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.
InterContinental Cleveland by IHG

InterContinental Cleveland by IHG

4.5 out of 5
Fairfax
Price was $1,158, price is now $856 per person
$856
per person
Sep 16 - Sep 20
found 16 hours ago
Roundtrip flight included
Los Angeles (LAX) 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.
Hilton Garden Inn Cleveland Downtown

Hilton Garden Inn Cleveland Downtown

3 out of 5
Downtown Cleveland
Save 100% on your flight
Price was $1,582, price is now $1,143 per person
$1,143
per person
Sep 16 - Sep 20
found 16 hours ago
Roundtrip flight included
Los Angeles (LAX) to Cleveland (CLE)
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. A bar/lounge, a 24-hour front desk, and a fireplace in the lobby are also provided.
The Westin Cleveland Downtown

The Westin Cleveland Downtown

4 out of 5
Downtown Cleveland
Save 100% on your flight
Price was $2,057, price is now $1,486 per person
$1,486
per person
Sep 16 - Sep 20
found 16 hours ago
Roundtrip flight included
Los Angeles (LAX) 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. Self parking, a coffee shop, and a snack bar/deli are also offered.
Landing Apartments near Rivergate Park Area

Landing Apartments near Rivergate Park Area

4 out of 5
Cuyahoga Valley
Save 100% on your flight
Price was $1,408, price is now $1,035 per person
$1,035
per person
Sep 16 - Sep 20
found 16 hours ago
Roundtrip flight included
Los Angeles (LAX) 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.
Hotel Cleveland, Autograph Collection

Hotel Cleveland, Autograph Collection

4 out of 5
Downtown Cleveland
Save 100% on your flight
Price was $1,681, price is now $1,273 per person
$1,273
per person
Sep 16 - Sep 20
found 16 hours ago
Roundtrip flight included
Los Angeles (LAX) 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.

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
$119 nightly
The price is $137 total per night
$137 total
Jul 8 - Jul 9
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
Wingate by Wyndham Geneva at SPIRE Academy

Wingate by Wyndham Geneva at SPIRE Academy

3 out of 5
1715 S Broadway Geneva OH
$111 nightly
The price is $128 total per night
$128 total
Jul 30 - Jul 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
$139 nightly
The price is $160 total per night
$160 total
Jul 8 - Jul 9
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

The Lodge at Geneva

3.5 out of 5
4888 N. Broadway Geneva OH
$274 nightly
The price is $312 total per night
$312 total
Jul 8 - Jul 9
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 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
$64 nightly
The price is $74 total per night
$74 total
Jul 19 - Jul 20
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
The Palms Motel

The Palms Motel

2 out of 5
5169 Lake Rd E Geneva OH
$79 nightly
The price is $91 total per night
$91 total
Jul 19 - Jul 20
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 $856. 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.