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.
Hyatt Regency Louisville

Hyatt Regency Louisville

4 out of 5
Downtown Louisville
Price was CA $1,303, price is now CA $1,076 per person
CA $1,076
per person
Jun 30 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
8.8/10 Excellent! (1,009 reviews)
The hotel is perfectly located and the amenities are great!

Reviewed on May 18, 2026

Cottonwood Airport & Expo Hotel Louisville

Cottonwood Airport & Expo Hotel Louisville

3.5 out of 5
Shively
Price was CA $1,846, price is now CA $1,443 per person
CA $1,443
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Louisville (SDF)
8.6/10 Excellent! (1,022 reviews)
Loved this hotel and staff. I’ve never stayed at (or even heard of the Cottonwood hotel chain), but I’m a huge fan. Excellent rates, clean facility, friendly staff, decent breakfast. I just wish they had more locations!

Reviewed on May 22, 2026

Renovated River Home Hot Tub Sauna Game Room

Renovated River Home Hot Tub Sauna Game Room

2 out of 5
Utica
Price was CA $5,108, price is now CA $4,195 per person
CA $4,195
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Louisville (SDF)
No reviews
The Reserve on Main

The Reserve on Main

4 out of 5
Downtown Louisville
Price was CA $6,244, price is now CA $5,191 per person
CA $5,191
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Louisville (SDF)
9.4/10 Exceptional! (3 reviews)
Super easy! Loved the vibe!

Reviewed on Apr 18, 2026

Holiday Inn Louisville Airport South by IHG

Holiday Inn Louisville Airport South by IHG

3 out of 5
Price was CA $1,717, price is now CA $1,445 per person
CA $1,445
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Louisville (SDF)
8.8/10 Excellent! (893 reviews)
Very surprised how well kept this hotel was. Usually hotels by the airport aren't that nice. This one was a little under-priced for the rating by others, so had kinda low expectations. Pleasantly surprised at how clean and nice it looked. Staff was very helpful. Finally, the breakfast was really one of the better breakfast buffets we had. Scrambled eggs, fried eggs, pork patties & sausage, bacon, biscuits & gravy, french toast, muffins, pastry and donuts. The waitress stocking the buffet stopped by our table twice and asked if there was any thing else we'd like. Great place to stay in Louisville that was a great value.

Reviewed on May 22, 2026

Jessamine County Hotel Deals

The Manchester

The Manchester

4 out of 5
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
The price is CA $260 per night from May 31 to Jun 1
CA $260
CA $326 total
May 31 - Jun 1
includes taxes & fees
9.6/10 Exceptional! (1,292 reviews)
"Had a great overnight stay. Shuttle was great to Distillary area and dining room rooftop was nice. We even played Trivia that night ( ugh we lost). Great nights rest before heading to Nashville. Would stay there again for certain."

Reviewed on May 18, 2026

The Manchester
Holiday Inn Express Lexington Horse Park Area by IHG

Holiday Inn Express Lexington Horse Park Area by IHG

3 out of 5
1935 Stanton Way, 1935 4 yes Lexington KY
Fully refundable
The price is CA $133 per night from May 31 to Jun 1
CA $133
CA $154 total
May 31 - Jun 1
includes taxes & fees
Holiday Inn Express Lexington Horse Park Area by IHG
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 $177 per night from Jun 21 to Jun 22
CA $177
CA $206 total
Jun 21 - Jun 22
includes taxes & fees
8.4/10 Very Good! (1,003 reviews)
"No complaints, great stay. Clean room, friendly & helpful staff."

Reviewed on May 22, 2026

Hilton Lexington/Downtown
See all 1,242 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
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Family Vacations

Frequently asked questions

How much does a Jessamine County vacation package cost?
The cheapest Jessamine County package is CA $1,076, 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.