Winchester Vacations from $450
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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.
Comfort Inn & Suites
Price was $559, price is now $450 per person
$450
per person
Dec 17 - Dec 23
found 15 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Lexington (LEX)
8/10 Very Good! (1,001 reviews)
Breakfast was reasonably healthy but could be improved. Staff was great. Limited number of nearby eating options.
Reviewed on Oct 10, 2025
21c Museum Hotel Lexington
Downtown Lexington
Price was $726, price is now $579 per person
$579
per person
Dec 17 - Dec 23
found 15 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Lexington (LEX)
8.8/10 Excellent! (1,001 reviews)
The overall vibe of the hotel was awesome. The bar was great and the hotel staff were helpful.
Reviewed on Oct 7, 2025
GuestHouse Lexington
Price was $598, price is now $478 per person
$478
per person
Dec 17 - Dec 23
found 15 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Lexington (LEX)
8.2/10 Very Good! (1,368 reviews)
I did not realize there was no elevator... would've been a deal breaker. The curtains i the room don't cover the window...bright lights all night sucked. .did not sleep well.
Reviewed on Oct 13, 2025
Discover the most popular places to visit in Winchester
Kentucky Horse Park
4.5/5(328 reviews)
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
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.
Fayette Mall
4.5/5(321 reviews)
You can find the perfect gifts to bring home at Fayette Mall during your stay in Lexington. Discover the area's acclaimed theater scene, or seek out its horseback riding.
What to do in Winchester
Lexington: Downtown Walking Food & History Tour
$99
per adult
Experience Rebecca Ruth Chocolate Tour & Museum!
$10
per adult
Bites of the Bluegrass Cocktails & Bites Tour
$105
per adult
Winchester Hotel Deals
Best Western Winchester Hotel
1307 W Lexington Ave, Winchester, KY
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $89 total per night from Nov 2 to Nov 3
$89 total
Nov 2 - Nov 3
Total with taxes and fees
8.4/10 Very Good! (982 reviews)
"Yes"
Reviewed on Oct 5, 2025
Spark by Hilton Lexington Hamburg
2381 Buena Vista Rd, Lexington, KY
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $80 total per night from Oct 28 to Oct 29
$80 total
Oct 28 - Oct 29
Total with taxes and fees
8.6/10 Excellent! (183 reviews)
"Staff was friendly and the place was clean n well kept"
Reviewed on Oct 6, 2025
GuestHouse Lexington
2261 Elkhorn Road, Lexington, KY
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $83 total per night from Oct 26 to Oct 27
$83 total
Oct 26 - Oct 27
Total with taxes and fees
8.2/10 Very Good! (1,404 reviews)
"I did not realize there was no elevator... would've been a deal breaker. The curtains i the room don't cover the window...bright lights all night sucked. .did not sleep well."
Reviewed on Oct 13, 2025
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.
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
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- 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
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- Hotels near Claiborne Farm
- Hotels near The Thoroughbred Center
- Hotels near Lexington Ice Center
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- 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.