Jessamine County Vacations & Trips from $1,179
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Your Jessamine County Vacation
When adventure calls, answer it with a customized vacation package to Jessamine County. Wherever your travels take you and whatever your plans are, get ready to immerse yourself in a destination with so much to offer. During your trip to Jessamine County, you'll want to include some of its leading cities. What can't you miss? Wilmore. From the moment you book your Jessamine County vacation to when you get back home, Expedia has you covered every step of the way.
The Latest Jessamine County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Louisville Marriott Downtown
Downtown Louisville
$1,224
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9/10 Wonderful! (1,000 reviews)
Property was nice! Room was as expected! Valet/service was much to be desired! Room service snd bar service was some of the worst I’ve ever encountered! Was told by room service they had water; but if I wanted then I had to come get them myself! She wasn’t delivering them! Bartender in the hotel lounge was so bad it was laughable!! Told us she was doing us a favor by waiting on us! Lost her mind when I ask for 3 small bowls to put nuts in so our party of eight didn’t have to pass around the same cardboard cup she put them in!
Reviewed on Aug 16, 2026
Hotel Distil, Autograph Collection
Downtown Louisville
$1,235
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9.6/10 Exceptional! (489 reviews)
Love this hotel. The bed was incredibly comfortable for a hotel bed. Linens were high end. Staff were great - neighborhood was great. Restaurant had a great breakfast. Would definitely stay again.
Reviewed on Aug 5, 2026
Find the Best Jessamine County Vacation Packages
Jessamine County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Blue Grass Airport (LEX) |
Jessamine County Hotel Deals
DoubleTree Suites by Hilton Hotel Lexington
2601 Richmond Rd Lexington KY
Fully refundableReserve now, pay when you stay
$106 nightly
$123 total
Aug 30 - Aug 31
Total with taxes and fees
The Manchester
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
$189 nightly
$220 total
Sep 1 - Sep 2
Total with taxes and fees
9.6/10 Exceptional! (1,395 reviews)
"Wonderful stay, very relaxed, friendly staff. Rooftop had a young vibe. Bar/lounge in hotel classy."
Reviewed on Aug 16, 2026
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
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.
Stay near popular Jessamine County attractions
Camp Nelson National Monument
9.4/10 (3 reviews)
You can spend time browsing the exhibits at Camp Nelson National Monument during your travels in Nicholasville. While in this family-friendly area, you can enjoy the restaurants.
Asbury Theological Seminary
Enjoy the collegiate vibe at Asbury Theological Seminary during your stay in Wilmore. Make some time to visit the shops while you're in the area.
Chrisman Mill Vineyards
7.0/10 (2 reviews)
You can enjoy a tasting or tour at Chrisman Mill Vineyards during your travels to Nicholasville. Discover the entertainment venues in this family-friendly area, or seek out its horseback riding.
First Vineyard
8.6/10 (4 reviews)
You can enjoy a tasting or tour at First Vineyard during your travels to Nicholasville. Discover the countryside and sunrises in this family-friendly area.
High Bridge Kentucky River Museum
You can spend time exploring the galleries in High Bridge Kentucky River Museum in Wilmore.
Connemara Golf Course
9.4/10 (3 reviews)
Play a round of golf in Nicholasville at Connemara Golf Course, and enjoy other activities such as horseback riding. Attend a sporting event or simply enjoy the lively bars while you're in the area.
Kirkland Athletic Complex
After visiting Kirkland Athletic Complex, make a plan to see the other sights and activities in Wilmore. Make some time to visit the shops while you're in the area.
Wilmore City Hall
Wilmore City Hall is just one of the places to see in Wilmore, so why not enjoy the other things to explore during your travels? Make some time to visit the shops while you're in the area.
What to do in Jessamine County
Bites of the Bluegrass Cocktails & Bites Tour
$125
per adult
100% of travellers recommend
Distillery District Food & History Tour in Lexington
$125
per adult
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
