Default HTG hotel image

Tollesboro Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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
$176 nightly
The price is $180
Oct 20 - Oct 21
Total with taxes and fees
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
$175 nightly
The price is $180
Oct 20 - Oct 21
Total with taxes and fees
Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!
A spacious room with a wooden floor, a stone fireplace, a red leather chair, a green armchair, and a grey sofa.

3. 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.
$118 nightly
The price is $126
Oct 21 - Oct 22
Total with taxes and fees
Charming country home on 433 acres
Terrace/patio

4. 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.
$165 nightly
The price is $177
Oct 20 - Oct 21
Total with taxes and fees
Quiet Country home, Pet friendly
A gravel driveway leading to a rustic building with a red roof, surrounded by a pond and trees.

5. 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.
$140 nightly
The price is $150
Oct 22 - Oct 23
Total with taxes and fees
Lazy Lake Cabin 2!!! Pet Friendly!!
A red building with a covered porch, two potted plants, a grill, and a ladder.

6. 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
$135 nightly
The price is $145
Oct 20 - Oct 21
Total with taxes and fees
Beautiful Country Sunsets I
A two-chair setup outside a house with a window, a small table, and a concrete floor.

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

Highland Hideaway - Tons of character, modern updates and art !
Flemingsburg
$170 nightly
The price is $188
Nov 4 - Nov 5
Total with taxes and fees
Highland Hideaway - Tons of character, modern updates and art !
An outdoor seating area with chairs and a fire pit, surrounded by a grassy field and a view of a forested hill.

8. The Stockholm-Spacious 1BR with Full Kitchen

The Stockholm-Spacious 1BR with Full Kitchen
Vanceburg
$135 nightly
The price is $145
Oct 21 - Oct 22
Total with taxes and fees
The Stockholm-Spacious 1BR with Full Kitchen
A wooden covered bridge with a stone pathway leading to a small stream.

9. 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
$150 nightly
The price is $161
Oct 21 - Oct 22
Total with taxes and fees
Secluded cabin located on 400 acres in the beautiful hills of Kentucky.
Cabin 2

10. 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.
$155 nightly
The price is $155
Oct 20 - Oct 21
Total with taxes and fees
Sleeps 4| Private Bathroom | Stunning Views
A two-story brick building with a central entrance flanked by columns, a front lawn, and trees in the background.

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

The Montgomery-Spacious 1BR with 2 Queen Beds
Vanceburg
$145 nightly
The price is $155
Oct 21 - Oct 22
Total with taxes and fees
The Montgomery-Spacious 1BR with 2 Queen Beds
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, (48 reviews)
"Very clean, and had everything we needed in the kitchen. Very cozy. Exactly what we were looking for."
United States
Debra
$182 nightly
The price is $200
Oct 20 - Oct 21
Total with taxes and fees
Cozy Sunset Cottage on the family farm near Cave Run Lake and Morehead State
A wooden deck with string lights, a covered seating area, and a view of a town at dusk.

13. 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
$368 nightly
The price is $383
Oct 20 - Oct 21
Total with taxes and fees
Peaceful cabin with spectacular river and scenic views.
A wooden deck with a round table and two chairs, a window, and a wooden wall.

14. 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.
$155 nightly
The price is $166
Oct 21 - Oct 22
Total with taxes and fees
Lazy Lake Cabin 1! Pet Friendly
A covered porch with stone walls, a staircase, and outdoor seating.

15. 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.
$556 nightly
The price is $595
Oct 20 - Oct 21
Total with taxes and fees
Spacious Lodge w/ Fire Pit & Hot Tub
A cabin interior with a wooden dining table, chairs, a ceiling fan, a microwave, and an oven.

16. 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.
$209 nightly
The price is $219
Oct 26 - Oct 27
Total with taxes and fees
Griffis Game Hunting and/or Getaway
Porch Swing

17. Private Hot Tub Cabin Bordering Shawnee State Forest | Fire Pt | Starlink

Private Hot Tub Cabin Bordering Shawnee State Forest | Fire Pt | Starlink
Blue Creek
9.8 out of 10, Exceptional, (17 reviews)
"Over all, a nice little get away "
United States
jonathan
$312 nightly
The price is $332
Oct 20 - Oct 21
Total with taxes and fees
Private Hot Tub Cabin Bordering Shawnee State Forest | Fire Pt | Starlink
A wooden cabin with a porch and a green roof, surrounded by gravel and a wooden fence.

18. 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.
$125 nightly
The price is $134
Oct 20 - Oct 21
Total with taxes and fees
Beautiful country sunsets II
A modern kitchen with white cabinets, a black refrigerator, and a wooden dining table with chairs.

19. 3-bedroom house in charming Morehead near Cave Run and Morehead State

3-bedroom house in charming Morehead near Cave Run and Morehead State
Morehead
10.0 out of 10, Exceptional, (4 reviews)
"It was clean and just as described. Perfect location for us visiting a child at Morehead State. We will be booking again!!"
United States
Stacy T.
$328 nightly
The price is $361
Nov 17 - Nov 18
Total with taxes and fees
3-bedroom house in charming Morehead near Cave Run and Morehead State
A log cabin interior with a wooden staircase, a kitchen area, and seating.

20. Kentucky Cabin Getaway w/ Loft Sleeping

Kentucky Cabin Getaway w/ Loft Sleeping
Mayslick
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful remote cabin with all the amenities of home. Every detail was planned out and perfect. We absolutely loved it."
United States
Diane L.
$419 nightly
The price is $463
Oct 20 - Oct 21
Total with taxes and fees
Kentucky Cabin Getaway w/ Loft Sleeping
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Tollesboro Hotel Reviews

Peaceful cabin with spectacular river and scenic views.

Peaceful cabin with spectacular river and scenic views.

10/10 Excellent
"AWESOME"
Adam M. 2-night trip
Posted 10 hours ago
Peaceful cabin with spectacular river and scenic views.

Find out more about Tollesboro

Everything you need to know about Tollesboro vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Tollesboro vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Tollesboro vacation 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 low season months. For more hustle and bustle, you may prefer to visit Tollesboro in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $145 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Tollesboro rentals

At Expedia, we put the best Tollesboro vacation 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 vacation.

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 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.