Windsor vacation rentals
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Top-rated vacation rentals in Windsor
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Guesthouse in Kingsville
4.96 out of 5 average rating, 207 reviewsCozy Kingsville Country Guest House
Enjoy your stay in this cozy guest house on the main strip of the charming village of Cottam, within the town of Kingsville. This attached suite will be all for you. Separated from the main house with your own private entrance in the front and rear. Relax on the spacious deck overlooking the lush green mature treed backyard, roast marshmallows at the fire pit or take a nice nap on the hammock. Located a short drive to downtown Kingsville, beaches, wineries, restaurants, craft breweries and more!
Oct 30 – Nov 6
Apartment in Windsor
4.94 out of 5 average rating, 182 reviewsOLDE WALKERVILLE Windsor Ontario
Do you need a nice quite, non-shared clean place to stay ? This cute one bedroom, living room /sleeper sofa, kitchen, full bath (washer/dryer 6 nights + ) Located on the second floor, above our family home, is ready for you to enjoy your stay. In Olde Walkerville, walking distance to restaurants, pubs, boutiques and, the river with walking and bike paths along with summer activities. Short drive to the Casino, Chrysler Theatre / St. Clair Arts, U.S.A Boarder, down town Train Station.
Nov 10 – 17
Home in Windsor
4.89 out of 5 average rating, 177 reviewsStunning Top Tier Modern Home Is Ready To Host You
Enjoy the luxurious feel of a modern home while you sit back and relax in Windsor’s hidden gem! Beautifully decorated and featuring a MASSIVE 1500 sq.ft living room with chic furniture, a pool table, state-of-the-art kitchen, and a high-ceiling 4 piece bathroom. Lots of nearby attractions! Spend a night out enjoying the views of the Detroit skyline after Game Night at Caesars! Head over to the University of Windsor to meet friends! Come home and nestle in the warmth of your clean & comfy bed!
Nov 3 – 10
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Windsor vacation rentals
Other great vacation rentals in Windsor
Barn in Essex
4.91 out of 5 average rating, 333 reviews14th Homestead Barn Loft
Mar 5 – 12
Farm stay in Essex
5.0 out of 5 average rating, 130 reviewsLuxury Farm Stay - Hot tub - Allow pets - Firepits
Feb 2 – 9
Cottage in Kingsville
4.89 out of 5 average rating, 188 reviewsLakeview Inn
Oct 9 – 16
Home in Windsor
4.89 out of 5 average rating, 110 reviewsStylish South Walkerville Home w Hot-Tub & Firepit
Feb 17 – 24
Home in Windsor
4.97 out of 5 average rating, 30 reviewsExecutive One-Bedroom Upper Unit
Jan 31 – Feb 7
Guest suite in Windsor
4.8 out of 5 average rating, 93 reviewsSpacious Wonder
Jun 13 – 20
Home in Windsor
4.8 out of 5 average rating, 76 reviews3 Bed Bright Modern Home in Heart of Walkerville
Apr 7 – 14
Home in Windsor
5.0 out of 5 average rating, 27 reviewsBoutique Suite on the River
Sep 9 – 16
Home in Windsor
4.94 out of 5 average rating, 54 reviewsThe Boho Oasis
Jul 9 – 16
Home in Windsor
5.0 out of 5 average rating, 22 reviewsThe Spot - Luxury Living
Oct 22 – 29
Apartment in Windsor
4.96 out of 5 average rating, 67 reviews"The Modern Loft" in Walkerville / 2Bed - 1 Bath
Aug 26 – Sep 2
Guesthouse in Windsor
4.89 out of 5 average rating, 35 reviewsCozy Guesthouse in South Windsor
May 30 – Jun 6
Other great vacation rentals in Windsor
Farm stay in Essex County
5.0 out of 5 average rating, 78 reviewsThe Fir&Feather Tree Farm 1Bedroom Suite & Hot tub
Sep 3 – 10
Apartment in Windsor
4.94 out of 5 average rating, 62 reviewsWalkerville Loft (Main floor unit)
May 23 – 30
Townhouse in Windsor
4.93 out of 5 average rating, 45 reviewsThe Chilver Place
Jun 23 – 30
Apartment in Windsor
5.0 out of 5 average rating, 13 reviewsART LOFT Luxury Apartment—Artist's Home
Jul 31 – Aug 7
Home in Windsor
4.98 out of 5 average rating, 42 reviewsHistoric Walkerville Lux Home
Aug 15 – 22
Home in Windsor
5.0 out of 5 average rating, 10 reviewsStylish Apt Near Downtown- Ideal for Long Stays!
Nov 4 – 11
Guesthouse in Essex
5.0 out of 5 average rating, 38 reviewsPremiere Cottage-Heart of Wine County/ Lake Access
Jul 3 – 10
Guest suite in Windsor
4.86 out of 5 average rating, 51 reviewsPrivate Suite with Fireplace and Breakfast Nook
Aug 1 – 8
Apartment in Windsor
4.89 out of 5 average rating, 36 reviewsROOF TOP 2-Bedroom PentHouse ! ! !
Mar 13 – 20
Apartment in Windsor
5.0 out of 5 average rating, 18 reviewsCharming & Cozy 2BR Unit in the heart of Windsor
Apr 15 – 22
Home in Windsor
4.93 out of 5 average rating, 88 reviewsDowntown 2 Bed 1 Bath Unit w/ Free Parking
Aug 16 – 23
Guest suite in LaSalle
4.95 out of 5 average rating, 56 reviewsLuxury Loft - Waterfront, Pool, Tennis, Kayaks!
Jul 7 – 14
Quick stats about vacation rentals in Windsor
Total rentals | 1.4K properties |
---|---|
Rentals with dedicated workspaces | 770 properties have a dedicated workspace |
Rentals with a pool | 100 properties have a pool |
Pet-friendly rentals | 330 properties allow pets |
Family-friendly rentals | 560 properties are a good fit for families |
Total number of reviews | 64K reviews |
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.
Are there pet-friendly vacation rentals in Windsor?
Four-legged friends are welcome in Windsor. Choose from more than 330 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Windsor?
Yes! Work meets play with ease at over 770 vacation rentals in Windsor featuring dedicated workspaces. Stay connected and productive in your home away from home.
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