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Compare 21 Vacation Homes in Tollesboro with updated reviews, rates, and availability.

The Manor at Maysville Golf Course View

9.6 out of 10, Exceptional, (15)
"This was our 2nd time staying at The Moss Manor and once again our stay was great. When we come back home to Ky if this property is available we will be staying again. Also very nice upgrades done in the house since our last stay. "
The Manor at Maysville Golf Course View

Jewel Box Cottage in Historic Maysville KY

9.2 out of 10, Wonderful, (7)
"The house was wonderful place for family to gather after funeral of my father. My mother wanted us to be able to gather together for stories, laughter & tears. This gave us privacy to do so. Booking & checking in was very easy. We found it very clean except for some "sticky" kitchen cabinet doors/drawers. The only "issue" we had was not finding outlets in the bedrooms......after a good night's rest we realized the next morning that they were located in the baseboards of the same color! Will...
The price is SAR 845
SAR 1,429 total
includes taxes & fees
3 Dec - 4 Dec
Jewel Box Cottage in Historic Maysville KY

URBAN GETAWAY - .6 Downtown Maysville/Entire House

9.4 out of 10, Exceptional, (25)
"Very comfortable. Accessible location to places we wanted to visit. "
The price is SAR 297
SAR 456 total
includes taxes & fees
1 Dec - 2 Dec
URBAN GETAWAY - .6 Downtown Maysville/Entire House

Riverview Getaway

9.8 out of 10, Exceptional, (8)
"Cozy, comfortable, and convenient!"
Riverview Getaway

Renovated KY Farmhouse Retreat w/ Pasture Views!

10.0 out of 10, Exceptional, (6)
"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, (38)
"We came to Maysville from Indiana to celebrate a friend’s birthday whose family is from the area. I found the apartment on Vrbo and it was everything we expected and then some!! Beautiful apartment, quaint neighborhood, wonderful restaurants within walking distance, and the hosts were very welcoming and responsive. I will say the stairs are every bit as steep as everyone describes, but we managed without any issues. I do caution anyone with limited abilities to consider the stairs before...
Beautifully renovated unit in the downtown Maysville’s entertainment district

Manchester Getaway on Ohio River Scenic Byway

8.0 out of 10, Very Good, (1)
"Definitely not the best to swim but great to fish cook and hangout with the family for some peaceful time"
Manchester Getaway on Ohio River Scenic Byway

Relax and Unwind at River Front Oasis w/ Hot Tub

10.0 out of 10, Exceptional, (3)
"Awesome...."
Relax and Unwind at River Front Oasis w/ Hot Tub

Step Back in Time at Cherry Manor- Downtown Historic Maysville

10.0 out of 10, Exceptional, (2)
"Cherry Manor was an absolute dream for my friends and I to celebrate my 40th!! The house is absolutely stunning and has everything needed for a relaxing time! The location is super convenient in town to explore the beautiful historic architecture. My friends and I made lasting memories that I will certainly cherish! Thank you so much, Ashlee, for sharing the gem and being so welcoming!!"
Step Back in Time at Cherry Manor- Downtown Historic Maysville

Charming country home on 433 acres

10.0 out of 10, Exceptional, (1)
"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!"
The price is SAR 225
SAR 442 total
includes taxes & fees
1 Dec - 2 Dec
Charming country home on 433 acres

River House with AC and WiFi in welcoming Ripley, Ohio

2.0 star property
River House with AC and WiFi in welcoming Ripley, Ohio

The Red Lodge!! Pet Friendly!

2.0 star property
The price is SAR 282
SAR 583 total
includes taxes & fees
5 Dec - 6 Dec
The Red Lodge!! Pet Friendly!

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!

Luxury and Character in Maysville, Kentucky

10.0 out of 10, Exceptional, (3)
"Great experience. Anne was very proactive and friendly and we received a heartwarming welcome. Our room was beautifully presented with gifts galore and snacks aplenty. Highly recommended."
Luxury and Character in Maysville, Kentucky

Cozy basement apartment

Cozy basement apartment

Backpackers Paradise

Backpackers Paradise

The Eagles Nest

The Eagles Nest

Lazy Lake Cabin 2!!! Pet Friendly!!

2.0 star property
The price is SAR 282
SAR 583 total
includes taxes & fees
28 Nov - 29 Nov
Lazy Lake Cabin 2!!! Pet Friendly!!

Ripley River House

2.0 star property
Ripley River House

Ripley River House

2.0 star property
Ripley River House
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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Other property types in Tollesboro

The Manor at Maysville Golf Course View

9.6 out of 10, Exceptional, (15)
"This was our 2nd time staying at The Moss Manor and once again our stay was great. When we come back home to Ky if this property is available we will be staying again. Also very nice upgrades done in the house since our last stay. "
The Manor at Maysville Golf Course View

Glamping Cabin | Huge Window | Over a Creek

10.0 out of 10, Exceptional, (3)
"Beautiful location ."
The price is SAR 357
SAR 526 total
includes taxes & fees
3 Dec - 4 Dec
Glamping Cabin | Huge Window | Over a Creek

Jewel Box Cottage in Historic Maysville KY

9.2 out of 10, Wonderful, (7)
"The house was wonderful place for family to gather after funeral of my father. My mother wanted us to be able to gather together for stories, laughter & tears. This gave us privacy to do so. Booking & checking in was very easy. We found it very clean except for some "sticky" kitchen cabinet doors/drawers. The only "issue" we had was not finding outlets in the bedrooms......after a good night's rest we realized the next morning that they were located in the baseboards of the same color! Will...
The price is SAR 845
SAR 1,429 total
includes taxes & fees
3 Dec - 4 Dec
Jewel Box Cottage in Historic Maysville KY
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.