Deals on vacations and trips to Windsor

Save when you book Windsor package deals

Choose two or more items and save on your trip:

Windsor flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Westin Cleveland Downtown

The Westin Cleveland Downtown

4 out of 5
Downtown Cleveland
Price was $293, price is now $247 per person
$247
per person
Dec 13 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Cleveland (CLE)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A snack bar/deli, dry cleaning, and free newspapers are also on offer.
Comfort Suites Hartville - North Canton

Comfort Suites Hartville - North Canton

2.5 out of 5
Price was $502, price is now $405 per person
$405
per person
Dec 11 - Dec 14
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Cleveland (CLE)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free perks like full breakfast and free self parking.
InterContinental Cleveland by IHG

InterContinental Cleveland by IHG

4.5 out of 5
Fairfax
Price was $443, price is now $366 per person
$366
per person
Dec 13 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Cleveland (CLE)
This luxury hotel features 2 restaurants, a bar/lounge, and a 24-hour gym. WiFi in public areas is free. Valet parking, a terrace, and a lobby fireplace are also offered.
Hotel Cleveland, Autograph Collection

Hotel Cleveland, Autograph Collection

4 out of 5
Downtown Cleveland
Price was $369, price is now $307 per person
$307
per person
Dec 13 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Cleveland (CLE)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Self parking is offered and multilingual staff can provide around-the-clock assistance.
Hampton Inn & Suites Cleveland-Beachwood

Hampton Inn & Suites Cleveland-Beachwood

2.5 out of 5
Price was $464, price is now $391 per person
$391
per person
Dec 6 - Dec 9
found 19 hours ago
Roundtrip flight included
Las Vegas (LAS) to Cleveland (CLE)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.

Top Windsor hotels deals

Red Roof Inn Cleveland - Mentor/ Willoughby

Red Roof Inn Cleveland - Mentor/ Willoughby

2 out of 5
4166 State Route 306, Willoughby, OH
Free Cancellation
Reserve now, pay when you stay
The price is $71 total per night
$71 total
per night
Dec 1 - Dec 2
Free self parking is available and the hotel's front desk is staffed around-the-clock. WiFi in public areas is free. A safe deposit box is also provided.
Pet friendly
Parking included
The Lodge at Geneva

The Lodge at Geneva

3.5 out of 5
4888 N. Broadway, Geneva, OH
Free Cancellation
Reserve now, pay when you stay
The price is $150 total per night
$150 total
per night
Nov 10 - Nov 11
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free self parking and free WiFi. There's a seasonal outdoor pool on site, and laundry facilities and concierge services are also offered.
Pool
Parking included
Holiday Inn Express & Suites Painesville - Concord by IHG

Holiday Inn Express & Suites Painesville - Concord by IHG

2.5 out of 5
11200 Gold Court, Painesville, OH
Free Cancellation
The price is $158 total per night
$158 total
per night
Nov 9 - Nov 10
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Comfort Inn

Comfort Inn

2.5 out of 5
7581 Auburn Rd, Rt 44 Off I-90, Painesville, OH
Free Cancellation
Reserve now, pay when you stay
The price is $115 total per night
$115 total
per night
Nov 16 - Nov 17
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the laundry service and free internet in public areas. Enjoy the gym and conveniences like a 24-hour front desk and barbecue grills.
Pool
Breakfast included
Red Roof Inn Ashtabula - Austinburg

Red Roof Inn Ashtabula - Austinburg

2 out of 5
1860 Austinburg-Ashtabula Rd, I-90 Exit 223, Austinburg, OH
Free Cancellation
Reserve now, pay when you stay
The price is $75 total per night
$75 total
per night
Dec 1 - Dec 2
A bar/lounge and a 24-hour front desk are featured at this hotel, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A safe deposit box and laundry facilities are also provided.
Breakfast included
Pet friendly
Cabin 1 The Sunrise Patio

Cabin 1 The Sunrise Patio

The price is $154 total per night
$154 total
per night
Nov 5 - Nov 6
This cabin includes a garden and barbecue grills.
Pet friendly
Outdoor Space
Don't see what you're looking for?
See all available properties in Windsor
View all properties
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.

Popular places to visit

Windsor Mills Covered Bridge

5/5(3 reviews)

Learn about the local history of Windsor when you take a trip to Windsor Mills Covered Bridge. Experience the area's festivals and entertainment venues.

Windsor Mills Covered Bridge

Frequently asked questions

How much are vacation packages to Windsor?
Packages, including flights and hotels in Windsor, start from as little as $247. Make your daydreams a reality and secure your dream vacation with Travelocity today.
Where can I get the best vacation package deals for Windsor?
You can snap up fantastic Windsor package deals with Travelocity. Pick from as many as 400 airlines and 1,000,000 worldwide properties and turn those travel dreams into reality.
Why should I purchase my Windsor vacation bundle with Travelocity?
Whether you're on the hunt for the ultimate unplugged escape or after the fun and excitement that only a big city can provide, booking everything with Travelocity saves you time, money and hassle. No need to comb through hundreds of websites to find the best deal — our Price Match Guarantee ensures you'll always get the lowest possible price, and our team of customer service experts are available round-the-clock.
Will I save money on my Windsor car rental if I book it with a hotel or flight?
With a Windsor vacation package, you can bundle your flight, car and hotel bookings and save loads. If you'd love to see the best of this wonderful part of the world, why not check out Progressive Field? This well-known attraction is 40 mi from Windsor. With your own rental car, you'll be there belong long.
Which airport is best for Windsor?
For many, a stay in Windsor means getting off the plane at Hopkins Intl. Airport (CLE). This busy airport is located 50 mi west of the downtown area. You could also opt to jet into Akron-Canton Airport (CAK) (50 mi away from central Windsor) or Erie Intl. Airport (ERI) (55 mi away from central Windsor).

Photos of local treasures

Browse Windsor vacation photos for more inspiration