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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Hillsboro holiday homes

A gravel driveway leading to a rustic building with a red roof, surrounded by a pond and trees.

1. Lazy Lake Cabin 2!!! Pet Friendly!!

Lazy Lake Cabin 2!!! Pet Friendly!!
Flemingsburg
4.0 out of 10, (2 reviews)
"Property was not clean. Rooms had exposed wiring and several other safety hazards. Ok room to rent if just looking for a place to rest your head. The couch also smelled like wet dog."
United States
Frederick L.
The price is £116
includes taxes & fees
5 Oct - 6 Oct
Lazy Lake Cabin 2!!! Pet Friendly!!
Terrace/patio

2. Quiet Country home, Pet friendly

Quiet Country home, Pet friendly
Wallingford
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 £136
includes taxes & fees
2 Nov - 3 Nov
Quiet Country home, Pet friendly
A spacious room with a wooden floor, a stone fireplace, a red leather chair, a green armchair, and a grey sofa.

3. Charming country home on 433 acres

Charming country home on 433 acres
wallingford
6.0 out of 10, (6 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 £98
includes taxes & fees
5 Oct - 6 Oct
Charming country home on 433 acres
A modern kitchen with white cabinets, a black refrigerator, and a wooden dining table with chairs.

4. 3-bedroom house in charming Morehead near Cave Run and Morehead State

3-bedroom house in charming Morehead near Cave Run and Morehead State
Morehead
10.0 out of 10, Exceptional, (4 reviews)
"It was clean and just as described. Perfect location for us visiting a child at Morehead State. We will be booking again!!"
United States
Stacy T.
The price is £267
includes taxes & fees
27 Oct - 28 Oct
3-bedroom house in charming Morehead near Cave Run and Morehead State
A wooden deck with a round table and two chairs, a window, and a wooden wall.

5. Lazy Lake Cabin 1! Pet Friendly

Lazy Lake Cabin 1! Pet Friendly
Flemingsburg
6.0 out of 10, (2 reviews)
"Pet friendly, very peaceful and quiet, host is awwsome and very responsive to any needs. Beautiful surroundings"
United States
Donna S.
The price is £128
includes taxes & fees
5 Oct - 6 Oct
Lazy Lake Cabin 1! Pet Friendly
A covered porch with stone walls, a staircase, and outdoor seating.

6. Spacious Lodge w/ Fire Pit & Hot Tub

Spacious Lodge w/ Fire Pit & Hot Tub
Wallingford
10.0 out of 10, Exceptional, (3 reviews)
"super nice place!"
United States
Trystan S.
The price is £432
includes taxes & fees
5 Oct - 6 Oct
Spacious Lodge w/ Fire Pit & Hot Tub
A room with two sofas, a wooden ceiling, and a door with curtains.

7. Lake Adventure Basecamp w/ Game Room

Lake Adventure Basecamp w/ Game Room
Morehead
9.6 out of 10, Exceptional, (54 reviews)
"Overall a very nice property, but there are some general maintenance items that need addressed to make this a great stay."
United States
Ryan B.
The price is £490
includes taxes & fees
6 Oct - 7 Oct
Lake Adventure Basecamp w/ Game Room
A Farmers' Market pavilion with a clear roof, a sign indicating it's powered by KJ, and operating hours from June through October.

8. Cozy, Bright Home in Historic Downtown

Cozy, Bright Home in Historic Downtown
Mount Sterling
8.6 out of 10, Excellent, (24 reviews)
"This is definitely an older home, but it was clean and comfortable and the Dolly memorabilia is amazing!"
United States
Glenda
The price is £97
includes taxes & fees
5 Oct - 6 Oct
Cozy, Bright Home in Historic Downtown
A building with a staircase leading to a door marked with the number 218.

9. 1 Bedroom Bourbon House on the Hill

1 Bedroom Bourbon House on the Hill
Mount Sterling
10.0 out of 10, Exceptional, (1 review)
"This property was very welcoming to our small dog."
United States
Anne D.
The price is £102
includes taxes & fees
5 Oct - 6 Oct
1 Bedroom Bourbon House on the Hill
A wooden interior with a fireplace, dining area, and a clock on the wall.

10. The Cave Run Lake Cabin

The Cave Run Lake Cabin
Wellington
9.6 out of 10, Exceptional, (80 reviews)
"Very nice property, in a nice neighborhood."
United States
Anne S.
The price is £182
includes taxes & fees
5 Oct - 6 Oct
The Cave Run Lake Cabin
A bedroom with a bed, nightstands, a ceiling fan, a mural of a sunset, and a window with blinds.

11. 5 o'clock somewhere in Mt Sterling

5 o'clock somewhere in Mt Sterling
Mount Sterling
9.4 out of 10, Exceptional, (3 reviews)
"A good stay in a friendly area."
United States
Trey S.
The price is £106
includes taxes & fees
5 Oct - 6 Oct
5 o'clock somewhere in Mt Sterling
A log cabin interior with a wooden staircase, a kitchen area, and seating.

12. Kentucky Cabin Getaway w/ Loft Sleeping

Kentucky Cabin Getaway w/ Loft Sleeping
Mayslick
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful remote cabin with all the amenities of home. Every detail was planned out and perfect. We absolutely loved it."
United States
Diane L.
The price is £343
includes taxes & fees
5 Oct - 6 Oct
Kentucky Cabin Getaway w/ Loft Sleeping
A view from a window with a wooden railing, overlooking a cabin and a covered vehicle in a forested area.

13. Peaceful 3-bedroom cabin near Cave Run Lake and RRG

Peaceful 3-bedroom cabin near Cave Run Lake and RRG
Wellington
The price is £320
includes taxes & fees
5 Oct - 6 Oct
Peaceful 3-bedroom cabin near Cave Run Lake and RRG
A rural road curving through a green landscape with a wooden fence, a stone wall, and a small building in the distance.

14. Historical 4-bedroom farmhouse in serene Sharpsburg with AC.

Historical 4-bedroom farmhouse in serene Sharpsburg with AC.
Sharpsburg
9.6 out of 10, Exceptional, (8 reviews)
"Delightful country setting that allowed our family to be together to prepare for our daughter’s wedding. "
United States
Lance S.
The price is £311
includes taxes & fees
5 Oct - 6 Oct
Historical 4-bedroom farmhouse in serene Sharpsburg with AC.
A wooden porch with a bench, a door, and a view of a red building and trees.

15. Canyon Ridge Retreats

Canyon Ridge Retreats
Wellington
10.0 out of 10, Exceptional, (1 review)
"Clean, quiet, and scenic! Would stay again!"
United States
Derek S.
The price is £389
includes taxes & fees
2 Nov - 3 Nov
Canyon Ridge Retreats
Exterior

16. Hunting Lodge in the City

Hunting Lodge in the City
Mount Sterling
The price is £110
includes taxes & fees
5 Oct - 6 Oct
Hunting Lodge in the City
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 Hillsboro Hotel Reviews

Starway to Heaven Cabin at Red River Gorge - Hot Tub - Great View

Starway to Heaven Cabin at Red River Gorge - Hot Tub - Great View

10/10 Excellent
"We loved our stay! We had a wonderful trip and really enjoyed the hot tub and the cleanliness of the cabin! Beautiful view off the back deck!"
Meghan H. 2-night trip
Posted 14 hours ago
Starway to Heaven Cabin at Red River Gorge - Hot Tub - Great View

Find out more about Hillsboro

Hillsboro Holiday Homes information

Number of reviews
109
Accommodation
41 Holiday Homes
Lowest Price
£97
Highest Price
£490