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Check prices for these dates

In two weeks
10 Oct - 12 Oct
In two months
21 Nov - 23 Nov
In three months
19 Dec - 21 Dec
In four months
16 Jan - 18 Jan
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!!

8.4 out of 10, Very good, (22)
"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!!
Mountaintop Cottage
Exterior

Mountaintop Cottage

2.0 star property
10.0 out of 10, Exceptional, (18)
"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 HK$1,050
HK$1,501 total
includes taxes & fees
1 Oct - 2 Oct
Mountaintop Cottage
Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!
Exterior

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

10.0 out of 10, Exceptional, (281)
"This is an adorable property on a beautiful farm! Hosts were very kind and attentive. We will definitely stay here the next time we are in Lexington! "
Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!
Cozy Cottage Perfect for Girls Night Away
Interior

Cozy Cottage Perfect for Girls Night Away

9.8 out of 10, Exceptional, (10)
"This place is just charming. We were in town for our daughter’s graduation from UK and your place was perfect. Spacious and so comfy. "
The price is HK$2,723
HK$5,138 total
includes taxes & fees
29 Sept - 30 Sept
Cozy Cottage Perfect for Girls Night Away
3 bedroom cottage on horse farm close to Kentucky Horse Park, Keeneland, the Ark
3 bedrooms, iron/ironing board, WiFi, bed sheets

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

10.0 out of 10, Exceptional, (3)
"Great stay! Will be back again. "
3 bedroom cottage on horse farm close to Kentucky Horse Park, Keeneland, the Ark
Cozy 1 bedroom cottage on picturesque horse farm
Exterior

Cozy 1 bedroom cottage on picturesque horse farm

10.0 out of 10, Exceptional, (41)
"The cottage and surroundings were beautiful. The location was perfect for our planned activities. We look forward to visiting again!"
Cozy 1 bedroom cottage on picturesque horse farm
Unique, Cozy Stay near Red River Gorge
Exterior

Unique, Cozy Stay near Red River Gorge

7.0 out of 10, Good, (8)
"Me and my girlfriend had a great time enjoy the area around were we were staying and had a great time and the people their were nice"
The price is HK$604
HK$1,133 total
includes taxes & fees
28 Sept - 29 Sept
Unique, Cozy Stay near Red River Gorge
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
Interior

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 HK$840
HK$1,819 total
includes taxes & fees
29 Sept - 30 Sept
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
Peaceful Mt Sterling Cabin: Deck & Fire Pit!
Interior

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!
Hike & Climb: Pet-friendly Red River Gorge Cabin!
Interior

Hike & Climb: Pet-friendly Red River Gorge Cabin!

3.0 star property
Hike & Climb: Pet-friendly Red River Gorge Cabin!
Location! Comfy Beds~Hot Tub~6mi KY Horse Park~Walkable
Outdoor dining

Location! Comfy Beds~Hot Tub~6mi KY Horse Park~Walkable

Location! Comfy Beds~Hot Tub~6mi KY Horse Park~Walkable
Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY
Exterior

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
Springside BoHo Getaway
Exterior

Springside BoHo Getaway

9.8 out of 10, Exceptional, (49)
"Jonathon provided a great stay. "
The price is HK$1,167
HK$2,367 total
includes taxes & fees
28 Sept - 29 Sept
Springside BoHo Getaway
Georgetown Home ~ 6 Mi to Kentucky Horse Park!
Front of property

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!
Interior

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!
Interior

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
Front of property

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
Lovely Lexington Home: 4 Mi to Downtown!
Interior

Lovely Lexington Home: 4 Mi to Downtown!

3.0 star property
Lovely Lexington Home: 4 Mi to Downtown!
Quaint Creekside Cottage w/ Porch & Backyard!
Interior

Quaint Creekside Cottage w/ Porch & Backyard!

3.0 star property
Quaint Creekside Cottage w/ Porch & Backyard!
Hike & Fish: Nature Escape Near Licking River!
Interior

Hike & Fish: Nature Escape Near Licking River!

3.0 star property
Hike & Fish: Nature Escape Near Licking River!
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

Spark by Hilton Lexington Hamburg

Spark by Hilton Lexington Hamburg

10/10 Excellent
"Clean"
Britney 1-night trip
Posted 3 days ago
Spark by Hilton Lexington Hamburg

Find out more about Winchester

Find out more about Winchester

Winchester Cottages information

Number of reviews
149
Accommodation
35 Cottages
Lowest Price
HK$1,133
Highest Price
HK$5,138

Frequently asked questions

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What is there to do in Winchester near my cottage?
The most useful travel accessory is a well-planned schedule. Southwind Golf Course is a good spot to start your adventures in Winchester.

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