Monticello Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NT$25,000 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Find the Best Monticello Vacation Packages

Monticello Hotel Deals

Best Western Lake Cumberland Inn

Best Western Lake Cumberland Inn

2030 E Highway 90 Monticello KY
Fully refundableReserve now, pay when you stay
NT$4,143
NT$4,567 total
Sep 6 - Sep 7
includes taxes & fees
Best Western Lake Cumberland Inn
Cumberland Falls State Resort Park

Cumberland Falls State Resort Park

7351 Hwy. 90 Williamsburg KY
NT$3,728
NT$4,110 total
Aug 27 - Aug 28
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
"We were not informed about the resort being closed until arrival. The cabins are duplexes, and are not well maintained or cleaned. Tried to checkout, but couldn’t until the morning. Mouse droppings everywhere including the beds, all drains clogged, the WiFi did not work, and the beds were smaller ..."

Reviewed on 2026/8/24

Cumberland Falls State Resort Park
Red Roof Inn Somerset, KY

Red Roof Inn Somerset, KY

1201 S Highway 27 Somerset KY
Fully refundableReserve now, pay when you stay
NT$2,071
NT$2,371 total
Sep 7 - Sep 8
includes taxes & fees
7/10 Good! (1,006 reviews)
"The first room that we went into the ceiling was leaking onto floor and damaged, the 2nd room that they gave us was dirty, mold on walls behind beds, did not look like walls had been cleaned in a long time, there was cat and dog hair on one of the beds. The staff was very nice and helpful. Not a ..."

Reviewed on 2026/8/25

Red Roof Inn Somerset, KY
See all 1,073 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.

Stay near popular Monticello attractions

Mill Springs Mill Park

This historic 1877 grist mill boasts one of the world's largest operating overshot water wheels at 40 feet in diameter. Watch milling demonstrations and purchase freshly ground cornmeal to take home.
See properties

Conley Bottom Marina

Explore the waterfront in Monticello with a trip to Conley Bottom Marina. Wander the lakeside in this relaxing area.
See properties

Wayne County Historical Museum

8.0/10 (9 reviews)
Step back in time at this local museum featuring Civil War dioramas and a restored one-room schoolhouse. Explore Wayne County's heritage through carefully preserved artifacts and the historic stagecoach display.
See properties

Lake Cumberland Winery

8.0/10 (21 reviews)
Tucked in Monticello's countryside, Lake Cumberland Winery offers tastings of locally crafted wines amid scenic surroundings. Sample their signature varieties while enjoying the peaceful Kentucky landscape.
See properties

Big Island

Big Island rises majestically from Lake Cumberland, creating a picturesque backdrop for Kentucky boaters. Explore its serene shores during spring through fall when the lake's azure waters are most inviting.
See properties

Fall Creek Recreation Area

Nestled on Lake Cumberland's shores, Fall Creek Campground features ten shaded waterfront sites amid hardwood forest. Reserve early for direct lake access, perfect for fishing, boating, and serene natural immersion.
See properties

Frequently asked questions

How much does a Monticello vacation package cost?
You'll find cheap prices on Expedia for your Monticello break. However, factors like the length of stay, hotel choice and season will determine how much your vacation to Monticello costs.
What are the cheapest months to go to Monticello?
January, February and June are the best times to search for cheap Monticello vacation packages. Opting to travel in quieter periods means you can typically find better prices on hotels and flights.
How many days is enough for Monticello?
Usually, a handful of days is enough to tick off the main attractions during your Monticello vacation. But if you prefer to have some time to rest or take day tours, think about extending your itinerary.
How to find the best Monticello package deals?
Bagging a cheap Monticello package deal is a breeze with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, add some filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most economical Monticello package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Monticello vacation as a package?
You can enjoy significant savings on your Monticello escape by booking a personalized vacation package. Click on the "Package" heading, then enter your destination and travel dates to browse some great hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Monticello?
If you're considering an impromptu Monticello vacation, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score sensational deals on your hotels and flights by booking well in advance.
How to plan a trip to Monticello?
  1. Pick the best time to travel: Your schedule, favorite season and the type of weather you enjoy can all impact your decision on when to go to Monticello.
  2. Set your budget: Factor in expenses such as food, flights and transportation when working out how much to put aside for your trip to Monticello. Then, pick a property that works with your budget, whether that's an affordable stay or a lavish getaway.
  3. Determine how many days away: Start by making a list of all the sights and activities you'd like to get to in Monticello. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to find a Monticello vacation package that brings all your bookings together.

Explore a world of travel with Expedia

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