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Compare 26 Cottages in Winchester with updated reviews, rates, and availability.

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!!

9.0 out of 10, Wonderful, (12)
"Nice little place. Enjoyed our stay. "
1 bed cottage, grill, fire pit, Very close to Red River Gorge!!
Springside BoHo Getaway
Master Bedroom

Springside BoHo Getaway

10.0 out of 10, Exceptional, (36)
"Everything was superbly put together except fo cleanliness of the kitchen and the Refrigerator."
The price is SAR 563
SAR 1,052 total
includes taxes & fees
23 Dec - 24 Dec
Springside BoHo Getaway
Cedar Creek Cottage - Hot Tub, Modern, Private!

Cedar Creek Cottage - Hot Tub, Modern, Private!

9.8 out of 10, Exceptional, (7)
"Red River Gorge kayaking is a must. Book deluxe kayaking way in advance because it sells out fast. The regular classic tour was good but only an hour in the cave. "
Cedar Creek Cottage - Hot Tub, Modern, Private!
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, (258)
"Host was gracious making sure we had everything we needed for our stay. It was a cozy cottage on a beautiful property close to attractions in Lexington."
The price is SAR 545
SAR 955 total
includes taxes & fees
23 Dec - 24 Dec
Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!
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 SAR 406
SAR 745 total
includes taxes & fees
23 Dec - 24 Dec
Bungalow | 1 Bed, 0.5 Bath
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!
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 1 bedroom cottage on picturesque horse farm
Exterior

Cozy 1 bedroom cottage on picturesque horse farm

10.0 out of 10, Exceptional, (22)
"Great stay, would do it gain for sure "
Cozy 1 bedroom cottage on picturesque horse farm
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!
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
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 SAR 1,315
SAR 2,490 total
includes taxes & fees
30 Dec - 31 Dec
Cozy Cottage Perfect for Girls Night Away
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!
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!
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
Quaint Creekside Cottage w/ Porch & Backyard!
Exterior

Quaint Creekside Cottage w/ Porch & Backyard!

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

Mountaintop Cottage

2.0 star property
10.0 out of 10, Exceptional, (3)
"Farm was perfect. Animals were beautiful and feeding them was an added bonus. Home was clean. Owner was very attentive and available. We will definitely be returning. "
Mountaintop Cottage
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, (1475)
"EVERYTHING GREAT. ROOM DID NOT HAVE A MICROWAVE OVEN. "
The price is SAR 342
SAR 377 total
includes taxes & fees
30 Dec - 31 Dec
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, (271)
"Quiet and peaceful retreat! Everything was as advertised and we had a great stay. "
The price is SAR 348
SAR 773 total
includes taxes & fees
8 Jan - 9 January 2025
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
Nestled in the beautiful mountains of the Red River Gorge Area

Nestled in the beautiful mountains of the Red River Gorge Area

9.0 out of 10, Wonderful, (6)
"Cabin was great but absolutely 0 service or wifi. Offered a great getaway from reality "
The price is SAR 651
SAR 1,031 total
includes taxes & fees
31 Dec - 1 January 2025
Nestled in the beautiful mountains of the Red River Gorge Area
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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