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Search Cottages in Winchester

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Compare 28 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!!

9.4 out of 10, Exceptional, (10)
"Nice little place. Enjoyed our stay. "
1 bed cottage, grill, fire pit, Very close to Red River Gorge!!
Mountaintop Cottage
Terrace/patio

Mountaintop Cottage

2.0 star property
10.0 out of 10, Exceptional, (2)
"This is such a wonderful property! The owner is great and so very helpful! Just beautiful! "
Mountaintop Cottage
Bungalow | 1 Bed, 0.5 Bath
The Bungalow

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 732 total
includes taxes & fees
27 Nov - 28 Nov
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, (14)
"Everything was great, except for the pool that wasn't clean"
1,600 Acres | Pool | Pond | Fishing | | WiFi near Red River Gorge, KY!
Homey Horse Farm Hideaway ~ 6 Mi to KY Horse Park!
Lexington Vacation Rental | Cottage | 1BR | 1BA | 800 Sq Ft

Homey Horse Farm Hideaway ~ 6 Mi to KY Horse Park!

9.8 out of 10, Exceptional, (57)
"We could not have asked for a more perfect place to stay. Would highly recommend to anyone thinking of staying here. "
Homey Horse Farm Hideaway ~ 6 Mi to KY Horse Park!
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, (21)
"Great stay, would do it gain for sure "
Cozy 1 bedroom cottage on picturesque horse farm
Springside BoHo Getaway
Master Bedroom

Springside BoHo Getaway

10.0 out of 10, Exceptional, (33)
"We enjoyed our stay at Springside BoHo. We liked the exposed brick and woodwork in the unit. The outdoor patio was perfect to have a drink and relax. Easy walking distance to local restaurants and shops. We would stay again. Thank you! "
The price is AED 551
AED 1,041 total
includes taxes & fees
1 Dec - 2 Dec
Springside BoHo Getaway
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
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!
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 1,818
AED 3,142 total
includes taxes & fees
1 Dec - 2 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
Homey Horse Farm Hideaway ~ 6 Mi to KY Horse Park!
Living area

Homey Horse Farm Hideaway ~ 6 Mi to KY Horse Park!

2.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful setting! "
Homey Horse Farm Hideaway ~ 6 Mi to KY Horse Park!
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!
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, (1460)
"Absolutely beautiful place!!!!"
The price is AED 316
AED 348 total
includes taxes & fees
8 Dec - 9 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, (265)
"The cottage was lovely. The property not so much. It was so steep all over that walking wasn't possile. Apron was small and driveway extremely steep."
The price is AED 340
AED 749 total
includes taxes & fees
2 Dec - 3 Dec
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB
Property grounds

Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB

10.0 out of 10, Exceptional, (121)
"Very clean and well taken care of! The owner was very flexible after we had to reschedule"
The price is AED 547
AED 891 total
includes taxes & fees
2 Dec - 3 Dec
Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB
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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