Jessamine County Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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 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.
Holiday Inn Express Louisville Airport Expo Center by IHG
Hayfield Dundee
CA $1,072
per person
Nov 17 - Nov 23
found 1 hour ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.6/10 Excellent! (1,007 reviews)
Expedia sucks. Send me emails to view my reservation and it only lets me thru the app which I don’t have and don’t want
Reviewed on Oct 10, 2026
Cottonwood Airport & Expo Hotel Louisville
Shively
CA $1,121
per person
Nov 17 - Nov 23
found 1 hour ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.6/10 Excellent! (1,008 reviews)
My daughter and I stayed at the Cottonwood Louisville Hotel for the weekend, and overall we had a nice stay. The hotel was clean, comfortable, and the staff was very nice and welcoming. My only wish was that there were more restaurants within walking distance, but besides that, everything was good. We enjoyed our stay and would consider staying here again.
Reviewed on Oct 7, 2026
Fairfield Inn & Suites by Marriott Louisville Downtown
Downtown Louisville
CA $1,085
per person
Nov 17 - Nov 23
found 1 hour ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.4/10 Very good! (1,009 reviews)
I really enjoyed my visit. The staffs was helpful to help me with directions and my next visit will be to go back there.
Reviewed on Oct 10, 2026
Jessamine County Hotel Deals
GuestHouse Lexington
2261 Elkhorn Road Lexington KY
Fully refundable
CA $96
CA $111 total
Oct 13 - Oct 14
includes taxes & fees
The Manchester
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
CA $247
CA $311 total
Nov 1 - Nov 2
includes taxes & fees
21c Museum Hotel Lexington
167 West Main Street Lexington KY
Fully refundableReserve now, pay when you stay
CA $194
CA $233 total
Nov 1 - Nov 2
includes taxes & 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.
Frequently asked questions
How much does a Jessamine County vacation package cost?
The cheapest Jessamine County package is CA $1,072, 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.
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.
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.
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.
High Bridge Park
After visiting High Bridge Park, make a plan to see the other sights and activities in Wilmore.
B. L. Fisher Library
After visiting B. L. Fisher Library, 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.
Hickman Creek Nature Center
You can take time to visit Hickman Creek Nature Center during your travels to Nicholasville. While in this family-friendly area, you can enjoy the restaurants.
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 $138
per adult
100% of travellers recommend
Bites of the Bluegrass Cocktails & Bites Tour
CA $175
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.
