Winchester Vacations

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Find the Best Winchester Vacation Packages

Winchester Hotel Deals

GLō Best Western Lexington
GLō Best Western Lexington
3 out of 5
1935 Stanton Way, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is AED 317 per night from Apr 7 to Apr 8
AED 317
AED 382 total
includes taxes & fees
7 Apr - 8 Apr
9.2/10 Wonderful! (2,284 reviews)
"Thought it was a little weird microwave was on the floor in corner , but other than it everything was great"

Reviewed on 22 March 2025

GLō Best Western Lexington
Quality Inn Lexington -Horse Park
Quality Inn Lexington -Horse Park
2.5 out of 5
1938 Stanton Way, Bldg A, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is AED 231 per night from Apr 6 to Apr 7
AED 231
AED 279 total
includes taxes & fees
6 Apr - 7 Apr
8.2/10 Very Good! (1,471 reviews)
"Had a wonderful experience here. Very clean, smelled good, easy stay with dogs. Really glad we chose this hotel!"

Reviewed on 19 March 2025

Quality Inn Lexington -Horse Park
Hilton Lexington/Downtown
Hilton Lexington/Downtown
3.5 out of 5
369 West Vine Street, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is AED 559 per night from Apr 6 to Apr 7
AED 559
AED 674 total
includes taxes & fees
6 Apr - 7 Apr
8.2/10 Very Good! (1,005 reviews)
Great place to stay
"Hotel was clean and comfortable. Staff was very helpful and knowledgeable. Highly recommend"

Reviewed on 19 March 2025

Hilton Lexington/Downtown
See all 1,089 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.

Frequently asked questions

How much does a Winchester vacation package cost?
You’ll find cheap prices on Expedia for your Winchester escape. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Winchester costs.
What are the cheapest months to go to Winchester?
December, January and February are the best times to search for cheap Winchester vacation packages. Traveling in quieter months means you can generally find better prices on accommodations and flights.
How to find the best Winchester package deals?
Use Expedia’s handy filters to help you find some of the best Winchester package deals. When you begin your search, simply set your maximum budget and then order the results by “Price: low to high.” If you’re looking to save, plan your adventure for midweek, or browse for Winchester package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it’s usually best to lock in your vacation package well in advance.
Is it cheaper to book a Winchester vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You’ll usually snag a better deal than booking each component individually. And you’ll still enjoy the freedom to create a personalized Winchester vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Winchester?
Secure fantastic discounts by booking your flights ahead of time with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Winchester adventure.
How to plan a trip to Winchester?

  1. Choose the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Winchester.
  2. Work out your budget: Make sure you have enough money to pay for everything from transportation and food to experiences and flights. Your hotel will probably be the largest expense during your trip to Winchester.
  3. Decide how long to go away for: Now that you know more about Winchester, you can work out the right length of your vacation. Pull together a rough itinerary and allocate enough time to get through everything on your must-do list.
  4. Combine your accommodations and airfare: After you’ve nailed down your travel dates and duration, lock in the ideal Winchester vacation package for you.

Discover the most popular places to visit in Winchester

In a hores eye #2

University of Kentucky

4.5/5(384 reviews)

Explore the campus of University of Kentucky, during your travels in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.

University of Kentucky
Kentucky Horse Park showing land animals

Kentucky Horse Park

4.5/5(328 reviews)

Explore the lovely green spaces of Kentucky Horse Park and enjoy the horseback riding in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Kentucky Horse Park
The Kentucky Castle

The Kentucky Castle

4.5/5(24 reviews)

Enjoy a trip to The Kentucky Castle and popular activities like horseback riding in Versailles. Attend a sporting event or simply enjoy the lively bars while you're in the area.

The Kentucky Castle