Monticello Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Lisa Klein

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Your Monticello Vacation

Our vacation packages to Monticello let you create your own adventure. Tailor your journey to suit your needs and interests and make every moment count in this fantastic city. Fill your trip to Monticello with visits to some of its top attractions. Where to first? Make a beeline for Wayne County Historical Museum. Your ideal Monticello vacation is clicks away. Browse flights, accommodations and more on Expedia for a trip that's tailored to suit your style.

Top Monticello Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Best Western Ashbury Inn

Best Western Ashbury Inn

2.5 out of 5
per person
Sep 17 - Sep 23
found 19 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.2/10 Very Good! (943 reviews)
Great value for the price with hot breakfast Beds were comfortable...

Reviewed on Jul. 29, 2025

The Brown Hotel

The Brown Hotel

4.5 out of 5
Downtown Louisville
per person
Sep 17 - Sep 23
found 19 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
9.4/10 Exceptional! (1,042 reviews)
Beautiful hotel, great location, helpful staff. Will definitely stay here again

Reviewed on Aug. 7, 2025

Derby City Gaming & Hotel - A Churchill Downs Property

Derby City Gaming & Hotel - A Churchill Downs Property

4 out of 5
per person
Sep 17 - Sep 23
found 19 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
9.4/10 Exceptional! (1,341 reviews)
My go-to hotel in Louisville.

Reviewed on Aug. 7, 2025

The Grady

The Grady

4 out of 5
Downtown Louisville
per person
Sep 17 - Sep 23
found 19 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
9.4/10 Exceptional! (1,009 reviews)
Classy and modern southern design. Staff are friendly and helpful.

Reviewed on Aug. 7, 2025

Holiday Inn Express & Suites Louisville Downtown by IHG

Holiday Inn Express & Suites Louisville Downtown by IHG

2.5 out of 5
Downtown Louisville
per person
Sep 17 - Sep 23
found 19 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.8/10 Excellent! (1,510 reviews)
It was nice hotel, downtown. Didn’t like that we had to pay 21$ a day for a parking pass. Front didn’t explain that they would take the 21 dollars out of the 50$ incident deposit.

Reviewed on Aug. 7, 2025

Ready to book your vacation to Monticello?

 

Choose your dates

Monticello Hotel Deals

Best Western Lake Cumberland Inn

Best Western Lake Cumberland Inn

2.5 out of 5
2030 E Highway 90, Monticello, KY
Fully refundableReserve now, pay when you stay
The price is CA $172 per night from Sep 1 to Sep 2
CA $172
CA $189 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (332 reviews)
"The only complaint we had was the tv didn’t work. But this trip to visit family we weren’t in the room much. Bed was comfortable and clean. Air worked great and bathroom was clean."

Reviewed on Aug. 2, 2025

Best Western Lake Cumberland Inn
Lake Cumberland Luxury #2! Amazing Lake views, hot tub, fire pit!

Lake Cumberland Luxury #2! Amazing Lake views, hot tub, fire pit!

Monticello
9.8/10 Exceptional! (8 reviews)
"We really enjoyed our stay. Communication with the host was great and we couldn't get over how beautiful the view was!"

Reviewed on Aug. 4, 2025

Get rates
Lake Cumberland Luxury #2! Amazing Lake views, hot tub, fire pit!
This charming cozy cottage has a private hot tub, deck for fishing.

This charming cozy cottage has a private hot tub, deck for fishing.

monticello
9.8/10 Exceptional! (149 reviews)
"Great place. Very quite and peaceful."

Reviewed on Jun. 18, 2025

Get rates
This charming cozy cottage has a private hot tub, deck for fishing.
See all 912 properties in Monticello
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
Family Vacations

Discover the most popular places to visit in Monticello

Lake Cumberland Winery

You can enjoy a tasting or tour at Lake Cumberland Winery during your travels to Monticello. Amble around this family-friendly area's lakeside, or seek out the fishing spots.

Lake Cumberland Winery

Frequently asked questions

How much does a Monticello vacation package cost?
Offering excellent value package deals from CA $1,255 on Expedia, you'll be thrilled with how little a vacation to Monticello costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Monticello?
You can usually find lower prices and greater availability in January, February and June. Take a look at our cheap Monticello vacation packages and you could score some great off-season discounts.
How many days is enough for Monticello?
Generally, a handful of days is enough to explore the major attractions during your Monticello vacation. However, if you want to have some time to chill out or go on day trips, think about extending your trip.
How to find the best Monticello package deals?
Use Expedia's handy filters to help you find some unbeatable Monticello package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or look for Monticello package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Monticello vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging stays and flights separately. Better still, you can customize your Monticello getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
How to plan a trip to Monticello?

  1. Pick your travel dates: What you plan to do in Monticello and your favourite season can help you decide when to travel.
  2. Plan your budget wisely: In addition to the price of your stay, you should factor in other expenses. These include flights, food and transportation. Also, set aside a little extra for unexpected expenses that could crop up during your trip to Monticello.
  3. Decide how long to go for: Now that you know more about Monticello, you can work out the perfect length of your vacation. Pull together a draft plan and give yourself enough time to get through everything on your must-do list.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to choose a Monticello vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.