Winchester Trips (flight + hotel)

Photo by Nawa Aseen

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Top hotels in Winchester

Baymont by Wyndham Winchester
Baymont by Wyndham Winchester
2.5 out of 5
960 Interstate Dr, Winchester, KY
Fully refundableReserve now, pay when you stay
The price is P4,322 per night from Jul 1 to Jul 2
P4,322
P4,765 total
Jul 1 - Jul 2
includes taxes & fees
7/10 Good! (704 reviews)
"as a 76 year old women i fell very safe here. i didn't notice any places to eat within walking distance of the property"

Reviewed on Jun 22, 2025

Baymont by Wyndham Winchester
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 P6,985 per night from Jul 6 to Jul 7
P6,985
P8,108 total
Jul 6 - Jul 7
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"Enjoyed my stay."

Reviewed on Jun 19, 2025

DoubleTree Suites by Hilton Hotel Lexington
Embassy Suites by Hilton Lexington/UK Coldstream
Embassy Suites by Hilton Lexington/UK Coldstream
3.5 out of 5
1801 Newtown Pike, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is P5,783 per night from Jul 6 to Jul 7
P5,783
P6,712 total
Jul 6 - Jul 7
includes taxes & fees
8.6/10 Excellent! (1,018 reviews)
"We had a nice quiet overnight stay to break up our long travel weekend. We booked a King suite for our family of 4. It was a great size! We were able to stretch out and not feel like we were in each other’s way. I usually hate hotels because of how noisy they can be, but I can say even with a convention ..."

Reviewed on Jun 23, 2025

Embassy Suites by Hilton Lexington/UK Coldstream
See all 1,139 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.

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 many days is enough for Winchester?
With a well-organized travel plan, you can easily visit the most popular Winchester sights in a few days. But if you prefer to discover lesser-known spots or take day trips, consider booking your Winchester vacation for longer.
Is it worth booking a vacation package to Winchester?
Known for its dining, nature and plenty of other highlights, you can be certain Winchester is a good vacation destination. Some of the most popular attractions to add to your itinerary? Don't miss Bluegrass Heritage Museum and Lykins Park during your Winchester vacation.
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.

Popular places to visit

The Red Mile Racetrack

Enjoy a trip to The Red Mile Racetrack and popular activities like horseback riding in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.

The Red Mile Racetrack

University of Kentucky Albert B. Chandler Hospital

Though University of Kentucky Albert B. Chandler Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Lexington while you are here.

University of Kentucky Albert B. Chandler Hospital

What to do in Winchester

Picture 1 for Activity Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass

Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass

P2,360
per adult
98% of travellers recommend
Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass
Self Guided Driving Tour to Four Kentucky Bourbon Distilleries

Self Guided Driving Tour to Four Kentucky Bourbon Distilleries

P1,685
per traveler
Self Guided Driving Tour to Four Kentucky Bourbon Distilleries
Experience Rebecca Ruth Chocolate Tour & Museum!

Experience Rebecca Ruth Chocolate Tour & Museum!

P562
per adult
Experience Rebecca Ruth Chocolate Tour & Museum!
See all activities in Winchester
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.