property
Orford
10.0 out of 10, Exceptional, (29 reviews)
"Amazing stay !"
Canada
Frederik
The price is NZ$518
includes taxes & fees
15 Oct - 16 Oct
Mi-Clos

12. 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$417
includes taxes & fees
20 Oct - 21 Oct
Sherby LUX: Central, Parking, Renovated, Sleeps 6

13. Waterfront cottage with spa, lots of activities nearby

Waterfront cottage with spa, lots of activities nearby
Saint-Rémi-de-Tingwick
9.0 out of 10, Wonderful, (2 reviews)
"Well-equipped and very clean home. We were very comfortable and had a wonderful stay. "
Canada
CAM Wizard, LLC
The price is NZ$578
includes taxes & fees
30 Sept - 1 Oct
Waterfront cottage with spa, lots of activities nearby

14. 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$436
includes taxes & fees
18 Oct - 19 Oct
The Jackrabbit (Mount Orford)

15. Le Cocoon 5 minutes from Mont Orford and Magog

Le Cocoon 5 minutes from Mont Orford and Magog
Orford
8.4 out of 10, Very good, (11 reviews)
"10 mins from mont orford, close to other hills.Comfortable, quiet, peaceful location. No TV channels available however"
Canada
steve b.
The price is NZ$452
includes taxes & fees
18 Oct - 19 Oct
Le Cocoon 5 minutes from Mont Orford and Magog

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

Montagnard-SPA-Mont-Orford-SEPAQ-Wood fireplace
Orford
9.0 out of 10, Wonderful, (31 reviews)
"Perfect location minutes from the ski hill and from shopping. Hot tub was a great way to relax after a hard day skiing. All amenities in the chalet were exactly as specified and more. "
Canada
Patrick M.
The price is NZ$360
includes taxes & fees
25 Oct - 26 Oct
Montagnard-SPA-Mont-Orford-SEPAQ-Wood fireplace

17. Magnificent Condo Au Coeur d'Orford

Magnificent Condo Au Coeur d'Orford
Orford
8.0 out of 10, Very good, (1 review)
"Très tranquille."
United States
Eugénie P.
The price is NZ$430
includes taxes & fees
8 Oct - 9 Oct
Magnificent Condo Au Coeur d'Orford

18. 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)
"We had a great time at this property. The island was a fun place for hors d'oeuvres, we enjoyed the hot tub and comfortable living space. The surrounding area was quiet and the property has beautiful views. We would certainly return again!"
United States
Alexandra D.
The price is NZ$1,009
includes taxes & fees
1 Oct - 2 Oct
Aux Berges du Pont Suspendu - Grand Lac Brompton

19. Le Vivaldi SPA Mont Orford SEPAQ

Le Vivaldi SPA Mont Orford SEPAQ
Orford
9.2 out of 10, Wonderful, (12 reviews)
"Nice cottage really well situated and easy communication with owner."
United States
Christian B.
The price is NZ$416
includes taxes & fees
1 Oct - 2 Oct
Le Vivaldi SPA Mont Orford SEPAQ

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

Sherby Prestige / King Bed / Central / Sleeps 6
Le Mont-Bellevue
8.4 out of 10, Very good, (26 reviews)
"Clean, cozy and close to all amenities. A great place to stay on a cold weather inter night!"
United States
Bill D.
The price is NZ$476
includes taxes & fees
6 Oct - 7 Oct
Sherby Prestige / King Bed / Central / Sleeps 6
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.
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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.