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Top Holiday Rentals in Tollesboro

Charming 2 Bedroom Cabin in Vanceburg-Your Gateway to Kentucky's Natural Beauty

10.0 out of 10, Exceptional, (1)
Charming 2 Bedroom Cabin in Vanceburg-Your Gateway to Kentucky's Natural Beauty

Spacious 4-bedroom 19th Century home in historic downtown Maysville!

10.0 out of 10, Exceptional, (2)
"We were overly impressed by this property and the location. The house was emasculate and had such great character in every room. Check in and communication with the property own were top notch. The main areas in the town are all within short walking distance of the home. We will definitely look for this home again next year when we come back to Maysville. We won Oktoberfest king 2025 so we’ll definitely be back!"
Spacious 4-bedroom 19th Century home in historic downtown Maysville!

Cozy Country Cabin close to West Union!

2.0 star property
10.0 out of 10, Exceptional, (20)
"The property was very clean and had everything we needed. We would stay again. "
Cozy Country Cabin close to West Union!

The Manor at Maysville Golf Course View

9.8 out of 10, Exceptional, (22)
"Our families got together for a lovely Christmas gathering here. The house was beautifully decorated!"
The Manor at Maysville Golf Course View

Peaceful cabin with spectacular river and scenic views.

9.8 out of 10, Exceptional, (16)
"Cozy cabin with a great view"
The price is £275
includes taxes & fees
25 Aug - 26 Aug
Peaceful cabin with spectacular river and scenic views.

Ljbak1987@icloud.com

10.0 out of 10, Exceptional, (2)
"This cabin was absolutely beautiful and perfect in every way! It had everything we could have possibly needed — from a thoughtfully stocked kitchen to body wash and soap in the bathrooms, which was such a nice touch. The kids’ area was a huge bonus and kept our little ones happy and entertained.The setting was just magical — the creek outside was peaceful and lovely, and we spent a lot of time just enjoying the relaxing atmosphere. We were in town for a family reunion, and this cabin made the...
Ljbak1987@icloud.com

Beautiful studio in historic downtown Maysville

9.6 out of 10, Exceptional, (10)
"It was very nice and a great location "
Beautiful studio in historic downtown Maysville

Home away from Home! - 1BR apartment in Maysville

10.0 out of 10, Exceptional, (5)
"Property manager is the sweetest and super helpful and available. The apartment was clean and comfortable. I highly recommend the eatery downstairs for lunch ir supper!!"
The price is £82
includes taxes & fees
14 Aug - 15 Aug
Home away from Home! - 1BR apartment in Maysville

Cozy Apartment in Maysville KY - Apt A

10.0 out of 10, Exceptional, (1)
"This was a very comfortable, historic home with beautiful architecture and minimalist decor to make for a relaxing and peaceful stay. We loved it!"
The price is £123
includes taxes & fees
16 Aug - 17 Aug
Cozy Apartment in Maysville KY - Apt A

Glamping Cabin | Huge Window | Over a Creek

10.0 out of 10, Exceptional, (4)
"Beautiful location ."
The price is £107
includes taxes & fees
14 Aug - 15 Aug
Glamping Cabin | Huge Window | Over a Creek

1 Mi to Hunting: Cozy & Secluded Stout Cabin

3.0 star property
1 Mi to Hunting: Cozy & Secluded Stout Cabin

Glamping Cabin | Huge Window | Cliff and Animal Views

The price is £107
includes taxes & fees
27 Aug - 28 Aug
Glamping Cabin | Huge Window | Cliff and Animal Views

Sleeps 12| Huge Windows | Stunning Views

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!"
The price is £283
includes taxes & fees
27 Aug - 28 Aug
Sleeps 12| Huge Windows | Stunning Views

Bear Necessities Cabin - What Else Do You Need?

The price is £141
includes taxes & fees
14 Aug - 15 Aug
Bear Necessities Cabin - What Else Do You Need?

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

2.0 star property
10.0 out of 10, Exceptional, (5)
"Very peaceful, amazing veiw perfect getaway will definitely stay again. "
Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!

Glamping Cabin | Huge Window | Tree House Feel

9.2 out of 10, Wonderful, (18)
"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"
The price is £107
includes taxes & fees
27 Aug - 28 Aug
Glamping Cabin | Huge Window | Tree House Feel

Unique and secluded A frame home on 31 acres with hot tub.

10.0 out of 10, Exceptional, (1)
"Very unique property with outstanding views. Nice amenities throughout (remote-operated ceiling fans, large screen TV, wifi, fully outfitted kitchen, large picture windows). The hot tub was fully functioning and appeared to be brand new. We appreciated the privacy that the property afforded and the several unique places in the home to retreat for reflection and/or conversation. "
Unique and secluded A frame home on 31 acres with hot tub.

1 Mi to Hunting: Cozy & Secluded Stout Cabin

10.0 out of 10, Exceptional, (5)
"The accommodation were great, clean and a lot of ni e touches like toothbrush, and personal hygiene items. Location vert clean and quiet. Close to portsmouth. Highly recommend stay here if you are in the adams county area."
1 Mi to Hunting: Cozy & Secluded Stout Cabin

Glamping Cabin | Huge Window | Nature Lovers Dream

9.8 out of 10, Exceptional, (9)
"Really enjoyed our stay! Beautiful scenery and well-maintained property. Having the property manager living on site was great as he was readily available to answer any questions. All the comforts of a hotel without the hotel."
The price is £107
includes taxes & fees
27 Aug - 28 Aug
Glamping Cabin | Huge Window | Nature Lovers Dream

Spacious Ewing Retreat w/ Game Room & Fireplace!

10.0 out of 10, Exceptional, (1)
"This was a very large farmhouse, that accommodated our group very well. Lots of beds, and large kitchen area made cooking and dining very easy for a large group! Plus, we were so far out in the country, the kids could make all the noise they wanted! Mark, our host, was on sight to check us in and explained where everything was located. Plus, he provided a list in the kitchen area, of local emergency contact phone numbers, that was very helpful. Having two kitchens / refrigerators was nice, for a...
Spacious Ewing Retreat w/ Game Room & Fireplace!
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

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?

Spacious 4-bedroom 19th Century home in historic downtown Maysville!: This holiday home rental outside of Tollesboro is located on a river, and offers a patio, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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. Fleming County Recreation Park 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.