Tollesboro Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Tollesboro holiday rentals

9.8 out of 10, Exceptional, (9 reviews)
"Over all, a nice little get away "
United States
jonathan
The price is NZ$494
includes taxes & fees
8 Mar - 9 Mar
Quiet Forest Cabin w/ Hot Tub Near Shawnee
9.4 out of 10, Exceptional, (16 reviews)
"Friendly host, beautiful setting, everything we needed for a nice weekend. We definitely will be returning was very excited to see they have camper hook ups."
United States
Chad R.
The price is NZ$268
includes taxes & fees
27 Feb - 28 Feb
Secluded cabin located on 500 acres in the beautiful hills of Kentucky.
10.0 out of 10, Exceptional, (7 reviews)
"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!"
United States
Amy H.
The price is NZ$507
includes taxes & fees
1 Mar - 2 Mar
Sleeps 12| Private Bathroom | Stunning Views
10.0 out of 10, Exceptional, (35 reviews)
"The cutest little place!! Perfect place for us and our hostess was fantastic. If we are ever back in this neck of the woods we will definitely stay here again!"
United States
Jennifer W.
The price is NZ$321
includes taxes & fees
1 Mar - 2 Mar
Cozy Sunset Cottage on the family farm near Cave Run Lake and Morehead State
9.8 out of 10, Exceptional, (31 reviews)
"Super nice host, very clean cabin."
United States
BRAD T.
The price is NZ$363
includes taxes & fees
2 Mar - 3 Mar
Griffis Game Hunting and/or Getaway
9.8 out of 10, Exceptional, (29 reviews)
"Great location. "
United States
John S.
The price is NZ$640
includes taxes & fees
27 Feb - 28 Feb
Peaceful cabin with spectacular river and scenic views.
9.6 out of 10, Exceptional, (8 reviews)
"Overall had a wonderful time. Hard to keep all the kids occupied since they're is no TV or internet, but over all had a fantastic time."
United States
Tambria F.
The price is NZ$596
includes taxes & fees
27 Feb - 28 Feb
Hickory Ridge Cabin | 3 Bed, 2 Bath

Cabin in Hillsboro

Beautiful Country Sunsets I
9.8 out of 10, Exceptional, (67 reviews)
"Beautiful country setting with amazing views. Just perfect. "
United States
Eli S.
The price is NZ$241
includes taxes & fees
2 Mar - 3 Mar
Beautiful Country Sunsets I

Holiday Home in Vanceburg

Riverview Getaway
10.0 out of 10, Exceptional, (13 reviews)
"Very nice little Vrbo. "
United States
Rebecca S.
The price is NZ$223
includes taxes & fees
9 Mar - 10 Mar
Riverview Getaway
6.8 out of 10, (3 reviews)
"Yes, it would have been perfect for leashed pets. Cabin was very cozy and fit our needs well. One thing we did notice that would've been great if they had some bowls for mixing pancakes and such. "
United States
Dane C.
The price is NZ$258
includes taxes & fees
8 Mar - 9 Mar
Sleeps 4| Private Bathroom | Stunning Views
9.8 out of 10, Exceptional, (8 reviews)
"Loved watching the storm through the big window and listening to the rain on the roof. "
United States
Crystal A.
The price is NZ$190
includes taxes & fees
2 Mar - 3 Mar
Glamping Cabin | Huge Window | Over a Creek
10.0 out of 10, Exceptional, (2 reviews)
"We had a great stay, we loved the horse and goats. It was peaceful and beautiful, exactly what we needed! Will definitely stay again! "
United States
Callie J.
The price is NZ$190
includes taxes & fees
2 Mar - 3 Mar
Glamping Cabin | Huge Window | Cliff and Animal Views
10.0 out of 10, Exceptional, (9 reviews)
"Very clean cabin and very cozy!"
United States
Debbie F.
The price is NZ$269
includes taxes & fees
27 Feb - 28 Feb
Bear Necessities Cabin - What Else Do You Need?
9.0 out of 10, Wonderful, (19 reviews)
"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"
Mexico
Víctor Manuel
The price is NZ$190
includes taxes & fees
8 Mar - 9 Mar
Glamping Cabin | Huge Window | Tree House Feel
9.6 out of 10, Exceptional, (10 reviews)
"Clean rooms, nice decor, pleasant spot. Loved the quiet on the porch area"
United States
David Z.
The price is NZ$464
includes taxes & fees
1 Mar - 2 Mar
Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA!
9.6 out of 10, Exceptional, (4 reviews)
"Nicely decorated property. This was perfect for our family and we’d definitely stay hear again when in Ripley. "
United States
John and Chris S.
The price is NZ$376
includes taxes & fees
27 Feb - 28 Feb
Spacious 3-bedroom apartment with WiFi, AC in charming Ripley

Holiday Home in Flemingsburg

Lazy Lake Cabin 1! Pet Friendly
10.0 out of 10, Exceptional, (1 review)
"Pet friendly, very peaceful and quiet, host is awwsome and very responsive to any needs. Beautiful surroundings"
United States
Donna S.
The price is NZ$277
includes taxes & fees
2 Mar - 3 Mar
Lazy Lake Cabin 1! Pet Friendly
10.0 out of 10, Exceptional, (2 reviews)
"Property owners were very welcoming. The tree house and property were well maintained. "
United States
Marci
The price is NZ$190
includes taxes & fees
1 Mar - 2 Mar
Glamping Cabin | Huge Window | Valley and Cliff Views
9.8 out of 10, Exceptional, (9 reviews)
"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."
United Kingdom
Abby M.
The price is NZ$190
includes taxes & fees
8 Mar - 9 Mar
Glamping Cabin | Huge Window | Nature Lovers Dream

Holiday Home in wallingford

Charming country home on 433 acres
5.6 out of 10, (5 reviews)
"Spacious inside and out. Interior offers a large living room with separate dining room. Plenty of yard and privacy. Short drive to town. Host was very accommodating!"
United States
Maria B.
The price is NZ$210
includes taxes & fees
1 Mar - 2 Mar
Charming country home on 433 acres
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.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Tollesboro Hotel Reviews

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, 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 NZ$190 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?

Unique and secluded A frame home on 31 acres with hot tub.: This holiday home rental outside of Tollesboro is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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. Kentucky Gateway Museum Center 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.