Winchester Vacations from $776
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Winchester Vacation
Take away the hard part of organizing your next epic adventure with a Winchester vacation package. Whether you're visiting for its landmarks, food or other highlights, this city offers endless possibilities for fun. Every trip to Winchester needs a well-thought-out itinerary. Fill yours with attractions like Bluegrass Heritage Museum, Lykins Park and Southwind Golf Course. Your ultimate Winchester vacation is just a few clicks away. Browse hotels, airfares and more on Expedia for an adventure that's tailored to suit your travel style.
The Latest Winchester vacation packages
Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Lexington
Downtown Lexington
$963
per person
Oct 9 - Oct 13
found 12 hours ago
Roundtrip flight included
Denver (DEN) to Lexington (LEX)
8.8/10 Excellent! (1,004 reviews)
We had a wonderful stay at the Hyatt. Shout out especially to Peter at the Registration desk who was so personable and helpful. Even though Barry Manilow had to cancel his concert, Peter sang Copacabana for us!
All of the staff and accommodations were amazing! I can very highly recommend Hyatt Regency Lexington.
Reviewed on Aug 5, 2026
Origin Lexington a Wyndham Hotel
$1,932
per person
Oct 23 - Oct 30
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Lexington (LEX)
9.4/10 Exceptional! (1,024 reviews)
Very Friendly Staff. Conveniently located to lots of shops and restaraunts. Room was very clean, modern and comfortable! 10/10
Reviewed on Aug 8, 2026
Hampton Inn I-75 Lexington/Hamburg Area
$998
per person
Oct 23 - Oct 30
just found
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Lexington (LEX)
8.6/10 Excellent! (1,006 reviews)
When we arrived we were told they were overbooked. There was no room for us.
They said Expedia booked customers were overbooked. Several hotels in the area were full. we had no where to stay. Expedia owes me a re fund and I will never use Expedia nor this Hotel chain again!
Reviewed on Aug 3, 2026
Stay near popular Winchester attractions
Winchester Traveling Trail
This serene mile-long pathway winds through meadows of Kentucky bluegrass, offering a peaceful escape. Benches and shaded areas make it perfect for a leisurely morning stroll with your leashed dog.
Bluegrass Heritage Museum
7.4/10 (13 reviews)
This Romanesque Revival building houses three floors of exhibits chronicling the Bluegrass region's rich heritage. Explore the preserved historic operating room and discover local artifacts spanning centuries.
Wiseman Park
Wiseman Park offers 3.6 acres of tranquil green space with tennis courts, basketball, and a playground in Winchester. Bring a picnic to enjoy under the shelter while children explore the recreational facilities.
Lykins Park
5.8/10 (6 reviews)
Lykins Park spans 40 acres with sports fields, playgrounds, and a disc golf course for active families. Catch the spectacular "Lights Over Lykins" fireworks display in July, a beloved Winchester tradition.
Southwind Golf Course
6.0/10 (2 reviews)
This challenging par-71 course captivates with strategic water hazards and dramatic elevation changes across 6,265 yards. Enjoy post-round relaxation at Stinky & Coco's patio overlooking the pristine fairways.
Cassell Creek Golf Course
7.6/10 (4 reviews)
This welcoming 18-hole course in Winchester offers an accessible golfing experience with open fairways and minimal hazards. Enjoy a relaxed round during spring or fall when the course conditions are at their prime.
Winchester Opera House
This 1873 opera house captivates with its elegant architecture and preserved wooden Grand Ballroom. Experience Winchester's cultural heritage through weddings and events in this meticulously restored historic venue.
The Holler
A local gathering spot known as "The Holler" where community members connect away from tourist crowds. Enjoy authentic regional culture and conversations with residents who share stories of the area.
What to do in Winchester
Winchester Hotel Deals
Baymont by Wyndham Winchester
960 Interstate Dr Winchester KY
Fully refundableReserve now, pay when you stay
$74 nightly
$82 total
Sep 7 - Sep 8
Total with taxes and fees
Marriott Lexington Griffin Gate Golf Resort & Spa
1800 Newtown Pike Lexington KY
Fully refundableReserve now, pay when you stay
$133 nightly
$155 total
Sep 6 - Sep 7
Total with taxes and fees
The Manchester
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
$194 nightly
$225 total
Sep 7 - Sep 8
Total with taxes and fees
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.
Find the Best Winchester Vacation Packages
Winchester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Blue Grass Airport (LEX) |
Population | 18,400 |
Max Temp Winter | 40ºF |
Max Temp Summer | 85ºF |
Top Sights | Bluegrass Heritage Museum, Southwind Golf Course and Lykins Park |
More vacations you might like
Frequently asked questions
How much does a Winchester vacation package cost?
You'll find cheap prices from $776 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. Opting to travel in less busy periods means you can typically find better prices on flights and accommodations.
How many days is enough for Winchester?
The ideal length of your Winchester vacation depends on what you'd like to see. Usually, a few days to a week will give you plenty of time to hit all the top sights and discover some hidden gems along the way.
Is it worth booking a vacation package to Winchester?
Whether you're planning to discover attractions like Bluegrass Heritage Museum and Lykins Park, or eager to experience its terrific dining and nature, a Winchester vacation guarantees an unforgettable adventure. Book your trip with Expedia and find out why Winchester is such a good vacation destination.
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.
Does Expedia offer Book Now, Pay Later Winchester vacation packages?
Secure your perfect escape to Winchester with help from Expedia's Book Now, Pay Later vacations. No need to scrimp and save or wait for your next paycheck — we've teamed up with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans let you spread the total cost over 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily stay on budget and snap up travel deals while they last.
Explore a world of travel with Expedia
- La Quinta Inn & Suites Hotels in Winchester
- Luxury Hotels in Lexington
- Hotels near Bluegrass Heritage Museum
- Cottages in Winchester
- Cabin Rentals in Winchester
- Motels in Lexington
- Pet-Friendly Hotels in Lexington
- Mount Sterling Hotels
- Casino Hotels in Winchester
- Hotels near Rupp Arena
- Non-Smoking Hotels in Winchester
- Georgetown Hotels
- Luxury Hotels in Winchester
- Hotels near University of Kentucky
- Lexington Hotels
- 3 Star Hotels in Winchester
- Hotels near Ark Encounter
- Marriott Hotels & Resorts in Winchester
- Business Hotels in Winchester
- Hotels with Suites in Winchester
- Hotels with an Outdoor Pool in Winchester
- Hotels with a Pool in Winchester
- Hotels with Connecting Rooms in Winchester
- 4 Star Hotels in Winchester
- Rv Parks in Winchester
- Hotels near Hamburg Pavilon
- Motels in Winchester
- Resorts in Winchester
- Cheap Hotels in Winchester
- Cabin Rentals in Kentucky
- Richmond Hotels
- Cheap Hotels in Lexington
- B&B in Winchester
- Guest Houses in Winchester
- Hotels with Hot Tubs in Lexington
- Hotels with an Indoor Pool in Winchester
- Downtown Lexington Hotels
- Extended Stay Hotels in Lexington
- Winchester Hotels
- Boutique Hotels in Winchester
- Hotels with Bars in Winchester
- Hotels near Lykins Park
- Hilton Hotels in Winchester
- Hotels near Kentucky Horse Park
- Hotels with Restaurants in Winchester
- Pet-Friendly Hotels in Winchester
- Flights from Louisville (SDF) to Lexington (LEX)
- Flights to Lexington
- Flights from Winchester
- Flights to Kentucky
- Flights from Dallas (DFW) to Lexington (LEX)
- Flights from Chicago (ORD) to Lexington (LEX)
- Flights to Winchester
- Flights from Atlanta (ATL) to Lexington (LEX)
- Flights from Blue Grass
- Flights from New York (JFK) to Lexington (LEX)
- Mount Sterling Vacations
- Talon Winery
- Raven Run Nature Sanctuary
- Bluegrass Heritage Museum
- Lykins Park
- Kentucky Horse Park
- Duncan Tavern Historic Center
- Fort Boonesborough State Park
- Shriners Hospitals for Children
- Visit Winchester
- Ashland Henry Clay Estate
- Kroger Field
- Lexington Sporting Club Youth Complex
- The Cane Ridge Meeting House
- The Thoroughbred Center
- Lake Reba
- Cassell Creek Golf Course
- Rupp Arena
- Jacobson Park
- Southwind Golf Course
- Claiborne Farm
- Nannine Clay Wallis Arboretum
- Grimes Mill Winery
- Lexington Opera House
- White Hall State Historic Site
- Ark Encounter
- Paradise Cove Aquatic Center
- The Kentucky Castle
- Thoroughbred Park
- Visit Lexington
- Loudoun House
- Lexington Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
