Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Jan 2 - Jan 4
In two months
Feb 13 - Feb 15
In three months
Mar 13 - Mar 15
In four months
Apr 10 - Apr 12

Our top choices for Windsor vacation rentals

Exterior
Most Equipped! - Condo le mieux équipé - Orford QC

Condo in Orford

Most Equipped! - Condo le mieux équipé - Orford QC
10.0 out of 10, Exceptional, (19)
"Great location, close to Mont Orford and Magog. Well equipped, comfortable stay. "
Canada
Monique & Jeff
Most Equipped! - Condo le mieux équipé - Orford QC
Property grounds
Cottage next to National Park, lakes, ski resort and so much more!

Vacation Home in Orford

Cottage next to National Park, lakes, ski resort and so much more!
9.4 out of 10, Exceptional, (22)
"This cottage is perfect for the entire family!"
Canada
Kevin L.
Cottage next to National Park, lakes, ski resort and so much more!
Fridge, microwave, oven, stovetop
Le Grand-Duc et Vicomte

Vacation Home in Tingwick

Le Grand-Duc et Vicomte
9.8 out of 10, Exceptional, (47)
"We had a great time. Lots of laughs and fun.The place was spotless.Would go again for sure !!! "
Canada
Leighah L.
Le Grand-Duc et Vicomte
Outdoor dining
Montagnard-SPA-Mont-Orford-SEPAQ-Wood fireplace

Chalet in Orford

Montagnard-SPA-Mont-Orford-SEPAQ-Wood fireplace
8.8 out of 10, Excellent, (23)
"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.
Montagnard-SPA-Mont-Orford-SEPAQ-Wood fireplace
Outdoor spa tub
Mount Orford - Spa - Neptune

Chalet in Orford

Mount Orford - Spa - Neptune
9.0 out of 10, Wonderful, (23)
"Great property with a very well furnished kitchen."
United States
Patrick D.
Mount Orford - Spa - Neptune
Smart TV, fireplace, books
À 5 minutes du Mont-Orford ! Avec accès au lac !

Condo in Orford

À 5 minutes du Mont-Orford ! Avec accès au lac !
9.2 out of 10, Wonderful, (16)
"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."
Canada
Julien D.
À 5 minutes du Mont-Orford ! Avec accès au lac !
TV
Paradise 2, Gorgeous and cozy cottage, perfect for getaways. 2 minutes away from Mount Orford

Chalet in Orford

Paradise 2, Gorgeous and cozy cottage, perfect for getaways. 2 minutes away from Mount Orford
9.8 out of 10, Exceptional, (46)
"This our 5th stay at Paradise 2. Always spotless and close to all the activities. Will be going back again!"
United States
Dawn M.
Paradise 2, Gorgeous and cozy cottage, perfect for getaways. 2 minutes away from Mount Orford
Dining
Chalet Escapade Orford - Great golf and ski escape 5 minutes from Mont-Orford

Chalet in Orford

Chalet Escapade Orford - Great golf and ski escape 5 minutes from Mont-Orford
9.8 out of 10, Exceptional, (11)
"We had a lovely weekend skiing at Orford and staying in this lovely property with our teens. Everything we needed for cooking was there and the whole chalet was spotless. We all loved the rain shower! The owner is so prompt to reply and incredibly helpful."
Canada
Christina C.
Chalet Escapade Orford - Great golf and ski escape 5 minutes from Mont-Orford
Property grounds
New Condo in Orford facing the mountain, pet-friendly

Condo in Orford

New Condo in Orford facing the mountain, pet-friendly
9.8 out of 10, Exceptional, (10)
"A beautiful condo. It exceeded our expectations. Thanks, Amelie!"
Canada
Sean D.
New Condo in Orford facing the mountain, pet-friendly
Outdoor dining
Le Paresseux - 5 min to Mount Orford, 2 minutes away from Ski Orford, fully equipped cottage

Chalet in Orford

Le Paresseux - 5 min to Mount Orford, 2 minutes away from Ski Orford, fully equipped cottage
9.8 out of 10, Exceptional, (21)
"Beautiful little Chalet, with full of charm. We had a wonderful time, the accommodations was comfortable and lovely, the owners were very respectful and kind. We will definitely return. "
United States
Micheline's
Le Paresseux - 5 min to Mount Orford, 2 minutes away from Ski Orford, fully equipped cottage
Beach
Woodpecker, Spa,Foyer,Bike,Ski!

Vacation Home in Orford

Woodpecker, Spa,Foyer,Bike,Ski!
10.0 out of 10, Exceptional, (24)
"One of the nice place ever been to relax and have fun "
Canada
Eduardo O.
Woodpecker, Spa,Foyer,Bike,Ski!
Terrace/patio
Station Chêne Rouge

Cabin in Hatley

Station Chêne Rouge
2.5 star property
9.8 out of 10, Exceptional, (88)
"Very beautiful place, unique. The owner was very nice and helpful. The chalet was perfect"
Canada
Ahmed S
Station Chêne Rouge
Fridge, microwave, oven, stovetop
Chalet Détente Orford - Cozy condo 5 minutes from Mont-Orford golf & ski resort

Chalet in Orford

Chalet Détente Orford - Cozy condo 5 minutes from Mont-Orford golf & ski resort
9.8 out of 10, Exceptional, (16)
"All was Awesome."
United States
jaroslaw b.
Chalet Détente Orford - Cozy condo 5 minutes from Mont-Orford golf & ski resort
Outdoor dining
The Jackrabbit (Mount Orford)

Chalet in Orford

The Jackrabbit (Mount Orford)
9.0 out of 10, Wonderful, (9)
"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 Jackrabbit (Mount Orford)
Outdoor dining
Hôtel à la maison - Havre en montagne & spa privé

Apartment in Orford

Hôtel à la maison - Havre en montagne & spa privé
9.6 out of 10, Exceptional, (22)
"Great place. Close to Mont Orford for skiing. Enjoyed the hot tub. "
Canada
Steven
Hôtel à la maison - Havre en montagne & spa privé
Interior
Hôtel à la maison - Le Massawippi

Apartment in Orford

Hôtel à la maison - Le Massawippi
9.8 out of 10, Exceptional, (20)
"Great stay, well equipped. "
Canada
Matthew G.
Hôtel à la maison - Le Massawippi
Smart TV, fireplace
Spacious 3 bedroom condo in the heart of Mount Orford's nature

Condo in Orford

Spacious 3 bedroom condo in the heart of Mount Orford's nature
10.0 out of 10, Exceptional, (8)
"We had a wonderful stay. We were visiting family in the area and exploring the Eastern Townships and the location was perfect for that. The condo is clean and beautiful. We really enjoyed the time spend there. "
Canada
Keri A.
Spacious 3 bedroom condo in the heart of Mount Orford's nature
Property grounds
La Vue O-Lac Magog Su

Chalet in Sherbrooke

La Vue O-Lac Magog Su
10.0 out of 10, Exceptional, (5)
"Great views of the lake. Convenient location to local ski hills. Very clean and comfortable property."
Canada
jakub
La Vue O-Lac Magog Su
Fridge, microwave, oven, stovetop
Sherby Prestige / King Bed / Central / Sleeps 6

Apartment in Sherbrooke

Sherby Prestige / King Bed / Central / Sleeps 6
8.4 out of 10, Very Good, (23)
" Very clean and comfortable- close to all amenities. We would definitely stay here again!Thank you "
Canada
Ryan S.
The price is ￥17,160
￥38,969 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Sherby Prestige / King Bed / Central / Sleeps 6
Indoor spa tub
Chic Ibiza, SPA, Ski, Foyer, Montagne

Apartment in Orford

Chic Ibiza, SPA, Ski, Foyer, Montagne
9.8 out of 10, Exceptional, (15)
"This property is clean, modern and close to amenities. We had a lovely visit and it has everything you could want. Thank you for a wonderful stay!"
Canada
Amy A.
Chic Ibiza, SPA, Ski, Foyer, Montagne
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

OTL Gouverneur Sherbrooke

OTL Gouverneur Sherbrooke

10/10 Excellent
"Great hotel"
Amelia 1-night trip
Posted 4 days ago
OTL Gouverneur Sherbrooke

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
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Look no further and take a look at our great range of rental properties in Windsor!

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?

Cottage next to National Park, lakes, ski resort and so much more! : Visitors like this Windsor vacation home rental. It is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

What’s there to see and do in Windsor?

While exploring the area, visit family-friendly sights like Musee de la Nature et des Sciences, 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.