Book Exclusive Winchester Vacation Packages

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Winchester flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Hilton Cincinnati Netherland Plaza

Hilton Cincinnati Netherland Plaza

4 out of 5
Downtown Cincinnati
Price was CA $993, price is now CA $896 per person
CA $896
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Cincinnati (CVG)
Book a stay at this luxury hotel in Cincinnati. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Great American Ball Park and Newport Aquarium are located nearby.
voco The Clair Cincinnati Downtown by IHG

voco The Clair Cincinnati Downtown by IHG

4 out of 5
Downtown Cincinnati
Price was CA $1,147, price is now CA $1,023 per person
CA $1,023
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Cincinnati (CVG)
Stay at this hotel in Cincinnati. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Great American Ball Park and Newport Aquarium are located nearby.
Graduate by Hilton Cincinnati

Graduate by Hilton Cincinnati

4 out of 5
Corryville
Price was CA $1,089, price is now CA $984 per person
CA $984
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Cincinnati (CVG)
Book a stay at this business-friendly hotel in Cincinnati. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Cincinnati Zoo and Botanical Garden and Great American Ball Park are located nearby.
Hampton Inn & Suites Cincinnati-Downtown

Hampton Inn & Suites Cincinnati-Downtown

2.5 out of 5
Downtown Cincinnati
Price was CA $1,134, price is now CA $1,034 per person
CA $1,034
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Cincinnati (CVG)
Book a stay at this business-friendly hotel in Cincinnati. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Great American Ball Park and Newport Aquarium are located nearby.
Wingate by Wyndham - Cincinnati - Blue Ash

Wingate by Wyndham - Cincinnati - Blue Ash

3 out of 5
Price was CA $1,045, price is now CA $968 per person
CA $968
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Cincinnati (CVG)
Stay at this hotel in Cincinnati. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Summit Park and Blue Ash Commons Shopping Center are located nearby.

Top Winchester hotels deals

Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !

Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !

Winchester OH
Get rates
Stay at this cabin in Winchester. Enjoy free WiFi, a garden, and laundry facilities. Popular attraction Adams Lake State Park is located nearby.
Kitchen
Washer
Countryside Inn & Suites

Countryside Inn & Suites

2.5 out of 5
100 Leininger Street Mount Orab OH
Free cancellation
Reserve now, pay when you stay
The price is CA $116 per night
CA $116
CA $131 total
Jul 5 - Jul 6
includes taxes & fees
Stay at this hotel in Mount Orab. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews.
Pool
Breakfast included
Quality Inn Seaman

Quality Inn Seaman

2.5 out of 5
55 Stern Dr Seaman OH
Free cancellation
The price is CA $121 per night
CA $121
CA $133 total
Jul 19 - Jul 20
includes taxes & fees
Stay at this hotel in Seaman. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews.
Pool
Breakfast included
Paragon Inn Hillsboro

Paragon Inn Hillsboro

2 out of 5
883 W Main St Hillsboro OH
Free cancellation
Reserve now, pay when you stay
The price is CA $107 per night
CA $107
CA $118 total
Jun 29 - Jun 30
includes taxes & fees
Stay at this motel in Hillsboro. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Hillsboro Public Library and Hillsboro Elks Country Club are located nearby.
Parking included
Free WiFi
Brown's Motel Aberdeen

Brown's Motel Aberdeen

2 out of 5
1055 US HWY 52 Aberdeen OH
Free cancellation
Reserve now, pay when you stay
The price is CA $71 per night
CA $71
CA $79 total
Jun 29 - Jun 30
includes taxes & fees
Stay at this motel in Aberdeen. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Kentucky Gateway Museum Center and Old Pogue Distillery are located nearby.
Breakfast included
Pet-friendly
Beverly hills inn

Beverly hills inn

2.5 out of 5
1830 U.S. 52 Aberdeen OH
Get rates
Book a stay at this business-friendly hotel in Aberdeen. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Old Pogue Distillery and Cummins Nature Preserve are located nearby.
Pool
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.

Winchester Vacations

Discovering the real essence of Winchester starts with delving into the little details. Are you ready to find out just where this unique place is and what things you can do there?

It's located 16 miles (26 kilometers) from Hillsboro and 20 miles (32 kilometers) away from Maysville.

Eager to meet a few locals? That shouldn't be too hard. 1,000 people call this corner of Ohio home.

Places to visit in Winchester

Add a little refinement to your vacation by visiting Meranda-Nixon Winery. Check out the winery, book a guided tour and try a sample or two of the finished product! Looking to shake things up a bit? Then try hiking! It's a popular activity you can't miss while you're in the Ohio region.

Where do you fly into for Winchester?

Heading into Cincinnati - Northern Kentucky International Airport (CVG)? After you've hopped off the plane and collected your belongings, downtown Winchester will be just 55 miles (89 kilometers) to the east from here.

Frequently asked questions

How much are vacation packages to Winchester?
With vacation packages being sold for just CA $896, there's no need to max out the credit card to travel to Winchester. Travelocity is here to help. Combine experiences, flights and hotels into a convenient package and receive some serious discounts. The more you book, the bigger the savings.
How long should my Winchester vacation be?
If you're looking for some guidance, most visitors spend around 2 nights vacationing in Winchester. But to discover the true essence of this destination, stay a few extra days. That way you can cross off more attractions and really soak up the local culture.
Where can I get the best vacation package deals for Winchester?
No matter your adventure, Travelocity can help you snap up the best Winchester package deal. All you have to do is mix and match from our 400 airlines and 1,000,000 properties around the world.
Why should I purchase my Winchester vacation bundle via Travelocity?
Travel is all about making cherished new memories and forgetting all your worries — which is why we have a professional team of customer service experts on hand around-the-clock should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best price available on our broad range of vacation packages. So what are you waiting for? There's no time like the present to secure the vacation you've always dreamed of.
Can I save money on my Winchester car rental if I bundle it with my hotel or flight?
Bundling your flight, hotel and car into a Winchester vacation package is a surefire way to land the best deal. Plus, having your own set of wheels gives you freedom to find your way to all those big-name sights you're eager to explore. Sitting 105 kilometers away from Winchester, Paramount Arts Center is one place that should be on your must-do list. Put together a driving playlist and make a day trip of it.
Which airport is best for Winchester?
A flight to Winchester means landing at Cincinnati - Northern Kentucky Intl. Airport (CVG). It's situated 88 kilometers west of the downtown area.
Where should I stay when visiting Winchester?
The Budget Host Inn is the first choice of many visitors. Book soon to avoid missing out.

Photos of local treasures

Browse Winchester vacation photos for more inspiration

A historic downtown area with a prominent clock tower and a green-roofed building.