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Tollesboro Vacation Rentals

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Our top choices for Tollesboro vacation rentals

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 CA $115
CA $243 total
includes taxes & fees
Nov 13 - Nov 14
Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!

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 CA $159
CA $252 total
includes taxes & fees
Nov 13 - Nov 14
Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!

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 CA $96
CA $148 total
includes taxes & fees
Nov 3 - Nov 4
Glamping Cabin | Huge Window | Over a Creek

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 CA $96
CA $148 total
includes taxes & fees
Nov 3 - Nov 4
Glamping Cabin | Huge Window | Cliff and Animal Views

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 CA $96
CA $148 total
includes taxes & fees
Nov 16 - Nov 17
Glamping Cabin | Huge Window | Tree House Feel

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 CA $140
CA $235 total
includes taxes & fees
Nov 12 - Nov 13
Quiet Country home, Pet friendly

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 CA $94
CA $164 total
includes taxes & fees
Nov 8 - Nov 9
Charming country home on 433 acres

8. The Stockholm-Spacious 1BR with Full Kitchen

The Stockholm-Spacious 1BR with Full Kitchen
Vanceburg
The price is CA $161
CA $190 total
includes taxes & fees
Nov 3 - Nov 4
The Stockholm-Spacious 1BR with Full Kitchen

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

The Montgomery-Spacious 1BR with 2 Queen Beds
Vanceburg
The price is CA $175
CA $205 total
includes taxes & fees
Nov 3 - Nov 4
The Montgomery-Spacious 1BR with 2 Queen Beds

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 CA $140
CA $220 total
includes taxes & fees
Nov 12 - Nov 13
Lazy Lake Cabin 1! Pet Friendly

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 CA $96
CA $148 total
includes taxes & fees
Nov 3 - Nov 4
Glamping Cabin | Huge Window | Nature Lovers Dream

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 CA $304
CA $510 total
includes taxes & fees
Nov 3 - Nov 4
Peaceful cabin with spectacular river and scenic views.

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 CA $96
CA $148 total
includes taxes & fees
Nov 3 - Nov 4
Glamping Cabin | Huge Window | Valley and Cliff Views

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

Highland Hideaway - Tons of character, modern updates and art !
Flemingsburg
The price is CA $175
CA $250 total
includes taxes & fees
Nov 28 - Nov 29
Highland Hideaway - Tons of character, modern updates and art !

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 CA $105
CA $175 total
includes taxes & fees
Dec 2 - Dec 3
Beautiful country sunsets II

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 CA $189
CA $205 total
includes taxes & fees
Nov 8 - Nov 9
Sleeps 4| Private Bathroom | Stunning Views

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 CA $569
CA $856 total
includes taxes & fees
Nov 12 - Nov 13
Spacious Lodge w/ Fire Pit & Hot Tub

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 CA $154
CA $220 total
includes taxes & fees
Nov 3 - Nov 4
Secluded cabin located on 400 acres in the beautiful hills of Kentucky.

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 CA $96
CA $148 total
includes taxes & fees
Nov 3 - Nov 4
Glamping Cabin | Huge Window | Unique Boulder Views

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 CA $168
CA $265 total
includes taxes & fees
Nov 4 - Nov 5
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

Find out more about Tollesboro

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Tollesboro. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.