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Compare 34 Cottages in Winchester with updated reviews, rates, and availability.

Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!
Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!
10.0 out of 10, Exceptional, (261)
The price is SAR 656
SAR 1,149 total
includes taxes & fees
2 Apr - 3 Apr

Cozy 1 bedroom cottage on picturesque horse farm
Cozy 1 bedroom cottage on picturesque horse farm
10.0 out of 10, Exceptional, (25)

1 bed cottage, grill, fire pit, Very close to Red River Gorge!!
1 bed cottage, grill, fire pit, Very close to Red River Gorge!!
8.8 out of 10, Excellent, (13)

Mountaintop Cottage
Mountaintop Cottage
10.0 out of 10, Exceptional, (6)
The price is SAR 506
SAR 724 total
includes taxes & fees
2 Apr - 3 Apr

Springside BoHo Getaway
Springside BoHo Getaway
10.0 out of 10, Exceptional, (39)
The price is SAR 563
SAR 1,050 total
includes taxes & fees
2 Apr - 3 Apr

Bungalow | 1 Bed, 0.5 Bath
Bungalow | 1 Bed, 0.5 Bath
10.0 out of 10, Exceptional, (3)
The price is SAR 405
SAR 755 total
includes taxes & fees
2 Apr - 3 Apr

1,600 Acres | Pool | Pond | Fishing | | WiFi near Red River Gorge, KY!
1,600 Acres | Pool | Pond | Fishing | | WiFi near Red River Gorge, KY!
8.4 out of 10, Very Good, (15)

Unique, Cozy Stay near Red River Gorge
Unique, Cozy Stay near Red River Gorge
9.0 out of 10, Wonderful, (2)
The price is SAR 272
SAR 504 total
includes taxes & fees
13 Apr - 14 Apr
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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Other property types in Winchester

Natural Bridge State Resort Park
Natural Bridge State Resort Park
8.6 out of 10, Excellent, (1510)
The price is SAR 454
SAR 500 total
includes taxes & fees
8 Apr - 9 Apr

Hot Tub & WiFi - Romantic Hideaway - Wooded Retreat near Red River Gorge, Kentucky!
Hot Tub & WiFi - Romantic Hideaway - Wooded Retreat near Red River Gorge, Kentucky!
9.2 out of 10, Wonderful, (75)
The price is SAR 577
SAR 999 total
includes taxes & fees
14 Apr - 15 Apr

Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!
Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!
9.6 out of 10, Exceptional, (138)
The price is SAR 425
SAR 864 total
includes taxes & fees
13 Apr - 14 Apr
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.
Recent reviews of Winchester hotels
Recent reviews of Winchester hotels

Hyatt Regency Lexington
5/5 Excellent
"It was a great stay"
A verified traveler stayed at Hyatt Regency Lexington
Posted 1 day ago