Windsor vacation rentals

KAYAK searches hundreds of travel sites at once for vacation home deals in Windsor

Here is why travelers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Recommended by KAYAK
Booking Insights
Recommended by KAYAK

Best Windsor vacation rentals

Self Contained Studio Near Windsor Attractions! - Windsor - Bedroom
Self Contained Studio Near Windsor Attractions!
Windsor, ENG, United Kingdom
7.4Good(4)
Apartment
Parking
Free Wi-Fi
C$ 194+
Check availability
King Edward Apartments - Windsor - Bedroom
King Edward Apartments
Windsor, ENG, United Kingdom
9.2Wonderful(409)
Apartment
Free Wi-Fi
C$ 358+
Check availability
Inviting 2-Bed Cottage in Windsor - Windsor - Living room
Inviting 2-Bed Cottage in Windsor
Windsor, ENG, United Kingdom
7.8Good(62)
Cottage
Free Wi-Fi
C$ 326+
Check availability
Hampden Apartments - The Anne - Windsor - Living room
Hampden Apartments - The Anne
Windsor, ENG, United Kingdom
8.6Very good(95)
Apartment
Parking
Free Wi-Fi
C$ 222+
Check availability
Snoozeden Westmead - Windsor Castle & Legoland - Windsor
Snoozeden Westmead - Windsor Castle & Legoland
Windsor, ENG, United Kingdom
4.9Mediocre(57)
Apartment
Parking
Free Wi-Fi
C$ 120+
Check availability
Windsorian Experience - Windsor
Windsorian Experience
Windsor, ENG, United Kingdom
9.4Wonderful(1243)
Homestay
Free Wi-Fi
C$ 185+
Check availability
Castle Room - Windsor
Castle Room
Windsor, ENG, United Kingdom
7.8Good(33)
Homestay
Parking
Free Wi-Fi
Pet friendly
C$ 116+
Check availability
The Clockhouse - Windsor
The Clockhouse
Windsor, ENG, United Kingdom
9.5Wonderful(231)
Apartment
Parking
Free Wi-Fi
C$ 261+
Check availability
Harte & Garter - Windsor
Harte & Garter
Windsor, ENG, United Kingdom
7.0Good(145)
Apartment
Free Wi-Fi
C$ 121+
Check availability
Victorian cottage - single occupancy - Windsor
Victorian cottage - single occupancy
Windsor, ENG, United Kingdom
8.7Very good(6)
Homestay
Parking
C$ 141+
Check availability
A cozy apartment - Windsor
A cozy apartment
Windsor, ENG, United Kingdom
8.8Very good(34)
Apartment
Parking
Free Wi-Fi
C$ 186+
Check availability
Penthouse Living by Lawsons - Windsor
Penthouse Living by Lawsons
Windsor, ENG, United Kingdom
9.2Wonderful(22)
Apartment
Free Wi-Fi
C$ 232+
Check availability
Lay Your Hat Apartments - Windsor
Lay Your Hat Apartments
Windsor, ENG, United Kingdom
9.1Wonderful(14)
Apartment
Free Wi-Fi
C$ 217+
Check availability
Heart of Windsor - Windsor
Heart of Windsor
Windsor, ENG, United Kingdom
9.4Wonderful(231)
Apartment
Parking
Free Wi-Fi
C$ 217+
Check availability
The Lego themed house - Windsor
The Lego themed house
Windsor, ENG, United Kingdom
8.8Very good(82)
Apartment
Parking
Free Wi-Fi
C$ 377+
Check availability
The Windsor Room - Windsor
The Windsor Room
Windsor, ENG, United Kingdom
8.4Very good(19)
Homestay
Parking
Free Wi-Fi
Pet friendly
C$ 121+
Check availability
Booking Insights

KAYAK’s insights for vacation rentals in Windsor

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Windsor with confidence.

What is the cheapest day of the week to book a vacation rental in Windsor?

Thursday offers the lowest rates in Windsor, with an average nightly price of C$ 132. The highest prices are found on Friday, with average rates at C$ 379.

How early should you book a vacation rental in Windsor?

Book at least 17 days before your stay begins to get the best price for your Windsor vacation rental.

Find deals

KAYAK's top tips for finding Windsor holiday rental deals

  • Parking is the most popular vacation rental property amenity in Windsor
  • Vacation rentals in Windsor are around 47% more expensive than hotels on average. Search here to compare prices for all accommodation types in Windsor.
  • The best vacation rental properties in Windsor are The Clockhouse (9.5, 231 reviews), Windsorian Experience (9.4, 1,243), and Heart of Windsor (9.4, 231), based on ratings and reviews from real travelers.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Windsor for 47 days.

FAQs when booking a vacation home in Windsor

  • What types of vacation rentals are available in Windsor?

    There are loads of different property types that you can make your vacation home in Windsor. You’ll find apartments, bungalows, cabins, chalets, condos, cottages, houses, homestays and villas.

  • Are there any pet-friendly vacation rentals in Windsor?

    There are a number of dog and pet-friendly Windsor vacation rentals, with around 7% allowing you to bring your pet along with you.

  • How much is a vacation rental in Windsor for this weekend?

    In the last 72 hours, users have found Windsor vacation rentals for this weekend for as low as C$ 503 per night. Search here for similar prices

  • How can I find vacation rentals near me in Windsor?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Windsor?

Our map will help you find the perfect place to stay in Windsor by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Windsor