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Windsor Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Windsor holiday rentals

A wooden cabin with a picnic table and a person standing by the window.

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 AU$207
includes taxes & fees
23 Sept - 24 Sept
Station Chêne Rouge
A living room with a sofa, coffee table, and a dining table with placemats. There is a TV stand with a TV and a bookshelf with books.

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 AU$170
includes taxes & fees
23 Sept - 24 Sept
Fully equipped apartments with 1 bedroom, onsuite in our century-old residence.
A living room with a sofa, coffee table, and a dining table. There is a TV on a stand and a bookshelf with books.

3. 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 AU$286
includes taxes & fees
23 Sept - 24 Sept
Fully equipped apartment with 2 bedrooms in our century-old residence.
A spacious living room with a large TV, comfortable seating, and large windows.

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 AU$367
includes taxes & fees
24 Sept - 25 Sept
Dynamite 2-Bedroom House WiFi Garage Sleeps 6
A modern kitchen with blue cabinets, stainless steel appliances, and a marble countertop.

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

Boutique Studio, Spa Bath & Parking, Sleeps 2
Le Mont-Bellevue
10.0 out of 10, Exceptional, (2 reviews)
"Très propre et bonnes informations sur le site."
Canada
Anthony
Boutique Studio, Spa Bath & Parking, Sleeps 2
A modern house with a wooden exterior, large windows, and a stone garden.

6. 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
The price is AU$432
includes taxes & fees
23 Sept - 24 Sept
Le Cleveland, Bord de l`eau, Foyer, Spa
A cozy tented room with a bed, a lamp, and a view of the outdoors.

7. Mi-Clos

Mi-Clos
2.0 star property
Orford
10.0 out of 10, Exceptional, (27 reviews)
"Amazing stay !"
Canada
Frederik
The price is AU$328
includes taxes & fees
29 Sept - 30 Sept
Mi-Clos
A modern kitchen with a refrigerator, a dining area with a table and chairs, a potted plant, and a TV mounted on the wall.

8. 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 AU$203
includes taxes & fees
1 Oct - 2 Oct
Entire unit with private Entrance in Sherbrooke
A modern kitchen with a double sink, a built-in washing machine, and a door with a panel design.

9. 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 AU$314
includes taxes & fees
24 Sept - 25 Sept
Sherby LUX: Central, Parking, Renovated, Sleeps 6
A wooden deck with a hot tub, string lights, and a wooden fence.

10. 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 AU$287
includes taxes & fees
24 Sept - 25 Sept
Chalet BIA Foyer & Spa

11. Charming apartment in heritage home

Charming apartment in heritage home
Le Mont-Bellevue
10.0 out of 10, Exceptional, (3 reviews)
"Cute place. Did not love the location."
United States
Nikki H.
The price is AU$251
includes taxes & fees
29 Sept - 30 Sept
Charming apartment in heritage home
A modern kitchen with wooden cabinets, a dining table set for four, and a staircase leading to an upper level.

12. 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 AU$372
includes taxes & fees
27 Sept - 28 Sept
Chalet BIA - Cap au Sud
A hot spring with steam rising from the water, surrounded by wooden beams and a view of trees through a window.

13. 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 AU$333
includes taxes & fees
23 Sept - 24 Sept
Le Vivaldi SPA Mont Orford SEPAQ
A dining table set for four with a view of a lake and hills.

14. 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 AU$814
includes taxes & fees
29 Sept - 30 Sept
Aux Berges du Pont Suspendu - Grand Lac Brompton
A modern kitchen with white cabinets, a stainless steel stove, and a hexagonal backsplash.

15. 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 AU$345
includes taxes & fees
23 Sept - 24 Sept
Sherby Prestige / King Bed / Central / Sleeps 6
A beach with clear blue water, sandy shore, and a forested hill in the background.

16. 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 AU$464
includes taxes & fees
27 Sept - 28 Sept
Waterfront cottage with spa, lots of activities nearby
A snow-covered outdoor area with a wooden deck, a hot tub, and a wooden structure with benches.

17. 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 AU$356
includes taxes & fees
18 Oct - 19 Oct
Le Cocoon 5 minutes from Mont Orford and Magog
A modern kitchen with a central island, stainless steel appliances, and a seating area with a sofa and a coffee table.

18. 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 AU$274
includes taxes & fees
21 Oct - 22 Oct
Downtown Sherby: Central, Parking, King Bed, Sleeps 3
A snow-covered outdoor area with a wooden deck, a hot tub, and a wooden structure with benches.

19. 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 AU$323
includes taxes & fees
29 Sept - 30 Sept
The Jackrabbit (Mount Orford)
A snow-covered outdoor area with a wooden deck, a hot tub, and a wooden structure with benches.

20. 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.
Montagnard-SPA-Mont-Orford-SEPAQ-Wood fireplace
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

Manoir Des Sables, an Ascend Collection Hotel

Manoir Des Sables, an Ascend Collection Hotel

8/10 Good
"All was good except the noise from the AC. It was very loud."
Tammy 2-night trip
Posted 2 hours ago
Manoir Des Sables, an Ascend Collection Hotel

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, 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 favourite 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 depend 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 AU$207 per night. Entering your travel dates in the search wizard might find you 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. 

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.