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Search Cottages in Winchester

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Check prices for these dates

Next weekend
9 Jum. I - 11 Jum. I
In two weeks
16 Jum. I - 18 Jum. I
In one month
30 Jum. I - 1 Jum. II
In two months
27 Jum. II - 29 Jum. II

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

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, (27)
"Great stay, would do it gain for sure "
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, (15)
"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, (9)
"I like everything about this property beautiful home beautiful scenery. Excellent host."
The price is SAR 506
SAR 723 total
includes taxes & fees
5 May - 6 May
Mountaintop Cottage
Springside BoHo Getaway
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Springside BoHo Getaway

10.0 out of 10, Exceptional, (42)
"Had an absolutely lovely stay with my family over the holiday weekend! Felt very warm and inviting inside, plus a great location by downtown. Would definitely stay here again!"
The price is SAR 563
SAR 1,042 total
includes taxes & fees
5 May - 6 May
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 751 total
includes taxes & fees
5 May - 6 May
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
5 May - 6 May
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 loved everything about our stay at the charming Lady Clay!! Can't recommend it enough!"
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)
"Well appointed cottage with everything you might need. Great layout and amenities. "
Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY
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
Georgetown Home ~ 6 Mi to Kentucky Horse Park!
Interior

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!
Interior

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

3.0 star property
Lexington Getaway w/ Backyard Deck < 2 Mi to UK!
~ 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!
Property grounds

Cozy Georgetown Cottage on a Working Horse Farm!

10.0 out of 10, Exceptional, (1)
"Had the most wonderful stay what a beautiful place."
Cozy Georgetown Cottage on a Working Horse Farm!
Family Home w/ Ping-pong & Fire Pit in Lexington
Interior

Family Home w/ Ping-pong & Fire Pit in Lexington

3.0 star property
Family Home w/ Ping-pong & Fire Pit in Lexington
15 Mi to Dtwn Lexington: Serene Wilmore Home!
Interior

15 Mi to Dtwn Lexington: Serene Wilmore Home!

3.0 star property
15 Mi to Dtwn Lexington: Serene Wilmore Home!
3 Mi to Kroger Field: Dtwn Home w/ Pool Table!
Interior

3 Mi to Kroger Field: Dtwn Home w/ Pool Table!

3.0 star property
3 Mi to Kroger Field: Dtwn Home w/ Pool Table!
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, (1539)
"Wonderful area"
The price is SAR 472
SAR 521 total
includes taxes & fees
5 May - 6 May
Natural Bridge State Resort Park
Tranquil Getaway in the Woods ~ Sunset Ridge
Terrace/patio

Tranquil Getaway in the Woods ~ Sunset Ridge

9.8 out of 10, Exceptional, (54)
"The cabin was beautiful and the scenery was great. Everything you need for a great getaway "
The price is SAR 394
SAR 558 total
includes taxes & fees
5 May - 6 May
Tranquil Getaway in the Woods ~ Sunset Ridge
Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!
Exterior

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

9.4 out of 10, Exceptional, (65)
"It was a perfect stay for a couple getaway. The hot tub was great, the fire pit was nice as well. Will definitely stay again. "
The price is SAR 406
SAR 822 total
includes taxes & fees
11 May - 12 May
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.