Holiday Packages in Windsor, Ontario

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Exact dates

Tips for booking hotels in Windsor

Gain useful insights to help choose a hotel in Windsor. Data was last updated on Fri Sep 12 2025.
Cheapest month:October
Most expensive month:November
Average price in Windsor:£91/night
Cheapest price found:£24/night
Cheapest day:Tuesday
Most expensive day:Friday
£44 - £110
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.
£93 - £234
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.

Popular Windsor vacation deals

Users browsing Cheapflights choose these holiday deals more than any other. Data was last updated on Fri Sep 12 2025.
Four Points by Sheraton Windsor Downtown
Four Points by Sheraton Windsor Downtown

Four Points by Sheraton Windsor Downtown

430 Ouellette Avenue, Windsor, ON, Canada
0.0 mi from city centre
Pool
Free Wi-Fi
£906
Avg. per night
View Deal
DoubleTree by Hilton Windsor Hotel & Suites
DoubleTree by Hilton Windsor Hotel & Suites

DoubleTree by Hilton Windsor Hotel & Suites

333 Riverside Drive West, Windsor, ON, Canada
0.0 mi from city centre
Pool
Free Wi-Fi
£854
Avg. per night
View Deal
Best Western Plus Waterfront Hotel
Best Western Plus Waterfront Hotel

Best Western Plus Waterfront Hotel

277 Riverside Drive West, Windsor, ON, Canada
0.0 mi from city centre
Pool
Free Wi-Fi
£885
Avg. per night
View Deal
Hampton Inn & Suites by Hilton Windsor
Hampton Inn & Suites by Hilton Windsor

Hampton Inn & Suites by Hilton Windsor

1840 Huron Church Road, Windsor, ON, Canada
0.0 mi from city centre
Pool
Free Wi-Fi
Parking
£915
Avg. per night
View Deal
Holiday Inn & Suites Windsor (Ambassador Bridge) By IHG
Holiday Inn & Suites Windsor (Ambassador Bridge) By IHG

Holiday Inn & Suites Windsor (Ambassador Bridge) By IHG

1855 Huron Church Road, Windsor, ON, Canada
0.0 mi from city centre
Pool
Free Wi-Fi
Parking
£901
Avg. per night
View Deal
Caesars Windsor Hotel and Casino
Caesars Windsor Hotel and Casino

Caesars Windsor Hotel and Casino

377 Riverside Drive East, Windsor, ON, Canada
0.0 mi from city centre
Pool
Free Wi-Fi
£929
Avg. per night
View Deal
Ye Olde Walkerville Bed & Breakfast
Ye Olde Walkerville Bed & Breakfast

Ye Olde Walkerville Bed & Breakfast

1104 Monmouth Road, Windsor, ON, Canada
0.0 mi from city centre
Free Wi-Fi
Air conditioning
£730
Avg. per night
View Deal
See all

Where to stay in Windsor

Utilise the map to find the perfect place to stay for your trip to Windsor. There are 100 hotels to choose from in Windsor.

FAQ about Windsor holiday packages

Find answers to frequently asked questions Cheapflights users have about Windsor holiday deals.

  • How much are vacation packages to Windsor?

    Windsor holidays can be booked for as little as £989.

  • What is the cheapest time of year to travel to Windsor?

    Windsor holidays in March typically cost around £75.

  • Can I save money on travel by booking a holiday package with Cheapflights?

    Yes! Holidays on Cheapflights are designed to help users save money by bundling their flight, car rental, and hotel.

  • What other destinations does Windsor have flight+hotel deals to?

    Remember to check back often to keep track of all the enticing offers for holiday packages to Windsor and more.

See more FAQs

Other popular holiday deals in Ontario

Consider booking a Flight+Hotel in one of these other areas of Ontario.
Ontario holidays
Toronto holidays
Niagara Falls holidays
Ottawa holidays
Brampton holidays
Mississauga holidays
London holidays
Richmond Hill holidays
Markham holidays
Niagara-on-the-Lake holidays
Kingston holidays