Windsor Holidays from £1,077

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Your Windsor Holiday

With a holiday package to Windsor, say goodbye to travel planning and hello to hassle-free adventure. Every detail of your journey has been taken care of before you go, so you can make the most of your time experiencing this awesome city. Your trip to Windsor wouldn't be complete without seeing a few popular attractions, such as Windsor Mills Covered Bridge. Whatever your travel plans or budget, putting together a tailored Windsor holiday is a breeze with Expedia.

The Latest Windsor Holiday Deals

Prices and availability subject to change. Additional terms may apply.
Hotel RL Cleveland Airport West

Hotel RL Cleveland Airport West

3.5 out of 5
per person
15 Jul - 20 Jul
Return direct flight included
London (LON) to Cleveland (CLE)
7.2/10 Good! (47 reviews)
Hotel staff was excellent and very kind!

Reviewed on 16 Apr 2024

Comfort Inn Mayfield Heights Cleveland East

Comfort Inn Mayfield Heights Cleveland East

2.5 out of 5
per person
15 Jul - 20 Jul
Return direct flight included
London (LON) to Cleveland (CLE)
8.2/10 Very Good! (1,000 reviews)
Great stay for a last minute booking!

Reviewed on 24 Apr 2024

Comfort Suites Twinsburg

Comfort Suites Twinsburg

2.5 out of 5
per person
15 Jul - 20 Jul
Return direct flight included
London (LON) to Cleveland (CLE)
8/10 Very Good! (557 reviews)
Second time staying at this hotel and it has been great both times!

Reviewed on 24 Apr 2024

Sprucewood Inn

Sprucewood Inn

2 out of 5
per person
15 Jul - 20 Jul
Return direct flight included
London (LON) to Cleveland (CLE)
6.8/10 (470 reviews)
For the price, it exceeded my expectations. Room was clean, staff was friendly. Better than your average motel, fridge, microwave.

Reviewed on 22 Apr 2024

Super 8 by Wyndham Twinsburg/Cleveland Area

Super 8 by Wyndham Twinsburg/Cleveland Area

2 out of 5
per person
15 Jul - 20 Jul
Return direct flight included
London (LON) to Cleveland (CLE)
7.2/10 Good! (675 reviews)
staff were WONDERFUL- so kind at check in and accommodating. Really, this makes the stay enjoyable

Reviewed on 9 Apr 2024

Econo Lodge Kent - Akron West

Econo Lodge Kent - Akron West

2 out of 5
per person
15 Jul - 20 Jul
Return direct flight included
London (LON) to Cleveland (CLE)
5.8/10 (535 reviews)
The staff are very friendly and they go above and beyond to make your stay pleasant.

Reviewed on 13 Apr 2024

Windsor Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Windsor Mills Covered Bridge and Riverdale Road Covered Bridge

Our pick of the best Windsor Hotel Deals

Red Roof Inn Cleveland - Mentor/ Willoughby
Red Roof Inn Cleveland - Mentor/ Willoughby
2 out of 5
4166 State Route 306, Willoughby, OH
Stay at this hotel in Willoughby. Enjoy free WiFi, free parking and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in their reviews. ...
7.4/10 Good! (1,003 reviews)
"Great location to visit Historic Kirtland"

Reviewed on 17 Apr 2024

Red Roof Inn Cleveland - Mentor/ Willoughby
The Lodge at Geneva
The Lodge at Geneva
3.5 out of 5
4888 N. Broadway, Geneva, OH
Stay at this 3.5-star hotel in Geneva-on-the-Lake. Enjoy free WiFi, free parking and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (473 reviews)
"This was a gorgeous place to stay!"

Reviewed on 20 Apr 2024

The Lodge at Geneva
Holiday Inn Express And Suites Painesville - Concord, an IHG Hotel
Holiday Inn Express And Suites Painesville - Concord, an IHG Hotel
2.5 out of 5
11200 Gold Court, Painesville, OH
Stay at this business-friendly hotel in Painesville. Enjoy free breakfast, free WiFi and free parking. Our guests praise the breakfast and the helpful staff ...
9.4/10 Exceptional! (661 reviews)
"Great atmosphere. Nice people."

Reviewed on 23 Apr 2024

Holiday Inn Express And Suites Painesville - Concord, an IHG Hotel
See all 476 properties in Windsor
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Windsor travel package cost?
Our Windsor travel packages, which begin at just £1,077, are an easy way to save big bucks. Handpick your favourite hotels, flights and rental car to create your perfect escape.
If I'm not able to travel, can I cancel my Windsor travel package?
Certainly, and we’re here to help. You may be able to amend or cancel your Windsor travel package at no cost within 24 hours of booking. However, you may incur a fee from your airline, hotel or car rental company if your booking is older than that. If life gets in the way of your holiday, look up our Customer Service Portal for more information.
How do I get a cheap travel package to Windsor?
One of the easiest ways to save money (and time) is to bundle your bookings with Expedia. Hotels, rental cars, flights and activities — we’ve got everything you need. Choose a combination that best suits you and watch your savings stack up. We know a travel package is never a one-size-fits-all. That’s why Expedia offers over 550 air carriers and 1,000,000 hotels around the globe, which lets you customize your Windsor holiday.
Does Expedia offer Book Now, Pay Later Windsor holidays?
We do. Expedia has teamed up with online lender Klarna to help you conveniently pay for your trip in instalments. Simply select the payment plan that works for you during the checkout process and take away the stress of budgeting for your next trip. Be sure to bundle your flights, accommodation and activities with Expedia to get the biggest bang for your travel buck. Browse our flexible payment options below:

  • Pay monthly holidays: Klarna has easy monthly payment plans that work for all types of budgets, so you can take that well-deserved holiday now.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay off your trip in multiple transactions.
  • Low deposit holidays: When you want to grab an awesome deal but your budget doesn’t quite cover it yet, Klarna’s low deposit holiday plan will help you get what you want.

Where should I stay in Windsor?
There’s so much to do in Windsor, so stay near its attractions and treat yourself to more time sightseeing. Windsor Mills Covered Bridge is one place to add to your to-do list.
What are the top hotels in Windsor?
Get your trip off to a good start by reserving a room at Americas Best Value Inn Austinburg. It’s one of most sought-after hotels in Windsor. Another leading option is Motel 6 Geneva, OH.
How far in advance should I book my Windsor holiday?
Browse Expedia to compare airfares as early as possible. You can usually purchase a ticket up to a year in advance. If you can’t see your preferred air carrier, or you have to book last minute, don’t despair. Low prices to Windsor sometimes appear within weeks of the date of departure.
What does an Expedia Windsor travel package include?
Hotels, flights and a reliable car for all your fun road trip adventures. Simply choose your favourite bundle and gain access to great discounts. Once you’ve made your booking, add on a few tours and experiences and watch your savings stack up. When it comes to organising your Windsor getaway, you’re the one in control!
What should I know before booking a Windsor travel package?
So many places to travel to, so many things to see and do. With a package, you can check more of them off your list. Bundle your hotels, rental cars and flights and score big savings.
Can I choose my airline with a Windsor Expedia travel package?
Expedia offers access to more than 550 airline partners worldwide, so you definitely can. Just choose the carrier you want and craft the perfect Windsor trip.

Discover the most popular places to visit in Windsor

Image for Windsor Mills Covered Bridge

Windsor Mills Covered Bridge

Learn about the local history of Windsor with a stop at Windsor Mills Covered Bridge. Experience the area's festivals and entertainment choices.

Windsor Mills Covered Bridge

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.