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Tollesboro Holiday Rentals

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Our top choices for Tollesboro holiday rentals

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

Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!
Stout
10.0 out of 10, Exceptional, (8 reviews)
"Very peaceful, amazing veiw perfect getaway will definitely stay again. "
United States
Kenneth
The price is AU$258
includes taxes & fees
15 June - 16 June
Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!

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

Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!
3.0 star property
Rome
The price is AU$254
includes taxes & fees
15 June - 16 June
Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!

Glamping Cabin | Huge Window | Cliff and Animal Views

Glamping Cabin | Huge Window | Cliff and Animal Views
Green Township
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 AU$165
includes taxes & fees
17 June - 18 June
Glamping Cabin | Huge Window | Cliff and Animal Views

Glamping Cabin | Huge Window | Over a Creek

Glamping Cabin | Huge Window | Over a Creek
Green Township
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 AU$165
includes taxes & fees
15 June - 16 June
Glamping Cabin | Huge Window | Over a Creek

Glamping Cabin | Huge Window | Tree House Feel

Glamping Cabin | Huge Window | Tree House Feel
Blue Creek
8.8 out of 10, Excellent, (20 reviews)
"The property is very remote, secluded and quiet. It is a pet friendly property that our dog very much enjoyed. For hikers this is a great location. We were very unlucky with the weather, so no fire pit or BBQing due to torrential rain (no one can control that). Amenities are solid. It is glamping. There is a gas station approx. 10 minutes away that serves some solid breakfast…Portsmouth is about 45 minutes away for some dinner options."
United States
Stuart
The price is AU$165
includes taxes & fees
15 June - 16 June
Glamping Cabin | Huge Window | Tree House Feel

Sleeps 4| Private Bathroom | Stunning Views

Sleeps 4| Private Bathroom | Stunning Views
Green Township
7.2 out of 10, Good, (5 reviews)
"We enjoyed staying at this unique cabin. Our children liked the animals and enjoyed petting some of them. "
United States
Al G.
The price is AU$223
includes taxes & fees
22 June - 23 June
Sleeps 4| Private Bathroom | Stunning Views

Beautiful Country Sunsets I

Beautiful Country Sunsets I
Hillsboro
9.6 out of 10, Exceptional, (68 reviews)
"Very nice, serene, and personable and the owners were excellent. Great sunrise and sunsets and the stars at night were amazing. "
United States
Simple
The price is AU$208
includes taxes & fees
25 June - 26 June
Beautiful Country Sunsets I

Bear Necessities Cabin - What Else Do You Need?

Bear Necessities Cabin - What Else Do You Need?
West Union
10.0 out of 10, Exceptional, (12 reviews)
"Great little spot! Cabin is super nice inside and out."
United States
Jason M.
The price is AU$246
includes taxes & fees
15 June - 16 June
Bear Necessities Cabin - What Else Do You Need?

Secluded cabin located on 400 acres in the beautiful hills of Kentucky.

Secluded cabin located on 400 acres in the beautiful hills of Kentucky.
Garrison
9.4 out of 10, Exceptional, (20 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 AU$231
includes taxes & fees
29 June - 30 June
Secluded cabin located on 400 acres in the beautiful hills of Kentucky.

Griffis Game Hunting and/or Getaway

Griffis Game Hunting and/or Getaway
West Union
9.8 out of 10, Exceptional, (31 reviews)
"Super nice host, very clean cabin."
United States
BRAD T.
The price is AU$312
includes taxes & fees
22 June - 23 June
Griffis Game Hunting and/or Getaway

Peaceful cabin with spectacular river and scenic views.

Peaceful cabin with spectacular river and scenic views.
Adams County
9.8 out of 10, Exceptional, (32 reviews)
"Great location. "
United States
John S.
The price is AU$579
includes taxes & fees
25 June - 26 June
Peaceful cabin with spectacular river and scenic views.

Cozy Sunset Cottage on the family farm near Cave Run Lake and Morehead State

Cozy Sunset Cottage on the family farm near Cave Run Lake and Morehead State
Morehead
10.0 out of 10, Exceptional, (41 reviews)
"Great place to stay, updated and clean"
United States
Ty R.
The price is AU$280
includes taxes & fees
6 July - 7 July
Cozy Sunset Cottage on the family farm near Cave Run Lake and Morehead State

Quiet Country home, Pet friendly

Quiet Country home, Pet friendly
Wallingford
10.0 out of 10, Exceptional, (1 review)
"Beautiful property especially if you like the peace and quiet of nature. The host was fantastic to work with and extremely friendly. "
United States
Julie G.
The price is AU$254
includes taxes & fees
15 June - 16 June
Quiet Country home, Pet friendly

Sleeps 12| Private Bathroom | Stunning Views

Sleeps 12| Private Bathroom | Stunning Views
Blue Creek
10.0 out of 10, Exceptional, (8 reviews)
"Neat house for a group with kids! The bunk house with the trap door was a blast for them. "
United States
Matt S.
The price is AU$442
includes taxes & fees
21 June - 22 June
Sleeps 12| Private Bathroom | Stunning Views

Lazy Lake Cabin 2!!! Pet Friendly!!

Lazy Lake Cabin 2!!! Pet Friendly!!
Flemingsburg
4.0 out of 10, (2 reviews)
"Property was not clean. Rooms had exposed wiring and several other safety hazards. Ok room to rent if just looking for a place to rest your head. The couch also smelled like wet dog."
United States
Frederick L.
The price is AU$216
includes taxes & fees
16 June - 17 June
Lazy Lake Cabin 2!!! Pet Friendly!!

Glamping Cabin | Huge Window | Nature Lovers Dream

Glamping Cabin | Huge Window | Nature Lovers Dream
Stout
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 AU$165
includes taxes & fees
16 June - 17 June
Glamping Cabin | Huge Window | Nature Lovers Dream

Glamping Cabin | Huge Window | Valley and Cliff Views

Glamping Cabin | Huge Window | Valley and Cliff Views
Green Township
10.0 out of 10, Exceptional, (3 reviews)
"Very family friendly lovely views great host and respectfully so clean very nice stay"
United Kingdom
Brett W.
The price is AU$165
includes taxes & fees
15 June - 16 June
Glamping Cabin | Huge Window | Valley and Cliff Views

Spacious 3-bedroom apartment with WiFi, AC in charming Ripley

Spacious 3-bedroom apartment with WiFi, AC in charming Ripley
Ripley
9.6 out of 10, Exceptional, (5 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 AU$324
includes taxes & fees
15 June - 16 June
Spacious 3-bedroom apartment with WiFi, AC in charming Ripley

Glamping Cabin | Huge Window | Unique Boulder Views

Glamping Cabin | Huge Window | Unique Boulder Views
Green Township
4.0 out of 10, (1 review)
The price is AU$165
includes taxes & fees
15 June - 16 June
Glamping Cabin | Huge Window | Unique Boulder Views

Lazy Lake Cabin 1! Pet Friendly

Lazy Lake Cabin 1! Pet Friendly
Flemingsburg
6.0 out of 10, (2 reviews)
"Pet friendly, very peaceful and quiet, host is awwsome and very responsive to any needs. Beautiful surroundings"
United States
Donna S.
The price is AU$238
includes taxes & fees
15 June - 16 June
Lazy Lake Cabin 1! Pet Friendly
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

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 favourite 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 depend 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 AU$165 per night. Entering your travel dates in the search wizard might find you 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. Russell Theatre and Laurel Oaks Golf Club 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.