Tollesboro Holiday Rentals

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Holiday Rentals in Tollesboro

URBAN GETAWAY - .6 Downtown Maysville/Entire House
9.8 out of 10, Exceptional, 15 reviews
"The property was great! Good location for me."
The price is NZ$198
includes taxes & fees
11 Jun - 12 Jun
URBAN GETAWAY - .6 Downtown Maysville/Entire House
Hippie Soul - Entertainment District .2 Downtown Maysville<br>
9.8 out of 10, Exceptional, 9 reviews
"Hippie Soul is a charming, beautiful property. It's well appointed & very comfortable. What a wonderful location. I'd absolutely stay here again."
The price is NZ$198
includes taxes & fees
11 Jun - 12 Jun
Hippie Soul - Entertainment District .2 Downtown Maysville<br>
Lazy Spread Cabin. Secluded wooded cabin tucked away with all the amenities
10.0 out of 10, Exceptional, 8 reviews
"Amazing property. Has everything you'd want in a rental."
Lazy Spread Cabin. Secluded wooded cabin tucked away with all the amenities
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Glamping Cabin | Huge Window | Nature Lovers Dream
9.8 out of 10, Exceptional, 7 reviews
"We Loved It!!! Cousin Greg was very pleasant. We had a Great time :-)"
The price is NZ$229
includes taxes & fees
5 Jun - 6 Jun
Glamping Cabin | Huge Window | Nature Lovers Dream
Newly renovated unit in downtown Maysville’s Entertainment District.
10.0 out of 10, Exceptional, 22 reviews
"This is a huge place that is perfectly located with river views, lovely furnishings, everything you need to make a lovely meal, and kind and thoughtful hosts. Travel to Maysville just so you can stay here!!"
Newly renovated unit in downtown Maysville’s Entertainment District.
Sleeps 12| Huge Windows | Stunning Views
10.0 out of 10, Exceptional, 5 reviews
"Excellent!"
The price is NZ$605
includes taxes & fees
27 Jun - 28 Jun
Sleeps 12| Huge Windows | Stunning Views
Relax and Unwind at River Front Oasis w/ Hot Tub
10.0 out of 10, Exceptional, 3 reviews
"Awesome...."
Relax and Unwind at River Front Oasis w/ Hot Tub
Spacious Ewing Retreat w/ Game Room & Fireplace!
Spacious Ewing Retreat w/ Game Room & Fireplace!
Glamping Cabin | Huge Window | Over a Creek
10.0 out of 10, Exceptional, 1 review
"The property was quaint and exactly what we needed for our getaway from technology. The grill provided is charcoal and I may have misread that somewhere. We will definately be back, just more prepared."
The price is NZ$229
includes taxes & fees
5 Jun - 6 Jun
Glamping Cabin | Huge Window | Over a Creek
Riverview Getaway
9.8 out of 10, Exceptional, 7 reviews
"Cozy, comfortable, and convenient!"
The price is NZ$175
includes taxes & fees
4 Jun - 5 Jun
Riverview Getaway
Renovated KY Farmhouse Retreat w/ Pasture Views!
10.0 out of 10, Exceptional, 6 reviews
"Beautiful property, loved seeing all the animals."
Renovated KY Farmhouse Retreat w/ Pasture Views!
Beautifully renovated unit in the downtown Maysville’s entertainment district
10.0 out of 10, Exceptional, 31 reviews
"Was a great location for us. View was great. We will stay again"
Beautifully renovated unit in the downtown Maysville’s entertainment district
Manchester Getaway on Ohio River Scenic Byway
Manchester Getaway on Ohio River Scenic Byway
Historic and Elegant
The price is NZ$362
includes taxes & fees
5 Jun - 6 Jun
Historic and Elegant
Glamping Cabin | Huge Window | Tree House Feel
9.2 out of 10, Wonderful, 15 reviews
"Exactly as advertised. Would definitely come back!"
The price is NZ$229
includes taxes & fees
5 Jun - 6 Jun
Glamping Cabin | Huge Window | Tree House Feel
Glamping Cabin | Huge Window | Valley and Cliff Views
10.0 out of 10, Exceptional, 1 review
"Enjoyed the area in general.Love the outdoors, so the cabin was really nice.Great craftsmanship and a lot of hard work has been put into the Glamping cabins.Hospitality went above and beyond. Thank you & much appreciated."
The price is NZ$229
includes taxes & fees
5 Jun - 6 Jun
Glamping Cabin | Huge Window | Valley and Cliff Views
Jewel Box Cottage in Historic Maysville KY
9.0 out of 10, Wonderful, 6 reviews
"The house is in great condition and was comfortable to stay in."
The price is NZ$622
includes taxes & fees
11 Jun - 12 Jun
Jewel Box Cottage in Historic Maysville KY
Glamping Cabin | Huge Window | Cliff and Animal Views
The price is NZ$229
includes taxes & fees
5 Jun - 6 Jun
Glamping Cabin | Huge Window | Cliff and Animal Views
1A Historic Downtown Maysville,KY
9.6 out of 10, Exceptional, 5 reviews
"Good location within walking distance of bars and restaurants"
1A Historic Downtown Maysville,KY
Renovated KY Farmhouse Retreat w/ Pasture Views!
3.0 star property
10.0 out of 10, Exceptional, 1 review
"Perfect if you actually want to relax and decompress...no noise no lights no city..."
Renovated KY Farmhouse Retreat w/ Pasture Views!
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See all available properties in Tollesboro
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.

Other types of properties in Tollesboro you may be interested in

French Quarter Inn
3.0 star property
8.8 out of 10, Excellent, 625 reviews
"Nice older hotel with history. In historic area on the river. Nice view. Quiet. "
The price is NZ$180
includes taxes & fees
10 Jun - 11 Jun
French Quarter Inn
Days Inn by Wyndham Maysville Kentucky
2.5 star property
6.8 out of 10, 265 reviews
"Excellent experience "
The price is NZ$126
includes taxes & fees
2 Jun - 3 Jun
Days Inn by Wyndham Maysville Kentucky
Quality Inn
2.5 star property
6.2 out of 10, 102 reviews
"This was a great location for us. Convenient to to restaurants, grocery store, church. There was confusion to where our room was, but the staff was excellent in helping. "
The price is NZ$122
includes taxes & fees
2 Jun - 3 Jun
Quality Inn
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Tollesboro holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Tollesboro. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Tollesboro. Seeing all the best attractions is bound to make you fall in love with Tollesboro. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Tollesboro short-term rentals, that won’t be hard to do.

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?

URBAN GETAWAY - .6 Downtown Maysville/Entire House: This holiday home rental outside of Tollesboro is located on a river, and has a patio, a garden and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

What can I see and do in Tollesboro?

While exploring the area, visit the sights like National Underground Railroad Museum, Kentucky Gateway Museum Center and Fleming County Recreation Park. Russell Theatre 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.

Recent reviews of Tollesboro properties
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