A rural landscape with barns, a silo, and a fenced area.

Search Holiday Homes in Flemingsburg

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Flemingsburg holiday homes

Terrace/patio

1. 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 £135
includes taxes & fees
12 Nov - 13 Nov
Quiet Country home, Pet friendly
An outdoor seating area with chairs and a fire pit under string lights.

2. Highland Hideaway - Tons of character, modern updates and art !

Highland Hideaway - Tons of character, modern updates and art !
Flemingsburg
The price is £144
includes taxes & fees
4 Nov - 5 Nov
Highland Hideaway - Tons of character, modern updates and art !
A covered porch with stone walls, a staircase, and outdoor seating.

3. Spacious Lodge w/ Fire Pit & Hot Tub

Spacious Lodge w/ Fire Pit & Hot Tub
Wallingford
10.0 out of 10, Exceptional, (4 reviews)
"super nice place!"
United States
Trystan S.
The price is £477
includes taxes & fees
11 Nov - 12 Nov
Spacious Lodge w/ Fire Pit & Hot Tub
A spacious room with a wooden floor, a stone fireplace, a red leather chair, a green armchair, and a grey sofa.

4. 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
29 Oct - 30 Oct
Charming country home on 433 acres
A gravel driveway leading to a rustic building with a red roof, surrounded by a pond and trees.

5. 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 £136
includes taxes & fees
12 Nov - 13 Nov
Lazy Lake Cabin 2!!! Pet Friendly!!
A wooden deck with a round table and two chairs, a window, and a wooden wall.

6. 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 £127
includes taxes & fees
5 Nov - 6 Nov
Lazy Lake Cabin 1! Pet Friendly
A log cabin interior with a wooden staircase, a kitchen area, and seating.

7. Kentucky Cabin Getaway w/ Loft Sleeping

Kentucky Cabin Getaway w/ Loft Sleeping
Mayslick
9.4 out of 10, Exceptional, (6 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 £334
includes taxes & fees
3 Nov - 4 Nov
Kentucky Cabin Getaway w/ Loft Sleeping
A modern kitchen with white cabinets, a black refrigerator, and a wooden dining table with chairs.

8. 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, (5 reviews)
The price is £267
includes taxes & fees
2 Nov - 3 Nov
3-bedroom house in charming Morehead near Cave Run and Morehead State
A room with two sofas, a wooden ceiling, and a door with curtains.

9. Lake Adventure Basecamp w/ Game Room

Lake Adventure Basecamp w/ Game Room
Morehead
9.6 out of 10, Exceptional, (54 reviews)
"Over all we had a wonderful stay, the house was spacious and bigger than the pictures show. Enjoyed our stay."
United States
Mary Jo W.
The price is £491
includes taxes & fees
29 Oct - 30 Oct
Lake Adventure Basecamp w/ Game Room
A living room with a sofa, a television, a cabinet, and a plant.

10. Cozy, Bright Home in Historic Downtown

Cozy, Bright Home in Historic Downtown
Mount Sterling
8.4 out of 10, Very good, (25 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 £96
includes taxes & fees
1 Nov - 2 Nov
Cozy, Bright Home in Historic Downtown
A building with a staircase leading to a door marked with the number 218.

11. 1 Bedroom Bourbon House on the Hill

1 Bedroom Bourbon House on the Hill
Mount Sterling
10.0 out of 10, Exceptional, (2 reviews)
"This property was very welcoming to our small dog."
United States
Anne D.
The price is £101
includes taxes & fees
31 Oct - 1 Nov
1 Bedroom Bourbon House on the Hill
A bedroom with a bed, nightstands, a ceiling fan, a mural of a sunset, and a window with blinds.

12. 5 o'clock somewhere in Mt Sterling

5 o'clock somewhere in Mt Sterling
Mount Sterling
9.0 out of 10, Wonderful, (4 reviews)
"A good stay in a friendly area."
United States
Trey S.
The price is £105
includes taxes & fees
29 Oct - 30 Oct
5 o'clock somewhere in Mt Sterling
A living room with a sofa, a coffee table, and a lamp.

13. Historic River Town Retreat w/ Screened Porch

Historic River Town Retreat w/ Screened Porch
Ripley
9.4 out of 10, Exceptional, (12 reviews)
"Really enjoyed our stay here! Very relaxing!!"
United States
Beth B.
The price is £356
includes taxes & fees
16 Nov - 17 Nov
Historic River Town Retreat w/ Screened Porch
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, (9 reviews)
"We had a great time with the family."
United States
Garrett W.
The price is £310
includes taxes & fees
1 Nov - 2 Nov
Historical 4-bedroom farmhouse in serene Sharpsburg with AC.
Exterior

15. Hunting Lodge in the City

Hunting Lodge in the City
Mount Sterling
The price is £109
includes taxes & fees
29 Oct - 30 Oct
Hunting Lodge in the City
A dining room with a wooden table and chairs, a chandelier, a fireplace, and a mirror on the wall.

16. The Williams House by Mustard Seed Hill - A Cozy Bourbon County Getaway

The Williams House by Mustard Seed Hill - A Cozy Bourbon County Getaway
Paris
8.8 out of 10, Excellent, (5 reviews)
"This property is an older home remodeled. the showers are only for SMALL people. they use horrible smelling air freshners. it took 2 days to get the chemical smell out. And the lights in the bathroom went out after the first day. The price on this home is way to high for the property. But on a good note, the fenced in back yard is huge. the dogs loved it. but the next door neighbor has aggressive pit bulls who go nuts at the fence when they are out. . And after letting the owner know about the...
United States
Randy H.
The price is £320
includes taxes & fees
1 Nov - 2 Nov
The Williams House by Mustard Seed Hill - A Cozy Bourbon County Getaway
A kitchen with a central island, two pendant lights, a stove, and wooden cabinets.

17. Historical 1812 Home featuring a Chef's Kitchen, Laundry, and AC

Historical 1812 Home featuring a Chef's Kitchen, Laundry, and AC
Millersburg
The price is £421
includes taxes & fees
9 Nov - 10 Nov
Historical 1812 Home featuring a Chef's Kitchen, Laundry, and AC
A house with a blue door, two windows with shutters, and a porch with a white railing.

18. Helena's Cottage: Romantic, Cozy Getaway with Lavish King Bed, Gas Fireplace

Helena's Cottage: Romantic, Cozy Getaway with Lavish King Bed, Gas Fireplace
Millersburg
The price is £268
includes taxes & fees
10 Nov - 11 Nov
Helena's Cottage: Romantic, Cozy Getaway with Lavish King Bed, Gas Fireplace
A two-story house with a beige exterior, numbered 1112, featuring a front porch with two wicker chairs and two wall-mounted lanterns.

19. The Neal House: Charming & Historic 3 Bedroom House

The Neal House: Charming & Historic 3 Bedroom House
Millersburg
The price is £375
includes taxes & fees
10 Nov - 11 Nov
The Neal House: Charming & Historic 3 Bedroom House
A two-story house with a front porch, a central door, and a small front yard.

20. The Parsonage: A Grand 19th Century 4 Bedroom Home

The Parsonage: A Grand 19th Century 4 Bedroom Home
Millersburg
The price is £404
includes taxes & fees
10 Nov - 11 Nov
The Parsonage: A Grand 19th Century 4 Bedroom Home
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Flemingsburg Hotel Reviews

Best Western Eagles Inn

Best Western Eagles Inn

10/10 Excellent
"Excellent place to stay for the night on a 12 day road-trip. Clean, quiet, friendly helpful staff. Great hot breakfast. 24 hr coffee, tea, hot chocolate available. Free parking. Located right off interstate many many restaurants etc available within 2-3 miles"
Cathy 1-night trip
Posted 10 hours ago
Best Western Eagles Inn

Find out more about Flemingsburg

Flemingsburg Holiday Homes information

Number of reviews
137
Accommodation
44 Holiday Homes
Lowest Price
£96
Highest Price
£491