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Search Winchester Cottage Rentals from CA $107

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Browse Select Winchester Cottages

1 bed cottage, grill, fire pit, Very close to Red River Gorge!!

8.6 out of 10, Excellent, (20)
"This cottage was such a great place to come back to after a long day of hiking and exploring Red River Gorge. Super cute in & outside with a beautiful landscape. We also had visits from a local cat every morning and night and he was so extremely sweet and made the trip all the more better."
1 bed cottage, grill, fire pit, Very close to Red River Gorge!!

Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!

10.0 out of 10, Exceptional, (272)
"Peaceful, relaxing, really enjoyed it"
The price is CA $186
CA $331 total
includes taxes & fees
Aug 18 - Aug 19
Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!

3 bedroom cottage on horse farm close to Kentucky Horse Park, Keeneland, the Ark

10.0 out of 10, Exceptional, (1)
"Amazing location, horses right outside the window. Perfect for the whole family"
The price is CA $274
CA $604 total
includes taxes & fees
Aug 11 - Aug 12
3 bedroom cottage on horse farm close to Kentucky Horse Park, Keeneland, the Ark

Mountaintop Cottage

2.0 star property
10.0 out of 10, Exceptional, (13)
"The cabin was in an excellent location and was very clean! The host was super helpful with providing directions and answering questions."
The price is CA $200
CA $282 total
includes taxes & fees
Aug 6 - Aug 7
Mountaintop Cottage

Unique, Cozy Stay near Red River Gorge

7.6 out of 10, Good, (5)
"Love it ❤️"
The price is CA $107
CA $201 total
includes taxes & fees
Aug 6 - Aug 7
Unique, Cozy Stay near Red River Gorge

Cozy 1 bedroom cottage on picturesque horse farm

10.0 out of 10, Exceptional, (37)
"Everything about our stay was perfect! We had everything we needed in the cottage and it was very clean. Walking out & seeing the horses & sitting on the porch was very relaxing. "
Cozy 1 bedroom cottage on picturesque horse farm

Springside BoHo Getaway

10.0 out of 10, Exceptional, (46)
"We truly enjoyed our stay for our girls trip! The beds were SOOOOO comfortable and the house was clean and well stocked with everything we needed. It was convenient to walk to the local restaurants. Would stay again for sure! "
The price is CA $207
CA $422 total
includes taxes & fees
Sep 1 - Sep 2
Springside BoHo Getaway

Bungalow | 1 Bed, 0.5 Bath

9.6 out of 10, Exceptional, (5)
"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 CA $149
CA $279 total
includes taxes & fees
Aug 6 - Aug 7
Bungalow | 1 Bed, 0.5 Bath

1,600 Acres | Pool | Pond | Fishing | | WiFi near Red River Gorge, KY!

8.6 out of 10, Excellent, (17)
"It was really nice clean.Beautiful place we would definitely stay again."
1,600 Acres | Pool | Pond | Fishing | | WiFi near Red River Gorge, KY!

Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre

3.0 star property
10.0 out of 10, Exceptional, (1)
"The cabin was adorable and had everything we needed for a weekend getaway. The host was very responsive, and we had a wonderful trip! "
The price is CA $149
CA $320 total
includes taxes & fees
Aug 6 - Aug 7
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre

Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY

10.0 out of 10, Exceptional, (13)
"Simply a great experience start to finish"
Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY

Cozy Cottage Perfect for Girls Night Away

10.0 out of 10, Exceptional, (9)
"We loved everything about our stay at the charming Lady Clay!! Can't recommend it enough!"
The price is CA $426
CA $831 total
includes taxes & fees
Aug 11 - Aug 12
Cozy Cottage Perfect for Girls Night Away

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!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Very nice property, very clean."
Georgetown Home ~ 6 Mi to Kentucky Horse Park!

Lexington Getaway w/ Backyard Deck < 2 Mi to UK!

3.0 star property
Lexington Getaway w/ Backyard Deck < 2 Mi to UK!

Lexington Home ~ 2 Mi to University of Kentucky!

3.0 star property
Lexington Home ~ 2 Mi to University of Kentucky!

10 Mi to Keeneland: Family Home w/ Deck & Yard

3.0 star property
10.0 out of 10, Exceptional, (1)
"I liked the porch and the pergola. My granddaughter ran around the house in bare feet and her feet got incredibly dirty. Floors probably need a good cleaning. That was the only begative i had."
10 Mi to Keeneland: Family Home w/ Deck & Yard

Quaint Creekside Cottage w/ Porch & Backyard!

3.0 star property
Quaint Creekside Cottage w/ Porch & Backyard!

Cozy Georgetown Cottage on a Working Horse Farm!

10.0 out of 10, Exceptional, (1)
"Had the most wonderful stay what a beautiful place."
Cozy Georgetown Cottage on a Working Horse Farm!

Family Home w/ Ping-pong & Fire Pit in Lexington

3.0 star property
Family Home w/ Ping-pong & Fire Pit in Lexington
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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Top Winchester Hotel Reviews