Holiday Homes in Eastern Kentucky

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Featured Holiday Homes in Eastern Kentucky

Our top choices for Eastern Kentucky holiday homes

Cozy Creekside Tiny Home w/ Full Kitchen - Walk to Distillery
Smart TV

Cozy Creekside Tiny Home w/ Full Kitchen - Walk to Distillery

The price is AU$231
includes taxes & fees
23 Sept - 24 Sept
Cozy Creekside Tiny Home w/ Full Kitchen - Walk to Distillery
Cheerful Three Bedroom Residential Home
Dining

Cheerful Three Bedroom Residential Home

The price is AU$726
includes taxes & fees
4 Sept - 5 Sept
Cheerful Three Bedroom Residential Home
Uncle Jim's Country Hide-a-way
Fridge, microwave, oven, stovetop

Uncle Jim's Country Hide-a-way

2.0 star property
10.0 out of 10, Exceptional, (13)
"We really enjoyed the peace and quiet and the animals "
The price is AU$411
includes taxes & fees
24 Aug - 25 Aug
Uncle Jim's Country Hide-a-way
Squirrel Kit-Hillside Cottage
1 bedroom, desk, WiFi, bed sheets

Squirrel Kit-Hillside Cottage

10.0 out of 10, Exceptional, (8)
"Great weekend getaway. Had a wonderful time at this property and I highly recommend, we will be going back for sure"
The price is AU$336
includes taxes & fees
4 Sept - 5 Sept
Squirrel Kit-Hillside Cottage
Cozy cabin with Full Kitchen on a pond in charming Corbin
Property grounds

Cozy cabin with Full Kitchen on a pond in charming Corbin

9.0 out of 10, Wonderful, (2)
"Such a cute cozy cabin. Very quiet and peaceful. Perfect for my hubs and I. Host was fantastic to deal with. Very good at communicating, super helpful and just all around a super nice and welcoming person. Housekeeping was spotless! Housekeeper was very accomodating, helpful and friendly. 10 out of 5 stars. "
The price is AU$202
includes taxes & fees
25 Aug - 26 Aug
Cozy cabin with Full Kitchen on a pond in charming Corbin
Froggy Bottom Tiny House
Terrace/patio

Froggy Bottom Tiny House

9.8 out of 10, Exceptional, (7)
"This is a true tiny home. The inside setup was perfect, allowing who ever is staying plenty of room for cooking, playing games or just simply relaxing while still getting that tiny house feeling. Beautiful area and so easy to get to. I will recommend froggy bottom"
Froggy Bottom Tiny House
Cozy Home in Heart of Prestonsburg
Interior

Cozy Home in Heart of Prestonsburg

10.0 out of 10, Exceptional, (8)
"Great location, quite, adequate"
The price is AU$273
includes taxes & fees
1 Sept - 2 Sept
Cozy Home in Heart of Prestonsburg
Charming 3-bedroom rustic cabin with WiFi in wonderful Williamsburg
Interior

Charming 3-bedroom rustic cabin with WiFi in wonderful Williamsburg

10.0 out of 10, Exceptional, (5)
The price is AU$518
includes taxes & fees
25 Aug - 26 Aug
Charming 3-bedroom rustic cabin with WiFi in wonderful Williamsburg
'Longspur' - One of our cute and tidy Lookout Cabins
Exterior

'Longspur' - One of our cute and tidy Lookout Cabins

'Longspur' - One of our cute and tidy Lookout Cabins
360 Degree Mountain View
5 bedrooms, iron/ironing board, free WiFi, bed sheets

360 Degree Mountain View

9.8 out of 10, Exceptional, (8)
"Family reunion great time! "
The price is AU$470
includes taxes & fees
24 Aug - 25 Aug
360 Degree Mountain View
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
2 bedrooms, iron/ironing board, free WiFi, bed sheets

4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,

10.0 out of 10, Exceptional, (12)
"We really enjoyed the house and property. The history of the home is very interesting. Everything was very comfortable. "
The price is AU$326
includes taxes & fees
4 Sept - 5 Sept
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
Private Suite on Eastern Kentucky Farm with Indoor Pickleball Court
Exterior

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$195
includes taxes & fees
25 Aug - 26 Aug
Private Suite on Eastern Kentucky Farm with Indoor Pickleball Court
Family-Fun Escape w/ Pool, Game Room, Firepit + Baby Gear
Dining

Family-Fun Escape w/ Pool, Game Room, Firepit + Baby Gear

9.8 out of 10, Exceptional, (31)
"The stay was great everything was awesome, everything was clean and the host was very friendly."
The price is AU$654
includes taxes & fees
27 Aug - 28 Aug
Family-Fun Escape w/ Pool, Game Room, Firepit + Baby Gear
Treetop Escape | Hot Tub | Fire Pit & Epic Views
Beach

Treetop Escape | Hot Tub | Fire Pit & Epic Views

10.0 out of 10, Exceptional, (19)
"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$444
includes taxes & fees
24 Aug - 25 Aug
Treetop Escape | Hot Tub | Fire Pit & Epic Views
The House on Park Avenue
Comfort House | Private kitchen

The House on Park Avenue

3.5 star property
The price is AU$622
includes taxes & fees
24 Aug - 25 Aug
The House on Park Avenue
King Luxe Retreat - Pets Welcome, Fenced Yard,
Private kitchen

King Luxe Retreat - Pets Welcome, Fenced Yard,

10.0 out of 10, Exceptional, (10)
"Very nice home to stay at for our trip. "
The price is AU$422
includes taxes & fees
24 Aug - 25 Aug
King Luxe Retreat - Pets Welcome, Fenced Yard,
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Property grounds

Charming 3-bedroom house with WiFi, AC in Pineville Kentucky

10.0 out of 10, Exceptional, (1)
The price is AU$432
includes taxes & fees
24 Aug - 25 Aug
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Overlook Oasis! RRG, A-frame Cabin, NEW HOT TUB, Grill! Pet friendly
Interior

Overlook Oasis! RRG, A-frame Cabin, NEW HOT TUB, Grill! Pet friendly

9.0 out of 10, Wonderful, (7)
"Listing has "New Hot Tub" in it...the hot tub and the supporting deck for it had not been built. The owner failed to mention this to us, until 24 hours before we showed up. Then asked if we wanted a discount or refund on the stay. We asked for a discount. Still waiting on that discount to be refunded to my account... This place is hard to get to, the directions on the listing aern't great. The listing shows that it sleeps 4....the love seat is barely big enough to fit 1 human on it. Maybe two...
The price is AU$470
includes taxes & fees
24 Aug - 25 Aug
Overlook Oasis! RRG, A-frame Cabin, NEW HOT TUB, Grill! Pet friendly
WiFi, Hot Tub, Pets, Prime Location in Red River Gorge!
Exterior

WiFi, Hot Tub, Pets, Prime Location in Red River Gorge!

9.4 out of 10, Exceptional, (23)
"Location is good for Gorge & Natural Bridge"
The price is AU$388
includes taxes & fees
4 Sept - 5 Sept
WiFi, Hot Tub, Pets, Prime Location in Red River Gorge!
The Nest - Cozy Loft, Deck & Firepit
Outdoor dining

The Nest - Cozy Loft, Deck & Firepit

The Nest - Cozy Loft, Deck & Firepit
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 Eastern Kentucky Hotel Reviews

Cumberland Falls State Resort Park

Cumberland Falls State Resort Park

10/10 Excellent
"Older property but loved the tranquility! "
Amy 1-night trip
Posted 1 day ago
Cumberland Falls State Resort Park