Holiday Homes in Eastern Kentucky

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Featured Holiday Homes in Eastern Kentucky

Private house near Cumberland Falls, Daniel Boone Forest and Laural River Lake
10.0 out of 10, Exceptional, (4)
"Wonderful place to stay. Nice quiet area to relax and unwind"
The price is AU$249
includes taxes & fees
21 Oct - 22 Oct
Private house near Cumberland Falls, Daniel Boone Forest and Laural River Lake
Cozy Home in Heart of Prestonsburg
10.0 out of 10, Exceptional, (8)
"We loved our stay at The Shotgun House! It was very clean, peaceful and safe. The bed was super comfortable, and we lacked for nothing as the host has the place fully stocked. Super easy check-in and out process. The location is perfect! You’re in town and within minutes of food, shopping and local entertainment. We will definitely stay again soon. "
The price is AU$272
includes taxes & fees
20 Oct - 21 Oct
Cozy Home in Heart of Prestonsburg
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
10.0 out of 10, Exceptional, (18)
"Our group had a wonderful time staying at Uncle Ernie's! Everything was neat, tidy, and felt like home. We definitely will be back next time we are in the area!"
The price is AU$323
includes taxes & fees
19 Oct - 20 Oct
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
10.0 out of 10, Exceptional, (2)
"We stayed here for a wedding weekend in Pineville, KY, and it was absolutely perfect from start to finish. The home was spotless, cozy, and had everything we could possibly need. The beds were so comfortable, and we instantly felt at home the moment we walked in.What truly set this stay apart was the host’s kindness and above-and-beyond hospitality. We got lost in the middle of the night trying to find the property, and the host stayed on the phone with us, patiently guiding us right to the...
The price is AU$339
includes taxes & fees
17 Oct - 18 Oct
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
360 Degree Mountain View
9.8 out of 10, Exceptional, (8)
"Very clean and comfortable. Everything we needed was there and available. "
The price is AU$508
includes taxes & fees
20 Oct - 21 Oct
360 Degree Mountain View
Charming 1-bedroom house in fabulous London with AC, WiFi
10.0 out of 10, Exceptional, (1)
"It met our needs for a nice getaway. We'll be back!"
The price is AU$333
includes taxes & fees
17 Oct - 18 Oct
Charming 1-bedroom house in fabulous London with AC, WiFi
Treetop Escape | Hot Tub | Fire Pit & Epic Views
10.0 out of 10, Exceptional, (22)
"Cute and fun cabin that’s about 20 minutes away from all the must see attractions and restaurants! The cabin is made for a family of four with great outdoor space. "
The price is AU$415
includes taxes & fees
11 Nov - 12 Nov
Treetop Escape | Hot Tub | Fire Pit & Epic Views
Guest Favorite | Forest Retreat | Hot Tub
10.0 out of 10, Exceptional, (10)
"Wonderful accommodations, beautiful setting, hikes and red river gorge as well as natural bridge were close by. We had a lovely weekend."
The price is AU$415
includes taxes & fees
11 Nov - 12 Nov
Guest Favorite | Forest Retreat | Hot Tub
Relax and Retreat four bedroom home
2.0 star property
10.0 out of 10, Exceptional, (7)
"Great hosts, great place!"
The price is AU$445
includes taxes & fees
17 Oct - 18 Oct
Relax and Retreat four bedroom home
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
9.2 out of 10, Wonderful, (5)
"We enjoyed our stay. "
The price is AU$486
includes taxes & fees
4 Nov - 5 Nov
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Overlook Oasis! RRG, A-frame Cabin, NEW HOT TUB, Grill! Pet friendly
9.0 out of 10, Wonderful, (7)
"Little hard to find using a gps but your directions got us there with no problem "
The price is AU$454
includes taxes & fees
27 Oct - 28 Oct
Overlook Oasis! RRG, A-frame Cabin, NEW HOT TUB, Grill! Pet friendly
3-bedroom house in charming Oneida with AC
The price is AU$599
includes taxes & fees
19 Oct - 20 Oct
3-bedroom house in charming Oneida with AC
1928 Home in the heart of Cumberland Gap
9.8 out of 10, Exceptional, (91)
"The host was easy to reach and the house was clean. Cumberland Gap has really nice trails to walk, and lots of antique stores. Shout out to the restaurant just down the street "1919" Great food We would definetly stay again."
The price is AU$397
includes taxes & fees
9 Nov - 10 Nov
1928 Home in the heart of Cumberland Gap
Cheerful Three Bedroom Residential Home
The price is AU$542
includes taxes & fees
19 Oct - 20 Oct
Cheerful Three Bedroom Residential Home
Private Suite on Eastern Kentucky Farm with Indoor Pickleball Court
8.8 out of 10, Excellent, (8)
"Jody and Darby were very friendly and welcoming! I was here for a month and would absolutely recommend it for someone staying in the area. I would recommend a car with either AWD or a high clearance. I would also recommend bringing an instapot, air fryer, or hot pot if you plan on cooking food here"
The price is AU$192
includes taxes & fees
22 Oct - 23 Oct
Private Suite on Eastern Kentucky Farm with Indoor Pickleball Court
Family-Fun Escape w/ Pool, Game Room, Firepit + Baby Gear
9.8 out of 10, Exceptional, (34)
"The stay was great everything was awesome, everything was clean and the host was very friendly."
The price is AU$662
includes taxes & fees
25 Oct - 26 Oct
Family-Fun Escape w/ Pool, Game Room, Firepit + Baby Gear
Welcoming 3-bedroom house with AC in charming Middlesboro
The price is AU$368
includes taxes & fees
5 Nov - 6 Nov
Welcoming 3-bedroom house with AC in charming Middlesboro
Newly Listed-Private 25-Acre Escape Near Red River Gorge
10.0 out of 10, Exceptional, (1)
The price is AU$540
includes taxes & fees
4 Nov - 5 Nov
Newly Listed-Private 25-Acre Escape Near Red River Gorge
The Ranger's Retreat
7.6 out of 10, Good, (7)
"We had a long drive and this was an awesome place to rest. Beds were very comfortable and the home had all the conveniences we needed."
The price is AU$620
includes taxes & fees
21 Oct - 22 Oct
The Ranger's Retreat
NEW Unique Silo | Hot Tub | King Beds | Sleeps 6
2.0 star property
The price is AU$565
includes taxes & fees
5 Nov - 6 Nov
NEW Unique Silo | Hot Tub | King Beds | Sleeps 6
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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