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.
Homewood Suites by Hilton Louisville Downtown, KY

Homewood Suites by Hilton Louisville Downtown, KY

3 out of 5
Downtown Louisville
Price was CA $1,590, price is now CA $1,345 per person
CA $1,345
per person
Mar 25 - Mar 29
found 6 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Louisville (SDF)
9.2/10 Wonderful! (1,004 reviews)
Room was clean and bathroom was updated. The staff were great, super friendly! Location was a short walk to convention center.

Reviewed on Feb 20, 2026

Louisville Marriott Downtown

Louisville Marriott Downtown

4 out of 5
Downtown Louisville
Price was CA $1,803, price is now CA $1,410 per person
CA $1,410
per person
Mar 25 - Mar 29
found 6 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Louisville (SDF)
9/10 Wonderful! (1,003 reviews)
Room was spotless. Staff was top notch. Amenities as expected but I did expect a microwave in the room. There wasn't one. 9/10 experience. Will definitely book again!

Reviewed on Jan 16, 2026

The Bellwether Hotel

The Bellwether Hotel

3.5 out of 5
Tyler Park
Price was CA $6,022, price is now CA $4,891 per person
CA $4,891
per person
Apr 28 - May 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Louisville (SDF)
8.6/10 Excellent! (31 reviews)
The coldest hotel room I’ve ever stayed in! We stayed in “The Olmstead” in January and maxing out the heater couldn’t quite make it a comfortable temperature in the room - I don’t think it got warmer than 65 in there. I think it’s a combo of the concrete floors and walls with high ceilings and one small unit placed near the ceiling. Otherwise a great room! But I wouldn’t stay there when it’s cold outside again.

Reviewed on Jan 4, 2026

Hotel Distil, Autograph Collection

Hotel Distil, Autograph Collection

4 out of 5
Downtown Louisville
Price was CA $1,944, price is now CA $1,585 per person
CA $1,585
per person
Mar 25 - Mar 29
found 6 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Louisville (SDF)
9.6/10 Exceptional! (422 reviews)
Great hotel & location

Reviewed on Feb 18, 2026

Moxy Louisville Downtown

Moxy Louisville Downtown

3.5 out of 5
Downtown Louisville
Price was CA $1,624, price is now CA $1,353 per person
CA $1,353
per person
Mar 25 - Mar 29
found 6 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Louisville (SDF)
9.2/10 Wonderful! (685 reviews)
Clean, great food, and awesome bar

Reviewed on Feb 19, 2026

The Annual Vacation Sale

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Jessamine County Hotel Deals

Holiday Inn Express Nicholasville by IHG

Holiday Inn Express Nicholasville by IHG

2.5 out of 5
164 Imperial Way Nicholasville KY
Fully refundable
The price is CA $125 per night from Mar 1 to Mar 2
CA $125
CA $137 total
Mar 1 - Mar 2
includes taxes & fees
8.6/10 Excellent! (612 reviews)
Clean, comfort and excellent service. The front desk person was so nice

Reviewed on Feb 15, 2026

Holiday Inn Express Nicholasville by IHG
The Manchester

The Manchester

4 out of 5
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
The price is CA $232 per night from Mar 22 to Mar 23
CA $232
CA $293 total
Mar 22 - Mar 23
includes taxes & fees
9.4/10 Exceptional! (1,166 reviews)
Friendly staff great room wonderful ambience lovely restaurant.. great valet all round an amazing stay..,Thanks Manchester

Reviewed on Feb 15, 2026

The Manchester
Hilton Lexington/Downtown

Hilton Lexington/Downtown

3.5 out of 5
369 West Vine Street Lexington KY
Fully refundableReserve now, pay when you stay
The price is CA $204 per night from Mar 8 to Mar 9
CA $204
CA $237 total
Mar 8 - Mar 9
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
Room was clean, staff was nice and all was good!

Reviewed on Feb 16, 2026

Hilton Lexington/Downtown
See all 1,210 properties in Jessamine County
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
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Frequently asked questions

How much does a Jessamine County vacation package cost?
The cheapest Jessamine County package is CA $1,345, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.