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.
Wildwood Inn Tropical Dome & Theme Suites

Wildwood Inn Tropical Dome & Theme Suites

2.5 out of 5
Price was $477, price is now $426 per person
$426
per person
Oct 23 - Oct 25
found 18 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Cincinnati (CVG)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and a picnic area are also provided.
Belterra Casino Resort

Belterra Casino Resort

3.5 out of 5
Price was $880, price is now $743 per person
$743
per person
Oct 9 - Oct 12
found 5 hours ago
Roundtrip flight included
Charlotte (CLT) 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.
Velvet Haus Downtown 3rd Floor Deck Backyard

Velvet Haus Downtown 3rd Floor Deck Backyard

2 out of 5
Over-the-Rhine
Price was $1,046, price is now $940 per person
$940
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Cincinnati (CVG)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden is also provided.
Hotel Covington Cincinnati Riverfront

Hotel Covington Cincinnati Riverfront

4 out of 5
Central Business District
Price was $1,114, price is now $1,012 per person
$1,012
per person
Nov 27 - Nov 29
found 24 hours ago
Roundtrip flight included
Philadelphia (PHL) 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.
Ashley Quarters Hotel Cincinnati Airport

Ashley Quarters Hotel Cincinnati Airport

2.5 out of 5
Price was $737, price is now $677 per person
$677
per person
Oct 9 - Oct 12
found 5 hours ago
Roundtrip flight included
Charlotte (CLT) to Cincinnati (CVG)
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental 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
French Quarter Inn

French Quarter Inn

3 out of 5
25 East McDonald Parkway Maysville KY
Free Cancellation
Reserve now, pay when you stay
$109 nightly
The price is $121 total per night
$121 total
Sep 6 - Sep 7
Total with taxes and fees
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
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
Sep 20 - Sep 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
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
Oct 4 - Oct 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
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
$55 nightly
The price is $61 total per night
$61 total
Sep 6 - Sep 7
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
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
$106 nightly
The price is $117 total per night
$117 total
Sep 6 - Sep 7
Total with taxes and fees
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.
Pool
Breakfast included
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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 $426, 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

A historic downtown area with a prominent clock tower and a green-roofed building.