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Compare 29 Cottages in Winchester with updated reviews, rates, and availability.

1 bed cottage, grill, fire pit, Very close to Red River Gorge!!
Exterior
1 bed cottage, grill, fire pit, Very close to Red River Gorge!!
9.0 out of 10, Wonderful, (4)
"Quaint little cabin. Close to Red river gorge. People were friendly "
1 bed cottage, grill, fire pit, Very close to Red River Gorge!!
Homey Horse Farm Hideaway ~ 6 Mi to KY Horse Park!
Lexington Vacation Rental | Cottage | 1BR | 1BA | 800 Sq Ft
Homey Horse Farm Hideaway ~ 6 Mi to KY Horse Park!
9.8 out of 10, Exceptional, (55)
"This was a beautiful and peaceful place to stay, with horses and colts everywhere. The cottage is so neat, clean, and inviting, and had every amenity you could think of. The owner is very friendly and the grounds are gorgeous. We will definitely make this a destination for future getaways."
Homey Horse Farm Hideaway ~ 6 Mi to KY Horse Park!
Cozy 1 bedroom cottage on picturesque horse farm
Exterior
Cozy 1 bedroom cottage on picturesque horse farm
10.0 out of 10, Exceptional, (20)
"The cottage is situated on a beautiful farm with horses all around. Within a short drive of Georgetown. Excellent facilities and very comfortable. "
Cozy 1 bedroom cottage on picturesque horse farm
Springside BoHo Getaway
Master Bedroom
Springside BoHo Getaway
10.0 out of 10, Exceptional, (30)
"Awesome location and such a boho chic place! Owner communication was outstanding. Only thing is the stairs to the loft was challenging to walk up if you’re not extremely sure footed. Also lighting is pretty non existent for the flight up/down. Otherwise, it was perfect."
The price is AED 551
AED 1,037 total
includes taxes & fees
23 Sep - 24 Sep
Springside BoHo Getaway
Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY
Fenced and gated entry for this private home on a wooded lot
Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY
10.0 out of 10, Exceptional, (11)
"Four adults stayed at the house for the Railbird Festival and it was absolutely perfect. The house was clean and decorated beautifully. We couldn’t have been happier. Thanks for a great weekend!"
Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY
Bungalow | 1 Bed, 0.5 Bath
The Bungalow
Bungalow | 1 Bed, 0.5 Bath
10.0 out of 10, Exceptional, (3)
"If you're looking for an off grid sleeping porch in the red river gorge, this one has a nice wooded view."
The price is AED 397
AED 739 total
includes taxes & fees
23 Sep - 24 Sep
Bungalow | 1 Bed, 0.5 Bath
Cedar Creek Cottage - Hot Tub, Modern, Private!
Cedar Creek Cottage - Hot Tub, Modern, Private!
9.6 out of 10, Exceptional, (5)
"Great place to stay, super clean and modern. The only thing is the driveway is not motorcyclist friendly so we parked on the other side of the house in the grass but no complaints otherwise"
Cedar Creek Cottage - Hot Tub, Modern, Private!
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, (13)
"Very nice place to stay, clean, quiet, and mostly as described. The view and pool were great. One clarification that could be made is that the pond is in the field with the cattle. And use caution when fishing, there is a hornets nest. Overall I’d recommend staying at this house."
1,600 Acres | Pool | Pond | Fishing | | WiFi near Red River Gorge, KY!
Hot Tub & WiFi - Mimi's Hideaway - Budget-Friendly Escape in Red River Gorge, Kentucky!
Hot Tub & WiFi - Mimi's Hideaway - Budget-Friendly Escape in Red River Gorge, Kentucky!
9.4 out of 10, Exceptional, (40)
"Cozy environment, loved the hot tub ,quite relaxing place,"
Hot Tub & WiFi - Mimi's Hideaway - Budget-Friendly Escape in Red River Gorge, Kentucky!
Unique, Cozy Stay near Red River Gorge
Unique, Cozy Stay near Red River Gorge
9.0 out of 10, Wonderful, (2)
"Love it ❤️"
Unique, Cozy Stay near Red River Gorge
Cozy Georgetown Cottage on a Working Horse Farm!
Georgetown Vacation Rental | 2BR | 1BA | 1,200 Sq Ft | 1 Step Required
Cozy Georgetown Cottage on a Working Horse Farm!
10.0 out of 10, Exceptional, (1)
Cozy Georgetown Cottage on a Working Horse Farm!
Cozy Cottage Perfect for Girls Night Away
The coziest pink couch!
Cozy Cottage Perfect for Girls Night Away
10.0 out of 10, Exceptional, (7)
"The house is adorable and was perfect for my daughter’s birthday sleepover!! The girls and Moms all loved it!"
The price is AED 1,429
AED 2,626 total
includes taxes & fees
23 Sep - 24 Sep
Cozy Cottage Perfect for Girls Night Away
Peaceful Mt Sterling Cabin: Deck & Fire Pit!
Property grounds
Peaceful Mt Sterling Cabin: Deck & Fire Pit!
3.0 star property
10.0 out of 10, Exceptional, (1)
Peaceful Mt Sterling Cabin: Deck & Fire Pit!
Georgetown Home ~ 6 Mi to Kentucky Horse Park!
Exterior
Georgetown Home ~ 6 Mi to Kentucky Horse Park!
3.0 star property
Georgetown Home ~ 6 Mi to Kentucky Horse Park!
Lexington Getaway w/ Backyard Deck < 2 Mi to UK!
Exterior
Lexington Getaway w/ Backyard Deck < 2 Mi to UK!
3.0 star property
Lexington Getaway w/ Backyard Deck < 2 Mi to UK!
Historic JC Cock House - Downtown Lexington KY
Welcome to the JC Cock House. A quaint cottage in the heart of the Bluegrass.
Historic JC Cock House - Downtown Lexington KY
10.0 out of 10, Exceptional, (1)
"Our family loved staying at the historic home in Lexington. The house and gardens are beautiful. John is a wonderful host who thought of everything for the house. Decorating is tops. Gardens are lovey and lush. Great stop for our weekend trip to KY."
Historic JC Cock House - Downtown Lexington KY
Homey Horse Farm Hideaway ~ 6 Mi to KY Horse Park!
Living area
Homey Horse Farm Hideaway ~ 6 Mi to KY Horse Park!
2.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful setting! "
Homey Horse Farm Hideaway ~ 6 Mi to KY Horse Park!
Quaint Creekside Cottage w/ Porch & Backyard!
Exterior
Quaint Creekside Cottage w/ Porch & Backyard!
3.0 star property
Quaint Creekside Cottage w/ Porch & Backyard!
Lexington Home ~ 2 Mi to University of Kentucky!
Living area
Lexington Home ~ 2 Mi to University of Kentucky!
3.0 star property
Lexington Home ~ 2 Mi to University of Kentucky!
Lexington Home ~ 5 Mi to University of Kentucky!
Living area
Lexington Home ~ 5 Mi to University of Kentucky!
3.0 star property
Lexington Home ~ 5 Mi to University of Kentucky!
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See all available properties in Winchester
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
Hiking
Natural Bridge State Resort Park
3.5 star property
8.6 out of 10, Excellent, (1413)
"We stayed for the weekend in the lodge. The breakfast and amenities were fine. We liked the location. There was so much to do! Everything was clean and functional. A little out-dated, but charming. We would definitely stay again and we're pleased with our stay. Dan at the Tavern made our night! "
The price is AED 408
AED 449 total
includes taxes & fees
24 Sep - 25 Sep
Natural Bridge State Resort Park
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
9.8 out of 10, Exceptional, (255)
"Really clean place as advertised. Great location"
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB
Property grounds
Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB
10.0 out of 10, Exceptional, (115)
"The property was very nice and clean. The owner was very easy to communicate with! "
The price is AED 547
AED 919 total
includes taxes & fees
26 Sep - 27 Sep
Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB
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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