Winchester Vacations from $542
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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.
Wildflower Ranch Inn
Price was $633, price is now $542 per person
$542
per person
Aug 6 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Lexington (LEX)
9.2/10 Wonderful! (23 reviews)
Beautiful historic property run by two artists who are great hosts. Conveniently located to many Bourbon Trail stops. The master’s suite with the whirlpool tub is incredible.
Reviewed on Apr 18, 2026
Country Inn & Suites by Radisson, Lexington, KY
Price was $801, price is now $578 per person
$578
per person
Jul 6 - Jul 9
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Lexington (LEX)
8/10 Very Good! (1,002 reviews)
The pool was closed for half our stay and it seemed fine and the lady at the front desk just wasn’t wanting to deal with people in the pool at night, so she “closed it for maintenance.”
Reviewed on May 22, 2026
Residence Inn by Marriott Lexington
Price was $862, price is now $630 per person
$630
per person
Jul 6 - Jul 9
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Lexington (LEX)
8.6/10 Excellent! (386 reviews)
My family spent the night before catching an early morning flight. The room met our need for a location close to the airport. Beds were squeaky and there was some noise from the street. Staff were friendly.
Reviewed on May 15, 2026
Montgomery Inn BnB
Price was $644, price is now $542 per person
$542
per person
Jul 8 - Jul 11
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Lexington (LEX)
9.4/10 Exceptional! (107 reviews)
We were doing a cross country trip in our airstream. We stayed one night at the BnB and absolutely loved the grounds, our room, and our host. She went above and beyond accommodating our airstream and our dogs.
Reviewed on May 11, 2026
Discover the most popular places to visit in Winchester
Kentucky Horse Park
Experience the exciting worlds of horses and horseracing at this equine theme park with multiple museums in the middle of Kentucky’s horse country.
University of Kentucky
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.
Keeneland Racing Course
Enjoy a trip to Keeneland Racing Course and popular activities like horseback riding in Lexington. You can attend a sporting event while in the area.
What to do in Winchester
Bites of the Bluegrass Cocktails & Bites Tour
$125
per adult
Distillery District Food & History Tour in Lexington
$125
per adult
Woodford Reserve, Castle & Key, and Stitzel Weller Bourbon Tour
$285
per adult
Winchester Hotel Deals
The Manchester
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
$203 nightly
The price is $236 total per night from Jun 14 to Jun 15
$236 total
Jun 14 - Jun 15
Total with taxes and fees
9.6/10 Exceptional! (1,292 reviews)
"Had a great overnight stay. Shuttle was great to Distillary area and dining room rooftop was nice. We even played Trivia that night ( ugh we lost). Great nights rest before heading to Nashville. Would stay there again for certain."
Reviewed on May 18, 2026
Hotel LEX, Trademark Collection by Wyndham
5532 Athens Boonesboro Rd Lexington KY
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $97 total per night from Jun 3 to Jun 4
$97 total
Jun 3 - Jun 4
Total with taxes and fees
8/10 Very Good! (710 reviews)
"Cute place to stop for a night. Definitely was an exisiting hotel that was bought out and quickly flipped."
Reviewed on May 23, 2026
Holiday Inn Express Lexington Horse Park Area by IHG
1935 Stanton Way, 1935 4 yes Lexington KY
Fully refundable
$94 nightly
The price is $110 total per night from May 31 to Jun 1
$110 total
May 31 - Jun 1
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
Explore a world of travel with Expedia
- Hotels near Bluegrass Heritage Museum
- Hotels near Community Park
- Hotels near Clark Regional Medical Center
- Hotels near Lykins Park
- Hotels near Southwind Golf Course
- Hotels near Cassell Creek Golf Course
- Hotels near Kentucky River Museum
- Hotels near Fort Boonesborough State Park
- Hotels near Grimes Mill Winery
- Hotels near Kentucky River
- Lexington Hotels
- Hotels near W S Webb Museum of Anthropology
- Hotels near Hamburg Pavilon
- Hotels near Raven Run Nature Sanctuary
- Hotels near Jacobson Park
- Mount Sterling Hotels
- Hotels near Hamburg Place
- Hotels near Liberty Area
- Cabin Rentals in Mount Sterling
- Hotels with a Pool in Mount Sterling
- Pet-Friendly Hotels in Mount Sterling
- Hotels with Hot Tubs in Mount Sterling
- Rv Parks in Mount Sterling
- Hotels with smoking rooms in Mount Sterling
- 4 Star Hotels in Mount Sterling
- Luxury Hotels in Mount Sterling
- B&B in Mount Sterling
- Motels in Mount Sterling
- 3 Star Hotels in Mount Sterling
- Hilton Hotels in Mount Sterling
- Marriott Hotels & Resorts in Mount Sterling
- Hotels with a Gym in Mount Sterling
- Apartments in Mount Sterling
- Cottages in Mount Sterling
- Hotels with an Outdoor Pool in Mount Sterling
- Family Hotels in Mount Sterling
- Hotels with Connecting Rooms in Mount Sterling
- Extended Stay Hotels in Mount Sterling
- Best Western Hotels in Mount Sterling
- Hotel Wedding Venues Hotels in Mount Sterling
- Red Roof Inn Hotels in Mount Sterling
- Resorts & Hotels with Spas in Mount Sterling
- Condo Rentals in Mount Sterling
- Farmstay in Mount Sterling
- Non-Smoking Hotels in Mount Sterling
- Hotels with an Indoor Pool in Mount Sterling
- Hotels near Claiborne Farm
- Hotels near The Thoroughbred Center
- Hotels near Lexington Ice Center
- Hotels near Talon Winery
- Hotels near Hopewell Museum
- Paris Hotels
- Hotels near The Cane Ridge Meeting House
- Camargo Hotels
- Cabin Rentals in Paris
- Bluegrass Heritage Museum
- Lykins Park
- Southwind Golf Course
- Cassell Creek Golf Course
- Fort Boonesborough State Park
- Boone Station State Historic Site
- Grimes Mill Winery
- Raven Run Nature Sanctuary
- Jacobson Park
- Mount Sterling Vacations
- Visit Mount Sterling
- White Hall State Historic Site
- Claiborne Farm
- The Thoroughbred Center
- Lexington Ice Center
- Talon Winery
- Hopewell Museum
- The Cane Ridge Meeting House
- Nannine Clay Wallis Arboretum
- Paris Vacations
- Duncan Tavern Historic Center
- Shriners Hospitals for Children
- Visit Paris
- Car rentals near Lykins Park
- Car rentals near Clintonville
- Car rentals near North Middletown
- Car rentals near Hamburg Pavilon
- Car rentals near Mount Sterling
- Enterprise Rental Cars in Mount Sterling
- Hertz Rental Cars in Mount Sterling
- Budget Rental Cars in Mount Sterling
- Luxury Car Rentals in Mount Sterling
- Car rentals near The Thoroughbred Center
- Car rentals near Camargo
- Car rentals near Paris
- Enterprise Rental Cars in Paris
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.