Deals on vacations and trips to Winchester

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Price found within the past 48 hours. Click for updated prices.
Ashley Quarters Hotel Cincinnati Airport

Ashley Quarters Hotel Cincinnati Airport

2.5 out of 5
Price was $507, price is now $425 per person
$425
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) 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.
Firehouse Lofts

Firehouse Lofts

4 out of 5
Downtown Cincinnati
Save 100% on your flight
Price was $1,722, price is now $1,398 per person
$1,398
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Cincinnati (CVG)
A rooftop terrace, free self parking, and a virtual front desk are featured at this aparthotel. WiFi in public areas is free. Express check-out is also provided.
voco The Clair Cincinnati Downtown by IHG

voco The Clair Cincinnati Downtown by IHG

4 out of 5
Downtown Cincinnati
Price was $785, price is now $649 per person
$649
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) 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.
Belterra Casino Resort

Belterra Casino Resort

3.5 out of 5
Price was $747, price is now $631 per person
$631
per person
Nov 30 - Dec 4
found 18 hours ago
Roundtrip non-stop flight included
Appleton (ATW) to Cincinnati (CVG)
This hotel features a golf course, a casino, and 4 restaurants. Traveling on business? Take advantage of the business center, laundry service, and free valet parking. Make the most of the gym and seasonal outdoor pool, and relax with drinks at one of the 3 bars/lounges.
Mana and Lila Boutique Aparthotel

Mana and Lila Boutique Aparthotel

2 out of 5
Downtown Cincinnati
Price was $899, price is now $762 per person
$762
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Cincinnati (CVG)
This aparthotel features a virtual front desk.

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
Quiet Farm Escape | Fishing, Nature & Views

Quiet Farm Escape | Fishing, Nature & Views

Winchester OH
$679 nightly
The price is $697 total per night
$697 total
Oct 20 - Oct 21
Total with taxes and fees
This vacation home features barbecue grills.
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
Nov 1 - Nov 2
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 laundry service. Enjoy the seasonal outdoor pool and conveniences like a terrace and free newspapers.
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
$82 nightly
The price is $93 total per night
$93 total
Nov 19 - Nov 20
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
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
Nov 19 - Nov 20
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
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
Nov 5 - Nov 6
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free on-the-go 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 $425, 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.