Jessamine County Vacation Packages
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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.
Top Jessamine County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Louisville Marriott Downtown
Downtown Louisville
CA $1,930
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Louisville (SDF)
9/10 Wonderful! (1,003 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
Elwood Hotel & Suites
CA $1,465
per person
Oct 19 - Oct 23
found 11 hours ago
Roundtrip flight included
Edmonton (YEG) to Lexington (LEX)
9.4/10 Exceptional! (1,141 reviews)
Needing to get money back for this stay, I brought up concerns to the front desk and received no help. Unfortunately did not get a name or pictures but I had to move rooms 3 times just to get to a room that I could stand to sleep in. I was offered no assistance moving my things from room to room. The first room smelled horribly or mildew, the second room had mold in the ac unit, the third still did not meet “exceptional” standards as listed with the room. I’m planning to get my money back.
Reviewed on Aug 24, 2026
Jessamine County Hotel Deals
DoubleTree Suites by Hilton Hotel Lexington
2601 Richmond Rd Lexington KY
Fully refundableReserve now, pay when you stay
CA $146
CA $169 total
Sep 6 - Sep 7
includes taxes & fees
8.8/10 Excellent! (1,045 reviews)
"Very spacious, clean room. Perfect option for move-in at UK."
Reviewed on Aug 24, 2026
The Manchester
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
CA $221
CA $280 total
Sep 7 - Sep 8
includes taxes & fees
9.6/10 Exceptional! (1,412 reviews)
"This is one of our favorite hotels of all time! Travelled everywhere- love all Four Seasons but the Manchester is home on the road — only better!"
Reviewed on Aug 25, 2026
Marriott Lexington Griffin Gate Golf Resort & Spa
1800 Newtown Pike Lexington KY
Fully refundableReserve now, pay when you stay
CA $142
CA $192 total
Sep 6 - Sep 7
includes taxes & fees
8.4/10 Very good! (824 reviews)
"The restaurant was understaffed and took forever to wait on us and even longer to bring our food and it wasn’t busy. The room had temporary fans in it and it appeared the sliding door to the balcony had been leaking. The next day I broke out in a rash from head to toe. This was probably a good place ..."
Reviewed on Aug 25, 2026
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 Jessamine County vacation package cost?
The cheapest Jessamine County package is CA $1,026, so your dream getaway can become a reality — without spending an arm and a leg. Combine flights, hotels and car rentals to custom build a package that matches your travel style.
How do I get a cheap travel package to Jessamine County?
Search for flights that fit in with your schedule, add a hotel to your booking and see how much you save with a Jessamine County vacation package. It's that simple! From flights and hotels to rental cars and tours, Expedia is where your cheap getaway begins. And with over 550 air carriers and 1,000,000 hotels all over the world to select from, you won't be short of choice.
What are the top hotels in Jessamine County?
Wilmore is one place that most travelers to Jessamine County put on their itinerary. For a memorable stay here, look up Holiday Inn Express Nicholasville, an IHG Hotel and Asbury Inn & Suites.
How far in advance should I book my Jessamine County vacation?
It all depends on the airline, but you can generally compare international flights on Expedia up to 12 months in advance. While it's a good idea to book ahead of time, lucky customers occasionally score a cheaper ticket just weeks before their intended journey.
What does an Expedia Jessamine County travel package include?
Car rentals, flights and hotels — we connect you to all the best deals. All you have to do is pick your favorite combination. After you've made your booking, you can add on the fun stuff like day tours and sightseeing activities. Our travel packages make it easy to put together an awesome Jessamine County getaway.
What should I know before booking a Jessamine County travel package?
You'll score big savings when you bundle your flights, hotels and rental cars into a package. Not just that, booking everything together makes trip planning easier. So why waste your money or time? Whether you're putting together an upscale romantic escape or an affordable family break, browse our vacation packages today.
Can I choose my airline with a Jessamine County Expedia vacation package?
Yes, and with more than 550 airlines to choose from around the world, you've got lots of choice. Browse the available options and see which airline fits your needs and budget.
If I'm not able to travel, can I cancel my Jessamine County vacation package?
We totally understand that life can throw you the odd curveball. If you've booked a Jessamine County vacation package and have to amend or cancel it, we can help. It's always worth browsing our Customer Service Portal first for information. But in general, if you've booked your package in the last 24 hours, you may be able to cancel or change your itinerary at no cost. If it's more than 24 hours, your airline, hotel or car rental company may charge a fee.
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.
High Bridge Kentucky River Museum
You can spend time exploring the galleries in High Bridge Kentucky River Museum in Wilmore.
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.
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.
High Bridge Park
After visiting High Bridge Park, make a plan to see the other sights and activities in Wilmore.
What to do in Jessamine County
Unique Horse Farm Tours with Insider Access to Private Farms
CA $83
per adult
90% of travellers recommend
Lexington: Downtown Walking Food & History Tour
CA $139
per adult
100% of travellers recommend
Bites of the Bluegrass Cocktails & Bites Tour
CA $176
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
