Monticello Vacation Rentals

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Our top choices for Monticello vacation rentals

Vacation Home in Monticello

The Cozy Cabell Cottage
9.8 out of 10, Exceptional, (52 reviews)
"This was the cutest little cottage! We stayed with my mom and baby while the boys camped on the lake, and it was the perfect little home base for meals and sleeping! Would definitely stay again!"
United States
Courtney M.
$174 nightly
The price is $191
Mar 16 - Mar 17
Total with taxes and fees
The Cozy Cabell Cottage
10.0 out of 10, Exceptional, (33 reviews)
"This beautiful home is made for a wonderful family getaway. My family had an amazing time relaxing and reconnecting in this well-appointed retrear. Stephanie, the host, was very comminicative throughout our stay. "
United States
Joshua H.
$453 nightly
The price is $487
Mar 17 - Mar 18
Total with taxes and fees
Modern 4BR Retreat~ King Ensuites w/ fireplaces~ Hot Tub~ Fire Pit~ Boat Ramp
$195 nightly
The price is $215
Mar 16 - Mar 17
Total with taxes and fees
Lakeside Escape - Charming home centrally located on Lake Cumberland

Camping in Jamestown

Glamping Back in Time
10.0 out of 10, Exceptional, (3 reviews)
"So novel and fun!"
United States
Sharon
$180 nightly
The price is $203
Mar 16 - Mar 17
Total with taxes and fees
Glamping Back in Time
10.0 out of 10, Exceptional, (16 reviews)
"Perfect getaway near Lake Cumberland"
United States
ANDREW G.
$181 nightly
The price is $200
Mar 17 - Mar 18
Total with taxes and fees
Newly renovated near Rowena, Grider and Wolf Creek Dam
10.0 out of 10, Exceptional, (89 reviews)
"super clean with everything you need for a great stay...super friendly hosts!!!"
United States
Barney H.
$188 nightly
The price is $202
Mar 16 - Mar 17
Total with taxes and fees
Boating Mecca: Near Dale Hollow Lake & Golf!
10.0 out of 10, Exceptional, (15 reviews)
"Great little house! Loved our stay!"
United States
shellyrhae C.
$110 nightly
The price is $123
Mar 23 - Mar 24
Total with taxes and fees
Cozy 1-bedroom house in charming Allardt with AC, WiFi
9.2 out of 10, Wonderful, (14 reviews)
"Such a lovely property. Very cozy and inviting. We will definitely stay again."
United States
Jennifer S.
$387 nightly
The price is $426
Mar 22 - Mar 23
Total with taxes and fees
NEW HOT TUB Cozy Cabin Cumberland River near Lake Cumberland~Firepit~New build
10.0 out of 10, Exceptional, (25 reviews)
"Wonderful, quaint space perfect for our small family! "
United States
Bianca F.
$226 nightly
The price is $255
Mar 17 - Mar 18
Total with taxes and fees
Cozy 2-bedroom cabin with WiFi, AC in welcoming Jamestown

Cabin in Burnside

Cozy Cabin
9.0 out of 10, Wonderful, (12 reviews)
"Clean room, cozy space"
United States
Christina C.
$197 nightly
The price is $217
Mar 16 - Mar 17
Total with taxes and fees
Cozy Cabin
9.0 out of 10, Wonderful, (8 reviews)
"This is not the typical Tourist cabin. It is a great place to stay to get away from everything. Very secluded but close to town if you need something. Will definitely reserve again in the future."
United States
Thomas B.
$188 nightly
The price is $212
Mar 22 - Mar 23
Total with taxes and fees
Whitetail Hollow- 2 bedroom 1 bath

Apartment in Jamestown

New Near Jamestown Dock - A
9.8 out of 10, Exceptional, (22 reviews)
"Great stay"
United States
Rob W.
$185 nightly
The price is $204
Mar 16 - Mar 17
Total with taxes and fees
New Near Jamestown Dock - A
9.6 out of 10, Exceptional, (26 reviews)
"This cabin is wonderful. We had a blast."
United States
INGIN L.
$271 nightly
The price is $298
Mar 22 - Mar 23
Total with taxes and fees
Charming cabin retreat: cozy, scenic, and perfect for a relaxing getaway!
9.4 out of 10, Exceptional, (38 reviews)
"Great place for cheap!"
United States
Jamie M.
$157 nightly
The price is $173
Mar 31 - Apr 1
Total with taxes and fees
Timy Home near Wolf Creek Marina & multiple boat ramps with a full kitchen
10.0 out of 10, Exceptional, (3 reviews)
"Everglow Hollow was great! We stayed for a long weekend and it was the perfect place to relax, while not being too far away from Lake Cumberland. Host also responded to questions right away and were very helpful. "
Canada
Morgan P.
$174 nightly
The price is $192
Mar 16 - Mar 17
Total with taxes and fees
LAKE CUMBERLAND Get-a-Way! Charming House. BOAT RAMP NEARBY - Wifi - RV Hookups
9.2 out of 10, Wonderful, (5 reviews)
"Had a wonderful time!!"
United States
RICK M.
$200 nightly
The price is $220
Mar 16 - Mar 17
Total with taxes and fees
Lake Cumberland "Lake Daze Cabin" near Clearwater
9.2 out of 10, Wonderful, (35 reviews)
"Very isolated and quiet Some of the blinds on the windows are broken and the light in the bedroom on the rt is not working. Beutiful country "
United States
cynthia B.
$178 nightly
The price is $207
Mar 17 - Mar 18
Total with taxes and fees
2 bedroom 1 bath cabin
9.4 out of 10, Exceptional, (28 reviews)
"Quiet, clean and peaceful"
United States
Neil
$178 nightly
The price is $201
Mar 22 - Mar 23
Total with taxes and fees
cozy cabin in the woods in a relaxing area with wrap around porch rocking chairs

Vacation Home in Byrdstown

Mema and Pa’s Place
10.0 out of 10, Exceptional, (15 reviews)
"Property was clean and quiet. "
United States
Jeremy F.
$199 nightly
The price is $222
Mar 16 - Mar 17
Total with taxes and fees
Mema and Pa’s Place
9.8 out of 10, Exceptional, (13 reviews)
"Really enjoyed the stay and will likely be back."
United States
Mike W.
$131 nightly
The price is $146
Mar 21 - Mar 22
Total with taxes and fees
The Honey Hut next to Big South Fork NRRA with AC, wifi, and horse stalls.
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.

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Top Monticello Hotel Reviews

Find out more about Monticello

Everything you need to know about Monticello vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Monticello vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Monticello vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Monticello vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Monticello. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Monticello in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $215 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Monticello rentals

At Expedia, we put the best Monticello vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Monticello rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Monticello vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Monticello. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Monticello?

Yes, we offer vacation rentals close to top points of interest in Monticello, or you can choose a secluded option if you're looking for a relaxing stay. Discover why Monticello is known for its marina and lakeside. Make sure you have time to check out the basketball games and wineries during your trip.

What are some of the best vacation rentals that Monticello has to offer?

6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍: Visitors like this Monticello vacation home rental. It offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. Other favorite homes for rent in Monticello are 4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View! and Lake Bluff Paradise on Lake Cumberland. Game room and seasonal hot tub!.

How many vacation rentals are there in Monticello?

With 45 Expedia vacation rentals, you're sure to find just the right place for your Monticello stay.

What’s there to see and do in Monticello?

Cumberland River and Big Island are a couple of scenic spots to enjoy the outdoors, whereas Wayne County Historical Museum is one of the cultural attractions. While here, Conley Bottom Marina and Lake Cumberland Winery are other places worth a visit.

What’s a vacation rental in Monticello like?

A vacation rental is a private property you can book for several days or longer in Monticello. Vacation rentals offer amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for small groups.