Montgomery County Holiday Rentals from €87: Search Short-Term Rentals

A river winding through a densely forested valley with rocky cliffs on one side.

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Our top choices for Montgomery County holiday rentals

1. The PawPlex a Cozy 1-bedroom apartment in marvelous Mount Sterling

Mount Sterling

Miguel

1 bedroom, iron/ironing board, WiFi, bed sheets

2. 5 o'clock somewhere in Mt Sterling

Mount Sterling

Trey S.

includes taxes & fees

13 Aug - 14 Aug

3. 1 Bedroom Bourbon House on the Hill

Mount Sterling

Anne D.

includes taxes & fees

25 Aug - 26 Aug

4. Cozy, Bright Home in Historic Downtown

Mount Sterling

Brittany K.

includes taxes & fees

17 Aug - 18 Aug

5. New, Cozy, Secluded Cabin

Jeffersonville

Edgar O.

includes taxes & fees

13 Aug - 14 Aug

6. Hunting Lodge in the City

Mount Sterling

includes taxes & fees

25 Aug - 26 Aug

Cabin, 2 Bedrooms, Kitchen | Living area

7. Natural Bridge State Resort Park

Slade

Jeff

includes taxes & fees

20 Aug - 21 Aug

8. BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK

Stanton

Donnie W.

includes taxes & fees

13 Aug - 14 Aug

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Top Montgomery County Hotel Reviews

Holiday Inn Express & Suites Mt Sterling North by IHG

8/10 Good

"The building needs some technical, but it's not prohibitive. Overall decent."

BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK

10/10 Excellent

"This was a birthday getaway for my son and husband and we had such an amazing, relaxing trip! The cabin was so clean and comfortable. It’s a great location and we loved everything about it! Host was great as well! We hope to return in the future! 10/10 :)"

Higher Standards-RRG-Hot Tub- Hand Crafted Detail

10/10 Excellent

"We LOVED the cabin and its private location--both are SUPERB! Our suggestions: (1) Given the cabin's lack of proximity to a grocery store, a few more provided amenities would be greatly appreciated; and(2) The only road to/from the cabin is several miles long and NOT advisable by 2WD vehicle--especially the LONG, STEEP concrete switchback and several of the heavily rutted and steep gravel sections--our front wheel drive Chevy Trax made it, but only with heavy tire/wheel slip (including on the concrete section due to its extreme grade). We would HIGHLY recommend only accessing the cabin with AWD, at a minimum, and ideally 4WD. Beyond those two friendly suggestions, we loved our stay--thanks so much!"

Mountain Modern | Hot Tub, Near Natural Bridge

10/10 Excellent

"We really enjoyed our stay\! The property was very nice, clean, and comfortable\. The only downside was that the directions to the property were difficult to follow, which made finding it a bit frustrating\. It also would have been nice to have a microwave and a Keurig coffee maker available\. Other than those minor issues, it was a great place to stay, and we would definitely consider staying here again\. The hot tub was fantastic!"

Turning Leaf Cabin 1 in the Red River Gorge• Pet Friendly• Hi Speed 🛜

8/10 Good

"This is a cute little cabin. It is conveniently located to a lot of trails and attractions. The people here are friendly. They were definitely dog friendly - which we love.If I could make a couple of suggestions - it would be to add more storage to the kitchen. There is no where to really put any non-refrigerated food. There is no counter space at all. A longer chain on the ceiling fan in the bedroom would have been nice instead of having to stand on the bed to turn off the light in order to keep the ceiling fan on. Lastly - it was disruptive to have someone working/doing laundry at 8 am right behind the wall where we were still trying to sleep on the morning of check out. Check out time is not till 10 am and we really could have used the sleep before heading out on our 3 hour trip home. Other than that our time here was great."

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Holiday Homes in Montgomery County

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Room 1

Change your mind

Treat yourself

Be picky

Our top choices for Montgomery County holiday rentals

1. The PawPlex a Cozy 1-bedroom apartment in marvelous Mount Sterling

2. 5 o'clock somewhere in Mt Sterling

3. 1 Bedroom Bourbon House on the Hill

4. Cozy, Bright Home in Historic Downtown

5. New, Cozy, Secluded Cabin

6. Hunting Lodge in the City

7. Natural Bridge State Resort Park

8. BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK

9. Mountaintop Cottage

10. Mountain Memories Cabin

11. Briar Patch Cabin RRG: Firepit, Sunset, WIFI

12. STOP SCROLLING!-HOT TUB-HIGH SPEED WIFI-SUPER CLEAN-NATURAL BRIDGE-NADA TUNNEL

13. Spacious Secluded Cabin on 100 Acres Near Red River Gorge

14. The Stillhouse Cabin, mins from Red River Gorge

15. Conveniently Located ~ WiFi ~ Central Heat & Air.

16. PRIVATE SHIPPING CONTAINER CABIN IN THE WOODS-RED RIVER GORGE-VERY CLEAN-HOT TUB

17. Cabin in Kentucky Horse Country

18. Plum Crazy: Frenchburg Cabin on 1 Acre

19. MY SHIPPING CONTAINER CABIN-SUPER CLEAN-KING BEDS-HOT TUB-VIEW-HI SPEED WIFI-RRG

20. Quaint, heavily forested cabin, mountain valley view.

Find holiday rentals that suit your style

Top Montgomery County Hotel Reviews

Holiday Inn Express & Suites Mt Sterling North by IHG

Black Bear Lodge Motel

Baymont by Wyndham Winchester

BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK

Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge

Wolf Pup- A Frame- Hillside Tiny Cottage Wi-Fi

Higher Standards-RRG-Hot Tub- Hand Crafted Detail

Mountain Modern | Hot Tub, Near Natural Bridge

Turning Leaf Cabin 1 in the Red River Gorge• Pet Friendly• Hi Speed 🛜

Find out more about Montgomery County

Holiday Homes in Montgomery County

Holiday Rentals in Montgomery County

Change your mind

Treat yourself

Be picky

Our top choices for Montgomery County holiday rentals

1. The PawPlex a Cozy 1-bedroom apartment in marvelous Mount Sterling

2. 5 o'clock somewhere in Mt Sterling

3. 1 Bedroom Bourbon House on the Hill

4. Cozy, Bright Home in Historic Downtown

5. New, Cozy, Secluded Cabin

6. Hunting Lodge in the City

7. Natural Bridge State Resort Park

8. BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK

9. Mountaintop Cottage

10. Mountain Memories Cabin

11. Briar Patch Cabin RRG: Firepit, Sunset, WIFI

12. STOP SCROLLING!-HOT TUB-HIGH SPEED WIFI-SUPER CLEAN-NATURAL BRIDGE-NADA TUNNEL

13. Spacious Secluded Cabin on 100 Acres Near Red River Gorge

14. The Stillhouse Cabin, mins from Red River Gorge

15. Conveniently Located ~ WiFi ~ Central Heat & Air.

16. PRIVATE SHIPPING CONTAINER CABIN IN THE WOODS-RED RIVER GORGE-VERY CLEAN-HOT TUB

17. Cabin in Kentucky Horse Country

18. Plum Crazy: Frenchburg Cabin on 1 Acre

19. MY SHIPPING CONTAINER CABIN-SUPER CLEAN-KING BEDS-HOT TUB-VIEW-HI SPEED WIFI-RRG

20. Quaint, heavily forested cabin, mountain valley view.

Find holiday rentals that suit your style

Top Montgomery County Hotel Reviews

Holiday Inn Express & Suites Mt Sterling North by IHG

Find out more about Montgomery County

Holiday Homes in Montgomery County