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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16

Browse Select Winchester Cottages

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

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

10.0 out of 10, Exceptional, (275)
"Peaceful, relaxing, really enjoyed it"
The price is CA $187
CA $336 total
includes taxes & fees
Aug 24 - Aug 25
Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!
1 bed cottage, grill, fire pit, Very close to Red River Gorge!!
Exterior detail

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

8.4 out of 10, Very good, (21)
"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!!
Springside BoHo Getaway
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Springside BoHo Getaway

10.0 out of 10, Exceptional, (47)
"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 $208
CA $430 total
includes taxes & fees
Aug 25 - Aug 26
Springside BoHo Getaway
Mountaintop Cottage
Terrace/patio

Mountaintop Cottage

2.0 star property
10.0 out of 10, Exceptional, (15)
"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 $201
CA $283 total
includes taxes & fees
Sep 14 - Sep 15
Mountaintop Cottage
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 CA $108
CA $202 total
includes taxes & fees
Aug 22 - Aug 23
Unique, Cozy Stay near Red River Gorge
Cozy 1 bedroom cottage on picturesque horse farm
Fridge, microwave, coffee/tea maker, toaster

Cozy 1 bedroom cottage on picturesque horse farm

10.0 out of 10, Exceptional, (38)
"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
Bungalow | 1 Bed, 0.5 Bath
Interior

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 $150
CA $281 total
includes taxes & fees
Aug 22 - Aug 23
Bungalow | 1 Bed, 0.5 Bath
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"
3 bedroom cottage on horse farm close to Kentucky Horse Park, Keeneland, the Ark
1,600 Acres | Pool | Pond | Fishing | | WiFi near Red River Gorge, KY!
Pool

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

8.8 out of 10, Excellent, (18)
"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
House (1 Bedroom) | 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 CA $187
CA $364 total
includes taxes & fees
Aug 24 - Aug 25
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY
Fridge, microwave, oven, stovetop

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
Interior

Cozy Cottage Perfect for Girls Night Away

10.0 out of 10, Exceptional, (9)
"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 CA $428
CA $845 total
includes taxes & fees
Aug 28 - Aug 29
Cozy Cottage Perfect for Girls Night Away
Peaceful Mt Sterling Cabin: Deck & Fire Pit!
House (2 Bedrooms) | Outdoor dining

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!
House (2 Bedrooms) | Interior

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

3.0 star property
Hike & Climb: Pet-friendly Red River Gorge Cabin!
Georgetown Home ~ 6 Mi to Kentucky Horse Park!
House (3 Bedrooms) | Interior

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!
House (3 Bedrooms) | 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
House (3 Bedrooms) | Interior

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!
House (2 Bedrooms) | Private kitchen

Quaint Creekside Cottage w/ Porch & Backyard!

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

Natural Bridge State Resort Park

Natural Bridge State Resort Park

10/10 Excellent
"Pool was wonderful when open. Friendly staff great accommodations for the price "
Karen 2-night trip
Posted 12 hours ago
Natural Bridge State Resort Park