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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct
1 bed cottage, grill, fire pit, Very close to Red River Gorge!!
Cozy cabin surrounded by lush greenery, featuring a front porch and picnic table.

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!
Stunning two-story home surrounded by a lush lawn and mature trees, offering a serene retreat.

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 HK$1,060
HK$1,886 total
includes taxes & fees
18 Aug - 19 Aug
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
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, (1)
"Amazing location, horses right outside the window. Perfect for the whole family"
The price is HK$1,562
HK$3,444 total
includes taxes & fees
11 Aug - 12 Aug
3 bedroom cottage on horse farm close to Kentucky Horse Park, Keeneland, the Ark
Mountaintop Cottage
Situated in a serene forest, this single-story building offers a peaceful retreat.

Mountaintop Cottage

2.0 star property
10.0 out of 10, Exceptional, (12)
"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$1,138
HK$1,610 total
includes taxes & fees
6 Aug - 7 Aug
Mountaintop Cottage
Unique, Cozy Stay near Red River Gorge
Situated amidst lush surroundings, this charming abode features a cozy front porch and a gabled roof.

Unique, Cozy Stay near Red River Gorge

7.6 out of 10, Good, (5)
"Love it ❤️"
The price is HK$610
HK$1,143 total
includes taxes & fees
6 Aug - 7 Aug
Unique, Cozy Stay near Red River Gorge
Cozy 1 bedroom cottage on picturesque horse farm
Stunning two-story house with a central entrance, flanked by columns, and a charming gabled roof.

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
Traditional two-story building with a symmetrical facade and evenly spaced windows.

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 HK$1,177
HK$2,458 total
includes taxes & fees
18 Aug - 19 Aug
Springside BoHo Getaway
Bungalow | 1 Bed, 0.5 Bath
Escape to a serene forest retreat with a cabin featuring a spacious deck and a large window offering breathtaking views.

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 HK$849
HK$1,589 total
includes taxes & fees
6 Aug - 7 Aug
Bungalow | 1 Bed, 0.5 Bath
1,600 Acres | Pool | Pond | Fishing | | WiFi near Red River Gorge, KY!
Relax by the pool surrounded by a deck with Adirondack chairs and a lounge area.

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
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$848
HK$1,826 total
includes taxes & fees
6 Aug - 7 Aug
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY
Stunning two-story home with a central entrance and two windows on each side, set behind a black metal gate.

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
Relax in a stylish living room with a sofa, armchairs, and a fireplace.

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 HK$2,426
HK$4,738 total
includes taxes & fees
11 Aug - 12 Aug
Cozy Cottage Perfect for Girls Night Away
Peaceful Mt Sterling Cabin: Deck & Fire Pit!
Situated in a natural setting, this cabin features a rustic exterior with a steeply pitched roof and a front porch.

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!
Stroll up to this charming single-story home with a cozy front porch and inviting windows.

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!
Enjoy the peaceful atmosphere of this two-story house with a spacious porch and covered deck, surrounded by a well-manicured lawn.

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
Quaint Creekside Cottage w/ Porch & Backyard!
Enjoy a peaceful stay in this charming single-story house with a cozy porch and beautiful views of the surrounding lawn and trees.

Quaint Creekside Cottage w/ Porch & Backyard!

3.0 star property
Quaint Creekside Cottage w/ Porch & Backyard!
Cozy Georgetown Cottage on a Working Horse Farm!
Guests can enjoy a peaceful retreat with a front porch and outdoor cooking facilities.

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
Interior

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

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

10/10 Excellent
"Staff was friendly and quick. Very clean facility, and was comfortable. Breakfast was hot and fresh. Will stay again next time through!"
Dave 1-night trip
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

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.