Deals on vacations and trips to Windsor

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Windsor flight + hotel vacation packages

The Tudor Arms Hotel Cleveland - a DoubleTree by Hilton

The Tudor Arms Hotel Cleveland - a DoubleTree by Hilton

4 out of 5
University Circle
per person
Jun 20 - Jun 24
Roundtrip non-stop flight included
Richmond (RIC) to Cleveland (CLE)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A free area shuttle is offered as well.
Sonesta Simply Suites Cleveland North Olmsted Airport

Sonesta Simply Suites Cleveland North Olmsted Airport

2.5 out of 5
per person
Jun 20 - Jun 24
Roundtrip non-stop flight included
Richmond (RIC) to Cleveland (CLE)
A gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Business travelers can take advantage of the business center.
InterContinental Cleveland, an IHG Hotel

InterContinental Cleveland, an IHG Hotel

4.5 out of 5
Fairfax
per person
Jun 20 - Jun 24
Roundtrip non-stop flight included
Richmond (RIC) 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.
InterContinental Suites Hotel Cleveland, an IHG Hotel

InterContinental Suites Hotel Cleveland, an IHG Hotel

4 out of 5
Fairfax
per person
Jun 20 - Jun 24
Roundtrip non-stop flight included
Richmond (RIC) to Cleveland (CLE)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A coffee shop, a terrace, and a lobby fireplace are also on offer.
The Westin Cleveland Downtown

The Westin Cleveland Downtown

4 out of 5
Downtown Cleveland
per person
Jun 20 - Jun 24
Roundtrip non-stop flight included
Richmond (RIC) 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.
Prices and availability subject to change. Additional terms may apply.

Top Windsor hotels deals

Best Western Plus Mentor-Cleveland Northeast

Best Western Plus Mentor-Cleveland Northeast

3 out of 5
8434 Mentor Avenue, Mentor, OH
Free Cancellation
Reserve now, pay when you stay
The price is $107 per night
$107
per night
Apr 28 - Apr 29
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.
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 $159 per night
$159
per night
May 6 - May 7
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.
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 $66 per night
$66
per night
Apr 25 - Apr 26
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.
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
Free Cancellation
The price is $112 per night
$112
per night
Apr 28 - Apr 29
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.
Breakfast included
Pool
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 $89 per night
$89
per night
Apr 21 - Apr 22
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 24-hour business center and free internet in public areas. Enjoy the gym and conveniences like a 24-hour front desk and barbecue grills.
Sleep Inn & Suites Near I-90 and Ashtabula

Sleep Inn & Suites Near I-90 and Ashtabula

2.5 out of 5
9350 Center Rd, Austinburg, OH
Free Cancellation
Reserve now, pay when you stay
The price is $84 per night
$84
per night
Apr 25 - Apr 26
This hotel features an indoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
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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

Image for Windsor Mills Covered Bridge

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?
Vacation packages, which include hotels and flights in Windsor, start from as low as $512. Turn your daydreams into reality and lock in your trip with Travelocity today.
Where can I get the best vacation package deals for Windsor?
One word — Travelocity. With no less than 400 partner airlines and 1,000,000 properties worldwide, it’s easy to craft a Windsor package deal that suits your needs.
Why should I book my Windsor vacation package via Travelocity?
With our Price Match Guarantee, we’ll match any cheaper price you find. Add on our 24/7 customer support and top-shelf service and your perfect vacation is well within reach.
Will I save money on my Windsor car rental if I combine it with hotels and flights?
Absolutely — combine your hotel, car and flight into a Windsor vacation package and you’ll save loads. With so much to see in the Windsor area, that rental car will make exploring easy. Once you’re behind the wheel, get out on the wide open road and cruise toward Conneaut Railroad Museum, an unmissable sight about 35 mi from Windsor.
What is the best time of year to go to Windsor?
If budget is what’s driving your travel decisions, you’ll score the best prices in . is generally the most expensive month. Most visitors venture to this location during May, June and July. If you’d rather avoid the crowds, visit in November, December and January.
Which airport is best for Windsor?
Hopkins Intl. Airport (CLE), located around 50 mi west of central Windsor, is most likely where you’ll step off the plane. Your other options are Akron-Canton Airport (CAK) (50 mi away from central Windsor) and Erie Intl. Airport (ERI) (55 mi away from central Windsor).
What is there to do in Windsor?
Take advantage of the fantastic photo opportunities at Windsor Mills Covered Bridge, one of the most visited attractions in Windsor. There’s a lot more to discover in this exciting city, so make sure you have enough time to visit some hidden gems.