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Check prices for these dates

Next weekend
11 Rab. II - 13 Rab. II
In two weeks
18 Rab. II - 20 Rab. II
In one month
2 Jum. I - 4 Jum. I
In two months
30 Jum. I - 1 Jum. II

Compare 27 Vacation Homes in Tollesboro with updated reviews, rates, and availability.

The Manor at Maysville Golf Course View
Smart TV, fireplace, stereo, computer monitors

The Manor at Maysville Golf Course View

9.8 out of 10, Exceptional, (17)
"My family and friends had a fantastic stay at the Manor! The space offers plenty of room, making it perfect for relaxing or getting work done. The Wi-Fi was excellent, which was a huge plus. The host was incredibly responsive, ensuring a smooth and hassle-free experience. Plus, the location is awesome—close to everything you need. Highly recommend!"
The Manor at Maysville Golf Course View
Spacious Ewing Retreat w/ Game Room & Fireplace!
Cookware/dishes/utensils

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!
Beautifully renovated unit in the downtown Maysville’s entertainment district
Interior

Beautifully renovated unit in the downtown Maysville’s entertainment district

10.0 out of 10, Exceptional, (39)
"What a beautiful property. It was an absolute pleasure to stay there. The host was easy to communicate with and super concerned that our stay was the best.It was. I will look to stay here in future trips to Maysville"
Beautifully renovated unit in the downtown Maysville’s entertainment district
Manchester Getaway on Ohio River Scenic Byway
Miscellaneous

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
Ljbak1987@icloud.com
Children's area

Ljbak1987@icloud.com

Ljbak1987@icloud.com
Charming country home on 433 acres
Property grounds

Charming country home on 433 acres

10.0 out of 10, Exceptional, (2)
"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 281
SAR 502 total
includes taxes & fees
30 Apr - 1 May
Charming country home on 433 acres
River House with AC and WiFi in welcoming Ripley, Ohio
Property grounds

River House with AC and WiFi in welcoming Ripley, Ohio

2.0 star property
River House with AC and WiFi in welcoming Ripley, Ohio
Relax and Unwind at River Front Oasis w/ Hot Tub
Miscellaneous

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
Renovated KY Farmhouse Retreat w/ Pasture Views!
Exterior

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!
Riverview Getaway
Fridge, microwave, coffee/tea maker, toaster

Riverview Getaway

9.8 out of 10, Exceptional, (8)
"Cozy, comfortable, and convenient!"
The price is SAR 244
SAR 402 total
includes taxes & fees
13 Apr - 14 Apr
Riverview Getaway
Furnished dormer room neighboring the Maysville Country Club.
Interior

Furnished dormer room neighboring the Maysville Country Club.

Furnished dormer room neighboring the Maysville Country Club.
Charming 4-bedroom house with WiFi and AC directly on the Ohio River with dock.
Terrace/patio

Charming 4-bedroom house with WiFi and AC directly on the Ohio River with dock.

Charming 4-bedroom house with WiFi and AC directly on the Ohio River with dock.
Luxury and Character in Maysville, Kentucky
Interior

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
Ripley River House
Property grounds

Ripley River House

2.0 star property
Ripley River House
Ripley River House
Property grounds

Ripley River House

2.0 star property
Ripley River House
The Eagles Nest
Private kitchen

The Eagles Nest

The Eagles Nest
Backpackers Paradise
Interior

Backpackers Paradise

Backpackers Paradise
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

Beautifully renovated unit in the downtown Maysville’s entertainment district
Interior

Beautifully renovated unit in the downtown Maysville’s entertainment district

10.0 out of 10, Exceptional, (39)
"What a beautiful property. It was an absolute pleasure to stay there. The host was easy to communicate with and super concerned that our stay was the best.It was. I will look to stay here in future trips to Maysville"
Beautifully renovated unit in the downtown Maysville’s entertainment district
Cozy Country Cabin close to West Union!
Terrace/patio

Cozy Country Cabin close to West Union!

2.0 star property
10.0 out of 10, Exceptional, (10)
"Delightful, spacious cabin. Away from it all with beautiful views but not too remote. Easy access from highway.We plan to return!"
Cozy Country Cabin close to West Union!
Beautiful studio in historic downtown Maysville
1 bedroom, free WiFi, bed sheets

Beautiful studio in historic downtown Maysville

9.0 out of 10, Wonderful, (2)
"The location is great, close to downtown. The apartment is above a bar so beware if you need a goodnight sleep because it can get loud with the bar patrons just below you but after 2:00am it gets super quiet as all the drunks have went home for the night. Larry(host) was super responsive and helpful. The apartment was a little Smokey smelling even though no smoking was allowed. Seems the smoke from the bar kinda creeps in, so beware if you have smoke allergies. With all that being said the...
Beautiful studio in historic downtown Maysville
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.