Deals on vacations and trips to Winchester

Save when you book Winchester package deals

Choose two or more items and save on your trip:

Winchester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Cincinnati RiverCenter

Embassy Suites by Hilton Cincinnati RiverCenter

3.5 out of 5
Price was $500, price is now $403 per person
$403
per person
Aug 6 - Aug 9
just found
Roundtrip flight included
Dallas (DFW) to Cincinnati (CVG)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and free cooked-to-order breakfast each morning.
Hotel Covington Cincinnati Riverfront

Hotel Covington Cincinnati Riverfront

4 out of 5
Price was $650, price is now $487 per person
$487
per person
Aug 6 - Aug 9
just found
Roundtrip flight included
Dallas (DFW) to Cincinnati (CVG)
This hotel features a restaurant and 2 bars/lounges. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and free airport shuttle. Enjoy the 24-hour gym and perks like a free area shuttle.
Belterra Casino Resort

Belterra Casino Resort

3.5 out of 5
Price was $738, price is now $555 per person
$555
per person
Jul 18 - Jul 22
found 7 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Cincinnati (CVG)
This hotel features a golf course, a casino, and 3 restaurants. Traveling on business? Take advantage of the business center, laundry service, and free valet parking. Enjoy the gym and unwind at the bar/lounge and poolside bar.
voco The Clair Cincinnati Downtown by IHG

voco The Clair Cincinnati Downtown by IHG

4 out of 5
Downtown Cincinnati
Price was $673, price is now $513 per person
$513
per person
Aug 6 - Aug 9
just found
Roundtrip flight included
Dallas (DFW) to Cincinnati (CVG)
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Relax with a drink at the bar/lounge and enjoy perks like free WiFi. Self parking, a coffee shop, and luggage storage are also offered.
Rising Star Casino Resort

Rising Star Casino Resort

2 out of 5
Save 100% on your flight
Price was $2,514, price is now $2,014 per person
$2,014
per person
Jul 18 - Jul 22
found 7 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Cincinnati (CVG)
A golf course, 3 restaurants, and an indoor pool are all featured at this smoke-free hotel. You'll appreciate the gym, bar/lounge, and snack bar/deli.

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
This cabin features free WiFi in public areas, a garden, and laundry facilities. Barbecue grills are provided for your convenience.
Beverly hills inn

Beverly hills inn

2.5 out of 5
1830 U.S. 52 Aberdeen OH
$55 nightly
The price is $61 total per night
$61 total
May 14 - May 15
Total with taxes and fees
A nightclub, 2 restaurants, and a 24-hour gym are all featured at this smoke-free hotel. Business travelers can take advantage of the laundry service. Enjoy the seasonal outdoor pool and perks like free self parking.
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
$86 nightly
The price is $97 total per night
$97 total
May 28 - May 29
Total with taxes and fees
An indoor pool, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A computer station and a safe deposit box are also provided.
Quality Inn Seaman

Quality Inn Seaman

2.5 out of 5
55 Stern Dr Seaman OH
Free Cancellation
$85 nightly
The price is $94 total per night
$94 total
Jun 4 - Jun 5
Total with taxes and fees
An outdoor pool is featured at this hotel, along with free self parking. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. A safe deposit box is provided and the front desk is staffed around-the-clock.
Paragon Inn Hillsboro

Paragon Inn Hillsboro

2 out of 5
883 W Main St Hillsboro OH
Free Cancellation
Reserve now, pay when you stay
$76 nightly
The price is $84 total per night
$84 total
May 16 - May 17
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and laundry facilities are on offer.
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
$50 nightly
The price is $56 total per night
$56 total
May 14 - May 15
Total with taxes and fees
This motel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free continental breakfast each morning. A picnic area and barbecue grills are also provided.
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.

Frequently asked questions

How much are vacation packages to Winchester?
With vacation packages being sold for just $403, 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 65 mi 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 55 mi 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

MAY 9, 2023 - WINCHESTER, KENTUCKY - aerial view of historic small town of Winchester with Town Clocktower and historic storefronts and buildings