Deals on vacations and trips to Winchester

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voco The Clair Cincinnati Downtown by IHG

voco The Clair Cincinnati Downtown by IHG

4 out of 5
Downtown Cincinnati
Price was $796, price is now $626 per person
$626
per person
Jul 3 - Jul 7
found 1 day 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.
Landing Apartments Near University Of Cincinnati

Landing Apartments Near University Of Cincinnati

4 out of 5
Corryville
Save 100% on your flight
Price was $1,638, price is now $1,244 per person
$1,244
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Houston (IAH) to Cincinnati (CVG)
This aparthotel features an outdoor pool and a 24-hour gym. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, barbecue grills, and a virtual front desk are also on offer.
Hyatt Place Cincinnati / Sharonville Convention Center

Hyatt Place Cincinnati / Sharonville Convention Center

3 out of 5
Price was $860, price is now $676 per person
$676
per person
Jul 9 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Cincinnati (CVG)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.
Hotel Covington Cincinnati Riverfront

Hotel Covington Cincinnati Riverfront

4 out of 5
Old Town
Price was $991, price is now $793 per person
$793
per person
Jul 3 - Jul 7
found 1 day 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
Central Business District
Price was $880, price is now $711 per person
$711
per person
Jul 3 - Jul 7
found 1 day 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.

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
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
Jun 28 - Jun 29
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
$55 nightly
The price is $61 total per night
$61 total
May 31 - Jun 1
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
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
Jun 21 - Jun 22
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
Paragon Inn Hillsboro

Paragon Inn Hillsboro

2 out of 5
883 W Main St Hillsboro OH
Free Cancellation
Reserve now, pay when you stay
$70 nightly
The price is $77 total per night
$77 total
Jun 30 - Jul 1
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
Country Nights Inn

Country Nights Inn

2.5 out of 5
11255 State Rte 41 West Union OH
Free Cancellation
Reserve now, pay when you stay
$80 nightly
The price is $88 total per night
$88 total
Jun 14 - Jun 15
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.
Parking included
Free WiFi
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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 $626, 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