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Check prices for these dates

Next weekend
11 Rab. II - 13 Rab. II
In two weeks
18 Rab. II - 20 Rab. II
In one month
2 Jum. I - 4 Jum. I
In two months
30 Jum. I - 1 Jum. II

Compare 34 Cottages in Winchester with updated reviews, rates, and availability.

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

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

10.0 out of 10, Exceptional, (261)
"Leslie and Al are wonderful hosts. They live on the property, but we certainly had all the privacy we wanted! Convenience of being in the country and close to town was such a blessing. The horses on the property are a joy to pet and feed. We will probably be back. Thanks, Leslie and Al!"
The price is SAR 656
SAR 1,149 total
includes taxes & fees
2 Apr - 3 Apr
Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!
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, (25)
"The stay was wonderful. "
Cozy 1 bedroom cottage on picturesque horse farm
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!!
Mountaintop Cottage
Terrace/patio

Mountaintop Cottage

2.0 star property
10.0 out of 10, Exceptional, (6)
"We appreciated the communication and comfort of the home. Definitely one of our top favorites we have rented on vrbo! The house is in a very remote location however the drive is worth it! "
The price is SAR 506
SAR 724 total
includes taxes & fees
2 Apr - 3 Apr
Mountaintop Cottage
Springside BoHo Getaway
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Springside BoHo Getaway

10.0 out of 10, Exceptional, (39)
"We enjoyed the property, we were comfortable and felt safe there. Fun boho environment with good food across from the street. Host was available, kind and great communication."
The price is SAR 563
SAR 1,050 total
includes taxes & fees
2 Apr - 3 Apr
Springside BoHo Getaway
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 SAR 405
SAR 755 total
includes taxes & fees
2 Apr - 3 Apr
Bungalow | 1 Bed, 0.5 Bath
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!
Unique, Cozy Stay near Red River Gorge
Exterior

Unique, Cozy Stay near Red River Gorge

9.0 out of 10, Wonderful, (2)
"Love it ❤️"
The price is SAR 272
SAR 504 total
includes taxes & fees
13 Apr - 14 Apr
Unique, Cozy Stay near Red River Gorge
Cozy Cottage Perfect for Girls Night Away
Interior

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 1,857
SAR 3,315 total
includes taxes & fees
2 Apr - 3 Apr
Cozy Cottage Perfect for Girls Night Away
Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY
Interior

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
Charming 3-bedroom detached cottage on horse farm near Lexington and Georgetown.
Fridge, microwave, oven, stovetop

Charming 3-bedroom detached cottage on horse farm near Lexington and Georgetown.

Charming 3-bedroom detached cottage on horse farm near Lexington and Georgetown.
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!
Historic JC Cock House - Downtown Lexington KY
Fridge, oven, stovetop, dishwasher

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
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!
Georgetown Home ~ 6 Mi to Kentucky Horse Park!
Dishwasher, paper towels

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!
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!
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!
TV

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 ~ 5 Mi to University of Kentucky!
House (3 Bedrooms) | Private kitchen | Oven, stovetop, dishwasher, blender

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
Seasonal outdoor pool

Natural Bridge State Resort Park

3.5 star property
8.6 out of 10, Excellent, (1510)
"Property very clean. Excellent breakfast. Close to Natural Bridge. "
The price is SAR 454
SAR 500 total
includes taxes & fees
8 Apr - 9 Apr
Natural Bridge State Resort Park
Hot Tub & WiFi - Romantic Hideaway - Wooded Retreat near Red River Gorge, Kentucky!
Terrace/patio

Hot Tub & WiFi - Romantic Hideaway - Wooded Retreat near Red River Gorge, Kentucky!

9.2 out of 10, Wonderful, (75)
"They helped us out ASAP before we drove out due to inclimate weather conditions. Offered us multiple other safe locations or cancellation/rescheduling and communicated consistently.Our cabin was clean as a whistle with every little thing we may have forgotten accomodated. It's super cute,comfortable and perfect for a getaway in the trees!!"
The price is SAR 577
SAR 999 total
includes taxes & fees
14 Apr - 15 Apr
Hot Tub & WiFi - Romantic Hideaway - Wooded Retreat near Red River Gorge, Kentucky!
Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!
Outdoor spa tub

Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!

9.6 out of 10, Exceptional, (138)
"Loved the cabin. I wish we had planned to stay longer. There are a lot of beautiful things to enjoy in the area."
The price is SAR 425
SAR 864 total
includes taxes & fees
13 Apr - 14 Apr
Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - 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.

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