Deals on vacations and trips to Winchester

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Winchester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Belterra Casino Resort

Belterra Casino Resort

3.5 out of 5
Price was $429, price is now $308 per person
$308
per person
May 29 - May 31
found 17 hours ago
Roundtrip flight included
Denver (DEN) 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
Price was $900, price is now $700 per person
$700
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Denver (DEN) 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.
voco The Clair Cincinnati Downtown by IHG

voco The Clair Cincinnati Downtown by IHG

4 out of 5
Downtown Cincinnati
Price was $883, price is now $691 per person
$691
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Denver (DEN) 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.
Radisson Hotel Cincinnati Riverfront

Radisson Hotel Cincinnati Riverfront

3.5 out of 5
Price was $671, price is now $531 per person
$531
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Denver (DEN) to Cincinnati (CVG)
This smoke-free hotel includes 2 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a snack bar/deli, and express check-out are also offered.
Holiday Inn Express & Suites Cincinnati Riverfront by IHG

Holiday Inn Express & Suites Cincinnati Riverfront by IHG

2.5 out of 5
Price was $794, price is now $641 per person
$641
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Denver (DEN) to Cincinnati (CVG)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.

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
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This cabin features free WiFi in public areas, a garden, and laundry facilities. Barbecue grills are provided for your convenience.
Kitchen
Washer
French Quarter Inn

French Quarter Inn

3 out of 5
25 East McDonald Parkway Maysville KY
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This hotel features a gym and a seasonal outdoor pool. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
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
$52 nightly
The price is $58 total per night
$58 total
May 12 - May 13
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
$84 nightly
The price is $95 total per night
$95 total
Apr 20 - Apr 21
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
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
$85 nightly
The price is $95 total per night
$95 total
Apr 19 - Apr 20
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-out. Laundry facilities, free newspapers, and barbecue grills are also on offer.
Breakfast included
Pet friendly
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
Apr 14 - Apr 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 $308, 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