Tollesboro Vacation Rentals

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Check prices for these dates

In two weeks
Feb 13 - Feb 15
In two months
Mar 27 - Mar 29
In three months
Apr 24 - Apr 26
In four months
May 22 - May 24

Our top choices for Tollesboro vacation rentals

Property grounds

Cabin in Garrison

Secluded cabin located on 500 acres in the beautiful hills of Kentucky.
9.4 out of 10, Exceptional, (16 reviews)
"Gorgeous property, great location, good communication. "
United States
Holly K.
The price is ￥16,779
￥24,496 total
includes taxes & fees
Feb 2 - Feb 3
Secluded cabin located on 500 acres in the beautiful hills of Kentucky.
1 bedroom, travel crib, WiFi, bed sheets

Vacation Home in Vanceburg

Riverview Getaway
10.0 out of 10, Exceptional, (12 reviews)
"Very nice little Vrbo. "
United States
Rebecca S.
The price is ￥9,915
￥20,413 total
includes taxes & fees
Feb 3 - Feb 4
Riverview Getaway
Interior

Cabin in West Union

Bear Necessities Cabin - What Else Do You Need?
10.0 out of 10, Exceptional, (9 reviews)
"Very clean cabin and very cozy!"
United States
Debbie F.
The price is ￥12,966
￥24,583 total
includes taxes & fees
Feb 4 - Feb 5
Bear Necessities Cabin - What Else Do You Need?
Property grounds

Cabin in Green Township

Glamping Cabin | Huge Window | Cliff and Animal Views
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 ￥10,525
￥17,389 total
includes taxes & fees
Feb 4 - Feb 5
Glamping Cabin | Huge Window | Cliff and Animal Views
Property grounds

Cabin in Green Township

Glamping Cabin | Huge Window | Over a Creek
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 ￥10,525
￥17,389 total
includes taxes & fees
Feb 4 - Feb 5
Glamping Cabin | Huge Window | Over a Creek
Terrace/patio

Cabin in Hillsboro

Beautiful Country Sunsets I
9.8 out of 10, Exceptional, (67 reviews)
"Beautiful country setting with amazing views. Just perfect. "
United States
Eli S.
The price is ￥12,966
￥22,047 total
includes taxes & fees
Feb 18 - Feb 19
Beautiful Country Sunsets I
Terrace/patio

Mobile Home in Morehead

Cozy Sunset Cottage on the family farm near Cave Run Lake and Morehead State
10.0 out of 10, Exceptional, (34 reviews)
"Clean, comfortable, great location, generous & thoughtful “extras” included."
United States
Carole W.
The price is ￥18,305
￥29,396 total
includes taxes & fees
Jan 29 - Jan 30
Cozy Sunset Cottage on the family farm near Cave Run Lake and Morehead State
Terrace/patio

Cabin in Blue Creek

Little Smokies Escape •HotTub •Shawnee State Park/Forest
9.8 out of 10, Exceptional, (9 reviews)
"Over all, a nice little get away "
United States
jonathan
The price is ￥23,491
￥45,788 total
includes taxes & fees
Feb 23 - Feb 24
Little Smokies Escape •HotTub •Shawnee State Park/Forest
Property grounds

Cabin in Green Township

Glamping Cabin | Huge Window | Tree House Feel
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 ￥10,525
￥17,389 total
includes taxes & fees
Feb 2 - Feb 3
Glamping Cabin | Huge Window | Tree House Feel
Terrace/patio

Vacation Home in Wallingford

Quiet Country home, Pet friendly
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 ￥11,578
￥23,137 total
includes taxes & fees
Jan 29 - Jan 30
Quiet Country home, Pet friendly
Terrace/patio

Cabin in Green Township

Sleeps 4| Private Bathroom | Stunning Views
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.
The price is ￥20,593
￥23,644 total
includes taxes & fees
Feb 1 - Feb 2
Sleeps 4| Private Bathroom | Stunning Views
Fridge, microwave, oven, stovetop

Cabin in West Union

Griffis Game Hunting and/or Getaway
9.8 out of 10, Exceptional, (31 reviews)
"Our work crew stayed here while in the area. It was perfect and cozy. Hosts were very responsive to any needs or questions!"
United States
April H.
The price is ￥20,593
￥33,832 total
includes taxes & fees
Feb 2 - Feb 3
Griffis Game Hunting and/or Getaway
Property grounds

Cabin in Blue Creek

Sleeps 12| Private Bathroom | Stunning Views
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.
The price is ￥38,135
￥47,898 total
includes taxes & fees
Feb 1 - Feb 2
Sleeps 12| Private Bathroom | Stunning Views
Interior

Vacation Home in Dover

Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA!
9.6 out of 10, Exceptional, (9 reviews)
"Clean rooms, nice decor, pleasant spot. Loved the quiet on the porch area"
United States
David Z.
The price is ￥30,340
￥41,302 total
includes taxes & fees
Jan 29 - Jan 30
Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA!
Terrace/patio

Cabin in Adams County

Peaceful cabin with spectacular river and scenic views.
9.8 out of 10, Exceptional, (29 reviews)
"Great location. "
United States
John S.
The price is ￥36,915
￥59,787 total
includes taxes & fees
Feb 11 - Feb 12
Peaceful cabin with spectacular river and scenic views.
Living area

Cabin in Ewing

Hickory Ridge Cabin | 3 Bed, 2 Bath
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 ￥33,544
￥55,775 total
includes taxes & fees
Feb 6 - Feb 7
Hickory Ridge Cabin | 3 Bed, 2 Bath
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Apartment in Ripley

Spacious 3-bedroom apartment with WiFi, AC in charming 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 ￥25,261
￥34,871 total
includes taxes & fees
Feb 7 - Feb 8
Spacious 3-bedroom apartment with WiFi, AC in charming Ripley
Exterior

Cabin in Green Township

Glamping Cabin | Huge Window | Valley and Cliff Views
10.0 out of 10, Exceptional, (2 reviews)
"Property owners were very welcoming. The tree house and property were well maintained. "
United States
Marci
The price is ￥10,525
￥17,389 total
includes taxes & fees
Feb 1 - Feb 2
Glamping Cabin | Huge Window | Valley and Cliff Views
Exterior

Cabin in Green Township

Glamping Cabin | Huge Window | Nature Lovers Dream
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 ￥10,525
￥17,389 total
includes taxes & fees
Feb 17 - Feb 18
Glamping Cabin | Huge Window | Nature Lovers Dream
Interior

Vacation Home in wallingford

Charming country home on 433 acres
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 ￥10,420
￥19,420 total
includes taxes & fees
Jan 29 - Jan 30
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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Top Tollesboro Hotel Reviews

Days Inn by Wyndham Maysville Kentucky

Days Inn by Wyndham Maysville Kentucky

10/10 Excellent
"We left before breakfast was served. Great room; very clean, easy access. Bed was comfortable but the pillows were a bit too hard and small. They were not full size. "
Dan 1-night trip
Posted 7 days ago
Days Inn by Wyndham Maysville Kentucky

Find out more about Tollesboro

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Look no further and take a look at our great range of rental properties in Tollesboro!

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?

The Manor at Maysville Golf Course View: This vacation home rental near Tollesboro is located next to a golf course and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 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.