Deals on vacations and trips to Windsor

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Windsor flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Quality Lodge

Quality Lodge

2.5 out of 5
Price was $458, price is now $383 per person
$383
per person
Oct 15 - Oct 17
found 18 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
ROOST Cleveland

ROOST Cleveland

4 out of 5
Downtown Cleveland
Price was $937, price is now $719 per person
$719
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Ontario Intl. Airport (ONT) to Cleveland (CLE)
A 24-hour gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Dry cleaning, luggage storage, and concierge services are also on offer.
Fidelity Hotel

Fidelity Hotel

4.5 out of 5
Downtown Cleveland
Save 100% on your flight
Price was $1,434, price is now $1,101 per person
$1,101
per person
Sep 18 - Sep 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
Hotel Kilbourne Downtown Sandusky

Hotel Kilbourne Downtown Sandusky

2.5 out of 5
Historic Downtown Sandusky
Price was $573, price is now $462 per person
$462
per person
Oct 15 - Oct 17
found 18 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Cleveland (CLE)
This hotel features 2 bars/lounges and a rooftop terrace. Enjoy a meal from the restaurant and perks like free self parking and free WiFi. A snack bar/deli and luggage storage are also provided.
Cedar Stables Inn and Suites

Cedar Stables Inn and Suites

2.5 out of 5
Price was $567, price is now $474 per person
$474
per person
Sep 11 - Sep 13
found 19 hours ago
Roundtrip non-stop flight included
Louisville (SDF) 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.

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
$63 nightly
The price is $73 total per night
$73 total
Sep 1 - Sep 2
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
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
Aug 30 - Aug 31
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
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
$112 nightly
The price is $129 total per night
$129 total
Aug 12 - Aug 13
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
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
$220 nightly
The price is $250 total per night
$250 total
Sep 10 - Sep 11
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
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
Aug 23 - Aug 24
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
The Palms Motel

The Palms Motel

2 out of 5
5169 Lake Rd E Geneva OH
Free Cancellation
Reserve now, pay when you stay
$139 nightly
The price is $160 total per night
$160 total
Aug 11 - Aug 12
Total with taxes and fees
A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A picnic area is also provided.
Pool
Parking included
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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 $383. 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.