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.
Explorer Rest & Recreation

Explorer Rest & Recreation

2 out of 5
Save 100% on your flight
Price was $345, price is now $237 per person
$237
per person
Oct 9 - Oct 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills and a virtual front desk are also provided.
Extended Stay America Premier Suites - Cleveland - Independence

Extended Stay America Premier Suites - Cleveland - Independence

2.5 out of 5
Price was $632, price is now $268 per person
$268
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
A 24-hour gym, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. Luggage storage and a safe deposit box are also provided.
Cedar Stables Inn and Suites

Cedar Stables Inn and Suites

2.5 out of 5
Save 100% on your flight
Price was $373, price is now $245 per person
$245
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Fidelity Hotel

Fidelity Hotel

4.5 out of 5
Downtown Cleveland
Save 100% on your flight
Price was $1,458, price is now $1,003 per person
$1,003
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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
Save 100% on your flight
Price was $1,566, price is now $1,084 per person
$1,084
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

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
$64 nightly
The price is $74 total per night
$74 total
Aug 30 - Aug 31
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
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
$117 nightly
The price is $134 total per night
$134 total
Aug 31 - Sep 1
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
$189 nightly
The price is $214 total per night
$214 total
Sep 17 - Sep 18
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
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
$102 nightly
The price is $117 total per night
$117 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
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
Sep 13 - Sep 14
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
Towneplace Suites By Marriott Geneva

Towneplace Suites By Marriott Geneva

3 out of 5
5327 Spire Circle Geneva OH
Free Cancellation
Reserve now, pay when you stay
$118 nightly
The price is $135 total per night
$135 total
Aug 30 - Aug 31
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
Pool
Breakfast 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 $237. 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.