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Check prices for these dates

Next weekend
7 Feb - 9 Feb
In two weeks
14 Feb - 16 Feb
In one month
28 Feb - 2 Mar
In two months
28 Mar - 30 Mar

Compare 27 Cottages in Winchester with updated reviews, rates, and availability.

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

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

10.0 out of 10, Exceptional, (259)
"Stayed here with my wife, son and our dog as a stop on a long road trip. Everything was great and the host was available and responsive. "
The price is AED 533
AED 917 total
includes taxes & fees
3 Feb - 4 Feb
Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!
Springside BoHo Getaway
Master Bedroom

Springside BoHo Getaway

10.0 out of 10, Exceptional, (37)
"This property was very nice and clean. It is well maintained and communication with the iwner was easy even over the holiday. "
The price is AED 643
AED 1,154 total
includes taxes & fees
3 Feb - 4 Feb
Springside BoHo Getaway
Cozy 1 bedroom cottage on picturesque horse farm
Exterior

Cozy 1 bedroom cottage on picturesque horse farm

10.0 out of 10, Exceptional, (23)
"Great stay, would do it gain for sure "
Cozy 1 bedroom cottage on picturesque horse farm
1,600 Acres | Pool | Pond | Fishing | | WiFi near Red River Gorge, KY!

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!
Bungalow | 1 Bed, 0.5 Bath
Snowy Day!

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 728 total
includes taxes & fees
3 Feb - 4 Feb
Bungalow | 1 Bed, 0.5 Bath
Mountaintop Cottage
Terrace/patio

Mountaintop Cottage

2.0 star property
10.0 out of 10, Exceptional, (4)
"Beautiful cottage in the woods with serene views and nature all around! Farm life with donkeys and cows that are friendly and vocal!! If you crave peace and quiet please stay here! Mr. Tipton is the best host!! "
The price is AED 477
AED 688 total
includes taxes & fees
3 Feb - 4 Feb
Mountaintop Cottage
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, (13)
"Nice little place. Enjoyed our stay. "
1 bed cottage, grill, fire pit, Very close to Red River Gorge!!
Unique, Cozy Stay near Red River Gorge

Unique, Cozy Stay near Red River Gorge

9.0 out of 10, Wonderful, (2)
"Love it ❤️"
Unique, Cozy Stay near Red River Gorge
Cozy Cottage Perfect for Girls Night Away
The coziest pink couch!

Cozy Cottage Perfect for Girls Night Away

10.0 out of 10, Exceptional, (7)
"The most adorable place ever! I have my reservations because I’ve had some very bad bookings, but this place was 100% amazing my little girl and her friends had the best time ever! I would totally book it for Mom’s weekend as well. There was no detail that was overlooked."
The price is AED 1,194
AED 2,302 total
includes taxes & fees
17 Feb - 18 Feb
Cozy Cottage Perfect for Girls Night Away
Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY
Fenced and gated entry for this private home on a wooded lot

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

10.0 out of 10, Exceptional, (13)
"The house was awesome. It was perfect for the two of us the detail everything was pointed so nicely down to the coffee cups. Definitely staying in this place again if I could give it more than five stars, I would clean."
Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY
Lexington Getaway w/ Backyard Deck < 2 Mi to UK!
Exterior

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

3.0 star property
Lexington Getaway w/ Backyard Deck < 2 Mi to UK!
Historic JC Cock House - Downtown Lexington KY
Welcome to the JC Cock House. A quaint cottage in the heart of the Bluegrass.

Historic JC Cock House - Downtown Lexington KY

10.0 out of 10, Exceptional, (1)
"Our family loved staying at the historic home in Lexington. The house and gardens are beautiful. John is a wonderful host who thought of everything for the house. Decorating is tops. Gardens are lovey and lush. Great stop for our weekend trip to KY."
Historic JC Cock House - Downtown Lexington KY
Peaceful Mt Sterling Cabin: Deck & Fire Pit!
Property grounds

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!
Exterior

Quaint Creekside Cottage w/ Porch & Backyard!

3.0 star property
Quaint Creekside Cottage w/ Porch & Backyard!
Georgetown Home ~ 6 Mi to Kentucky Horse Park!
Exterior

Georgetown Home ~ 6 Mi to Kentucky Horse Park!

3.0 star property
Georgetown Home ~ 6 Mi to Kentucky Horse Park!
Cozy Georgetown Cottage on a Working Horse Farm!
Georgetown Vacation Rental | 2BR | 1BA | 1,200 Sq Ft | 1 Step Required

Cozy Georgetown Cottage on a Working Horse Farm!

10.0 out of 10, Exceptional, (1)
Cozy Georgetown Cottage on a Working Horse Farm!
Lexington Home ~ 2 Mi to University of Kentucky!
Living area

Lexington Home ~ 2 Mi to University of Kentucky!

3.0 star property
Lexington Home ~ 2 Mi to University of Kentucky!
Lexington Home ~ 5 Mi to University of Kentucky!
Living area

Lexington Home ~ 5 Mi to University of Kentucky!

3.0 star property
Lexington Home ~ 5 Mi to University of Kentucky!
Gorgeous Lexington Retreat ~ 2 Mi From UK!
Living area

Gorgeous Lexington Retreat ~ 2 Mi From UK!

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. "
Gorgeous Lexington Retreat ~ 2 Mi From UK!
Walk to UK Campus: Charming Home w/ Patio!
Game room

Walk to UK Campus: Charming Home w/ Patio!

3.0 star property
Walk to UK Campus: Charming Home w/ Patio!
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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Other property types in Winchester

Natural Bridge State Resort Park
Hiking

Natural Bridge State Resort Park

3.5 star property
8.6 out of 10, Excellent, (1488)
"Cottage was nice, but needs some repairs and updates. It was very clean, we had everything we needed, and it was warm. All the trails in the park was closed so we enjoyed some in the Red River Gorge, which was only a 15-20 minute drive. Lots of good restaurants in the area as well."
The price is AED 316
AED 348 total
includes taxes & fees
3 Feb - 4 Feb
Natural Bridge State Resort Park
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!

Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!

9.8 out of 10, Exceptional, (277)
"Very good"
The price is AED 340
AED 720 total
includes taxes & fees
5 Feb - 6 Feb
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
Theodore Tiny Cabin- RRG Hot Tub! Pet Friendly!

Theodore Tiny Cabin- RRG Hot Tub! Pet Friendly!

10.0 out of 10, Exceptional, (12)
"Gorgeous Fall foliage @ a quaint cabin close to everything "
Theodore Tiny Cabin- RRG Hot Tub! Pet Friendly!
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.

Frequently asked questions

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