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.
Hampton Inn & Suites Cleveland/Independence

Hampton Inn & Suites Cleveland/Independence

2.5 out of 5
Price was $539, price is now $441 per person
$441
per person
Oct 23 - Oct 26
found 16 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Cleveland (CLE)
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.
Kimpton Schofield Hotel by IHG

Kimpton Schofield Hotel by IHG

4.5 out of 5
Downtown Cleveland
Price was $723, price is now $578 per person
$578
per person
Oct 23 - Oct 26
found 16 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) 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.
The Westin Cleveland Downtown

The Westin Cleveland Downtown

4 out of 5
Downtown Cleveland
Price was $741, price is now $594 per person
$594
per person
Oct 23 - Oct 26
found 16 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) 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 snack bar/deli, dry cleaning, and free newspapers are also on offer.
The Willoughby House

The Willoughby House

3 out of 5
Price was $611, price is now $503 per person
$503
per person
Oct 3 - Oct 5
found 17 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Cleveland (CLE)
A restaurant and a bar/lounge are featured at this bed & breakfast. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking.
Embassy Suites by Hilton Cleveland Rockside

Embassy Suites by Hilton Cleveland Rockside

3.5 out of 5
Price was $659, price is now $550 per person
$550
per person
Oct 23 - Oct 26
found 16 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Cleveland (CLE)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the 24-hour gym and free perks like cooked-to-order breakfast and WiFi in public areas. Self parking, a business center, and a snack bar/deli are also offered.

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
$70 nightly
The price is $81 total per night
$81 total
Aug 26 - Aug 27
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
$110 nightly
The price is $126 total per night
$126 total
Sep 1 - Sep 2
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.
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
$89 nightly
The price is $102 total per night
$102 total
Aug 26 - Aug 27
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
Free Cancellation
Reserve now, pay when you stay
$210 nightly
The price is $239 total per night
$239 total
Sep 1 - Sep 2
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
Comfort Inn

Comfort Inn

2.5 out of 5
7581 Auburn Rd, Rt 44 Off I-90, Painesville, OH
Free Cancellation
Reserve now, pay when you stay
$99 nightly
The price is $114 total per night
$114 total
Sep 7 - Sep 8
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the laundry service and free internet in public areas. Enjoy the gym and conveniences like a 24-hour front desk and barbecue grills.
Pool
Breakfast included
Red Roof Inn Ashtabula - Austinburg

Red Roof Inn Ashtabula - Austinburg

2 out of 5
1860 Austinburg-Ashtabula Rd, I-90 Exit 223, Austinburg, OH
Free Cancellation
Reserve now, pay when you stay
$73 nightly
The price is $84 total per night
$84 total
Sep 2 - Sep 3
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.

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 $441. 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