Deals on vacations and trips to Winchester

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Winchester flight + hotel vacation packages

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Belterra Casino Resort

Belterra Casino Resort

3.5 out of 5
Save 100% on your flight
Price was $626, price is now $431 per person
$431
per person
Aug 6 - Aug 10
found 1 day ago
Roundtrip 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.
Hotel Covington Cincinnati Riverfront

Hotel Covington Cincinnati Riverfront

4 out of 5
Save 100% on your flight
Price was $770, price is now $581 per person
$581
per person
Aug 6 - Aug 10
found 1 day ago
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.
Landing Apartments Near University Of Cincinnati

Landing Apartments Near University Of Cincinnati

4 out of 5
Corryville
Save 100% on your flight
Price was $846, price is now $643 per person
$643
per person
Aug 6 - Aug 10
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Cincinnati (CVG)
This aparthotel features an outdoor pool and a 24-hour gym. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, barbecue grills, and a virtual front desk are also on offer.
Embassy Suites by Hilton Cincinnati RiverCenter

Embassy Suites by Hilton Cincinnati RiverCenter

3.5 out of 5
Price was $581, price is now $461 per person
$461
per person
Aug 6 - Aug 10
found 1 day ago
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.
Holiday Inn Express Hotel & Suites Richwood-Cincinnati South by IHG

Holiday Inn Express Hotel & Suites Richwood-Cincinnati South by IHG

2.5 out of 5
Price was $579, price is now $466 per person
$466
per person
Aug 6 - Aug 10
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Cincinnati (CVG)
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. Enjoy the hot tub and free perks like buffet breakfast and free self parking.

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.
Kitchen
Washer
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.
Pool
Pet friendly
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.
Pool
Breakfast included
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.
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
$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.
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
$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.
Breakfast included
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.

Frequently asked questions

How much are vacation packages to Winchester?
With vacation packages being sold for just $431, 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