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Windsor vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Windsor

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Guesthouse in Kingsville

4.96 out of 5 average rating, 207 reviews

Cozy 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

R1,561 ZAR per night
Guest favorite

Apartment in Windsor

4.94 out of 5 average rating, 182 reviews

OLDE 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

R1,638 ZAR per night
Guest favorite

Home in Windsor

4.89 out of 5 average rating, 177 reviews

Stunning 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

R2,647 ZAR per night

Popular amenities for Windsor vacation rentals

Stay near Windsor's top sights

Little Caesars Arena159 locals recommend
Comerica Park212 locals recommend
Ford Field164 locals recommend
Caesars Windsor102 locals recommend
Fox Theatre75 locals recommend
Hart Plaza66 locals recommend

Other great vacation rentals in Windsor

Superhost

Barn in Essex

4.91 out of 5 average rating, 333 reviews

14th Homestead Barn Loft

Mar 5 – 12

R2,967 ZAR per night
Guest favorite

Farm stay in Essex

5.0 out of 5 average rating, 130 reviews

Luxury Farm Stay - Hot tub - Allow pets - Firepits

Feb 2 – 9

R4,886 ZAR per night
Guest favorite

Cottage in Kingsville

4.89 out of 5 average rating, 188 reviews

Lakeview Inn

Oct 9 – 16

R2,962 ZAR per night
Guest favorite

Home in Windsor

4.89 out of 5 average rating, 110 reviews

Stylish South Walkerville Home w Hot-Tub & Firepit

Feb 17 – 24

R2,809 ZAR per night
Guest favorite

Home in Windsor

4.97 out of 5 average rating, 30 reviews

Executive One-Bedroom Upper Unit

Jan 31 – Feb 7

R1,647 ZAR per night
Superhost

Guest suite in Windsor

4.8 out of 5 average rating, 93 reviews

Spacious Wonder

Jun 13 – 20

R945 ZAR per night
Superhost

Home in Windsor

4.8 out of 5 average rating, 76 reviews

3 Bed Bright Modern Home in Heart of Walkerville

Apr 7 – 14

R1,725 ZAR per night
Guest favorite

Home in Windsor

5.0 out of 5 average rating, 27 reviews

Boutique Suite on the River

Sep 9 – 16

R1,629 ZAR per night
Guest favorite

Home in Windsor

4.94 out of 5 average rating, 54 reviews

The Boho Oasis

Jul 9 – 16

R1,546 ZAR per night
Guest favorite

Home in Windsor

5.0 out of 5 average rating, 22 reviews

The Spot - Luxury Living

Oct 22 – 29

R1,295 ZAR per night
Guest favorite

Apartment in Windsor

4.96 out of 5 average rating, 67 reviews

"The Modern Loft" in Walkerville / 2Bed - 1 Bath

Aug 26 – Sep 2

R2,631 ZAR per night
Guest favorite

Guesthouse in Windsor

4.89 out of 5 average rating, 35 reviews

Cozy Guesthouse in South Windsor

May 30 – Jun 6

R772 ZAR per night

Other great vacation rentals in Windsor

Guest favorite

Farm stay in Essex County

5.0 out of 5 average rating, 78 reviews

The Fir&Feather Tree Farm 1Bedroom Suite & Hot tub

Sep 3 – 10

R1,661 ZAR per night
Guest favorite

Apartment in Windsor

4.94 out of 5 average rating, 62 reviews

Walkerville Loft (Main floor unit)

May 23 – 30

R1,499 ZAR per night
Guest favorite

Townhouse in Windsor

4.93 out of 5 average rating, 44 reviews

The Chilver Place

Jun 23 – 30

R1,922 ZAR per night
Guest favorite

Apartment in Windsor

5.0 out of 5 average rating, 13 reviews

ART LOFT Luxury Apartment—Artist's Home

Jul 31 – Aug 7

R2,397 ZAR per night
Guest favorite

Home in Windsor

4.98 out of 5 average rating, 42 reviews

Historic Walkerville Lux Home

Aug 15 – 22

R3,656 ZAR per night
Superhost

Home in Windsor

5.0 out of 5 average rating, 10 reviews

Stylish Apt Near Downtown- Ideal for Long Stays!

Nov 4 – 11

R1,990 ZAR per night
Guest favorite

Guesthouse in Essex

5.0 out of 5 average rating, 38 reviews

Premiere Cottage-Heart of Wine County/ Lake Access

Jul 3 – 10

R2,796 ZAR per night
Guest favorite

Guest suite in Windsor

4.86 out of 5 average rating, 51 reviews

Private Suite with Fireplace and Breakfast Nook

Aug 1 – 8

R1,416 ZAR per night
Superhost

Apartment in Windsor

4.89 out of 5 average rating, 36 reviews

ROOF TOP 2-Bedroom PentHouse ! ! !

Mar 13 – 20

R2,234 ZAR per night
Guest favorite

Apartment in Windsor

5.0 out of 5 average rating, 17 reviews

Charming & Cozy 2BR Unit in the heart of Windsor

Apr 15 – 22

R1,700 ZAR per night
Guest favorite

Home in Windsor

4.93 out of 5 average rating, 88 reviews

Downtown 2 Bed 1 Bath Unit w/ Free Parking

Aug 16 – 23

R1,750 ZAR per night
Guest favorite

Guest suite in LaSalle

4.95 out of 5 average rating, 56 reviews

Luxury Loft - Waterfront, Pool, Tennis, Kayaks!

Jul 7 – 14

R2,804 ZAR per night

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.

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Essex County
  5. Windsor