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Tollesboro Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Tollesboro holiday rentals

A wooden cabin interior with a sofa, a television, and a sliding barn door.

1. 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, (9 reviews)
"Very peaceful, amazing veiw perfect getaway will definitely stay again. "
United States
Kenneth
The price is AU$248
includes taxes & fees
14 Nov - 15 Nov
Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!
A wooden cabin interior with a sofa, a television, and a sliding barn door.

2. 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$257
includes taxes & fees
13 Nov - 14 Nov
Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!
A rustic cabin with a wooden staircase leading to a deck, surrounded by trees and a clear sky.

3. Glamping Cabin | Huge Window | Over a Creek

Glamping Cabin | Huge Window | Over a Creek
Green Township
9.2 out of 10, Wonderful, (11 reviews)
"Had a wonderful time! Bathrooms and cabin were very clean and it was very quiet. Just what we needed."
United States
Kristen W.
The price is AU$152
includes taxes & fees
1 Nov - 2 Nov
Glamping Cabin | Huge Window | Over a Creek
A wooden cabin with a staircase leading to a balcony, surrounded by snow-covered trees.

4. Glamping Cabin | Huge Window | Cliff and Animal Views

Glamping Cabin | Huge Window | Cliff and Animal Views
Green Township
9.6 out of 10, Exceptional, (4 reviews)
"Nice place, exceptionally nice and professional host and will definitely be reserving this place again real soon!"
United States
Gregory B.
The price is AU$152
includes taxes & fees
1 Nov - 2 Nov
Glamping Cabin | Huge Window | Cliff and Animal Views
A wooden gazebo with a sloped roof and a wooden deck, surrounded by trees and a mountainous backdrop.

5. Glamping Cabin | Huge Window | Tree House Feel

Glamping Cabin | Huge Window | Tree House Feel
Blue Creek
8.6 out of 10, Excellent, (23 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 AU$152
includes taxes & fees
16 Nov - 17 Nov
Glamping Cabin | Huge Window | Tree House Feel
Terrace/patio

6. 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$241
includes taxes & fees
30 Nov - 1 Dec
Quiet Country home, Pet friendly
A spacious room with a wooden floor, a stone fireplace, a red leather chair, a green armchair, and a grey sofa.

7. Charming country home on 433 acres

Charming country home on 433 acres
wallingford
6.0 out of 10, (6 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 AU$182
includes taxes & fees
8 Nov - 9 Nov
Charming country home on 433 acres
A multi-level wooden staircase with a railing, connecting different floors of a building.

8. The Stockholm-Spacious 1BR with Full Kitchen

The Stockholm-Spacious 1BR with Full Kitchen
Vanceburg
The price is AU$208
includes taxes & fees
1 Nov - 2 Nov
The Stockholm-Spacious 1BR with Full Kitchen
A spacious living room with a wooden staircase, a large window, and a variety of seating including a sofa and a chair.

9. The Montgomery-Spacious 1BR with 2 Queen Beds

The Montgomery-Spacious 1BR with 2 Queen Beds
Vanceburg
The price is AU$224
includes taxes & fees
2 Nov - 3 Nov
The Montgomery-Spacious 1BR with 2 Queen Beds
A wooden deck with a round table and two chairs, a window, and a wooden wall.

10. 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$239
includes taxes & fees
30 Nov - 1 Dec
Lazy Lake Cabin 1! Pet Friendly
A small cabin with a wooden exterior, a porch, and a visible interior with a bed and a table.

11. Glamping Cabin | Huge Window | Nature Lovers Dream

Glamping Cabin | Huge Window | Nature Lovers Dream
Stout
9.8 out of 10, Exceptional, (10 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$152
includes taxes & fees
1 Nov - 2 Nov
Glamping Cabin | Huge Window | Nature Lovers Dream
A wooden deck with string lights, a covered seating area, and a view of a town at dusk.

12. Peaceful cabin with spectacular river and scenic views.

Peaceful cabin with spectacular river and scenic views.
Adams County
9.8 out of 10, Exceptional, (41 reviews)
"Very peaceful and relaxing. And VERY clean!!"
United States
Timothy
The price is AU$509
includes taxes & fees
2 Nov - 3 Nov
Peaceful cabin with spectacular river and scenic views.
A small cabin with a wooden exterior, a porch, and a visible interior with a bed and a table.

13. Glamping Cabin | Huge Window | Valley and Cliff Views

Glamping Cabin | Huge Window | Valley and Cliff Views
Green Township
10.0 out of 10, Exceptional, (4 reviews)
"Very family friendly lovely views great host and respectfully so clean very nice stay"
United Kingdom
Brett W.
The price is AU$152
includes taxes & fees
1 Nov - 2 Nov
Glamping Cabin | Huge Window | Valley and Cliff Views
An outdoor seating area with chairs and a fire pit under string lights.

14. Highland Hideaway - Tons of character, modern updates and art !

Highland Hideaway - Tons of character, modern updates and art !
Flemingsburg
The price is AU$256
includes taxes & fees
18 Nov - 19 Nov
Highland Hideaway - Tons of character, modern updates and art !
A wooden cabin with a porch and a green roof, surrounded by gravel and a wooden fence.

15. Beautiful country sunsets II

Beautiful country sunsets II
Hillsboro
10.0 out of 10, Exceptional, (30 reviews)
"Cozy. Clean and had everything we needed"
United States
Rebecca M.
Beautiful country sunsets II
Cabin 2

16. Sleeps 4| Private Bathroom | Stunning Views

Sleeps 4| Private Bathroom | Stunning Views
Green Township
7.0 out of 10, Good, (6 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$211
includes taxes & fees
8 Nov - 9 Nov
Sleeps 4| Private Bathroom | Stunning Views
A covered porch with stone walls, a staircase, and outdoor seating.

17. Spacious Lodge w/ Fire Pit & Hot Tub

Spacious Lodge w/ Fire Pit & Hot Tub
Wallingford
10.0 out of 10, Exceptional, (4 reviews)
"super nice place!"
United States
Trystan S.
The price is AU$854
includes taxes & fees
1 Dec - 2 Dec
Spacious Lodge w/ Fire Pit & Hot Tub
A wooden covered bridge with a stone pathway leading to a small stream.

18. 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
9.6 out of 10, Exceptional, (24 reviews)
"Great cabin"
United States
Phillip
The price is AU$239
includes taxes & fees
1 Nov - 2 Nov
Secluded cabin located on 400 acres in the beautiful hills of Kentucky.
A rustic cabin with a wooden staircase leading to a deck, surrounded by trees and a clear sky.

19. 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$140
includes taxes & fees
2 Nov - 3 Nov
Glamping Cabin | Huge Window | Unique Boulder Views
A house with a covered porch, wooden steps, and a star decoration on the wall.

20. 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, (49 reviews)
"Very clean, and had everything we needed in the kitchen. Very cozy. Exactly what we were looking for."
United States
Debra
The price is AU$273
includes taxes & fees
2 Nov - 3 Nov
Cozy Sunset Cottage on the family farm near Cave Run Lake and Morehead State
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

Griffis Game Hunting and/or Getaway

Griffis Game Hunting and/or Getaway

10/10 Excellent
"If you are in this area, I recommend this comfy cute cabin."
Charles M. 3-night trip
Posted 4 days ago
Griffis Game Hunting and/or Getaway

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$152 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. Kentucky Gateway Museum Center and Washington Visitors Center 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.