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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 33 Cottages in Winchester with updated reviews, rates, and availability.

Mountaintop Cottage
Terrace/patio

Mountaintop Cottage

2.0 star property
10.0 out of 10, Exceptional, (9)
"I like everything about this property beautiful home beautiful scenery. Excellent host."
The price is AED 477
AED 688 total
includes taxes & fees
10 Jun - 11 Jun
Mountaintop Cottage
Unique, Cozy Stay near Red River Gorge
Exterior

Unique, Cozy Stay near Red River Gorge

8.0 out of 10, Very Good, (3)
"Love it ❤️"
The price is AED 285
AED 515 total
includes taxes & fees
1 Jun - 2 Jun
Unique, Cozy Stay near Red River Gorge
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!

8.4 out of 10, Very Good, (15)
"Everything was great, except for the pool that wasn't clean"
1,600 Acres | Pool | Pond | Fishing | | WiFi near Red River Gorge, KY!
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!!

8.8 out of 10, Excellent, (15)
"Nice little place. Enjoyed our stay. "
1 bed cottage, grill, fire pit, Very close to Red River Gorge!!
Bungalow | 1 Bed, 0.5 Bath
Interior

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 740 total
includes taxes & fees
3 Jun - 4 Jun
Bungalow | 1 Bed, 0.5 Bath
Springside BoHo Getaway
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Springside BoHo Getaway

10.0 out of 10, Exceptional, (44)
"Had an absolutely lovely stay with my family over the holiday weekend! Felt very warm and inviting inside, plus a great location by downtown. Would definitely stay here again!"
The price is AED 551
AED 1,033 total
includes taxes & fees
3 Jun - 4 Jun
Springside BoHo Getaway
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
Interior

Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre

3.0 star property
The price is AED 422
AED 883 total
includes taxes & fees
29 Jun - 30 Jun
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
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, (31)
"Great stay, would do it gain for sure "
Cozy 1 bedroom cottage on picturesque horse farm
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!
Cozy Cottage Perfect for Girls Night Away
Interior

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 AED 1,157
AED 2,238 total
includes taxes & fees
12 Jun - 13 Jun
Cozy Cottage Perfect for Girls Night Away
Lexington Home ~ 2 Mi to University of Kentucky!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Lexington Home ~ 2 Mi to University of Kentucky!

3.0 star property
Lexington Home ~ 2 Mi to University of Kentucky!
Georgetown Home ~ 6 Mi to Kentucky Horse Park!
House (3 Bedrooms) | Front of property

Georgetown Home ~ 6 Mi to Kentucky Horse Park!

3.0 star property
Georgetown Home ~ 6 Mi to Kentucky Horse Park!
~ 2 Mi From UK: Gorgeous Lexington Retreat!
Interior

~ 2 Mi From UK: Gorgeous Lexington Retreat!

3.0 star property
10.0 out of 10, Exceptional, (1)
"The house is charming, extremely clean and comfy. The linens and access to helpful kitchen items is a bonus. The ease of booking and gaining access waa seamless. The only little thing was that the sofa bed was in the same room with queen bed. We didnt need to use it but if our other guest had joined the trip it would have been difficult. The king and queen beds are very comfy. "
~ 2 Mi From UK: Gorgeous Lexington Retreat!
Peaceful Mt Sterling Cabin: Deck & Fire Pit!
House (2 Bedrooms) | Private kitchen | Microwave, oven, stovetop, highchair

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!
Quaint Creekside Cottage w/ Porch & Backyard!
Miscellaneous

Quaint Creekside Cottage w/ Porch & Backyard!

3.0 star property
Quaint Creekside Cottage w/ Porch & Backyard!
Cozy Georgetown Cottage on a Working Horse Farm!
Property grounds

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!
3 Mi to Kroger Field: Dtwn Home w/ Pool Table!
Interior

3 Mi to Kroger Field: Dtwn Home w/ Pool Table!

3.0 star property
3 Mi to Kroger Field: Dtwn Home w/ Pool Table!
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!
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
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!
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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