Tollesboro Holiday Rentals from NZ$193: Search Short-Term Rentals

Q: 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.

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Our top choices for Tollesboro holiday rentals

A wooden cabin interior with a sofa, a television, and a sliding barn door.

1. Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!

Stout

Kenneth

includes taxes & fees

4 Sept - 5 Sept

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

2. Glamping Cabin | Huge Window | Nature Lovers Dream

Stout

Abby M.

includes taxes & fees

6 Sept - 7 Sept

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

Blue Creek

"The property is very remote, secluded and quiet. It is a pet friendly property that our dog very much enjoyed. For hikers this is a great location. We were very unlucky with the weather, so no fire pit or BBQing due to torrential rain (no one can control that). Amenities are solid. It is glamping. There is a gas station approx. 10 minutes away that serves some solid breakfast…Portsmouth is about 45 minutes away for some dinner options."

Stuart

includes taxes & fees

6 Sept - 7 Sept

4. Glamping Cabin | Huge Window | Over a Creek

Green Township

Kristen W.

includes taxes & fees

6 Sept - 7 Sept

A spacious room with a wooden floor, a stone fireplace, a red leather chair, a green armchair, and a grey sofa.

5. Charming country home on 433 acres

wallingford

Maria B.

includes taxes & fees

16 Sept - 17 Sept

6. Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!

Rome

includes taxes & fees

5 Sept - 6 Sept

7. Quiet Country home, Pet friendly

Wallingford

Julie G.

includes taxes & fees

21 Sept - 22 Sept

A gravel driveway leading to a rustic building with a red roof, surrounded by a pond and trees.

8. Lazy Lake Cabin 2!!! Pet Friendly!!

Flemingsburg

Frederick L.

includes taxes & fees

16 Sept - 17 Sept

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Top Tollesboro Hotel Reviews

Super 8 by Wyndham Maysville KY

8/10 Good

"The rooms seem to have been refreshed, which was nice. The hotel was good & it was a good value."

Moon River Bed and Breakfast

10/10 Excellent

"We had a wonderful stay at Moon River Bed & Breakfast Inn in Maysville this July and couldn’t have been happier with the experience. The inn is beautiful, warm, and full of character—the kind of place that feels like part of the experience rather than simply somewhere to sleep. The hospitality was exceptional. We felt genuinely welcomed and well cared for throughout our stay, and the attention to detail made everything comfortable and relaxing. The location was also perfect for enjoying Maysville and the surrounding area. We travel to Maysville regularly, and Moon River was such a refreshing change from the typical hotel experience. It has the charm and personal touches that make you look forward to coming back at the end of the day. We thoroughly enjoyed our stay and would absolutely return. If you’re visiting Maysville and want somewhere memorable, comfortable, and welcoming, Moon River Bed & Breakfast Inn is an easy recommendation. Five stars!"

Secluded cabin located on 400 acres in the beautiful hills of Kentucky.

10/10 Excellent

"Communication was excellent. Darcy had contacted me a few hours before check-in letting me know that the refrigerator wasn’t keeping cold and they were having a new one delivered and just wanted to make sure that it was delivered basically before I had arrived. By the time we got there, it had been delivered and was hooked up and cold. Absolutely beautiful property. That nighttime sky and the stars are unforgettable."

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$193 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.

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Check prices for these dates

Our top choices for Tollesboro holiday rentals

1. Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!

2. Glamping Cabin | Huge Window | Nature Lovers Dream

3. Glamping Cabin | Huge Window | Tree House Feel

4. Glamping Cabin | Huge Window | Over a Creek

5. Charming country home on 433 acres

6. Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!

7. Quiet Country home, Pet friendly

8. Lazy Lake Cabin 2!!! Pet Friendly!!

9. Peaceful cabin with spectacular river and scenic views.

10. Cozy 1-bedroom apartment in charming Maysville - Apt B

11. Beautiful Country Sunsets I

12. Glamping Cabin | Huge Window | Valley and Cliff Views

13. Sleeps 4| Private Bathroom | Stunning Views

14. Glamping Cabin | Huge Window | Cliff and Animal Views

15. Griffis Game Hunting and/or Getaway

16. Cozy Sunset Cottage on the family farm near Cave Run Lake and Morehead State

17. Secluded cabin located on 400 acres in the beautiful hills of Kentucky.

18. Lazy Lake Cabin 1! Pet Friendly

19. Sleeps 12| Private Bathroom | Stunning Views

20. Shawnee Forest Cabin · Hot Tub · Fire Pit · Creek

Find holiday rentals that suit your style

Top Tollesboro Hotel Reviews

Super 8 by Wyndham Maysville KY

Peaceful cabin with spectacular river and scenic views.

French Quarter Inn

Moon River Bed and Breakfast

Beverly hills inn

Secluded cabin located in Amish country

Secluded cabin located on 400 acres in the beautiful hills of Kentucky.

Glamping Cabin | Huge Window | Over a Creek

Griffis Game Hunting and/or Getaway

Find out more about Tollesboro

Frequently asked questions

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