Tollesboro Vacation Rentals

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Nov 28 - Nov 29
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Nov 29 - Nov 30
This weekend
Nov 28 - Nov 30
Next weekend
Dec 5 - Dec 7

Vacation Rentals in Tollesboro

Exterior
Glamping Cabin | Huge Window | Cliff and Animal Views

Glamping Cabin | Huge Window | Cliff and Animal Views

Green Township
10.0 out of 10, Exceptional, (1)
"We had a lovely time at this cabin -- I stayed with my sweetheart and our doberman puppy, and the place was quiet, rustic, beautiful. I would be happy to come back here again. Our dog met goats for the first time! That was hilarious and unexpected. There's a beautiful horse on the property, and we had a nice time giving him scritches on the neck. The price was lovely for the accommodation, and the huge window looking out on the wooded cliff was a wonderful bonus. Thank you!"
United States
Olga
$114 nightly
The price is $114
Dec 2 - Dec 3
Total with taxes and fees
Glamping Cabin | Huge Window | Cliff and Animal Views
Fridge, microwave, stovetop, coffee/tea maker
Bear Necessities Cabin - What Else Do You Need?

Bear Necessities Cabin - What Else Do You Need?

West Union
10.0 out of 10, Exceptional, (7)
"Great little spot! Cabin is super nice inside and out."
United States
Jason M.
$155 nightly
The price is $161
Dec 5 - Dec 6
Total with taxes and fees
Bear Necessities Cabin - What Else Do You Need?
Fridge, stovetop, toaster, cookware/dishes/utensils
Sleeps 4| Private Bathroom | Stunning Views

Sleeps 4| Private Bathroom | Stunning Views

Green Township
10.0 out of 10, Exceptional, (1)
$155 nightly
The price is $155
Dec 1 - Dec 2
Total with taxes and fees
Sleeps 4| Private Bathroom | Stunning Views
Fridge, microwave, coffee/tea maker, toaster
Riverview Getaway

Riverview Getaway

Vanceburg
10.0 out of 10, Exceptional, (11)
"Such a cute little town. Place is right next to a bar and the lake. Really nice spot and really clean"
Canada
Emma
$125 nightly
The price is $134
Nov 30 - Dec 1
Total with taxes and fees
Riverview Getaway
Interior
Beautiful Country Sunsets I

Beautiful Country Sunsets I

Hillsboro
9.8 out of 10, Exceptional, (67)
"Beautiful country setting with amazing views. Just perfect. "
United States
Eli S.
$135 nightly
The price is $145
Dec 1 - Dec 2
Total with taxes and fees
Beautiful Country Sunsets I
Property grounds
Glamping Cabin | Huge Window | Over a Creek

Glamping Cabin | Huge Window | Over a Creek

Green Township
9.8 out of 10, Exceptional, (7)
"Beautiful location ."
United States
Shelly R.
$114 nightly
The price is $114
Dec 7 - Dec 8
Total with taxes and fees
Glamping Cabin | Huge Window | Over a Creek
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)
"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
Nov 30 - Dec 1
Total with taxes and fees
Glamping Cabin | Huge Window | Tree House Feel
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, (15)
"Great getaway from city life. Darcy was a great host."
United States
Alexander S.
$150 nightly
The price is $161
Nov 30 - Dec 1
Total with taxes and fees
Secluded cabin located on 500 acres in the beautiful hills of Kentucky.
Property grounds
Charming country home on 433 acres

Charming country home on 433 acres

wallingford
10.0 out of 10, Exceptional, (2)
"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
Nov 30 - Dec 1
Total with taxes and fees
Charming country home on 433 acres
Fridge, microwave, oven, stovetop
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, (32)
"Love the relaxed atmosphere "
United States
Darlene A.
$160 nightly
The price is $171
Dec 3 - Dec 4
Total with taxes and fees
Cozy Sunset Cottage on the family farm near Cave Run Lake and Morehead State
1 bedroom, WiFi
Home away from Home! - 1BR apartment in Maysville

Home away from Home! - 1BR apartment in Maysville

Maysville
10.0 out of 10, Exceptional, (13)
"Amazing stay. We would definitely recommend this place to anyone!"
United States
John H.
$105 nightly
The price is $107
Dec 13 - Dec 14
Total with taxes and fees
Home away from Home! - 1BR apartment in Maysville
Exterior
Griffis Game Hunting and/or Getaway

Griffis Game Hunting and/or Getaway

West Union
9.8 out of 10, Exceptional, (27)
"Awesome cabin. Super clean and fun!"
United States
Phillip M.
$212 nightly
The price is $222
Dec 3 - Dec 4
Total with taxes and fees
Griffis Game Hunting and/or Getaway
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, (27)
"This property is very secluded for those who need a getaway from the hustle and bustle. Beautiful views."
United States
Michelle S.
$348 nightly
The price is $363
Nov 30 - Dec 1
Total with taxes and fees
Peaceful cabin with spectacular river and scenic views.
Exterior
Glamping Cabin | Huge Window | Valley and Cliff Views

Glamping Cabin | Huge Window | Valley and Cliff Views

Green Township
10.0 out of 10, Exceptional, (2)
"Property owners were very welcoming. The tree house and property were well maintained. "
United States
Marci
$114 nightly
The price is $114
Nov 30 - Dec 1
Total with taxes and fees
Glamping Cabin | Huge Window | Valley and Cliff Views
Exterior
Glamping Cabin | Huge Window | Nature Lovers Dream

Glamping Cabin | Huge Window | Nature Lovers Dream

Green Township
9.8 out of 10, Exceptional, (9)
"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
Dec 1 - Dec 2
Total with taxes and fees
Glamping Cabin | Huge Window | Nature Lovers Dream
Property grounds
Sleeps 12| Private Bathroom | Stunning Views

Sleeps 12| Private Bathroom | Stunning Views

Blue Creek
10.0 out of 10, Exceptional, (6)
"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
Dec 1 - Dec 2
Total with taxes and fees
Sleeps 12| Private Bathroom | Stunning Views
Fridge, microwave, oven, stovetop
Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA!

Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA!

Dover
9.6 out of 10, Exceptional, (8)
"This was a great stay. Very easy to find and in a good area. Very clean and nice. "
United States
Amanda R.
$230 nightly
The price is $246
Nov 30 - Dec 1
Total with taxes and fees
Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA!
Smart TV
Spacious 3-bedroom apartment with WiFi, AC in charming Ripley

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

Ripley
9.4 out of 10, Exceptional, (3)
"Perfect location for my pilgrimage visit to John Rankin’s home. Incredibly spacious, historic flat. "
United States
Kathy M.
$230 nightly
The price is $230
Nov 30 - Dec 1
Total with taxes and fees
Spacious 3-bedroom apartment with WiFi, AC in charming Ripley
Interior
Glamping Cabin | Huge Window | Unique Boulder Views

Glamping Cabin | Huge Window | Unique Boulder Views

Green Township
4.0 out of 10, (1)
$114 nightly
The price is $114
Nov 30 - Dec 1
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.
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Top Tollesboro Hotel Reviews

Super 8 by Wyndham Maysville KY

Super 8 by Wyndham Maysville KY

10/10 Excellent
"Staff was nice "
Guy 1-night trip
Posted 5 days ago
Super 8 by Wyndham Maysville KY

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?

Riverview Getaway: This vacation home rental near Tollesboro has air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and a coffee maker.

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.