Tollesboro Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Tollesboro vacation rentals

A small cabin with a wooden exterior, a porch, and a visible interior with a bed and a table.

1. 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.
$96 nightly
The price is $96
Nov 15 - Nov 16
Total with taxes and fees
Glamping Cabin | Huge Window | Valley and Cliff Views
A rustic wooden structure with a wooden deck leading to a warmly lit interior, surrounded by trees.

2. Glamping Cabin | Huge Window | Over a Creek

Glamping Cabin | Huge Window | Over a Creek
Green Township
9.2 out of 10, Wonderful, (12 reviews)
"Had a great relaxing time everything was as expected."
United States
brandon b.
$96 nightly
The price is $96
Nov 15 - Nov 16
Total with taxes and fees
Glamping Cabin | Huge Window | Over a Creek
A rustic wooden structure with a wooden deck leading to a warmly lit interior, surrounded by trees.

3. 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 experience was amazing had a wonderful view and privacy I didn't have phone reception so I couldn't communicate very well. It was an adventure and we loved it so much that we are coming back to celebrate our 30th anniversary anniversary"
United States
Tonya U.
$106 nightly
The price is $106
Nov 26 - Nov 27
Total with taxes and fees
Glamping Cabin | Huge Window | Tree House Feel
A spacious room with a wooden floor, a stone fireplace, a red leather chair, a green armchair, and a grey sofa.

4. 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.
$110 nightly
The price is $117
Nov 22 - Nov 23
Total with taxes and fees
Charming country home on 433 acres
Terrace/patio

5. 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.
$157 nightly
The price is $168
Nov 23 - Nov 24
Total with taxes and fees
Quiet Country home, Pet friendly
A rustic wooden structure with a wooden deck leading to a warmly lit interior, surrounded by trees.

6. 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.
$96 nightly
The price is $96
Nov 15 - Nov 16
Total with taxes and fees
Glamping Cabin | Huge Window | Cliff and Animal Views
A small cabin with a wooden exterior, a porch, and a visible interior with a bed and a table.

7. 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.
$96 nightly
The price is $96
Nov 15 - Nov 16
Total with taxes and fees
Glamping Cabin | Huge Window | Nature Lovers Dream
An outdoor seating area with chairs and a fire pit under string lights.

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

Highland Hideaway - Tons of character, modern updates and art !
Flemingsburg
$162 nightly
The price is $179
Nov 29 - Nov 30
Total with taxes and fees
Highland Hideaway - Tons of character, modern updates and art !
A multi-level wooden staircase with a railing, connecting different floors of a building.

9. The Stockholm-Spacious 1BR with Full Kitchen

The Stockholm-Spacious 1BR with Full Kitchen
Vanceburg
$127 nightly
The price is $136
Nov 21 - Nov 22
Total with taxes and fees
The Stockholm-Spacious 1BR with Full Kitchen
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.
$147 nightly
The price is $157
Nov 23 - Nov 24
Total with taxes and fees
Lazy Lake Cabin 1! Pet Friendly
A wooden cabin with a porch and a green roof, surrounded by gravel and a wooden fence.

11. Beautiful Sunsets in the Countryside II

Beautiful Sunsets in the Countryside II
Hillsboro
10.0 out of 10, Exceptional, (31 reviews)
"Cozy. Clean and had everything we needed"
United States
Rebecca M.
$117 nightly
The price is $125
Dec 2 - Dec 3
Total with taxes and fees
Beautiful Sunsets in the Countryside II
A spacious living room with a wooden staircase, a large window, and a variety of seating including a sofa and a chair.

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

The Montgomery-Spacious 1BR with 2 Queen Beds
Vanceburg
$137 nightly
The price is $147
Nov 23 - Nov 24
Total with taxes and fees
The Montgomery-Spacious 1BR with 2 Queen Beds
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, (42 reviews)
"Very peaceful and relaxing. And VERY clean!!"
United States
Timothy
$350 nightly
The price is $365
Nov 15 - Nov 16
Total with taxes and fees
Peaceful cabin with spectacular river and scenic views.
A red building with a covered porch, two potted plants, a grill, and a ladder.

14. 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
$127 nightly
The price is $136
Dec 13 - Dec 14
Total with taxes and fees
Beautiful Country Sunsets I
A wooden covered bridge with a stone pathway leading to a small stream.

15. 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
$147 nightly
The price is $157
Nov 29 - Nov 30
Total with taxes and fees
Secluded cabin located on 400 acres in the beautiful hills of Kentucky.
A wooden covered structure with a wooden deck and stairs leading to a small cabin.

16. Glamping Cabin | Huge Window | Unique Boulder Views

Glamping Cabin | Huge Window | Unique Boulder Views
Green Township
4.0 out of 10, (1 review)
$106 nightly
The price is $106
Nov 15 - Nov 16
Total with taxes and fees
Glamping Cabin | Huge Window | Unique Boulder Views
Cabin 2

17. 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.
$147 nightly
The price is $147
Nov 15 - Nov 16
Total with taxes and fees
Sleeps 4| Private Bathroom | Stunning Views
A house with a covered porch, wooden steps, and a star decoration on the wall.

18. 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)
"Absolutely loved this property, definitely will be back!"
United States
madalyn r.
$166 nightly
The price is $183
Nov 18 - Nov 19
Total with taxes and fees
Cozy Sunset Cottage on the family farm near Cave Run Lake and Morehead State
A cabin interior with a wooden dining table, chairs, a ceiling fan, a microwave, and an oven.

19. Griffis Game Hunting and/or Getaway

Griffis Game Hunting and/or Getaway
West Union
9.8 out of 10, Exceptional, (40 reviews)
"Such a cute place!! We didn’t stay at the house enough to enjoy all of the amenities, but the cabin was very clean and cozy. The beds are really comfortable. The host was great too!"
United States
Daisha M.
$192 nightly
The price is $202
Nov 16 - Nov 17
Total with taxes and fees
Griffis Game Hunting and/or Getaway
A covered porch with stone walls, a staircase, and outdoor seating.

20. 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.
$528 nightly
The price is $565
Nov 18 - Nov 19
Total with taxes and fees
Spacious Lodge w/ Fire Pit & Hot Tub
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

A bedroom with a bed, a dresser, a vanity with a mirror, and a door leading to another room.
Moon River Bed and Breakfast

Moon River Bed and Breakfast

Moon River Bed and Breakfast
Maysville

10/10 Excellent

Denny is the host and he does a great job. I’ve stayed a couple of times for business and I plan on staying again next time.
United States
John
Reviewed November 11, 2026
Moon River Bed and Breakfast

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 $95 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.