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.
Comfort Suites Mason near Kings Island

Comfort Suites Mason near Kings Island

2.5 out of 5
Price was CA $1,143, price is now CA $1,119 per person
CA $1,119
per person
Dec 26 - Jan 2
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Cincinnati (CVG)
Book a stay at this business-friendly hotel in Mason. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Kings Island and Great Wolf Lodge Cincinnati Mason are located nearby.
Tru By Hilton Monroe

Tru By Hilton Monroe

2.5 out of 5
Price was CA $1,432, price is now CA $1,324 per person
CA $1,324
per person
Dec 26 - Jan 2
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Cincinnati (CVG)
Stay at this hotel in Monroe. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Traders World and Miami Valley Gaming are located nearby.
The Well House Hamilton, Tapestry Collection By Hilton

The Well House Hamilton, Tapestry Collection By Hilton

3.5 out of 5
Price was CA $1,328, price is now CA $1,273 per person
CA $1,273
per person
Dec 28 - Jan 1
found 5 hours ago
Roundtrip flight included
Hamilton (YHM) to Cincinnati (CVG)
Stay at this hotel in Hamilton. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Fitton Center For Creative Arts and Lane Public Library are located nearby.
Suburban Studios Mason Near Kings Island

Suburban Studios Mason Near Kings Island

2 out of 5
Price was CA $1,153, price is now CA $1,126 per person
CA $1,126
per person
Dec 26 - Jan 2
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Cincinnati (CVG)
Stay at this hotel in Mason. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Kings Island and Great Wolf Lodge Cincinnati Mason are located nearby.
TownePlace Suites by Marriott Cincinnati Mason

TownePlace Suites by Marriott Cincinnati Mason

4 out of 5
Price was CA $1,287, price is now CA $1,275 per person
CA $1,275
per person
Dec 28 - Jan 1
found 5 hours ago
Roundtrip flight included
Hamilton (YHM) to Cincinnati (CVG)
Book a stay at this business-friendly hotel in Mason. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Kings Island and The Golf 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 $121 per night
CA $121
CA $137 total
Dec 7 - Dec 8
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
Beverly hills inn

Beverly hills inn

2.5 out of 5
1830 U.S. 52 Aberdeen OH
Free cancellation
Reserve now, pay when you stay
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
Super 8 by Wyndham Maysville KY

Super 8 by Wyndham Maysville KY

2 out of 5
550 Tucker Dr Maysville KY
Free cancellation
Reserve now, pay when you stay
The price is CA $69 per night
CA $69
CA $77 total
Dec 9 - Dec 10
includes taxes & fees
Book a stay at this business-friendly hotel in Maysville. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Washington Visitors Center and Kenton Station Golf Course are located nearby.
Pet-friendly
Parking included
Days Inn by Wyndham Maysville Kentucky

Days Inn by Wyndham Maysville Kentucky

2.5 out of 5
484 Moody Dr Maysville KY
Free cancellation
Reserve now, pay when you stay
The price is CA $73 per night
CA $73
CA $81 total
Dec 9 - Dec 10
includes taxes & fees
Book a stay at this 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 National Underground Railroad Museum and Kentucky Gateway Museum Center are located nearby.
Breakfast included
Pet-friendly
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 $136 per night
CA $136
CA $150 total
Dec 4 - Dec 5
includes taxes & fees
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
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 $1,119, 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