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In two weeks
12 Dec - 14 Dec
In two months
23 Jan - 25 Jan
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20 Mar - 22 Mar

Vacation Homes in Winchester

Interior
River Relaxation - Calm Riverfront Home in Winchester Kentucky

River Relaxation - Calm Riverfront Home in Winchester Kentucky

Winchester
7.0 out of 10, Good, (4)
"We loved the house, the hosts were great and super communicative! The house is also close to Lexington and Winchester so we had plenty to do and places to eat out! "
United States
Maeve R.
The price is AED 414
AED 1,177 total
includes taxes & fees
1 Dec - 2 Dec
River Relaxation - Calm Riverfront Home in Winchester Kentucky
Terrace/patio
Peregrine Cabin - Off the Grid, hike-in cabin

Peregrine Cabin - Off the Grid, hike-in cabin

Stanton
10.0 out of 10, Exceptional, (13)
"We absolutely loved being tucked into the woods. We had a great experience and it was the perfect trip for our anniversary. "
United States
Kenetra F.
The price is AED 412
AED 678 total
includes taxes & fees
1 Dec - 2 Dec
Peregrine Cabin - Off the Grid, hike-in cabin
Property grounds
This house is a 2 bedroom(s), 1 bathrooms, located in Georgetown, KY.

This house is a 2 bedroom(s), 1 bathrooms, located in Georgetown, KY.

Georgetown
8.4 out of 10, Very Good, (32)
"We enjoyed our stay here very much. Thank you!"
United States
julianne k.
The price is AED 294
AED 650 total
includes taxes & fees
1 Dec - 2 Dec
This house is a 2 bedroom(s), 1 bathrooms, located in Georgetown, KY.
Fridge, microwave, oven, stovetop
My Old Kentucky Home

My Old Kentucky Home

Lexington
10.0 out of 10, Exceptional, (27)
"Cool property, with a great location. Owner had great communication."
United States
Anonymous traveler
The price is AED 364
AED 1,032 total
includes taxes & fees
5 Dec - 6 Dec
My Old Kentucky Home
3 bedrooms, desk, iron/ironing board, free WiFi
Spacious King Suite | Game Room | Patio | Firepit

Spacious King Suite | Game Room | Patio | Firepit

Georgetown
9.8 out of 10, Exceptional, (10)
"This house was perfect accommodations for our group of 3 couples. It was very clean and well stocked. The neighborhood is quiet. The location in Georgetown was convenient to Lexington attractions as well as to restaurants in downtown Georgetown. We recommend this VRBO highly. "
United States
Richard P.
The price is AED 289
AED 958 total
includes taxes & fees
2 Dec - 3 Dec
Spacious King Suite | Game Room | Patio | Firepit
Fridge, microwave, stovetop, coffee/tea maker
Cozy, Bright Home in Historic Downtown

Cozy, Bright Home in Historic Downtown

Mount Sterling
8.6 out of 10, Excellent, (20)
"We attended a wedding in the area and enjoyed our stay here."
United States
Anonymous traveler
The price is AED 231
AED 458 total
includes taxes & fees
1 Dec - 2 Dec
Cozy, Bright Home in Historic Downtown
Outdoor spa tub
Hot Tub! The Glow Hill - Ark 30 min - Horse Prk 13 min - Rupp - 20 min

Hot Tub! The Glow Hill - Ark 30 min - Horse Prk 13 min - Rupp - 20 min

Georgetown
10.0 out of 10, Exceptional, (3)
"Enjoyed my stay. Hosts were easy to communicate with and the rental was clean and quiet. "
United States
Barton
The price is AED 321
AED 742 total
includes taxes & fees
2 Dec - 3 Dec
Hot Tub! The Glow Hill - Ark 30 min - Horse Prk 13 min - Rupp - 20 min
Private kitchen
Bluegrass Retreat

Bluegrass Retreat

Georgetown
9.2 out of 10, Wonderful, (25)
"Cute quaint neighborhood, big back yard space, host very responsive. "
United States
Jenny M.
The price is AED 245
AED 736 total
includes taxes & fees
2 Dec - 3 Dec
Bluegrass Retreat
3 bedrooms, iron/ironing board, WiFi, bed sheets
Great Locatoin- Mins to Rupp-Kroger Field-Downtown Lexington- Modern Retro 70's

Great Locatoin- Mins to Rupp-Kroger Field-Downtown Lexington- Modern Retro 70's

Lexington
10.0 out of 10, Exceptional, (7)
"Nice and quiet street. Easy check in. Host was very responsive and made sure we were taken care of. "
United States
Michael D.
The price is AED 448
AED 1,181 total
includes taxes & fees
1 Dec - 2 Dec
Great Locatoin- Mins to Rupp-Kroger Field-Downtown Lexington- Modern Retro 70's
Fridge, microwave, oven, stovetop
Relaxing | Hot Tub | Fire Pit | S’mores | Garage

Relaxing | Hot Tub | Fire Pit | S’mores | Garage

LEXINGTON
9.2 out of 10, Wonderful, (45)
"Great place to stay! "
United States
Jeremy S.
The price is AED 243
AED 767 total
includes taxes & fees
1 Dec - 2 Dec
Relaxing | Hot Tub | Fire Pit | S’mores | Garage
Interior
Charming Kentucky Stone House

Charming Kentucky Stone House

Lexington
10.0 out of 10, Exceptional, (3)
"Super cute, updates amenities. Very clean and comfortable. Will defiantly stay there again. "
United States
melissa s.
The price is AED 324
AED 977 total
includes taxes & fees
1 Dec - 2 Dec
Charming Kentucky Stone House
Interior
New Barndo/ATV Parking/Private Access to Red River

New Barndo/ATV Parking/Private Access to Red River

Stanton
10.0 out of 10, Exceptional, (3)
"We stayed here for one night and wish we could have stayed longer. The property was incredible. Very thoughtfully decorated, spacious, and has everything you need plus more. Highly recommend!"
United States
Stephen S.
The price is AED 428
AED 1,189 total
includes taxes & fees
2 Dec - 3 Dec
New Barndo/ATV Parking/Private Access to Red River
Exterior
East Suite-🕊️ Bleubird Studio + Suites -Art Gallery • Yoga • Boutique Stay

East Suite-🕊️ Bleubird Studio + Suites -Art Gallery • Yoga • Boutique Stay

Georgetown
10.0 out of 10, Exceptional, (60)
"I so enjoyed staying at Jane‘s lovely place. Super clean and comfortable and thoughtfully laid out. Will definitely book again next time I’m in town."
United States
Katherine M.
The price is AED 436
AED 825 total
includes taxes & fees
1 Dec - 2 Dec
East Suite-🕊️ Bleubird Studio + Suites -Art Gallery • Yoga • Boutique Stay
Outdoor spa tub
Mint Condition at The Ridge

Mint Condition at The Ridge

2.0 star property
Powell County
The price is AED 364
AED 756 total
includes taxes & fees
14 Dec - 15 Dec
Mint Condition at The Ridge
Terrace/patio
‘Clara’ Just Off I-75! 2 Full Bedrooms!

‘Clara’ Just Off I-75! 2 Full Bedrooms!

Lexington
8.0 out of 10, Very Good, (22)
"Nice location for what we needed. Easy check in. Older unit with character. "
United States
Anne S.
The price is AED 191
AED 558 total
includes taxes & fees
1 Dec - 2 Dec
‘Clara’ Just Off I-75! 2 Full Bedrooms!
Fridge, microwave, oven, stovetop
Kim's Retreat: 3-BR Cabin w/ Hot Tub near Natural Bridge & Red River Gorge

Kim's Retreat: 3-BR Cabin w/ Hot Tub near Natural Bridge & Red River Gorge

Stanton
9.0 out of 10, Wonderful, (18)
"Very nice. Much more secluded than I thought it would be and a little further from civilization, but if that is what you're looking for it's perfect. Be aware that there is a cliff close by so if you have kids, let them know not to go near it! Great communication with the owners. Hot tub was amazing. "
United States
Jessica B.
The price is AED 402
AED 966 total
includes taxes & fees
1 Dec - 2 Dec
Kim's Retreat: 3-BR Cabin w/ Hot Tub near Natural Bridge & Red River Gorge
Fridge, microwave, oven, stovetop
"The Carlisle" WARM MODERN STAY w/ Yard -Greyline

"The Carlisle" WARM MODERN STAY w/ Yard -Greyline

Castlewood
10.0 out of 10, Exceptional, (4)
"Nicely furnished and very comfortable. Communication was smooth and check-in was easy."
United States
John C.
"The Carlisle" WARM MODERN STAY w/ Yard -Greyline
Exterior
Hot Tub/Playground/12 min to Horse Park/30min Ark

Hot Tub/Playground/12 min to Horse Park/30min Ark

Georgetown
10.0 out of 10, Exceptional, (23)
"Quiet, clean, convenient"
United States
Renee W.
The price is AED 411
AED 1,173 total
includes taxes & fees
2 Dec - 3 Dec
Hot Tub/Playground/12 min to Horse Park/30min Ark
Fridge, microwave, oven, stovetop
"The Dawning House" - Peaceful Modern Stay w/ Yard

"The Dawning House" - Peaceful Modern Stay w/ Yard

Georgetown
10.0 out of 10, Exceptional, (4)
"Nice time visiting my son "
United States
Lisa M.
The price is AED 350
AED 985 total
includes taxes & fees
1 Dec - 2 Dec
"The Dawning House" - Peaceful Modern Stay w/ Yard
Exterior
Cozy 1-bedroom in Lexington

Cozy 1-bedroom in Lexington

Lexington
9.2 out of 10, Wonderful, (10)
"The property was clean and well kept, the location is perfect and communication was immediate. I will definitely rent again!"
United States
Becky S.
The price is AED 327
AED 934 total
includes taxes & fees
31 Dec - 1 January 2026
Cozy 1-bedroom in Lexington
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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Top Winchester Hotel Reviews

Hilton Lexington/Downtown

Hilton Lexington/Downtown

10/10 Excellent
"Great location! "
MARIA 1-night trip
Posted 3 days ago
Hilton Lexington/Downtown