Monticello holiday lettings

We found 105 holiday rentals — enter your dates for availability

Select from 45 homes, 10 cottages and other holiday rentals in Monticello to find one that's perfect for your trip. Holiday homes provide the best amenities for your stay with friends, family or just your pet, such as a garden and pool. No matter what you're looking for, you'll find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

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The secluded area of Monticello awaits your stay

Enjoy the wineries and other features of Monticello. This relaxing city is known for its lake, boating and fishing. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Sightseeing in and around Monticello

Are you searching for attractions to visit while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Monticello has to offer. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • SomerSplash (23.3 mi / 37.5 km)
  • Dale Hollow Lake State Resort Park Golf Course (27.4 mi / 44 km)
  • Lake Cumberland Winery (7.9 mi / 12.6 km)
  • Natural Arch Scenic Area (15.9 mi / 25.6 km)
  • The Links Resort Golf Course (14.7 mi / 23.7 km)

Exploring the natural features in Monticello

Whether you're looking for adventure or just want to take in the scenery, Monticello is a great spot to appreciate mother nature. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Lake Cumberland State Resort Park (12.7 mi / 20.4 km)
  • Wolf Creek National Fish Hatchery (16.7 mi / 26.9 km)
  • Yahoo Falls (18.5 mi / 29.8 km)
  • Pickett State Park (19.1 mi / 30.7 km)
  • Angel Falls Trial (26.4 mi / 42.5 km)
  • Twin Arches (27.1 mi / 43.6 km)

Frequently asked questions

What is the best area to stay in Monticello when booking a holiday rental?
When considering a holiday rental in Monticello, Kentucky, the area around the serene Lake Cumberland is particularly appealing. This picturesque location offers a range of properties, from charming cabins to spacious homes, providing a superb base for families or groups seeking a tranquil getaway.

Staying near Lake Cumberland not only allows you to enjoy stunning waterfront views but also gives you easy access to top attractions such as the Lake Cumberland State Resort Park, where you can partake in outdoor activities like hiking, fishing, and boating. Additionally, the nearby Wolf Creek Dam is a marvel of engineering and is worth a visit for those interested in learning about the region's history and natural beauty.

Another lovely neighbourhood to consider is the downtown area of Monticello, which boasts a quaint charm with its local shops and eateries. You can explore the vibrant community while enjoying the hospitality of the locals. This area also provides proximity to several parks, making it ideal for leisurely strolls or picnics.
How much does it cost to rent a holiday home in Monticello?
Prices for holiday rentals in Monticello vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Monticello to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Monticello holiday house rentals?
You can find great discounts on house rentals in Monticello on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of holiday rental accomodation in Monticello?
In Monticello, holiday houses are the most popular type of holiday rental, with approximately 123 available throughout the area. These homes are typically spacious and well-equipped, featuring multiple bedrooms, full kitchens, and outdoor spaces such as decks or patios—ideal for enjoying the surrounding natural beauty. Additionally, there are around 30 cottages that offer a quaint and charming stay, often located near local attractions. For those seeking a rustic experience, about 18 cabins are available, providing a cosy atmosphere and often located in wooded areas. There are also several chalets and apartments, which cater to different preferences and group sizes.
Are there any family house rentals in Monticello?
In Monticello, Kentucky, there are numerous family-friendly holiday rentals available, with around 47 options to choose from. This charming town offers a variety of accommodations suitable for families, many of which feature spacious living areas and full kitchens, allowing for comfortable group gatherings and home-cooked meals.

Visitors can find properties with amenities such as outdoor spaces for children to play, as well as cosy lounges great for family movie nights. The area is also close to scenic spots like Lake Cumberland, where families can enjoy boating, fishing, and swimming during the warmer months.

Additionally, Monticello's proximity to the Daniel Boone National Forest provides opportunities for hiking and exploring the great outdoors, ensuring a delightful stay for families looking to connect with nature.
Can I rent a holiday home with a pool or hot tub in Monticello?
In Monticello, Kentucky, there are several holiday homes available for rent that feature pools and hot tubs, with around 10 options to choose from. This charming area, located near Lake Cumberland, offers a variety of properties across different neighbourhoods, providing a great blend of relaxation and outdoor activities.

Travellers can expect a range of amenities in these rentals, including private swimming pools, hot tubs, spacious outdoor areas, and fully equipped kitchens, ideal for family gatherings or group retreats. Many properties are designed for comfort, featuring cosy living rooms and sometimes even game rooms for entertainment.
Can I find long-stay holiday rentals in Monticello?
A long-stay holiday rental in Monticello is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Monticello?
In Monticello, Kentucky, there are a variety of pet-friendly house rentals available, with around 24 options to choose from. Many of these properties offer comfortable amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air. Some rentals may even feature fenced yards, making them particularly suitable for those travelling with dogs.

The area around Monticello provides stunning natural beauty, with nearby Lake Cumberland offering opportunities for outdoor activities like fishing, boating, and hiking. The lake's surrounding parks also allow for leisurely walks with pets, ensuring that both guests and their furry companions can enjoy the great outdoors together.
Are there any remote work holiday rentals in Monticello?
In Monticello, Kentucky, there are numerous remote work-friendly holiday rentals available, with around 189 options to choose from. This charming area offers a variety of properties suited for those needing a comfortable workspace while enjoying a getaway. Many rentals come equipped with Wi-Fi, ensuring that guests can stay connected and productive during their stay.

The town is surrounded by beautiful landscapes, ideal for outdoor activities such as hiking and fishing, which provide a refreshing break from work. Additionally, properties often feature amenities like spacious living areas, fully equipped kitchens, and sometimes even outdoor spaces to relax after a long day of remote work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Monticello holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Monticello with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Monticello?
In Monticello, popular holiday rental amenities include fully equipped kitchens, which allow guests to prepare their own meals. Many properties feature outdoor decks or patios, providing a lovely space to relax and enjoy the surroundings. Onsite parking is commonly available, making it convenient for travellers with vehicles. Additionally, rentals often come with coffee and tea makers for that morning brew, along with blenders for those who enjoy smoothies or other blended drinks.
When is the best time to visit Monticello for a holiday rental?
The peak travel season in Monticello runs from June to August, making it the prime time for travellers to enjoy warm weather and outdoor activities. July, in particular, is the most popular month, offering a vibrant setting as visitors flock to the area to experience its stunning lakes and scenic parks.

During this time, temperatures typically range from 20 to 30 degrees Celsius, creating ideal conditions for fishing, boating, and hiking. Monticello is home to several beautiful recreational areas, including Lake Cumberland, where you can spend your days on the water or explore picturesque trails nearby.

For those looking for a more budget-friendly option, consider visiting in October. This month offers a serene atmosphere, great for enjoying the beautiful autumn foliage without the crowds. The cooler temperatures, averaging around 10 to 20 degrees Celsius, make it a lovely time for leisurely strolls and exploring the local culture at a relaxed pace.

Ultimately, your ideal time to visit Monticello may depend on whether you seek the lively summer activities or the tranquil beauty of autumn.
How early should I book a Monticello holiday rental?
Book your Monticello holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Monticello?
In Monticello, Kentucky, visitors can enjoy a variety of attractions that highlight the area's natural beauty and local culture. The breathtaking Lake Cumberland is a major draw, offering opportunities for boating, fishing, and swimming, with several parks and marinas dotting its shores. Nearby, the Wolf Creek Dam provides scenic views and is a popular spot for picnicking and hiking.

For those interested in history, the Monticello Depot serves as a reminder of the town's railway heritage, while the nearby Wayne County Historical Museum showcases local artefacts and exhibits that tell the story of the region. The quaint downtown area features charming shops and eateries, allowing visitors to experience the local flavour while soaking in the small-town atmosphere.
Can I change or cancel my Monticello home rental booking on Vrbo?
To find Monticello holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Monticello holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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