Tollesboro Vacation Rentals from CA $131: Short-Term Rentals for 2025

Q: What's the top vacation rental that Tollesboro has to offer?

The Manor at Maysville Golf Course View : This vacation home rental near Tollesboro is located next to a golf course and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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Vacation Rentals in Tollesboro

Relax on the cabin's spacious deck, surrounded by lush greenery, with comfortable seating for socializing or unwinding.

"The property was very clean and had everything we needed. We would stay again. "

Enjoy a peaceful evening on the deck with a view of the city skyline.

"Cozy cabin with a great view"

CA $542 total

includes taxes & fees

Aug 17 - Aug 18

Cozy living room with a fireplace, sofa, and two side tables.

"Our families got together for a lovely Christmas gathering here. The house was beautifully decorated!"

Escape to a serene forest retreat with a deck and walking path.

"Beautiful location ."

CA $194 total

includes taxes & fees

Aug 4 - Aug 5

Cozy living space with a flat-screen TV, sofa, and patterned rug.

"Great place to stay. Overlooks the town Very nice and cozy "

Stunning courtyard with a brick pathway and beautifully landscaped gardens.

Set amidst the snowy forest, this cabin complex features a central deck and staircase leading to a second-story cabin, blending seamlessly into the winter landscape.

CA $194 total

includes taxes & fees

Aug 4 - Aug 5

Relax on the porch with a scenic view of the forest, surrounded by autumn foliage.

Kitchen with central island, sink, and microwave, offering a view of the outdoors.

"Very peaceful, amazing veiw perfect getaway will definitely stay again. "

Escape to a secluded cabin surrounded by trees and a gentle slope, offering a tranquil retreat.

"This cabin was exactly what we were looking for: Cozy, peaceful, clean, comfortable and all the amenities. Located near several great hiking spots within a short drive. Great indoor and outdoor space. Host was very friendly and responsive. Highly recommend this place!"

CA $514 total

includes taxes & fees

Aug 4 - Aug 5

Escape to a secluded cabin surrounded by trees and a gentle slope.

"The perfect place to connect with nature and enjoy a beautiful landscape the attention was great the beautiful place the super comfortable cabin I would come back again"

CA $194 total

includes taxes & fees

Aug 4 - Aug 5

Kitchen features a central island with ample workspace, white cabinetry, and a stainless steel refrigerator.

"Very unique property with outstanding views. Nice amenities throughout (remote-operated ceiling fans, large screen TV, wifi, fully outfitted kitchen, large picture windows). The hot tub was fully functioning and appeared to be brand new. We appreciated the privacy that the property afforded and the several unique places in the home to retreat for reflection and/or conversation. "

Escape to a serene forest retreat with a cozy cabin-style accommodation featuring a bed and dining area.

"Really enjoyed our stay! Beautiful scenery and well-maintained property. Having the property manager living on site was great as he was readily available to answer any questions. All the comforts of a hotel without the hotel."

CA $194 total

includes taxes & fees

Aug 4 - Aug 5

Prepare meals in this kitchen with a window offering a view of the street.

"Such a cute little town. Place is right next to a bar and the lake. Really nice spot and really clean"

CA $148 total

includes taxes & fees

Aug 4 - Aug 5

Kitchen equipped with microwave, coffee maker, and sink with a window above.

"This was a very large farmhouse, that accommodated our group very well. Lots of beds, and large kitchen area made cooking and dining very easy for a large group! Plus, we were so far out in the country, the kids could make all the noise they wanted! Mark, our host, was on sight to check us in and explained where everything was located. Plus, he provided a list in the kitchen area, of local emergency contact phone numbers, that was very helpful. Having two kitchens / refrigerators was nice, for a...

Relax on the porch with a scenic view of the forest, featuring a path leading to a rustic cabin.

"The accommodation were great, clean and a lot of ni e touches like toothbrush, and personal hygiene items. Location vert clean and quiet. Close to portsmouth. Highly recommend stay here if you are in the adams county area."

Enjoy al fresco dining at this outdoor cooking station with oven and grill.

"Definitely not the best to swim but great to fish cook and hangout with the family for some peaceful time"

Cozy retreat with a large bed, nightstand, and fireplace.

"Property manager is the sweetest and super helpful and available. The apartment was clean and comfortable. I highly recommend the eatery downstairs for lunch ir supper!!"

Escape to a secluded cabin surrounded by forest, featuring a cozy porch and a simple living area with a bed and table.

"Property owners were very welcoming. The tree house and property were well maintained. "

CA $194 total

includes taxes & fees

Aug 4 - Aug 5

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Top Tollesboro Hotel Reviews

Beverly hills inn

10/10 Excellent

"The workers were extra friendly and very helpful. The food was great and the atmosphere was phenomenal. Definitely recommend this to everyone."

Peaceful cabin with spectacular river and scenic views.

10/10 Excellent

"This wonderful cabin, high top of hill above the Ohio river, and across from the east end of Maysville Kentucky is just almost beyond words. The big porch across the front with rocking chairs to watch the barges go up and down the river and the trains go up and down on the Kentucky side. Even though it’s quite rustic with original cabin walls on part of it, the appointments are lovely; almost as though the owners live there. Unusual in a rental and really appreciate it!I track birds on my phone based on their song; 12 different ones at a time! We only live two hours away and so many that we never have at home.It rained one morning and the most amazing rainbow happened that started on the Kentucky side and came all the way across to literally right behind our cabin! It hung there for over a half an hour.Very close to my family‘s home and we were able to go and look at things that are sweet memories to me."

Country Nights Inn

10/10 Excellent

"The couple (I believe they are a couple) who own this place are incredible. So, nice, so accommodating, such a lovely couple of people. However, I do need to be honest. The place was not great. * Let me preface and say that I am not a high maintenance person, if there are scuffs, dents and dings in places - I don't care, that's normal. But, I do need to point out that the sheets reeked of cigarette smoke. It got so bad at the end of the night when I laid my head on the pillow that I needed to spray my perfume on them pretty heavily just to be able to sleep. There were a couple of dead bug bodies smooshed to the wall, where you could tell someone smashed them and just left them and no one cleaned them up. There was a booger on the wall next to the bed and that was pretty obvious to the naked eye if you were looking. The hair dryer, and the soap dispensers were covered in dust. The water pressure in the tub was so/so - it would be normal for five minutes then shoot out at high speed and be super loud then go back to normal. The air conditioner worked well but it was a little loud and annoying at time, but after a while, I was able to ignore it. And, lastly there was a security light right outside my room, which I get is needed, and I don't wish anyone to fall or not be able to see outside, but I think if they're going to keep it in that location then they should invest in better curtains/ blinds, because the light was extremely visible at night. "

Find out more about Tollesboro

Everything you need to know about Tollesboro 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 Tollesboro vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... 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 Tollesboro vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Tollesboro vacation rentals: An excellent choice for every season

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

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Tollesboro vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Tollesboro vacation rentals we have selected for you start as low as CA $131 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Tollesboro rentals

At Expedia, we put the best Tollesboro 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 Tollesboro 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 Tollesboro 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 Tollesboro. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Frequently asked questions

Are there vacation rentals in Tollesboro?

Yes, we give you a choice of vacation rentals close to the most popular sights in Tollesboro, or you can choose a more secluded option if you're looking for a relaxing stay.

What's the top vacation rental that Tollesboro has to offer?

The Manor at Maysville Golf Course View: This vacation home rental near Tollesboro is located next to a golf course and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What can I see and do in Tollesboro?

Explore the area and family-friendly sights such as National Underground Railroad Museum, or get out into nature at a spot like Flemingsburg Recreation Park. Fleming County Recreation Park and Kenton Station Golf Course are a couple of places you'll find in the larger area.

What are vacation rentals like in Tollesboro?

Vacation rentals are privately owned accommodations you can stay in for a few days or a quick weekend in Tollesboro. Vacation rentals feature extras such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for families.

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Tollesboro Vacation Rentals

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Vacation Rentals in Tollesboro

Charming 2 Bedroom Cabin in Vanceburg-Your Gateway to Kentucky's Natural Beauty

Charming 2 Bedroom Cabin in Vanceburg-Your Gateway to Kentucky's Natural Beauty

Cozy Country Cabin close to West Union!

Cozy Country Cabin close to West Union!

Peaceful cabin with spectacular river and scenic views.

Peaceful cabin with spectacular river and scenic views.

The Manor at Maysville Golf Course View

The Manor at Maysville Golf Course View

Glamping Cabin | Huge Window | Over a Creek

Glamping Cabin | Huge Window | Over a Creek

Beautiful studio in historic downtown Maysville

Beautiful studio in historic downtown Maysville

Luxury and Character in Maysville, Kentucky

Luxury and Character in Maysville, Kentucky

Glamping Cabin | Huge Window | Cliff and Animal Views

Glamping Cabin | Huge Window | Cliff and Animal Views

1 Mi to Hunting: Cozy & Secluded Stout Cabin

1 Mi to Hunting: Cozy & Secluded Stout Cabin

Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!

Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!

Sleeps 12| Huge Windows | Stunning Views

Sleeps 12| Huge Windows | Stunning Views

Glamping Cabin | Huge Window | Tree House Feel

Glamping Cabin | Huge Window | Tree House Feel

Unique and secluded A frame home on 31 acres with hot tub.

Unique and secluded A frame home on 31 acres with hot tub.

Glamping Cabin | Huge Window | Nature Lovers Dream

Glamping Cabin | Huge Window | Nature Lovers Dream

Riverview Getaway

Riverview Getaway

Spacious Ewing Retreat w/ Game Room & Fireplace!

Spacious Ewing Retreat w/ Game Room & Fireplace!

1 Mi to Hunting: Cozy & Secluded Stout Cabin

1 Mi to Hunting: Cozy & Secluded Stout Cabin

Manchester Getaway on Ohio River Scenic Byway

Manchester Getaway on Ohio River Scenic Byway

Home away from Home! - 1BR apartment in Maysville

Home away from Home! - 1BR apartment in Maysville

Glamping Cabin | Huge Window | Valley and Cliff Views

Glamping Cabin | Huge Window | Valley and Cliff Views

Top Tollesboro Hotel Reviews

Beverly hills inn

Find out more about Tollesboro

Find out more about Tollesboro

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Explore a world of travel with Expedia

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