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Tollesboro Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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!
3.0 star property
Rome
The price is HK$894
HK$1,416 total
includes taxes & fees
4 Oct - 5 Oct
Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!
Terrace/patio

2. 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 HK$785
HK$1,386 total
includes taxes & fees
5 Oct - 6 Oct
Quiet Country home, Pet friendly
A wooden cabin interior with a sofa, a television, and a sliding barn door.

3. 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 HK$643
HK$1,413 total
includes taxes & fees
4 Oct - 5 Oct
Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!
A rustic wooden structure with a wooden deck leading to a warmly lit interior, surrounded by trees.

4. Glamping Cabin | Huge Window | Over a Creek

Glamping Cabin | Huge Window | Over a Creek
Green Township
9.2 out of 10, Wonderful, (11 reviews)
"Beautiful location ."
United States
Shelly R.
The price is HK$496
HK$849 total
includes taxes & fees
2 Oct - 3 Oct
Glamping Cabin | Huge Window | Over a Creek
A rustic wooden structure with a wooden deck leading to a warmly lit interior, surrounded by trees.

5. 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 HK$496
HK$849 total
includes taxes & fees
2 Oct - 3 Oct
Glamping Cabin | Huge Window | Cliff and Animal Views
A rustic wooden structure with a wooden deck leading to a warmly lit interior, surrounded by trees.

6. Glamping Cabin | Huge Window | Tree House Feel

Glamping Cabin | Huge Window | Tree House Feel
Green Township
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 HK$496
HK$849 total
includes taxes & fees
2 Oct - 3 Oct
Glamping Cabin | Huge Window | Tree House Feel
A wooden deck with string lights, a covered seating area, and a view of a town at dusk.

7. Peaceful cabin with spectacular river and scenic views.

Peaceful cabin with spectacular river and scenic views.
Adams County
9.8 out of 10, Exceptional, (39 reviews)
"Very peaceful and relaxing. And VERY clean!!"
United States
Timothy
The price is HK$1,899
HK$3,240 total
includes taxes & fees
6 Oct - 7 Oct
Peaceful cabin with spectacular river and scenic views.
Cabin 2

8. 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 HK$1,059
HK$1,216 total
includes taxes & fees
4 Oct - 5 Oct
Sleeps 4| Private Bathroom | Stunning Views
A wooden deck with a round table and two chairs, a window, and a wooden wall.

9. 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 HK$785
HK$1,302 total
includes taxes & fees
5 Oct - 6 Oct
Lazy Lake Cabin 1! Pet Friendly
A spacious room with a wooden floor, a stone fireplace, a red leather chair, a green armchair, and a grey sofa.

10. 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 HK$530
HK$987 total
includes taxes & fees
4 Oct - 5 Oct
Charming country home on 433 acres
A rustic wooden structure with a wooden deck leading to a warmly lit interior, surrounded by trees.

11. 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 HK$1,962
HK$2,472 total
includes taxes & fees
4 Oct - 5 Oct
Sleeps 12| Private Bathroom | Stunning Views
A house with a covered porch, wooden steps, and a star decoration on the wall.

12. 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, (47 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 HK$942
HK$1,563 total
includes taxes & fees
5 Oct - 6 Oct
Cozy Sunset Cottage on the family farm near Cave Run Lake and Morehead State
A two-story brick building with a central entrance flanked by columns, a front lawn, and trees in the background.

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

The Montgomery-Spacious 1BR with 2 Queen Beds
Vanceburg
The price is HK$981
HK$1,218 total
includes taxes & fees
2 Oct - 3 Oct
The Montgomery-Spacious 1BR with 2 Queen Beds
A covered porch with stone walls, a staircase, and outdoor seating.

14. Spacious Lodge w/ Fire Pit & Hot Tub

Spacious Lodge w/ Fire Pit & Hot Tub
Wallingford
10.0 out of 10, Exceptional, (3 reviews)
"super nice place!"
United States
Trystan S.
The price is HK$2,826
HK$4,611 total
includes taxes & fees
5 Oct - 6 Oct
Spacious Lodge w/ Fire Pit & Hot Tub
A two-story brick building with a central entrance flanked by columns, a front lawn, and trees in the background.

15. The Stockholm-Spacious 1BR with Full Kitchen

The Stockholm-Spacious 1BR with Full Kitchen
Vanceburg
The price is HK$902
HK$1,134 total
includes taxes & fees
2 Oct - 3 Oct
The Stockholm-Spacious 1BR with Full Kitchen
A wooden covered bridge with a stone pathway leading to a small stream.

16. 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 HK$863
HK$1,260 total
includes taxes & fees
5 Oct - 6 Oct
Secluded cabin located on 400 acres in the beautiful hills of Kentucky.
A small cabin with a wooden exterior, a porch, and a visible interior with a bed and a table.

17. 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 HK$496
HK$849 total
includes taxes & fees
2 Oct - 3 Oct
Glamping Cabin | Huge Window | Valley and Cliff Views
A small cabin with a wooden exterior, a porch, and a visible interior with a bed and a table.

18. Glamping Cabin | Huge Window | Nature Lovers Dream

Glamping Cabin | Huge Window | Nature Lovers Dream
Green Township
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 HK$496
HK$849 total
includes taxes & fees
2 Oct - 3 Oct
Glamping Cabin | Huge Window | Nature Lovers Dream
A red building with a covered porch, two potted plants, a grill, and a ladder.

19. Beautiful Country Sunsets I

Beautiful Country Sunsets I
Hillsboro
9.6 out of 10, Exceptional, (69 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 HK$667
HK$1,134 total
includes taxes & fees
14 Oct - 15 Oct
Beautiful Country Sunsets I
A cabin interior with a wooden dining table, chairs, a ceiling fan, a microwave, and an oven.

20. Griffis Game Hunting and/or Getaway

Griffis Game Hunting and/or Getaway
West Union
9.8 out of 10, Exceptional, (36 reviews)
"Super nice host, very clean cabin."
United States
BRAD T.
The price is HK$1,059
HK$1,732 total
includes taxes & fees
5 Oct - 6 Oct
Griffis Game Hunting and/or Getaway
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

Beverly hills inn

Beverly hills inn

8/10 Good
"This lodging was a pleasant surprise at a remarkable price! After spending a couple of nights in not-so-wonderful lodgings (even though they had an 8 rating), we had decided to take a loss and find other lodging if this was not acceptable. It was so much better and we stayed! Our room was quiet, clean and comfortable."
Pamela 1-night trip
Posted 1 day ago
Beverly hills inn

Find out more about Tollesboro

Search for holiday rentals in Tollesboro on Expedia! You can easily find your home rentals, villas, holiday apartments in Tollesboro using one of the methods below:

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Look no further and take a look at our great range of rental properties in Tollesboro!

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.