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.
Radisson Hotel Cincinnati Riverfront

Radisson Hotel Cincinnati Riverfront

3.5 out of 5
Price was $538, price is now $444 per person
$444
per person
May 9 - May 12
found 12 hours ago
Roundtrip flight included
Boston (BOS) 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.
Hotel Covington Cincinnati Riverfront

Hotel Covington Cincinnati Riverfront

4 out of 5
Price was $783, price is now $613 per person
$613
per person
May 9 - May 12
found 12 hours ago
Roundtrip flight included
Boston (BOS) 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.
Embassy Suites by Hilton Cincinnati RiverCenter

Embassy Suites by Hilton Cincinnati RiverCenter

3.5 out of 5
Price was $593, price is now $470 per person
$470
per person
May 9 - May 12
found 12 hours ago
Roundtrip flight included
Boston (BOS) 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.
voco The Clair Cincinnati Downtown by IHG

voco The Clair Cincinnati Downtown by IHG

4 out of 5
Downtown Cincinnati
Price was $703, price is now $564 per person
$564
per person
May 9 - May 12
found 12 hours ago
Roundtrip flight included
Boston (BOS) 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.
21c Museum Hotel Cincinnati

21c Museum Hotel Cincinnati

4.5 out of 5
Downtown Cincinnati
Price was $660, price is now $546 per person
$546
per person
May 9 - May 12
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Cincinnati (CVG)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Relax with a drink at the bar/lounge and enjoy perks like free WiFi. Valet parking, a 24-hour business center, and dry cleaning are also offered.

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
$110 nightly
The price is $122 total per night
$122 total
Mar 1 - Mar 2
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
Mar 15 - Mar 16
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
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
$50 nightly
The price is $55 total per night
$55 total
Mar 13 - Mar 14
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
Super 8 by Wyndham Maysville KY

Super 8 by Wyndham Maysville KY

2 out of 5
550 Tucker Dr Maysville KY
Free Cancellation
Reserve now, pay when you stay
$66 nightly
The price is $73 total per night
$73 total
Mar 4 - Mar 5
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. Express check-in, express check-out, and a computer station are also on offer.
Pet friendly
Parking 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
$65 nightly
The price is $73 total per night
$73 total
Mar 7 - Mar 8
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
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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 $444, 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
MAY 9, 2023 - WINCHESTER, KENTUCKY - aerial view of historic small town of Winchester with Town Clocktower and historic storefronts and buildings