Tollesboro Holiday Rentals

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Our top choices for Tollesboro holiday rentals

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
9.6 out of 10, Exceptional, (17 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 NZ$275
includes taxes & fees
15 Apr - 16 Apr
Secluded cabin located on 500 acres in the beautiful hills of Kentucky.

Shawnee Cabin Retreat | Hot Tub + Fire Pit

Shawnee Cabin Retreat | Hot Tub + Fire Pit
Blue Creek
9.6 out of 10, Exceptional, (10 reviews)
"Nice cabin nice area. Had fun hunting "
United States
Matthew C.
The price is NZ$479
includes taxes & fees
15 Apr - 16 Apr
Shawnee Cabin Retreat | Hot Tub + Fire Pit

Riverview Getaway

Riverview Getaway
Vanceburg
10.0 out of 10, Exceptional, (13 reviews)
"Great Place"
United States
Chip B.
The price is NZ$229
includes taxes & fees
14 Apr - 15 Apr
Riverview Getaway

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.
The price is NZ$195
includes taxes & fees
16 Apr - 17 Apr
Glamping Cabin | Huge Window | Over a Creek

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, (38 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.
The price is NZ$330
includes taxes & fees
14 Apr - 15 Apr
Cozy Sunset Cottage on the family farm near Cave Run Lake and Morehead State

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 NZ$195
includes taxes & fees
15 Apr - 16 Apr
Glamping Cabin | Huge Window | Cliff and Animal Views

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.
The price is NZ$608
includes taxes & fees
15 Apr - 16 Apr
Peaceful cabin with spectacular river and scenic views.

Sleeps 4| Private Bathroom | Stunning Views

Sleeps 4| Private Bathroom | Stunning Views
Green Township
7.0 out of 10, Good, (4 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 NZ$266
includes taxes & fees
14 Apr - 15 Apr
Sleeps 4| Private Bathroom | Stunning Views

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 NZ$229
includes taxes & fees
10 May - 11 May
Beautiful country sunsets II

Bear Necessities Cabin - What Else Do You Need?

Bear Necessities Cabin - What Else Do You Need?
West Union
9.8 out of 10, Exceptional, (10 reviews)
"Very clean cabin and very cozy!"
United States
Debbie F.
The price is NZ$279
includes taxes & fees
14 Apr - 15 Apr
Bear Necessities Cabin - What Else Do You Need?

Glamping Cabin | Huge Window | Tree House Feel

Glamping Cabin | Huge Window | Tree House Feel
Blue Creek
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
The price is NZ$195
includes taxes & fees
14 Apr - 15 Apr
Glamping Cabin | Huge Window | Tree House Feel

Griffis Game Hunting and/or Getaway

Griffis Game Hunting and/or Getaway
West Union
9.8 out of 10, Exceptional, (31 reviews)
"Very cozy cabin. Quality family time."
United States
cindy S.
The price is NZ$373
includes taxes & fees
14 Apr - 15 Apr
Griffis Game Hunting and/or Getaway

Sleeps 12| Private Bathroom | Stunning Views

Sleeps 12| Private Bathroom | Stunning Views
Blue Creek
10.0 out of 10, Exceptional, (7 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 NZ$528
includes taxes & fees
14 Apr - 15 Apr
Sleeps 12| Private Bathroom | Stunning Views

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 NZ$303
includes taxes & fees
11 May - 12 May
Quiet Country home, Pet friendly

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.
The price is NZ$284
includes taxes & fees
14 Apr - 15 Apr
Lazy Lake Cabin 1! Pet Friendly

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.
The price is NZ$620
includes taxes & fees
8 May - 9 May
Hickory Ridge Cabin | 3 Bed, 2 Bath

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.
The price is NZ$386
includes taxes & fees
14 Apr - 15 Apr
Spacious 3-bedroom apartment with WiFi, AC in charming Ripley

Glamping Cabin | Huge Window | Valley and Cliff Views

Glamping Cabin | Huge Window | Valley and Cliff Views
Green Township
10.0 out of 10, Exceptional, (3 reviews)
"Property owners were very welcoming. The tree house and property were well maintained. "
United States
Marci
The price is NZ$195
includes taxes & fees
14 Apr - 15 Apr
Glamping Cabin | Huge Window | Valley and Cliff Views

Glamping Cabin | Huge Window | Nature Lovers Dream

Glamping Cabin | Huge Window | Nature Lovers Dream
Stout
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 NZ$195
includes taxes & fees
19 Apr - 20 Apr
Glamping Cabin | Huge Window | Nature Lovers Dream

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 NZ$216
includes taxes & fees
23 Apr - 24 Apr
Charming country home on 433 acres
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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Find out more about Tollesboro

Everything you need to know about Tollesboro holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Tollesboro holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Tollesboro holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Tollesboro holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Tollesboro holiday rentals we have selected for you start as low as NZ$195 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Tollesboro rentals

At Expedia, we put the best Tollesboro holiday 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 holiday.

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 holiday rentals in Tollesboro?

Yes, there are holiday rentals close to the most popular sights in Tollesboro, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Tollesboro has to offer?

Unique and secluded A frame home on 31 acres with hot tub.: This holiday home rental outside of Tollesboro is located on a river, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 wider area.

What are holiday rentals like in Tollesboro?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Tollesboro. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for a small group gathering.