Winchester Vacations

Book a Hotel + Flight together to unlock savings

Photo by Nawa Aseen

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to SAR 390 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Find the Best Winchester Vacation Packages

Winchester Hotel Deals

The Manchester
The Manchester
4 out of 5
941 Manchester St, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is SAR 605 per night from Jun 29 to Jun 30
SAR 605
SAR 767 total
29 Jun - 30 Jun
includes taxes & fees
9.4/10 Exceptional! (864 reviews)
"Very nice, hotel and rooms. It would be easier if parking and breakfast were included in the price of the stay. Would stay again if in Lexington."

Reviewed on 5 June 2025

The Manchester
GuestHouse Lexington
GuestHouse Lexington
2.5 out of 5
2261 Elkhorn Road, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is SAR 224 per night from Jul 6 to Jul 7
SAR 224
SAR 260 total
6 Jul - 7 Jul
includes taxes & fees
8.2/10 Very Good! (1,195 reviews)
Convenient location and clean!
"Surprisingly well. Very nice and helpful reception from front desk. When I did walk in the room, it was dated but the sheets looked and felt clean, towels were clean, and the bathroom was clean. Very important to me."

Reviewed on 4 June 2025

GuestHouse Lexington
DoubleTree Suites by Hilton Hotel Lexington
DoubleTree Suites by Hilton Hotel Lexington
4 out of 5
2601 Richmond Rd, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is SAR 407 per night from Jun 29 to Jun 30
SAR 407
SAR 473 total
29 Jun - 30 Jun
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"Great service!"

Reviewed on 2 June 2025

DoubleTree Suites by Hilton Hotel Lexington
See all 1,124 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

Kentucky Horse Park showing land animals

Kentucky Horse Park

4.5/5(328 reviews)

Explore Kentucky Horse Park, a favorite green space in Lexington, and also enjoy the area's horseback riding. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Kentucky Horse Park
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
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