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.
Fidelity Hotel

Fidelity Hotel

4.5 out of 5
Downtown Cleveland
Price was $506, price is now $416 per person
$416
per person
Dec 3 - Dec 5
found 4 hours ago
Roundtrip flight included
New York (JFK) to Cleveland (CLE)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a communal living room, and dry cleaning are also offered.
Cedar Stables Inn and Suites

Cedar Stables Inn and Suites

2.5 out of 5
Price was $707, price is now $608 per person
$608
per person
Nov 20 - Nov 23
found 3 hours ago
Roundtrip flight included
Seattle (SEA) to Cleveland (CLE)
A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. Express check-out and a safe deposit box are also provided.
Quality Lodge

Quality Lodge

2.5 out of 5
Price was $653, price is now $568 per person
$568
per person
Nov 20 - Nov 23
found 3 hours ago
Roundtrip flight included
Seattle (SEA) to Cleveland (CLE)
A seasonal outdoor pool, free self parking, and barbecue grills are featured at this motel. WiFi in public areas is free. A picnic area and luggage storage are also provided.
Landing Apartments near Rivergate Park Area

Landing Apartments near Rivergate Park Area

4 out of 5
Cuyahoga Valley
Price was $622, price is now $544 per person
$544
per person
Nov 6 - Nov 8
found 1 day ago
Roundtrip flight included
New York (NYC) to Cleveland (CLE)
This apartment features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the free WiFi in public areas and onsite conference center. Free self parking, barbecue grills, and a virtual front desk are also on offer.
Holiday Inn Cleveland Clinic by IHG

Holiday Inn Cleveland Clinic by IHG

3 out of 5
Fairfax
Price was $471, price is now $418 per person
$418
per person
Dec 3 - Dec 5
found 4 hours ago
Roundtrip flight included
New York (JFK) to Cleveland (CLE)
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the sauna, bar/lounge, and laundry facilities.

Top Windsor hotels deals

Best Western Plus Mentor-Cleveland Northeast

Best Western Plus Mentor-Cleveland Northeast

2.5 out of 5
8434 Mentor Avenue Mentor OH
Free Cancellation
Reserve now, pay when you stay
$105 nightly
The price is $121 total per night
$121 total
Oct 4 - Oct 5
Total with taxes and fees
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.
Pool
Breakfast included
The Lodge at Geneva-on-the-Lake

The Lodge at Geneva-on-the-Lake

3.5 out of 5
4888 North Broadway (SR 534) Geneva-on-the-Lake OH
Free Cancellation
Reserve now, pay when you stay
$139 nightly
The price is $157 total per night
$157 total
Sep 28 - Sep 29
Total with taxes and fees
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
Pete's Lakefront Motel

Pete's Lakefront Motel

2 out of 5
5225 Old Lake Rd Geneva OH
Free Cancellation
Reserve now, pay when you stay
$145 nightly
The price is $166 total per night
$166 total
Oct 17 - Oct 18
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A seasonal outdoor pool is also provided.
On private beach
Pool
Wingate by Wyndham Geneva at SPIRE Academy

Wingate by Wyndham Geneva at SPIRE Academy

3 out of 5
1715 S Broadway Geneva OH
Free Cancellation
Reserve now, pay when you stay
$101 nightly
The price is $116 total per night
$116 total
Oct 4 - Oct 5
Total with taxes and fees
A 24-hour gym, free self parking, and laundry facilities are featured at this motel. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. Staff at the 24-hour front desk can provide around-the-clock assistance.
Breakfast included
Pet friendly
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
$61 nightly
The price is $70 total per night
$70 total
Sep 28 - Sep 29
Total with taxes and fees
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
Red Roof Inn Ashtabula - Austinburg

Red Roof Inn Ashtabula - Austinburg

2 out of 5
1860 Austinburg-Ashtabula Rd Austinburg OH
Free Cancellation
Reserve now, pay when you stay
$70 nightly
The price is $80 total per night
$80 total
Oct 18 - Oct 19
Total with taxes and fees
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
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.

Stay near popular Windsor attractions

Windsor Mills Covered Bridge

10.0/10 (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.
See properties

Frequently asked questions

How much are vacation packages to Windsor?
Packages, including flights and hotels in Windsor, start from as little as $416. 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

A wooden covered bridge over a river surrounded by lush greenery.
A wooden covered bridge with an American flag, surrounded by autumn foliage.