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Tollesboro Vacation Rentals

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Check prices for these dates

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

Our top choices for Tollesboro vacation 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 ￥12,920
￥27,118 total
includes taxes & fees
Nov 15 - Nov 16
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 ￥17,962
￥28,427 total
includes taxes & fees
Nov 13 - Nov 14
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 ￥10,872
￥15,441 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥10,872
￥15,441 total
includes taxes & fees
Nov 2 - Nov 3
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
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 ￥10,872
￥16,702 total
includes taxes & fees
Nov 22 - Nov 23
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 ￥15,756
￥26,484 total
includes taxes & fees
Nov 12 - Nov 13
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 ￥10,635
￥18,472 total
includes taxes & fees
Nov 11 - Nov 12
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 ￥18,119
￥22,772 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥19,695
￥24,460 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥15,756
￥26,146 total
includes taxes & fees
Nov 12 - Nov 13
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
Green Township
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 ￥10,872
￥15,441 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥34,317
￥57,518 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥10,872
￥15,441 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥19,711
￥29,546 total
includes taxes & fees
Nov 18 - Nov 19
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.
The price is ￥11,817
￥19,736 total
includes taxes & fees
Nov 22 - Nov 23
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 ￥21,271
￥23,162 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥64,152
￥96,464 total
includes taxes & fees
Nov 11 - Nov 12
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 ￥17,332
￥24,797 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥10,872
￥16,702 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥18,907
￥30,001 total
includes taxes & fees
Nov 2 - Nov 3
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

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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Frequently asked questions

Are there vacation rentals in Tollesboro?

Yes, we give you a choice of vacation rentals close to the most popular sights in Tollesboro, or you can choose a more secluded option if you're looking for a relaxing stay.

What's the top vacation rental that Tollesboro has to offer?

Unique and secluded A frame home on 31 acres with hot tub.: This vacation home rental near Tollesboro is located on a river and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 larger area.

What are vacation rentals like in Tollesboro?

Vacation rentals are privately owned accommodations you can stay in for a few days or a quick weekend in Tollesboro. Vacation rentals feature extras such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for families.