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Find vacation rentals that suit your style

Cabins

Apartments
Our top choices for Winchester cabin rentals

1. Natural Bridge State Resort Park
Natural Bridge State Resort ParkSlade
8.6 out of 10, Excellent, (2,141 reviews)
$70 nightly
The price is $77
Dec 6 - Dec 7
Total with taxes and fees

2. 1800’s Historical Log Cabin near I-75 Interstate
1800’s Historical Log Cabin near I-75 InterstateLexington
9.4 out of 10, Exceptional, (86 reviews)
$209 nightly
The price is $243
Nov 16 - Nov 17
Total with taxes and fees

3. Unique Stay in a 1907 Log Cabin on The Kentucky River
Unique Stay in a 1907 Log Cabin on The Kentucky RiverLexington
9.6 out of 10, Exceptional, (114 reviews)
$155 nightly
The price is $180
Nov 17 - Nov 18
Total with taxes and fees

4. Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge
Sunset Ridge Cabin – Hilltop Sunset Views Near Red River GorgeIrvine
10.0 out of 10, Exceptional, (134 reviews)
$184 nightly
The price is $202
Nov 16 - Nov 17
Total with taxes and fees

5. Cabin in Kentucky Horse Country
Cabin in Kentucky Horse CountryBourbon County
10.0 out of 10, Exceptional, (82 reviews)
$428 nightly
The price is $465
Nov 16 - Nov 17
Total with taxes and fees

6. Romantic RRG Cabin • Private Hot Tub • Amazing Views • Near Natural Bridge
Romantic RRG Cabin • Private Hot Tub • Amazing Views • Near Natural BridgeStanton
10.0 out of 10, Exceptional, (141 reviews)
$235 nightly
The price is $259
Nov 16 - Nov 17
Total with taxes and fees

7. New, Cozy, Secluded Cabin
New, Cozy, Secluded CabinJeffersonville
8.4 out of 10, Very good, (9 reviews)
$179 nightly
The price is $196
Nov 17 - Nov 18
Total with taxes and fees

8. Dappled Grey Cabin with hot tub at Red River Gorge
Dappled Grey Cabin with hot tub at Red River GorgeStanton
10.0 out of 10, Exceptional, (8 reviews)
$162 nightly
The price is $166
Nov 17 - Nov 18
Total with taxes and fees

9. Social Distance/127 Private Acres -Hot Tub -Wi-Fi
Social Distance/127 Private Acres -Hot Tub -Wi-FiIrvine
9.6 out of 10, Exceptional, (4 reviews)
$315 nightly
The price is $326
Nov 30 - Dec 1
Total with taxes and fees

10. Mountain Memories Cabin
Mountain Memories CabinStanton
10.0 out of 10, Exceptional, (100 reviews)
$149 nightly
The price is $164
Nov 16 - Nov 17
Total with taxes and fees

11. Trailer Parking/Hot Tub/King Size Beds/Mt Views
Trailer Parking/Hot Tub/King Size Beds/Mt ViewsStanton
10.0 out of 10, Exceptional, (1 review)
$262 nightly
The price is $288
Nov 17 - Nov 18
Total with taxes and fees

12. Private RRG Cabin • Hot Tub • 2BR • Secluded in the Woods
Private RRG Cabin • Hot Tub • 2BR • Secluded in the WoodsStanton
10.0 out of 10, Exceptional, (345 reviews)
$257 nightly
The price is $283
Nov 19 - Nov 20
Total with taxes and fees

13. Romantic Red River Gorge Cabin • Private Hot Tub • Secluded Escape
Romantic Red River Gorge Cabin • Private Hot Tub • Secluded EscapeStanton
10.0 out of 10, Exceptional, (51 reviews)
$235 nightly
The price is $259
Nov 16 - Nov 17
Total with taxes and fees

14. Romantic Red River Gorge Cabin • Hot Tub • Quiet Escape
Romantic Red River Gorge Cabin • Hot Tub • Quiet EscapeStanton
10.0 out of 10, Exceptional, (183 reviews)
$235 nightly
The price is $259
Nov 16 - Nov 17
Total with taxes and fees

15. 3 Miles Hollerwood/ATV Parking/Mountain Views
3 Miles Hollerwood/ATV Parking/Mountain ViewsZoe
9.8 out of 10, Exceptional, (10 reviews)
$218 nightly
The price is $240
Nov 16 - Nov 17
Total with taxes and fees

16. Private | Hot Tub | Stargazing | Mountain View
Private | Hot Tub | Stargazing | Mountain ViewStanton
9.8 out of 10, Exceptional, (8 reviews)
$307 nightly
The price is $330
Dec 16 - Dec 17
Total with taxes and fees

17. Sandstone-Cozy Cliffside Cabin, Hot Tub + Fire Pit
Sandstone-Cozy Cliffside Cabin, Hot Tub + Fire PitStanton
$280 nightly
The price is $309
Nov 24 - Nov 25
Total with taxes and fees

18. Cozy RRG Cabin • King Beds • Hot Tub • Views
Cozy RRG Cabin • King Beds • Hot Tub • ViewsStanton
10.0 out of 10, Exceptional, (392 reviews)
$265 nightly
The price is $292
Nov 23 - Nov 24
Total with taxes and fees

19. Plum Crazy: Hot Tub Cabin in Frenchburg
Plum Crazy: Hot Tub Cabin in FrenchburgFrenchburg
9.6 out of 10, Exceptional, (17 reviews)
$265 nightly
The price is $292
Nov 16 - Nov 17
Total with taxes and fees

20. Quaint, heavily forested cabin, mountain valley view.
Quaint, heavily forested cabin, mountain valley view.Slade
8.4 out of 10, Very good, (47 reviews)
$190 nightly
The price is $209
Nov 17 - Nov 18
Total with taxes and fees
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.
Learn more about Winchester
Stroll through charming downtown streets lined with local shops and eateries. Tee off at Cassell Creek or Southwind Golf Course, then explore local history at the Bluegrass Heritage Museum.
































































