Top Winter Vacations - Vacation Rentals in Caesar's Windsor

Beautifully renovated home in historic Walkerville. From US $199
         

10.0 (31 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
7BR house 19 ppl DT Windsor WD Free Parking From US $885
         

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10.0 (2 Reviews)
Villa
  • Air Conditioner
  • Parking
  • View
Ye Olde Walkerville Bed & Breakfast From US $107
         

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9.6 (384 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Windsor Retreat - Chic and Cozy 3beds and 2 Baths From US $172
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
DoubleTree by Hilton Windsor Hotel & Suites From US $132
         

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9.2 (1114 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
The Boho Oasis: Luxurious Studio Apartment, Quiet Court, Close to All Amenities! From US $92
         

10.0 (33 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Comfort Inn & Suites Ambassador Bridge From US $86
         

8.0 (1466 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
The Boho Oasis: Spacious Deluxe Apartment, Close to All Amenities, Safe & Quiet From US $106
         

10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Modern 2BR with Remote Workspace, Patio, BBQ & Gym From US $170
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Two Bedroom Luxury apartment in Walkerville. From US $137
         

10.0 (3 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Black Door Bungalow From US $104
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Luxury New Build 4BR Home | Modern Comfort & Style From US $230
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Best Kept Secret in Walkerville! Cheerful 2BD Home From US $208
         

10.0 (1 Review)
House
  • Air Conditioner
  • Pet Friendly
  • TV
loft Apt On Wyndotte | 2bed 1bath | Nr tunnel From US $200
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • TV
Quaint Clean 2BR close to downtown Windsor with Lndry & Prkng Inc From US $199
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Explore Windsor - Private Getaway in the Core From US $174
         

Pro Tip: Topwintervacations makes it easy to compare the best listings on Topwintervacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Topwintervacations homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Caesar's Windsor.

Weather in Caesar's Windsor

View the weather forecast for Caesar's Windsor before booking your Caesar's 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

Caesar's Windsor Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Caesar's Windsor?
How many vacation rentals are available in Caesar's Windsor?

Currently, the total number of properties listed in 2026 is over 380 in the Caesar's Windsor area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Caesar's Windsor.