Book Exclusive Winchester Vacation Packages

Choose one or more items to build your trip:

Winchester flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Ashley Quarters Hotel

Ashley Quarters Hotel

2.5 out of 5
per person
Apr. 12 - Apr. 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Cincinnati (CVG)
Book a stay at this business-friendly hotel in Florence. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Turfway Park Racing & Gaming and Turfway Crossing are located nearby.
DoubleTree Suites by Hilton Hotel Cincinnati - Blue Ash

DoubleTree Suites by Hilton Hotel Cincinnati - Blue Ash

4 out of 5
per person
Apr. 12 - Apr. 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Cincinnati (CVG)
Stay at this 4-star business-friendly hotel in Sharonville. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Sharon Woods Golf Course and Heritage Village Museum are located nearby.
21c Museum Hotel Cincinnati

21c Museum Hotel Cincinnati

4.5 out of 5
Downtown Cincinnati
per person
Apr. 12 - Apr. 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Cincinnati (CVG)
Stay at this 4.5-star luxury hotel in Cincinnati. Enjoy free WiFi, a full-service spa, and a rooftop terrace. 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.
The Cincinnatian Hotel Curio Collection by Hilton

The Cincinnatian Hotel Curio Collection by Hilton

4 out of 5
Downtown Cincinnati
per person
Apr. 12 - Apr. 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Cincinnati (CVG)
Book a stay at this historic hotel in Cincinnati. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hard Rock Casino Cincinnati and Great American Ball Park are located nearby.
Hilton Cincinnati Netherland Plaza

Hilton Cincinnati Netherland Plaza

4 out of 5
Downtown Cincinnati
per person
Apr. 12 - Apr. 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Cincinnati (CVG)
Book a stay at this historic 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.

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 !

Get rates
Stay at this cabin in Winchester. Enjoy free WiFi, a garden, and patios. Popular attraction Adams Lake State Park is located nearby.
Kitchen
Washer
French Quarter Inn

French Quarter Inn

3 out of 5
25 East McDonald Parkway, Maysville, KY
Free cancellation
Reserve now, pay when you stay
The price is CA $157 per night
CA $157
CA $175 total
includes taxes & fees
8 Feb - 9 Feb
Stay at this 3-star business-friendly hotel in Maysville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Russell Theatre and Kentucky Gateway Museum Center are located nearby.
Pool
Breakfast included
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 $112 per night
CA $112
CA $127 total
includes taxes & fees
9 Feb - 10 Feb
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
Days Inn by Wyndham Hillsboro

Days Inn by Wyndham Hillsboro

2.5 out of 5
103 Harry Sauner Rd, Hillsboro, OH
Free cancellation
Reserve now, pay when you stay
The price is CA $129 per night
CA $129
CA $142 total
includes taxes & fees
1 Mar - 2 Mar
Book a stay at this business-friendly hotel in Hillsboro. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Hillsboro Public Library and Hillsboro Elks Country Club are located nearby.
Pool
Breakfast included
Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond

Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond

Get rates
Book a stay at this family-friendly vacation home in Peebles. Enjoy free WiFi, a garden, and a pool table. Popular attraction Serpent Mound is located nearby.
Kitchen
Washer
New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .

New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .

Get rates
Stay at this cabin in West Union. Enjoy free WiFi, a garden, and patios. Our guests praise the helpful staff in our reviews. Popular attraction Adams Lake State Park is located nearby.
Kitchen
Washer
Don't see what you're looking for?
See all available properties in Winchester
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.

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 $902, 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