Monticello vacation rentals

We found 99 vacation rentals — enter your dates for availability

Select from 43 homes, 10 cottages, and other vacation rentals in Monticello to find one that's perfect for your trip. Vacation homes offer the best amenities for your stay with friends, family, or just your pet, like cable TV and a washer and dryer. At the end of the day, you'll be sure to find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Monticello

Showing deals for:Mar 27 - Apr 3

Image gallery for Uniquely styled octagon shaped home. Just 2 miles to the lake

Exterior
10 out of 10, Exceptional, (17 reviews)
Exceptional
(17 reviews)

Uniquely styled octagon shaped home. Just 2 miles to the lake

Monticello

8% off
Price is $184
$1,290 for 7 nights
All fees included
Uniquely styled octagon shaped home. Just 2 miles to the lake

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Find out more about Monticello

Why visit Monticello

  • Outdoor Adventures: Monticello is perfect for outdoor enthusiasts, offering scenic parks and eco-friendly activities.
  • Beautiful Scenery: Experience stunning views at Mill Creek, ideal for relaxing and enjoying nature.
  • Family-Friendly Activities: Monticello caters to families with various attractions that promote bonding and adventure.
  • Charming Accommodations: Choose from cozy cabins, spacious vacation homes, or quaint cottages for your stay.
  • Welcoming Community: Explore friendly neighborhoods that enhance your experience with local charm and hospitality.

Popular types of accommodation in Monticello

Discover the charm of Monticello with a variety of vacation rentals that cater to your needs. Whether you're seeking a cozy cabin, a spacious private vacation home, or a quaint cottage, Monticello has it all. Our diverse selection ensures you find the perfect home away from home. Explore mansion rentals across the United States or indulge in charming cottage rentals that make your stay unforgettable. Your ideal Monticello getaway awaits.

  • Houses: The top choice for visitors in Monticello, these homes offer spacious and comfortable settings, perfect for families or groups.
  • Cabins: A favorite among nature lovers, cabins provide a cozy retreat surrounded by the beauty of the outdoors.
  • Cottages: Charming and quaint, cottages are ideal for a romantic getaway or a peaceful solo retreat.
  • Condos: Convenient and modern, condos offer a blend of comfort and amenities for a hassle-free stay.
  • Chalets: These unique lodgings offer a mountain lodge experience, perfect for those seeking adventure and relaxation.**

Top attractions in and around Monticello

Monticello, Kentucky, offers a delightful escape for outdoor enthusiasts and adventure seekers. Visitors can explore scenic marinas, parks, and national/state parks that provide eco-friendly and family-friendly experiences. Whether you're looking to enjoy nature, spend time with loved ones, or embark on an outdoor adventure, Monticello has a variety of attractions that cater to your interests, making it an ideal destination for a memorable vacation.

  • Lake Cumberland State Resort Park: Located 13 miles from Monticello, this stunning state park offers breathtaking scenery, outdoor adventures like hiking and fishing, and a serene atmosphere perfect for nature lovers.
  • Conley Bottom Marina: Situated in Monticello, this marina is the ideal spot for outdoor enthusiasts, featuring beach vibes, boat rentals, and various water sports that promise a fun-filled day on Lake Cumberland.
  • Wayne County Historical Museum: Located in Monticello, this museum showcases the rich cultural heritage of the area, featuring fascinating exhibits and artifacts that tell the story of Wayne County's history.

Things to do recommended for couples

For a romantic getaway in Monticello, don’t miss Lake Cumberland Winery. Enjoy the charming atmosphere while sipping on exquisite wines together. The perfect blend of romance and entertainment makes it an ideal spot for couples looking to unwind and create lasting memories.

Things to do recommended for families

Families visiting Monticello can explore the Natural Arch Scenic Area, located 16 miles away. This recreational spot offers wellness and relaxation vibes, making it a perfect getaway for outdoor activities and family bonding amidst nature's beauty.

Things to do recommended for groups

Groups visiting Monticello can enjoy a round of golf at The Links Resort Golf Course, set in a beautiful outdoor environment just 15 miles away. For shopping enthusiasts, Somerset Mall offers a vibrant shopping experience 19 miles from Monticello, perfect for family outings and city vibes.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Monticello

When planning your trip, whether you're traveling with friends, family, pets, or seeking extended stays, be sure to prioritize your preferences in the search filters. Here are some helpful Vrbo booking tips for you.

  • Traveling to Monticello with a group: Think about how many bedrooms you'll require, along with features like a fully-equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Monticello with young kids: Traveling with young kids can be quite challenging. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Monticello: For many families, a vacation wouldn't be the same without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Monticello: If you're in search of vacation rentals that offer special rates for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include features like a parking space, a modern kitchen, or a private pool in your search criteria as well.

Where to stay in and around Monticello

Monticello, Kentucky, offers a delightful blend of outdoor adventures and serene landscapes perfect for a family-friendly getaway. Explore scenic views at Mill Creek, where nature's beauty surrounds you, or enjoy the inviting atmosphere of nearby neighborhoods filled with friendly locals. Whether you're seeking a relaxing country vacation or thrilling outdoor activities, Monticello promises unforgettable experiences that cater to every traveler's desire for adventure and tranquility.

  • Lake Cumberland: Located 12 miles from Monticello, Lake Cumberland is a stunning natural destination known for its expansive lake and outdoor adventures. The area offers breathtaking scenery and a plethora of activities for nature enthusiasts, including hiking trails and campgrounds. Visitors can enjoy fishing, boating, and picnicking in the beautiful surroundings of the national state park. The lake itself serves as a focal point for recreation, making it a perfect spot for those seeking an adventurous getaway amidst nature.
  • Jamestown: Situated 16 miles from Monticello, Jamestown is a charming city that attracts outdoor lovers and adventure seekers. With its scenic landscapes and recreational areas, Jamestown offers plenty of opportunities for hiking and camping. The proximity to the national state park and the picturesque lake enhances the travel experience, providing visitors with a tranquil environment to explore. Whether you’re looking to hike scenic trails or relax in a serene campground, Jamestown is a delightful stop on your vacation itinerary.
  • Mill Springs: Nestled within the area of Monticello, Mill Springs is a quaint village that showcases the beauty of the Kentucky landscape. It's an ideal spot for travelers interested in outdoor activities, offering recreational areas, hiking trails, and campgrounds. The village's close proximity to the lake and national state park allows for plenty of exploration and adventure. Mill Springs is a peaceful destination that invites visitors to immerse themselves in nature and enjoy the serene ambiance of the region.

Best time to go to Monticello

If you're planning a trip to Monticello, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.6°F (2.0°C)Light RainMostly CloudyAverageSlightly Low
February40.1°F (4.5°C)Light RainMostly CloudyAverageSlightly Low
March48.0°F (8.9°C)Light RainMostly CloudyAverageSlightly Low
April56.8°F (13.8°C)Light RainMostly SunnyAverageAverage
May65.8°F (18.8°C)Light RainMostly SunnyAverageAverage
June73.6°F (23.1°C)Light RainMostly SunnySlightly HighSlightly High
July76.3°F (24.6°C)Light RainMostly SunnySlightly HighSlightly High
August74.8°F (23.8°C)Light RainMostly SunnySlightly HighSlightly High
September69.4°F (20.8°C)Light RainMostly SunnyAverageAverage
October58.6°F (14.8°C)Light RainMostly SunnySlightly LowAverage
November47.5°F (8.6°C)Light RainMostly SunnySlightly LowAverage
December41.4°F (5.2°C)Light RainMostly CloudySlightly LowAverage

Booking with Vrbo is simple

Planning to save on your upcoming journey? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, booking a longer stay can lead to considerable savings. To discover a Vrbo property that aligns with your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you make the most of your trip.

Unlock savings with One Key

Reserve an eligible Vrbo for your group getaway and earn OneKeyCash on your entire reservation. Being the planner truly has its rewards. When you join our travel rewards program, One Key, you’ll gain access to exclusive member discounts and accumulate OneKeyCash on qualifying bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers an easy-to-use platform for planning your trips. You can create new itineraries, resume planning from where you last stopped, or view and arrange your travel plans all in one place. Your saved or booked properties will be neatly grouped under categories like Potential, Upcoming, or Current Trips. To begin utilizing Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The remote 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 accommodations with space to entertain friends and family, Vrbo 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

Do you want to find things to do while you're in town? Venture out of your vacation home and experience everything that makes Monticello a fun place to get away. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Lake Cumberland Winery (7.9 mi / 12.6 km)
  • SomerSplash (23.3 mi / 37.5 km)
  • Dale Hollow Lake State Resort Park Golf Course (27.4 mi / 44 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 an active traveler or just want to spend some time taking 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 center:

  • Lake Cumberland State Resort Park (12.7 mi / 20.4 km)
  • Wolf Creek National Fish Hatchery (16.7 mi / 26.9 km)
  • Pulaski County Park (18.4 mi / 29.6 km)
  • Yahoo Falls (18.5 mi / 29.8 km)
  • Pickett State Park (19.1 mi / 30.7 km)
  • Bandy Creek Visitors Center (25.1 mi / 40.3 km)

Frequently asked questions

What is the best area to stay in Monticello when booking a vacation rental?
When planning a vacation in Monticello, Kentucky, one of the best areas to consider for your stay is near the scenic Lake Cumberland. This region is particularly attractive for those who enjoy outdoor activities and beautiful waterfront views. The proximity to Lake Cumberland State Resort Park offers a wealth of recreational opportunities, including boating, fishing, and hiking. Staying in this area provides easy access to stunning natural landscapes and serene lakeside settings, making it ideal for a relaxing getaway.

Another appealing neighborhood is the downtown area of Monticello. Here, you'll find a charming blend of local shops, restaurants, and cultural sites, creating a vibrant atmosphere. The historic downtown area is also close to attractions like the Wayne County Historical Museum, where visitors can learn about the rich history of the region.
How much does it cost to rent a vacation home in Monticello?
Prices for vacation 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 vacation 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.
Where are the best areas for renting a beach house in Monticello?
For renting a beach house in Monticello, Kentucky, travelers should focus on the area surrounding Lake Cumberland, which is known for its beautiful shores and recreational activities. The neighborhoods along the northern shoreline, particularly near the Waitsboro Recreation Area, offer vacation rentals with stunning lake views and direct access to the water. Many of these properties feature amenities like private docks, outdoor grills, and spacious decks, great for enjoying summer evenings by the lake.

Additionally, the area around the Lake Cumberland State Resort Park provides a variety of rental options, including cabins and lakefront homes. These accommodations often come equipped with full kitchens, cozy living rooms, and access to hiking trails and picnic areas, making them ideal for families or groups seeking a blend of relaxation and outdoor adventure.

For those interested in boating or fishing, rentals near the confluence of the Cumberland River and Lake Cumberland are particularly appealing. Here, properties may include features such as boat ramps, fish cleaning stations, and ample parking for trailers, suiting outdoor enthusiasts.
What is the most popular type of vacation rental accomodation in Monticello?
In Monticello, vacation houses are the most popular rental option, with about 43 available throughout the area. These houses are typically situated in tranquil neighborhoods, providing a peaceful retreat for families and groups. Most vacation houses come with multiple bedrooms, fully equipped kitchens, spacious living areas, and outdoor spaces like decks or patios where guests can enjoy the natural surroundings.

Additionally, there are several cottages, cabins, and chalets scattered around, offering a cozy atmosphere and unique charm. These rentals often feature rustic decor and may include amenities like fireplaces, hot tubs, or proximity to local lakes for fishing and boating.
Are there any family house rentals in Monticello?
In Monticello, Kentucky, families can choose from a variety of vacation rentals, with around 48 options available. This charming town, located near the shores of Lake Cumberland, offers homes that cater well to families seeking a fun getaway. Many of these properties come equipped with spacious living areas, full kitchens for preparing meals together, and outdoor spaces great for children to enjoy.

Visitors will appreciate amenities such as air conditioning and Wi-Fi, ensuring a comfortable stay. The nearby lake provides opportunities for boating, fishing, and swimming, making it an ideal spot for family-friendly activities.
Can I rent a vacation home with a pool or hot tub in Monticello?
In Monticello, Kentucky, there are several vacation homes available for rent that include pools and hot tubs, with around 12 options to choose from. This picturesque area, situated near Lake Cumberland, offers a variety of accommodations that cater to different preferences. Many of these properties feature private pools and hot tubs, great for relaxing after a day of exploring the outdoors or enjoying water activities on the lake.

Travelers can expect amenities such as fully equipped kitchens for home-cooked meals, spacious living areas for family gatherings, and outdoor spaces for barbecues and enjoying the scenic surroundings.
Can I find long-stay vacation rentals in Monticello?
A long-stay vacation rental in Monticello is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Monticello?
In Monticello, Kentucky, there are numerous pet-friendly house rentals available, with around 22 options for travelers with furry companions. Many of these rentals offer spacious rooms, allowing for comfortable stays for both guests and their pets. Expect amenities such as fully equipped kitchens, outdoor spaces, and cozy living areas, which can make your stay feel like a home away from home.

The region is known for its beautiful natural surroundings, including nearby Lake Cumberland, where outdoor activities abound. Although specific pet-friendly points of interest are not highlighted, the area's expansive parks and open spaces provide excellent opportunities for walking and enjoying nature with your pets.
Are there any remote work vacation rentals in Monticello?
In Monticello, Kentucky, there is a good selection of remote work vacation rentals available, with around 58 options to choose from. These properties are equipped to support remote work, featuring amenities such as Wi-Fi, dedicated desks, desk chairs, and even laptop workspaces, which can enhance productivity during your stay. Many rentals also provide a comfortable environment with spacious living areas and full kitchens, allowing for a balanced mix of work and relaxation.

The area is known for its beautiful natural surroundings, including Lake Cumberland, which offers opportunities for outdoor activities during breaks from work. With local shops and dining options close by, travelers can enjoy both the convenience of amenities and the charm of Monticello. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Monticello vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Monticello with parking available—perfect for families or travelers 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 vacation rental amenities include WiFi, kitchens equipped with essential appliances like blenders and coffee/tea makers, and outdoor patios for enjoying the fresh air. These amenities cater to travelers looking for comfort and convenience during their stay, allowing them to prepare meals and relax in a cozy setting.
When is the best time to visit Monticello for a vacation rental?
The most popular time to visit Monticello is during the peak season from June to August, when visitors flock to enjoy the warm summer weather and a variety of outdoor activities. This vibrant period is ideal for those seeking adventures such as hiking, fishing, and boating on the beautiful Lake Cumberland, where the stunning natural surroundings enhance the experience.

July stands out as the highlight of this season, offering the warmest temperatures, typically ranging from the mid-70s to low 90s Fahrenheit. This inviting climate encourages outdoor exploration, whether you're embarking on a scenic hike or simply relaxing by the water. The lively atmosphere during this time means you'll encounter fellow travelers and have access to community events that celebrate the local culture.

For those looking for a more budget-friendly option, consider visiting in October, when the fall foliage transforms the landscape into a picturesque setting.
How early should I book a Monticello vacation rental?
Book your Monticello vacation 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 vacation 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 showcase the area's natural beauty and recreational opportunities. Lake Cumberland is a major highlight, offering boating, fishing, and stunning views. Vacation rentals near the lake allow easy access to various water activities and the surrounding state parks, such as Lake Cumberland State Resort Park, which features hiking trails and picnic areas.

The downtown area of Monticello provides a glimpse into local culture, with quaint shops and eateries. Nearby, the Daniel Boone National Forest offers extensive trails for hiking and camping, making it a great spot for outdoor enthusiasts.
Can I change or cancel my Monticello home rental booking on Vrbo?
To find Monticello vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, 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 organizing 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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