Holiday rentals in Windsor

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Top-rated holiday rentals in Windsor

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

Guest favourite
Home in Windsor
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!
17–24 JulIndividual Host,
£137 per night
4.9 out of 5 average rating, 176 reviews
Guest favourite
Guest house in Kingsville
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!
26 May – 2 JunIndividual Host,
£81 per night
4.96 out of 5 average rating, 205 reviews
Guest favourite
Flat in Windsor
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.
25 Sept – 2 OctIndividual Host,
£71 per night
4.94 out of 5 average rating, 182 reviews

Popular amenities for Windsor holiday 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 holiday rentals in Windsor

Guest favourite
Villa in Windsor
Cheerful 4-bedroom home by the river.
20–27 DecIndividual Host,
£153 per night
4.89 out of 5 average rating, 128 reviews
Superhost
Flat in Windsor
ROOF TOP 2-Bedroom PentHouse ! ! !
12–19 OctIndividual Host,
£101 per night
4.88 out of 5 average rating, 34 reviews
Guest favourite
Home in Windsor
The Spot - Luxury Living
1–8 OctIndividual Host,
£63 per night
5.0 out of 5 average rating, 23 reviews
Guest favourite
Guest suite in Windsor
Spacious Wonder
9–16 JunIndividual Host,
£46 per night
4.79 out of 5 average rating, 90 reviews
Guest favourite
Home in Windsor
"The Oasis" a Walkerville dream / 2 Bed - 1 Bath
1–8 JunIndividual Host,
£104 per night
4.91 out of 5 average rating, 80 reviews
Guest favourite
Home in Windsor
Executive One-Bedroom Upper Unit
14–21 AugIndividual Host,
£83 per night
4.97 out of 5 average rating, 29 reviews
Superhost
Flat in Windsor
Affordable Urban Bachelor
30 Aug – 6 SeptIndividual Host,
£57 per night
4.79 out of 5 average rating, 34 reviews
Guest favourite
Home in Windsor
The Boho Oasis
14–21 MayIndividual Host,
£78 per night
4.94 out of 5 average rating, 52 reviews
Guest favourite
Home in Windsor
Boutique Suite on the River
30 Jun – 7 JulIndividual Host,
£73 per night
5.0 out of 5 average rating, 26 reviews
Guest favourite
Home in Windsor
Historic Walkerville Lux Home
6–13 NovIndividual Host,
£181 per night
4.98 out of 5 average rating, 41 reviews
Guest favourite
Guest suite in Amherstburg
Stylish Private Guest Suite
12–19 JunIndividual Host,
£97 per night
4.96 out of 5 average rating, 69 reviews
Guest favourite
Home in Windsor
Downtown 2 Bed 1 Bath Unit w/ Free Parking
3–10 JunProfessional Host,
£83 per night
4.93 out of 5 average rating, 86 reviews

Quick stats about holiday 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

Destinations to explore

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