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.
HomeField Inn.

HomeField Inn.

2 out of 5
Price was $622, price is now $511 per person
$511
per person
Jun 6 - Jun 11
found 1 day ago
Roundtrip flight included
New York (NYC) to Cleveland (CLE)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A virtual front desk are provided for your convenience.
The Inn at Fulton

The Inn at Fulton

2 out of 5
Save 100% on your flight
Price was $1,246, price is now $776 per person
$776
per person
Jun 6 - Jun 11
found 1 day ago
Roundtrip flight included
New York (NYC) to Cleveland (CLE)
This aparthotel includes free WiFi in public areas and laundry facilities.
The Washington Boutique Hotel

The Washington Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $1,040, price is now $778 per person
$778
per person
Jun 21 - Jun 24
found 21 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Cleveland (CLE)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Laundry facilities and a virtual front desk are also provided.
InterContinental Cleveland by IHG

InterContinental Cleveland by IHG

4.5 out of 5
Fairfax
Price was $779, price is now $644 per person
$644
per person
Jun 20 - Jun 22
found 1 day ago
Roundtrip non-stop flight included
Islip (ISP) 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.
Cedar Point's Hotel Breakers

Cedar Point's Hotel Breakers

3.5 out of 5
Price was $872, price is now $724 per person
$724
per person
Jun 21 - Jun 24
found 21 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Cleveland (CLE)
This smoke-free hotel includes 4 restaurants, an outdoor pool, and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the 24-hour gym and perks like free self parking and free WiFi.

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
$61 nightly
The price is $70 total per night
$70 total
Apr 12 - Apr 13
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
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
$101 nightly
The price is $117 total per night
$117 total
Apr 8 - Apr 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
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
$160 nightly
The price is $181 total per night
$181 total
Apr 15 - Apr 16
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
Cabin 1 The Sunrise Patio

Cabin 1 The Sunrise Patio

Geneva OH
$150 nightly
The price is $159 total per night
$159 total
May 1 - May 2
Total with taxes and fees
This cabin includes a garden and barbecue grills.
Pet friendly
Free WiFi
Americas Best Value Inn Austinburg

Americas Best Value Inn Austinburg

2 out of 5
2352 State Route 45 N Austinburg OH
Free Cancellation
Reserve now, pay when you stay
$70 nightly
The price is $80 total per night
$80 total
Apr 19 - Apr 20
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. The front desk is staffed around-the-clock and laundry facilities are on offer.
Breakfast included
Pet friendly
Wingate by Wyndham Geneva at SPIRE Academy

Wingate by Wyndham Geneva at SPIRE Academy

2.5 out of 5
1715 S Broadway Geneva OH
Free Cancellation
Reserve now, pay when you stay
$97 nightly
The price is $111 total per night
$111 total
Apr 8 - Apr 9
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
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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

Windsor Mills Covered Bridge

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?
Packages, including flights and hotels in Windsor, start from as little as $511. 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

old Windsor Mill Covered Bridge in Ohio, USA
Historic Windsor Mills Covered Bridge in Autumn - Ashtabula County, Ohio