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.
Tru by Hilton Mason Kings Island

Tru by Hilton Mason Kings Island

2.5 out of 5
Price was $472, price is now $422 per person
$422
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Cincinnati (CVG)
This hotel features an indoor pool and a gym. 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.
Belterra Casino Resort

Belterra Casino Resort

3.5 out of 5
Price was $757, price is now $626 per person
$626
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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.
Holiday Inn Express and Suites Dry Ridge by IHG

Holiday Inn Express and Suites Dry Ridge by IHG

2.5 out of 5
Price was $564, price is now $490 per person
$490
per person
Feb 20 - Feb 23
found 2 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Cincinnati (CVG)
This hotel doesn't skimp on freebies - guests receive free continental breakfast and free WiFi. Traveling on business? Take advantage of the 2 onsite conference rooms. Enjoy the indoor pool and conveniences like a 24-hour front desk and laundry facilities.
Comfort Suites Dry Ridge

Comfort Suites Dry Ridge

2.5 out of 5
Price was $592, price is now $520 per person
$520
per person
Feb 20 - Feb 23
found 2 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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. Guests will appreciate freebies like self-serve breakfast and free self parking.
Comfort Inn Airport Turfway Road

Comfort Inn Airport Turfway Road

2.5 out of 5
Price was $519, price is now $457 per person
$457
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Cincinnati (CVG)
A 24-hour gym, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. There's express check-out and multilingual staff can provide around-the-clock assistance.

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.
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
Jan 26 - Jan 27
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.
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
$48 nightly
The price is $53 total per night
$53 total
Jan 12 - Jan 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.
French Quarter Inn

French Quarter Inn

3 out of 5
25 East McDonald Parkway Maysville KY
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $122 total per night
$122 total
Jan 12 - Jan 13
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.
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
$98 nightly
The price is $108 total per night
$108 total
Jan 13 - Jan 14
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.
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
$58 nightly
The price is $64 total per night
$64 total
Jan 14 - Jan 15
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.
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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 $422, 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

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