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Windsor flight + hotel vacation packages

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Fidelity Hotel

Fidelity Hotel

4.5 out of 5
Downtown Cleveland
Price was $732, price is now $586 per person
$586
per person
Nov 6 - Nov 8
found 5 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.
ROOST Cleveland

ROOST Cleveland

4 out of 5
Downtown Cleveland
Price was $1,046, price is now $781 per person
$781
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Charleston (CHS) to Cleveland (CLE)
A 24-hour gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. A snack bar/deli, a communal living room, and luggage storage are also on offer.
Landing Apartments near Rivergate Park Area

Landing Apartments near Rivergate Park Area

4 out of 5
Cuyahoga Valley
Price was $1,173, price is now $899 per person
$899
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Charleston (CHS) 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.
Kimpton Schofield Hotel by IHG

Kimpton Schofield Hotel by IHG

4.5 out of 5
Downtown Cleveland
Price was $829, price is now $646 per person
$646
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Charleston (CHS) 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, laundry service, and valet parking. A coffee shop, a lobby fireplace, and WiFi in public areas are also on offer.
Hotel Indigo Cleveland Downtown by IHG

Hotel Indigo Cleveland Downtown by IHG

3.5 out of 5
Downtown Cleveland
Price was $743, price is now $616 per person
$616
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Charleston (CHS) 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 terrace, a computer station, and luggage storage are also on offer.

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
$147 nightly
The price is $168 total per night
$168 total
Oct 24 - Oct 25
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 27 - Sep 28
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
$74 nightly
The price is $84 total per night
$84 total
Oct 11 - Oct 12
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
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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.

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 $586. 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.