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Check prices for these dates

Next weekend
28 Saf. - 2 Rab. I
In two weeks
7 Rab. I - 9 Rab. I
In one month
21 Rab. I - 23 Rab. I
In two months
18 Rab. II - 20 Rab. II

Compare 26 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 SAR 544
SAR 936 total
includes taxes & fees
24 Feb - 25 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, (38)
"Great place. Great host. We will be back!"
The price is SAR 656
SAR 1,162 total
includes taxes & fees
24 Feb - 25 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 SAR 405
SAR 763 total
includes taxes & fees
24 Feb - 25 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 SAR 486
SAR 701 total
includes taxes & fees
26 Mar - 27 Mar
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, (8)
"We rented this house for a 30th birthday weekend. It was as adorable as pictured with the girliest small touches that really set it apart from other options. We walked several places for shopping and eating. I hadn’t realized there was only one shower but it worked out just fine. Would definitely stay again. "
The price is SAR 1,219
SAR 2,329 total
includes taxes & fees
24 Feb - 25 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)
"Simply a great experience start to finish"
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, (1496)
"Hiking trail was nice"
The price is SAR 322
SAR 355 total
includes taxes & fees
24 Feb - 25 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, (279)
"Loved the location but 4 wheel drive is highly recommend. Very steep driveway."
The price is SAR 347
SAR 744 total
includes taxes & fees
24 Feb - 25 Feb
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!

Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!

9.4 out of 10, Exceptional, (62)
"We needed a short convenient layover in the middle of a trip and this worked perfectly. "
The price is SAR 386
SAR 817 total
includes taxes & fees
24 Feb - 25 Feb
Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, 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.

Frequently asked questions

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