Winchester Vacation Packages

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Top Winchester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Cincinnati Netherland Plaza

Hilton Cincinnati Netherland Plaza

4 out of 5
Downtown Cincinnati
per person
Sep 1 - Sep 4
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Cincinnati (CVG)
7.8/10 Good! (1,027 reviews)
Went for the CMF, great location. Lots of restaurants and entertainment in walking distance. Very roomy.

Reviewed on Jul. 28, 2025

Hyatt Regency Cincinnati

Hyatt Regency Cincinnati

4 out of 5
Downtown Cincinnati
per person
Sep 1 - Sep 4
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Cincinnati (CVG)
9/10 Wonderful! (1,450 reviews)
Hallway carpet had a mildew smell.

Reviewed on Jul. 28, 2025

voco The Clair Cincinnati Downtown by IHG

voco The Clair Cincinnati Downtown by IHG

3 out of 5
Downtown Cincinnati
per person
Sep 1 - Sep 4
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Cincinnati (CVG)
9.2/10 Wonderful! (1,025 reviews)
Staff was nice. Food in the restaurant amazing! Will definitely stay again.

Reviewed on Jul. 28, 2025

The Cincinnatian Hotel Curio Collection by Hilton

The Cincinnatian Hotel Curio Collection by Hilton

4 out of 5
Downtown Cincinnati
per person
Sep 1 - Sep 4
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Cincinnati (CVG)
7.6/10 Good! (1,001 reviews)
Lack of towels supplied. Room had accumulated dust in the slatted pocket doors. Location was great, staff was great, beds were comfortable. Stock more towels and a thorough cleaning would make this hotel really nice.

Reviewed on Jul. 23, 2025

Embassy Suites by Hilton Cincinnati RiverCenter

Embassy Suites by Hilton Cincinnati RiverCenter

3.5 out of 5
per person
Sep 1 - Sep 4
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Cincinnati (CVG)
7.4/10 Good! (1,020 reviews)
Valet is not 24 hours had pay for valet than self park because no valetvwas after midnight

Reviewed on Jul. 27, 2025

Ready to book your vacation to Winchester?

 

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Winchester Hotel Deals

Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !

Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !

Winchester
10/10 Exceptional! (267 reviews)
"We had an enjoyable stay at Deer Path cabins. Jim was friendly and accommodating. We enjoyed talking to him while fishing at the pond. The cabin was clean and welcoming!"

Reviewed on Jul. 23, 2025

Get rates
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
Beverly hills inn

Beverly hills inn

2.5 out of 5
1830 U.S. 52, Aberdeen, OH
Fully refundableReserve now, pay when you stay
The price is CA $62 per night from Jul 29 to Jul 30
CA $62
CA $69 total
Jul 29 - Jul 30
includes taxes & fees
8.6/10 Excellent! (76 reviews)
"I love this place!!"

Reviewed on Jul. 22, 2025

Beverly hills inn
Countryside Inn & Suites

Countryside Inn & Suites

2.5 out of 5
100 Leininger Street, Mount Orab, OH
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from Aug 11 to Aug 12
CA $118
CA $134 total
Aug 11 - Aug 12
includes taxes & fees
7/10 Good! (516 reviews)
"always clean, and friendly easy check in"

Reviewed on Jul. 9, 2025

Countryside Inn & Suites
See all 139 properties in Winchester
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.
All Inclusive Vacations
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Frequently asked questions

How much does a Winchester vacation package cost?
Offering excellent value package deals from CA $894 on Expedia, you'll be pleasantly surprised at how much a vacation to Winchester costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Winchester?
To pick up cheap Winchester vacation packages, plan your getaway outside of peak times such as school holidays. You'll typically find lower prices and better availability when it's less busy.
How many days is enough for Winchester?
Typically, a handful of days is enough to see the main attractions during your Winchester vacation. But if you want to have some time to kick back or take day tours, consider extending your itinerary.
How to find the best Winchester package deals?
Bagging a cheap Winchester package deal is a cinch with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can personalize your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to view the most economical Winchester package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Winchester vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and stays separately. Better still, you can customize your Winchester getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Winchester?
Score amazing discounts by booking your flights in advance with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Winchester getaway.
How to plan a trip to Winchester?

  1. Pick your travel dates: The things you plan to do in Winchester and your favourite season can help you decide when to get away.
  2. Figure out your budget: Ensure you have enough money to cover everything from meals and transportation to flights and activities. Your accommodations will probably be the largest expense during your trip to Winchester.
  3. Determine how many days away: Start by compiling a list of the activities and sights you'd like to get to in Winchester. Then, estimate how long you'll need for each, including any travel time.
  4. Combine your accommodations and airfare: After you've nailed down your trip dates and duration, lock in the right Winchester vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.