
Vacation rentals in Windsor
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Top-rated vacation rentals in Windsor
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Popular amenities for Windsor vacation rentals
House rentals in Windsor

Modern & Cozy Home Retreat
We had really great experience. Alin is a great host we got response in 5 to 10mins. Place was clean and had everything we needed. Felt like home.

Beautiful 3Bedroom 2Bath Home free parking&laundry
Shastina was a wonderful host and the house was perfect!! She responded promptly to any questions or messages, and was incredibly kind and helpful. The house felt safe and comfortable, it was easy to walk to the city or there were always Ubers around to pick up for further distances. I would 100% stay here again!

Stylish Getaway steps to DT Kingsville, Spa & Lake
Queen and Mill is a fabulous find! The location is perfect and an easy walk to friendly downtown Kingsville for shops and restaurants. The house itself was exactly as advertised - very tastefully decorated and welcoming. Thoughtful touches such as a welcome basket, wine and a bonfire starter kit made our stay extra special. The house easily accommodated a 3 generation family of 6 adults and the fenced in backyard offers extra space to visit, relax and have fun. Lindsey was quick to respond to the few questions we had; instructions were clear and easy to follow. It was a smooth stay from start to finish! We wouldn’t hesitate to stay here again - don’t pass it up!

Stylish Apt Near Downtown- Ideal for Long Stays!
Great location, good value, clean. Nice residential neighborhood. Check-in was easy and host was responsive. Solid internet. Lots of nice places to eat and get coffee in Little Italy to the south and a little north on Wyandotte. Very walkable which was important to me because I didn’t have a car. Would stay there again.

Hot Tub, TV & Sound bar with fire pit to enjoy.
Gregory’s Place was amazing. Me and my friends had a great time. We enjoyed some time in the hot tub and it was amazing. The place was clean and really beautiful. We played a lot of Pacman which was really awesome. Thanks for having us Gregory!!

stylish house in south windsor-2 bedrooms
Always completely satisfied with any of there beautiful brand new homes! Thanks as always guys!

The Lake House Ontario
Our stay here was amazing! Very well stocked home- ample kitchen stuff, towels, blankets, games etc. Backyard is beautiful, with many seating options! Beds were comfortable. We are able to check early which was appreciated! Joan was easy to deal with and responsive. Newly renovated bathroom with jetted and tub and large shower was so nice!

little cozy house 2 bedroom
Nice and clean place. Would definitely stay there again.
Dog friendly vacation rentals in Windsor

The Coziest Cottage in Essex County's Wine Country
Stayed for 2 nights with my young family and dog, couldn’t be more happy! Beautiful place, amazing yard, fully stocked with everything you would need plus more ! Enjoyed the fire pit in the evening. Such a cute cottage, I wish I could live there. I will 100% be back

Lakeside getaway
The house is very cozy, clean, comfy and is in a safe and quite neighborhood steps away from the beach. My husband is a chef and he enjoyed cooking in the spacious kitchen and outdoor BBQ area. Great private backyard. The host is very prompt in responding to inquiries and very helpful.

Navy Yard Flats (Flat A) - Historic Amherstburg
We really enjoyed our stay at the Navy Yard Flats. Prime location, beautiful unit, responsive host. Jason was lovely. Very helpful and went above & beyond. We liked the central location. Parking was manageable for us. Our boys loved playing in the park across the street and ice cream shop next door. I loved the cafes close by. If you are a light sleep or have Littles, I would bring a fan for the one bedroom. Overall it was a great stay and we will be booking again with Jason this summer.

Quiet LaSalle Newly Renovated Entire Country Home
John is a very courteous and caring host! If you are looking for a quiet peaceful getaway then this is the place!

Sawiak Waterfront Haven
This is my second time staying at Lukas’s lake house. As long as it’s there, I’ll be back. Thanks Lukas!

Main on Main ~ Stylish Studio Downtown Kingsville
Elaine's place has the interesting character of an old house but with modern amenities. The location is great - quiet, but a very short walk to coffee shops, grocery stores, restaurants, etc. She responded immediately when I communicated with her - she's a great host.

It's a 'Shore' thing - Executive Retreat
We recently stayed at this beautiful cottage on the lake, and it was truly the perfect escape. From the moment we arrived, it was clear that the host had thought of everything. The cottage was very clean , cozy, and fully stocked with all the essentials—and then some. Fresh linens, kitchen supplies, firewood, even board games and snacks were waiting for us. The view of the lake was stunning, especially at sunrise. We spent our days enjoying meals on the deck while watching the water. In the evenings, we relaxed by the fire pit We didn’t have to worry about a single thing the whole time we were there—it really felt like a home away from home.

Chardonnay Bay- June Special! stay 2 get 1 free!
Sarah & Joes place , Chardonnay Bay was perfect for a little getaway. They were very friendly , and always responded promptly. The instructions made finding it and checking in a breeze. The home was spotless and very well equipped. The bed was comfy with all the linens and towels and comforts of home. A very short walk to the quiet cute beach , and a great local restaurant/ bar - the wreck. Would stay again and would recommend to anyone. Thanks for everything!
Dog friendly house rentals Windsor

*KID & FAMILY FRIENDLY* Shores of Erie Guest House
We travelled to Colchester with two kids under 8 for a wedding. Taylor’s space was clean, had everything we needed to make our stay comfortable and was a close walk to the beach, park and icecream! Taylor is a great host and we will definitely stay again next time we are in the area.

Luxury water front 3BR house
Very clean, beautiful and quiet house located Front Rd. Very convenient to downtown. The backyard deck is very beautiful in front of water. We really enjoyed staying for two nights. The host is very kind and responsive. She sent us messages everyday to ask whether we need any help and satisfy staying over there. We definitely come back again if we come to Windsor in the future.

Cozy 1919 House, River Rouge/Detroit.
This place was everything I needed it to be for my family! It was walking distance to my grandparents house which made this vacation sooo much easier! The house was very spacious and our big girls loved the rooms in the basement. The little ones we had definitely enjoyed the little swings set in the backyard also. I also love the fact that Connie is very easy to communicate with and very responsive! I will absolutely be back to stay at this place next time we come back to visit!!

3BD Cozy Chic Home Near *Airport*Beaumont*Downtown
We loved the home and the peaceful neighborhood. Make sure to walk over to Dellah Coffee & Brunch House for unique breakfast items and coffee. Great location and access to freeways and attractions in the area.

Erie's Edge lakefront, Point Pelee, Hillman Marsh
This house is amazing! Patsy and Charlsie put a lot of thought into creature comforts - chargers for electronics in strategic locations, plenty of blankets for lounging, lots of seating, Keurig with kcups, as well as shampoo/conditioner. Not to mention plenty of reading material for those early mornings. The house is very cozy and well maintained. We felt immediately at home. We never felt like we were in someone else’s home. The deck area is beautiful but the weather was uncooperative so we were not able to enjoy it as much as we wanted. Wheatley itself is very quaint with a few excellent options for food - iScreams, and Renny’s to name a couple- but Leamington is a short drive away and has more choices. We had a great time and had no trouble communicating with Patsy or Charlsie. They were proactive in getting information to us and very responsive when we had questions. I highly recommend this location! Patsy and Charlsie really know how to host an AirBnB! Two thumbs up!

Turkey Creek Hideaway
This airbnb is top notch. So comfortable. So close to everything and yet tucked away, private and practically a nature reserve. My pup and I enjoyed mornings lounging by the river, walks on all the nearby trails, the fire pit. There are all kinds of birds including blue herons in the area…we had the most surreal encounter with a fawn on one of our walks. Truly magical place. Home is very comfortable. Hosts are next door and very helpful/responsive and also respectful of privacy. Highly recommend.

JEN's DEN / Lake Erie Resort/Fishermens Delight!
Great spot for couple days of fishing. Local bar was the spot to walk to for dinner

David's Dwelling: Spa-like bathrooms, Full Wetbar!
Had a truly comfortable and memorable stay. The amenities were well maintained and thoughtfully provided. Everything was clean and organized upon arrival. We highly recommend.
Quick stats about vacation rentals in Windsor
Total rentals
1.6K properties
Total number of reviews
77K reviews
Family-friendly rentals
620 properties are a good fit for families
Pet-friendly rentals
400 properties allow pets
Rentals with a pool
50 properties have a pool
Rentals with dedicated workspaces
890 properties have a dedicated workspace
Frequently Asked Questions
How is the weather in Windsor?
Windsor has a humid continental climate with four distinct seasons. Summers can be hot, reaching up to 86°F (30°C), while winters are cold with temperatures dropping to around 20°F (-6°C). Snowfall is common in winter, which makes for great winter sports activities.
What are some of the best things to do in Windsor?
In Windsor, you can explore the unique outdoor art at Windsor Sculpture Park, tour the historic Willistead Manor, or enjoy a day of fun at the Adventure Bay Family Water Park. Nature lovers also enjoy hiking the trails in Devonwood Conservation Area.
What is the best time of year to visit Windsor?
The most popular time to visit Windsor is during the summer months from June to August. This is when you can enjoy the Windsor Summer Fest, an annual festival with carnival rides, concerts, and fireworks. The warm weather also allows for exploration of the city's outdoor attractions.
What are the best places to stay in Windsor?
Downtown Windsor is a popular area to stay due to its easy access to restaurants, shops, and attractions like the Art Gallery of Windsor. Walkerville, known for its historic charm, and Riverside, with its waterfront views, are also frequently suggested.
What are the best places to visit in Windsor?
Visitors often enjoy exploring the Windsor Sculpture Park, filled with quirky outdoor art, or touring the historic Willistead Manor. The Adventure Bay Family Water Park is also a frequent favorite, especially for those traveling with children.
What are some hiking trails in Windsor?
Windsor is home to several hiking trails. The Ganatchio Trail, running along the Detroit River, is perfect for waterfront views, while the Little River Extension offers winding paths through lush greenery. For a forested hike, try the Devonwood Conservation Area.
What are some family activities to do in Windsor?
Take the family for a fun-filled day at the Adventure Bay Family Water Park, or explore the exhibits at the Windsor Science Centre. For a more relaxed day, pack a picnic and head to the Peche Island, a 100-acre island with trails, wildlife, and picnic spots.
What are some of the best day trip ideas in Windsor?
You could take a day trip to Point Pelee National Park, an excellent destination for bird watching and hiking, located just 60 minutes (60 miles/97 km) away. Alternatively, visit the Detroit Science Centre, a quick 10 minutes (3 miles/5 km) trip across the Detroit River.
What types of vacation rentals are available in Windsor?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Windsor. From over 720 house rentals to over 500 apartment rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.
Are there vacation rentals with a dedicated workspace in Windsor?
Yes! Work meets play with ease at over 890 vacation rentals in Windsor featuring dedicated workspaces. Stay connected and productive in your home away from home.
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- Ford Field
- Little Caesars Arena
- Point Pelee National Park
- Comerica Park
- Michigan Stadium
- Wesburn Golf & Country Club
- Oakland Hills Country Club
- Detroit Golf Club
- Detroit Zoo
- University of Michigan Museum of Art
- Warren Community Center
- Roseland Golf & Curling Club
- Maumee Bay State Park
- Orchard Lake Country Club
- Grosse Ile Golf & Country Club
- Motown Museum
- Franklin Hills Country Club
- Rolling Hills Water Park
- Bloomfield Hills Country Club
- Seven Lakes State Park
- Essex Golf & Country Club
- Ambassador Golf Club
- Coachwood Golf & Country Club
- Country Club of Detroit