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

Flat 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.

10–17 Nov

£71 per night
Guest favourite

Guest house in Kingsville

4.96 out of 5 average rating, 208 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!

30 Oct – 6 Nov

£76 per night
Guest favourite

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!

3–10 Nov

£137 per night

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

Superhost

Flat in Windsor

4.89 out of 5 average rating, 36 reviews

ROOF TOP 2-Bedroom PentHouse ! ! !

13–20 Mar

£117 per night
Superhost

Home in The Core

4.8 out of 5 average rating, 76 reviews

3 Bed Bright Modern Home in Heart of Walkerville

7–14 Apr

£108 per night
Guest favourite

Home in The Core

5.0 out of 5 average rating, 27 reviews

Boutique Suite on the River

9–16 Sept

£73 per night
Guest favourite

Home in Windsor

4.94 out of 5 average rating, 54 reviews

The Boho Oasis

9–16 Jul

£80 per night
Guest favourite

Home in Windsor

5.0 out of 5 average rating, 22 reviews

The Spot - Luxury Living

22–29 Oct

£68 per night
Guest favourite

Guest house in Windsor

4.89 out of 5 average rating, 35 reviews

Cozy Guesthouse in South Windsor

30 May – 6 Jun

£40 per night
Guest favourite

Flat in The Core

4.96 out of 5 average rating, 67 reviews

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

26 Aug – 2 Sept

£136 per night
Guest favourite

Townhouse in Windsor

4.88 out of 5 average rating, 8 reviews

Comfy house near shopping mall.

29 Apr – 6 May

£100 per night
Guest favourite

Home in West Side

5.0 out of 5 average rating, 41 reviews

The Whimsical Inn

9–16 Sept

£115 per night
Superhost

Flat in Windsor

5.0 out of 5 average rating, 3 reviews

newly built 2BR/2BA condo

7–14 Jun

£102 per night
Guest favourite

Farm stay in Essex County

5.0 out of 5 average rating, 78 reviews

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

3–10 Sept

£82 per night
Guest favourite

Flat in Windsor

4.94 out of 5 average rating, 62 reviews

Walkerville Loft (Main floor unit)

23–30 May

£77 per night

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