Holiday Rentals in Tollesboro

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Holiday Rentals in Tollesboro

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

10.0 out of 10, Exceptional, (1)
Charming 2 Bedroom Cabin in Vanceburg-Your Gateway to Kentucky's Natural Beauty

Spacious 4-bedroom 19th Century home in historic downtown Maysville!

10.0 out of 10, Exceptional, (2)
"We were overly impressed by this property and the location. The house was emasculate and had such great character in every room. Check in and communication with the property own were top notch. The main areas in the town are all within short walking distance of the home. We will definitely look for this home again next year when we come back to Maysville. We won Oktoberfest king 2025 so we’ll definitely be back!"
Spacious 4-bedroom 19th Century home in historic downtown Maysville!

Bear Necessities Cabin - What Else Do You Need?

10.0 out of 10, Exceptional, (1)
"Great little spot! Cabin is super nice inside and out."
The price is €161
includes taxes & fees
2 Sept - 3 Sept
Bear Necessities Cabin - What Else Do You Need?

Glamping Cabin | Huge Window | Over a Creek

10.0 out of 10, Exceptional, (5)
"Beautiful location ."
The price is €110
includes taxes & fees
1 Sept - 2 Sept
Glamping Cabin | Huge Window | Over a Creek

Peaceful cabin with spectacular river and scenic views.

9.8 out of 10, Exceptional, (18)
"Cozy cabin with a great view"
The price is €320
includes taxes & fees
31 Aug - 1 Sept
Peaceful cabin with spectacular river and scenic views.

The Manor at Maysville Golf Course View

9.8 out of 10, Exceptional, (22)
"Our families got together for a lovely Christmas gathering here. The house was beautifully decorated!"
The Manor at Maysville Golf Course View

Cozy Country Cabin close to West Union!

2.0 star property
10.0 out of 10, Exceptional, (20)
"The property was very clean and had everything we needed. We would stay again. "
Cozy Country Cabin close to West Union!

Glamping Cabin | Huge Window | Tree House Feel

9.2 out of 10, Wonderful, (18)
"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"
The price is €110
includes taxes & fees
31 Aug - 1 Sept
Glamping Cabin | Huge Window | Tree House Feel

Glamping Cabin | Huge Window | Cliff and Animal Views

The price is €110
includes taxes & fees
31 Aug - 1 Sept
Glamping Cabin | Huge Window | Cliff and Animal Views

1 Mi to Hunting: Cozy & Secluded Stout Cabin

3.0 star property
1 Mi to Hunting: Cozy & Secluded Stout Cabin

Glamping Cabin | Huge Window | Nature Lovers Dream

9.8 out of 10, Exceptional, (9)
"We had a spectacular stay! Comfortable, Quiet, and Clean!Only a small suggestion Put a handle on the inside of the screen door and WD-40 the big door on cabin 1."
The price is €110
includes taxes & fees
28 Sept - 29 Sept
Glamping Cabin | Huge Window | Nature Lovers Dream

Sleeps 12| Huge Windows | Stunning Views

10.0 out of 10, Exceptional, (6)
"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!"
The price is €327
includes taxes & fees
23 Sept - 24 Sept
Sleeps 12| Huge Windows | Stunning Views

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

2.0 star property
10.0 out of 10, Exceptional, (5)
"Very peaceful, amazing veiw perfect getaway will definitely stay again. "
Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!

Charming country home on 433 acres

10.0 out of 10, Exceptional, (2)
Charming country home on 433 acres

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

10.0 out of 10, Exceptional, (1)
"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. "
Unique and secluded A frame home on 31 acres with hot tub.

Ljbak1987@icloud.com

10.0 out of 10, Exceptional, (2)
"This cabin was absolutely beautiful and perfect in every way! It had everything we could have possibly needed — from a thoughtfully stocked kitchen to body wash and soap in the bathrooms, which was such a nice touch. The kids’ area was a huge bonus and kept our little ones happy and entertained.The setting was just magical — the creek outside was peaceful and lovely, and we spent a lot of time just enjoying the relaxing atmosphere. We were in town for a family reunion, and this cabin made the...
Ljbak1987@icloud.com

1 Mi to Hunting: Cozy & Secluded Stout Cabin

10.0 out of 10, Exceptional, (5)
"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."
1 Mi to Hunting: Cozy & Secluded Stout Cabin

Riverview Getaway

9.8 out of 10, Exceptional, (9)
"Such a cute little town. Place is right next to a bar and the lake. Really nice spot and really clean"
The price is €119
includes taxes & fees
28 Sept - 29 Sept
Riverview Getaway

Quiet Country home, Pet friendly

2.0 star property
Quiet Country home, Pet friendly

Manchester Getaway on Ohio River Scenic Byway

8.0 out of 10, Very good, (1)
"Definitely not the best to swim but great to fish cook and hangout with the family for some peaceful time"
Manchester Getaway on Ohio River Scenic Byway
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 Tollesboro Hotel Reviews

Find out more about Tollesboro

Find out more about Tollesboro

Everything you need to know about Tollesboro holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Tollesboro holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Tollesboro holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Tollesboro holiday rentals we have selected for you start as low as €110 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 holiday 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 holiday.

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. 

Frequently asked questions

Are there holiday rentals in Tollesboro?

Yes, there are holiday rentals close to the most popular sights in Tollesboro, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Tollesboro has to offer?

Spacious 4-bedroom 19th Century home in historic downtown Maysville!: This holiday home rental outside of Tollesboro is located on a river, and offers a patio, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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 wider area.

What are holiday rentals like in Tollesboro?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Tollesboro. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for a small group gathering.