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
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 5

Our top choices for Tollesboro vacation rentals

Property grounds

Secluded cabin located on 500 acres in the beautiful hills of Kentucky.

Secluded cabin located on 500 acres in the beautiful hills of Kentucky.
Garrison
9.4 out of 10, Exceptional, (16 reviews)
"Friendly host, beautiful setting, everything we needed for a nice weekend. We definitely will be returning was very excited to see they have camper hook ups."
United States
Chad R.
$150 nightly
The price is $161
Mar 10 - Mar 11
Total with taxes and fees
Secluded cabin located on 500 acres in the beautiful hills of Kentucky.
Terrace/patio

Quiet Forest Cabin w/ Hot Tub Near Shawnee

Quiet Forest Cabin w/ Hot Tub Near Shawnee
Blue Creek
9.8 out of 10, Exceptional, (9 reviews)
"Nice cabin nice area. Had fun hunting "
United States
Matthew C.
$296 nightly
The price is $307
Mar 10 - Mar 11
Total with taxes and fees
Quiet Forest Cabin w/ Hot Tub Near Shawnee
1 bedroom, travel crib, WiFi, bed sheets

Riverview Getaway

Riverview Getaway
Vanceburg
10.0 out of 10, Exceptional, (13 reviews)
"Very nice little Vrbo. "
United States
Rebecca S.
$125 nightly
The price is $134
Mar 10 - Mar 11
Total with taxes and fees
Riverview Getaway
Terrace/patio

Sleeps 4| Private Bathroom | Stunning Views

Sleeps 4| Private Bathroom | Stunning Views
Green Township
6.8 out of 10, (3 reviews)
"Yes, it would have been perfect for leashed pets. Cabin was very cozy and fit our needs well. One thing we did notice that would've been great if they had some bowls for mixing pancakes and such. "
United States
Dane C.
$155 nightly
The price is $155
Mar 10 - Mar 11
Total with taxes and fees
Sleeps 4| Private Bathroom | Stunning Views
Terrace/patio

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, (37 reviews)
"The cutest little place!! Perfect place for us and our hostess was fantastic. If we are ever back in this neck of the woods we will definitely stay here again!"
United States
Jennifer W.
$180 nightly
The price is $193
Mar 10 - Mar 11
Total with taxes and fees
Cozy Sunset Cottage on the family farm near Cave Run Lake and Morehead State
Property grounds

Glamping Cabin | Huge Window | Over a Creek

Glamping Cabin | Huge Window | Over a Creek
Green Township
9.8 out of 10, Exceptional, (8 reviews)
"Loved watching the storm through the big window and listening to the rain on the roof. "
United States
Crystal A.
$114 nightly
The price is $114
Mar 11 - Mar 12
Total with taxes and fees
Glamping Cabin | Huge Window | Over a Creek
Property grounds

Glamping Cabin | Huge Window | Cliff and Animal Views

Glamping Cabin | Huge Window | Cliff and Animal Views
Green Township
10.0 out of 10, Exceptional, (2 reviews)
"We had a great stay, we loved the horse and goats. It was peaceful and beautiful, exactly what we needed! Will definitely stay again! "
United States
Callie J.
$114 nightly
The price is $114
Mar 10 - Mar 11
Total with taxes and fees
Glamping Cabin | Huge Window | Cliff and Animal Views
Property grounds

Sleeps 12| Private Bathroom | Stunning Views

Sleeps 12| Private Bathroom | Stunning Views
Blue Creek
10.0 out of 10, Exceptional, (7 reviews)
"This cabin was exactly what we were looking for: Cozy, peaceful, clean, comfortable and all the amenities. Located near several great hiking spots within a short drive. Great indoor and outdoor space. Host was very friendly and responsive. Highly recommend this place!"
United States
Amy H.
$315 nightly
The price is $315
Mar 10 - Mar 11
Total with taxes and fees
Sleeps 12| Private Bathroom | Stunning Views
Living area

Hickory Ridge Cabin | 3 Bed, 2 Bath

Hickory Ridge Cabin | 3 Bed, 2 Bath
Ewing
9.6 out of 10, Exceptional, (8 reviews)
"Overall had a wonderful time. Hard to keep all the kids occupied since they're is no TV or internet, but over all had a fantastic time."
United States
Tambria F.
$343 nightly
The price is $365
Mar 13 - Mar 14
Total with taxes and fees
Hickory Ridge Cabin | 3 Bed, 2 Bath
Interior

Bear Necessities Cabin - What Else Do You Need?

Bear Necessities Cabin - What Else Do You Need?
West Union
10.0 out of 10, Exceptional, (9 reviews)
"Very clean cabin and very cozy!"
United States
Debbie F.
$147 nightly
The price is $152
Mar 10 - Mar 11
Total with taxes and fees
Bear Necessities Cabin - What Else Do You Need?
Outdoor dining

Lazy Lake Cabin 1! Pet Friendly

Lazy Lake Cabin 1! Pet Friendly
Flemingsburg
10.0 out of 10, Exceptional, (1 review)
"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
Mar 10 - Mar 11
Total with taxes and fees
Lazy Lake Cabin 1! Pet Friendly
Terrace/patio

Peaceful cabin with spectacular river and scenic views.

Peaceful cabin with spectacular river and scenic views.
Adams County
9.8 out of 10, Exceptional, (29 reviews)
"Great location. "
United States
John S.
$315 nightly
The price is $328
Mar 10 - Mar 11
Total with taxes and fees
Peaceful cabin with spectacular river and scenic views.
Property grounds

Glamping Cabin | Huge Window | Tree House Feel

Glamping Cabin | Huge Window | Tree House Feel
Green Township
9.0 out of 10, Wonderful, (19 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
$114 nightly
The price is $114
Mar 10 - Mar 11
Total with taxes and fees
Glamping Cabin | Huge Window | Tree House Feel
Fridge, microwave, oven, stovetop

Griffis Game Hunting and/or Getaway

Griffis Game Hunting and/or Getaway
West Union
9.8 out of 10, Exceptional, (31 reviews)
"Super nice host, very clean cabin."
United States
BRAD T.
$212 nightly
The price is $222
Mar 16 - Mar 17
Total with taxes and fees
Griffis Game Hunting and/or Getaway
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Spacious 3-bedroom apartment with WiFi, AC in charming Ripley

Spacious 3-bedroom apartment with WiFi, AC in charming Ripley
Ripley
9.6 out of 10, Exceptional, (4 reviews)
"Nicely decorated property. This was perfect for our family and we’d definitely stay hear again when in Ripley. "
United States
John and Chris S.
$230 nightly
The price is $230
Mar 10 - Mar 11
Total with taxes and fees
Spacious 3-bedroom apartment with WiFi, AC in charming Ripley
Exterior

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.
$114 nightly
The price is $114
Mar 10 - Mar 11
Total with taxes and fees
Glamping Cabin | Huge Window | Nature Lovers Dream
Interior

Charming country home on 433 acres

Charming country home on 433 acres
wallingford
5.6 out of 10, (5 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
Mar 10 - Mar 11
Total with taxes and fees
Charming country home on 433 acres
Interior

Glamping Cabin | Huge Window | Unique Boulder Views

Glamping Cabin | Huge Window | Unique Boulder Views
Green Township
4.0 out of 10, (1 review)
$114 nightly
The price is $114
Mar 10 - Mar 11
Total with taxes and fees
Glamping Cabin | Huge Window | Unique Boulder Views
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

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now
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

Quality Inn Maysville

Quality Inn Maysville

6/10 Okay
"There was no hot tub or pool available. "
Paula 2-night trip
Posted 12 hours ago
Quality Inn Maysville

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 $114 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.

Explore a world of travel with Expedia

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 Kenton Station Golf Course 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.