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Tollesboro Vacation Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sep - 13 Sep
In four months
9 Oct - 11 Oct

Our top choices for Tollesboro vacation rentals

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)
"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 AED 253
AED 419 total
includes taxes & fees
24 Jun - 25 Jun
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.
The price is AED 253
AED 419 total
includes taxes & fees
28 Jun - 29 Jun
Glamping Cabin | Huge Window | Cliff and Animal Views
House (1 Bedroom) | Interior

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 AED 338
AED 658 total
includes taxes & fees
22 Jun - 23 Jun
Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!
Terrace/patio

Sleeps 4| Private Bathroom | Stunning Views

Sleeps 4| Private Bathroom | Stunning Views
Green Township
7.2 out of 10, Good, (5 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 AED 496
AED 569 total
includes taxes & fees
23 Jun - 24 Jun
Sleeps 4| Private Bathroom | Stunning Views
Terrace/patio

Beautiful Country Sunsets I

Beautiful Country Sunsets I
Hillsboro
9.6 out of 10, Exceptional, (68 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
The price is AED 312
AED 531 total
includes taxes & fees
23 Jun - 24 Jun
Beautiful Country Sunsets I
TV

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, (8 reviews)
"Very peaceful, amazing veiw perfect getaway will definitely stay again. "
United States
Kenneth
The price is AED 301
AED 662 total
includes taxes & fees
22 Jun - 23 Jun
Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!
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, (12 reviews)
"Great little spot! Cabin is super nice inside and out."
United States
Jason M.
The price is AED 344
AED 626 total
includes taxes & fees
29 Jun - 30 Jun
Bear Necessities Cabin - What Else Do You Need?
Property grounds

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
9.4 out of 10, Exceptional, (20 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.
The price is AED 422
AED 610 total
includes taxes & fees
6 Jul - 7 Jul
Secluded cabin located on 400 acres in the beautiful hills of Kentucky.
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.
The price is AED 496
AED 789 total
includes taxes & fees
23 Jun - 24 Jun
Griffis Game Hunting and/or Getaway
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, (41 reviews)
"Great place to stay, updated and clean"
United States
Ty R.
The price is AED 441
AED 720 total
includes taxes & fees
7 Jul - 8 Jul
Cozy Sunset Cottage on the family farm near Cave Run Lake and Morehead State
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, (33 reviews)
"Great location. "
United States
John S.
The price is AED 889
AED 1,517 total
includes taxes & fees
30 Jun - 1 Jul
Peaceful cabin with spectacular river and scenic views.
Exterior

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.
The price is AED 275
AED 551 total
includes taxes & fees
23 Jun - 24 Jun
Lazy Lake Cabin 2!!! Pet Friendly!!
Terrace/patio

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 AED 367
AED 649 total
includes taxes & fees
22 Jun - 23 Jun
Quiet Country home, Pet friendly
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.
The price is AED 275
AED 492 total
includes taxes & fees
16 Jul - 17 Jul
Charming country home on 433 acres
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.
The price is AED 253
AED 419 total
includes taxes & fees
24 Jun - 25 Jun
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, (8 reviews)
"Neat house for a group with kids! The bunk house with the trap door was a blast for them. "
United States
Matt S.
The price is AED 918
AED 1,153 total
includes taxes & fees
29 Jun - 30 Jun
Sleeps 12| Private Bathroom | Stunning Views
Interior

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 AED 253
AED 419 total
includes taxes & fees
22 Jun - 23 Jun
Glamping Cabin | Huge Window | Unique Boulder Views
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, (5 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.
The price is AED 608
AED 840 total
includes taxes & fees
22 Jun - 23 Jun
Spacious 3-bedroom apartment with WiFi, AC in charming Ripley
Outdoor dining

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 AED 367
AED 610 total
includes taxes & fees
22 Jun - 23 Jun
Lazy Lake Cabin 1! Pet Friendly
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

8/10 Good
"This property is exactly what one would expect for the price. No frills. The morning breakfast was nice as was the coffee."
douglas 1-night trip
Posted 9 hours ago
Super 8 by Wyndham Maysville KY

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. Laurel Oaks Golf Club and Adams Lake State Park 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.