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Our top choices for Winchester vacation homes

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.
$311 nightly
The price is $343
Dec 28 - Dec 29
Total with taxes and fees
River Relaxation - Calm Riverfront Home in Winchester Kentucky

Cozy Tiny Home Retreat - Near RRG Hiking + Hot Tub

Cozy Tiny Home Retreat - Near RRG Hiking + Hot Tub
2.0 star property
Stanton
10.0 out of 10, Exceptional, (1)
"Perfect small cozy cabin for a couple get away. Thank you. We really enjoyed our stay."
United States
Carrie F.
$177 nightly
The price is $195
Dec 25 - Dec 26
Total with taxes and fees
Cozy Tiny Home Retreat - Near RRG Hiking + Hot Tub

Charming Kentucky Stone House

Charming Kentucky Stone House
Lexington
10.0 out of 10, Exceptional, (4)
"My wife and daughter stayed and said it was nice, clean, and easy to navigate, too. They would stay again!"
United States
Justin M.
$205 nightly
The price is $238
Jan 5 - Jan 6, 2026
Total with taxes and fees
Charming Kentucky Stone House

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
$213 nightly
The price is $247
Dec 29 - Dec 30
Total with taxes and fees
My Old Kentucky Home

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.
$194 nightly
The price is $225
Jan 1 - Jan 2, 2026
Total with taxes and fees
Cozy 1-bedroom in Lexington

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.
$162 nightly
The price is $176
Dec 26 - Dec 27
Total with taxes and fees
Peregrine Cabin - Off the Grid, hike-in cabin

Pet-Friendly Bluegrass Retreat w/ Fenced Yard

Pet-Friendly Bluegrass Retreat w/ Fenced Yard
Georgetown
9.4 out of 10, Exceptional, (28)
"Cute quaint neighborhood, big back yard space, host very responsive. "
United States
Jenny M.
$178 nightly
The price is $196
Jan 24 - Jan 25, 2026
Total with taxes and fees
Pet-Friendly Bluegrass Retreat w/ Fenced Yard

Hot Tub Glow Hill Home Near KY Horse Park, Ark and Rupp Arena

Hot Tub Glow Hill Home Near KY Horse Park, Ark and Rupp Arena
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
$233 nightly
The price is $256
Dec 26 - Dec 27
Total with taxes and fees
Hot Tub Glow Hill Home Near KY Horse Park, Ark and Rupp Arena

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.
$175 nightly
The price is $177
Dec 25 - Dec 26
Total with taxes and fees
This house is a 2 bedroom(s), 1 bathrooms, located in Georgetown, KY.

Cozy Modern 3-bd, Pet Friendly, 12 miles from RRG!

Cozy Modern 3-bd, Pet Friendly, 12 miles from RRG!
Stanton
10.0 out of 10, Exceptional, (41)
"Convenient location to explore Red River Gorge, nice kitchen, nice, updated home"
United States
Lisa
$203 nightly
The price is $230
Dec 25 - Dec 26
Total with taxes and fees
Cozy Modern 3-bd, Pet Friendly, 12 miles from RRG!

Cozy, Bright Home in Historic Downtown

Cozy, Bright Home in Historic Downtown
Mount Sterling
8.8 out of 10, Excellent, (21)
"We attended a wedding in the area and enjoyed our stay here."
United States
Anonymous traveler
$120 nightly
The price is $132
Dec 31 - Jan 1, 2026
Total with taxes and fees
Cozy, Bright Home in Historic Downtown

‘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.
$139 nightly
The price is $161
Jan 11 - Jan 12, 2026
Total with taxes and fees
‘Clara’ Just Off I-75! 2 Full Bedrooms!

Cecil's Cozy Cottage

Cecil's Cozy Cottage
Lexington
9.4 out of 10, Exceptional, (69)
"House was very clean, quiet and well equipped!"
United States
Richard H.
$220 nightly
The price is $224
Jan 7 - Jan 8, 2026
Total with taxes and fees
Cecil's Cozy Cottage

Spacious King Suite | Game Room | Patio | Firepit

Spacious King Suite | Game Room | Patio | Firepit
Georgetown
9.8 out of 10, Exceptional, (10)
"This property met all of our expectations and then some. We very much appreciated the ping pong table and cornhole boards in the garage. They provided a great way for us to unwind and enjoy time as a family. We also loved how centrally located it was to the local attractions. The beds were very comfortable and we found plenty of space for our family of 6 to sleep comfortably. Overall we were very impressed and would definitely stay here again! "
United States
Whitney A.
$279 nightly
The price is $307
Jan 8 - Jan 9, 2026
Total with taxes and fees
Spacious King Suite | Game Room | Patio | Firepit

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.
$296 nightly
The price is $326
Dec 25 - Dec 26
Total with taxes and fees
Hot Tub/Playground/12 min to Horse Park/30min Ark

Location, Location, Location

Location, Location, Location
Northside District
9.2 out of 10, Wonderful, (67)
"Great location!"
United States
Karla R.
$212 nightly
The price is $216
Jan 4 - Jan 5, 2026
Total with taxes and fees
Location, Location, Location

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, (8)
"Nice and quiet street. Easy check in. Host was very responsive and made sure we were taken care of. "
United States
Michael D.
$277 nightly
The price is $322
Dec 29 - Dec 30
Total with taxes and fees
Great Locatoin- Mins to Rupp-Kroger Field-Downtown Lexington- Modern Retro 70's

Luxe Home Downtown - Sleeps 6. Off-street parking

Luxe Home Downtown - Sleeps 6. Off-street parking
Northside District
9.6 out of 10, Exceptional, (21)
"Great stay great house"
United States
jody J.
$232 nightly
The price is $251
Jan 6 - Jan 7, 2026
Total with taxes and fees
Luxe Home Downtown - Sleeps 6. Off-street parking

Beautiful 4-bedroom home, close to Downtown/UK

Beautiful 4-bedroom home, close to Downtown/UK
Lexington
10.0 out of 10, Exceptional, (3)
"We had a great stay at this property. The house was clean and 100% ready to go. Great location. "
United States
Jonathan H.
$272 nightly
The price is $296
Jan 5 - Jan 6, 2026
Total with taxes and fees
Beautiful 4-bedroom home, close to Downtown/UK

Pet-friendly home w/ fenced yard in Georgetown

Pet-friendly home w/ fenced yard in Georgetown
Georgetown
8.8 out of 10, Excellent, (25)
"Perfect location great for the weekend couldn't be happier"
United States
Beth M.
$210 nightly
The price is $231
Jan 11 - Jan 12, 2026
Total with taxes and fees
Pet-friendly home w/ fenced yard in Georgetown
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

Find out more about Winchester

Winchester Vacation Homes information

Number of reviews
418
Accommodation
437 Vacation Homes
Lowest Price
$132
Highest Price
$343

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