620+ Vacation Rentals & Holiday Homes in Windsor |
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Windsor Accommodations - Hotels & Rentals

About Windsor Vacation Rentals

Discover More than 620 Incredible Getaway Rentals Available in Windsor. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Windsor.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Windsor, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Windsor. The Average Size of Places to Stay Near Windsor is 1055.69 ft², with Prices Averaging US $203 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Windsor. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Windsor

Type Count
Vacation Homes 270
Holiday Apartments 163
Cottages 87
Villas 5

Use these Quick Filters to Find a Vacation Rental in Windsor

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Windsor with Online Reservations.

Weather in Windsor, ON

View the weather forecast for Windsor before booking your Windsor Vacation Rentals to confirm your best time to go.

December - February
High 23°F       Low 2°F
March - May
High 65°F       Low 12°F
June - August
High 76°F       Low 49°F
September - November
High 65°F       Low 8°F

Activities WindsorGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World WindsorGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


Caesars Casino
Detroit Windsor Tunnel
Point Pelee National Park
Caesar's Windsor
University of Windsor
Adventure Bay Family Water Park
The Colosseum
Jackson Park
St. Clair College
Devonshire Mall
Windsor Family Credit Union Centre
Leamington Arts Centre
Ambassador Golf Club
Coventry Gardens
Dieppe Gardens
Leamington Municipal Marina
Willistead Manor
Ontario Travel Information Centre - Windsor
Olde Walkerville Neighborhood
Walkerville Brewery

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


McGregor 395 Properties
South Central 224 Properties
Bridgeview 202 Properties
East Windsor 179 Properties
Leamington 139 Properties
Sandwich Towne 116 Properties
Tecumseh 114 Properties
Riverside 78 Properties
Walkerville 57 Properties
Amherstburg 28 Properties
Wheatley 28 Properties
LaSalle 25 Properties

Frequently Asked Questions About Windsor?

What are the top hotels, lake houses & vacation rentals in Windsor?

We provide an array of great vacation destinations in Windsor. If you are looking to stay in or around the Windsor area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Windsor:

How many Hotels & Vacation Rentals have private pools in Windsor?

We have 11 Hotels & Vacation Rentals featuring a private pool in and near Windsor. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel, lake house, or vacation rental in Windsor is best for families?

Searching for a family-friendly getaway in Windsor? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Windsor?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 620 in the Windsor area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Windsor.

Nearby Neighborhood (7) 
Neighborhood Property Count
Walkerville Vacation Rentals in Windsor, Ontario 57
Bridgeview Vacation Rentals in Windsor, Ontario 202
East Windsor Vacation Rentals in Windsor, Ontario 179
Riverside Vacation Rentals in Windsor, Ontario 78
Romney Vacation Rentals in Windsor, Ontario 59
South Central Vacation Rentals in Windsor, Ontario 224
Sandwich Towne Vacation Rentals in Windsor, Ontario 116

People Also Ask

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