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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, (263)
The price is SAR 657
SAR 1,158 total
includes taxes & fees
27 Apr - 28 Apr

Cozy 1 bedroom cottage on picturesque horse farm
Cozy 1 bedroom cottage on picturesque horse farm
10.0 out of 10, Exceptional, (27)

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, (15)

Mountaintop Cottage
Mountaintop Cottage
10.0 out of 10, Exceptional, (8)
The price is SAR 507
SAR 724 total
includes taxes & fees
10 May - 11 May

Springside BoHo Getaway
Springside BoHo Getaway
10.0 out of 10, Exceptional, (40)
The price is SAR 563
SAR 1,059 total
includes taxes & fees
21 Apr - 22 Apr

Bungalow | 1 Bed, 0.5 Bath
Bungalow | 1 Bed, 0.5 Bath
10.0 out of 10, Exceptional, (3)

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
20 Apr - 21 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, (1526)
The price is SAR 435
SAR 480 total
includes taxes & fees
29 Apr - 30 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, (141)
The price is SAR 425
SAR 864 total
includes taxes & fees
11 May - 12 May

Tranquil Getaway in the Woods ~ Sunset Ridge
Tranquil Getaway in the Woods ~ Sunset Ridge
9.8 out of 10, Exceptional, (53)
The price is SAR 394
SAR 558 total
includes taxes & fees
22 Apr - 23 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

Days Inn Lexington SE/Hamburg
5/5 Excellent
"Staff is wonderful! Clean pet friendly place close to both interstate and town for shopping. Wonderful place to stay!! "
A verified traveler stayed at Days Inn Lexington SE/Hamburg
Posted 15 hours ago