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Vacation Homes in Winchester

Cozy, Bright Home in Historic Downtown
8.6 out of 10, Excellent, (20)
"Very Cute house, good downtown location. Owner very quick to respond and friendly."
United States
Casey H.
$113 nightly
The price is $125
Nov 9 - Nov 10
Total with taxes and fees
Cozy, Bright Home in Historic Downtown
New Barndo/ATV Trailer Park/Outdoor Shower/HotTub
9.8 out of 10, Exceptional, (10)
"This home was just what we needed for a relaxing weekend in the Kentucky mountains. The home was clean, fully stocked with everything we needed, and very easy to check in and out. The hiking at the red River gorge was amazing and the people in Kentucky were so lovely!"
United States
Jean K.
$288 nightly
The price is $317
Nov 18 - Nov 19
Total with taxes and fees
New Barndo/ATV Trailer Park/Outdoor Shower/HotTub
My Old Kentucky Home
10.0 out of 10, Exceptional, (27)
"Great stay. Went to a UK game and it was great. Close to rupp and a great place to stay for a game. "
United States
Kevin G.
$242 nightly
The price is $281
Nov 9 - Nov 10
Total with taxes and fees
My Old Kentucky Home
Kim's Retreat: 3-BR Cabin w/ Hot Tub near Natural Bridge & Red River Gorge
9.0 out of 10, Wonderful, (17)
"Overall the stay was nice but compare to other rental, I did not rate as high. Travel on one lane road to get to cabin which was not mentioned. Lots of blind spots and dangerous with oncoming vehicles"
United States
William K.
Kim's Retreat: 3-BR Cabin w/ Hot Tub near Natural Bridge & Red River Gorge
Charming Kentucky Stone House
10.0 out of 10, Exceptional, (3)
"Super cute, updates amenities. Very clean and comfortable. Will defiantly stay there again. "
United States
melissa s.
$224 nightly
The price is $260
Nov 10 - Nov 11
Total with taxes and fees
Charming Kentucky Stone House
Cozy Corner - Little House in Downtown Lexington
10.0 out of 10, Exceptional, (2)
"Cute little house. Great communication with host. Walk able neighborhood."
United States
Molli P.
$219 nightly
The price is $254
Nov 12 - Nov 13
Total with taxes and fees
Cozy Corner - Little House in Downtown Lexington
Hot Tub! The Glow Hill - Ark 30 min - Horse Prk 13 min - Rupp - 20 min
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
$208 nightly
The price is $229
Nov 10 - Nov 11
Total with taxes and fees
Hot Tub! The Glow Hill - Ark 30 min - Horse Prk 13 min - Rupp - 20 min
This house is a 2 bedroom(s), 1 bathrooms, located in Georgetown, KY.
8.4 out of 10, Very Good, (32)
"Clean and cozy with a great view."
United States
Branden D.
$175 nightly
The price is $177
Nov 9 - Nov 10
Total with taxes and fees
This house is a 2 bedroom(s), 1 bathrooms, located in Georgetown, KY.
Cozy 1-bedroom in Lexington
9.2 out of 10, Wonderful, (10)
"The location was great. Very close to the Bourbon trail. The place was very clean. The layout was very odd. The bed is very tall and difficult for my wife (5' tall) to climb onto. I needed to place a milk crate on the floor for her to step on."
United States
Dan G.
$210 nightly
The price is $244
Nov 10 - Nov 11
Total with taxes and fees
Cozy 1-bedroom in Lexington
Spacious King Suite / Game Room / Patio / Firepit
9.8 out of 10, Exceptional, (9)
"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.
$264 nightly
The price is $291
Nov 18 - Nov 19
Total with taxes and fees
Spacious King Suite / Game Room / Patio / Firepit
Charming Home Near UK Campus! Perfect for Family Visits.
10.0 out of 10, Exceptional, (28)
"The BEST rental we have stayed in! Clean, great location, tons of extras (snacks, bathroom items, coffee, and more) they thought of everything! The space is perfect just as pictured. The owner was very responsive and accommodating. We will be staying here again next time we are in Lexington."
United States
Natalie R.
Charming Home Near UK Campus! Perfect for Family Visits.
Red RIver Gorge, Hollerwood, High Speed Wi-Fi, KY Dragway
10.0 out of 10, Exceptional, (1)
"great place! will be back!"
United States
maggie m.
$217 nightly
The price is $239
Nov 11 - Nov 12
Total with taxes and fees
Red RIver Gorge, Hollerwood, High Speed Wi-Fi, KY Dragway
Bluegrass Retreat
9.2 out of 10, Wonderful, (25)
"We had a short trip for a family event. The home was clean and comfortable, and the neighborhood was quiet. thank you for hosting us!"
United States
Katie L.
$211 nightly
The price is $233
Nov 16 - Nov 17
Total with taxes and fees
Bluegrass Retreat
"The Carlisle" WARM MODERN STAY w/ Yard -Greyline
10.0 out of 10, Exceptional, (4)
"My siblings and I enjoyed our brief stay. House was very comfortable. Kitchen well stocked. "
United States
John O.
$230 nightly
The price is $266
Nov 11 - Nov 12
Total with taxes and fees
"The Carlisle" WARM MODERN STAY w/ Yard -Greyline
💙Modern Downtown with Parking - Keeneland - Horse Park
9.8 out of 10, Exceptional, (21)
"Property was close to campus, downtown, restaurants, etc. Neighborhood was quiet! If I found myself back in Lexington I would certainly stay again!"
United States
jeremy r.
$238 nightly
The price is $276
Nov 11 - Nov 12
Total with taxes and fees
💙Modern Downtown with Parking - Keeneland - Horse Park
Candlelight Cabin Red River Gorge
10.0 out of 10, Exceptional, (29)
"Loved our stay here, we had everything we could possibly need!"
United States
Ronda B.
$305 nightly
The price is $327
Dec 1 - Dec 2
Total with taxes and fees
Candlelight Cabin Red River Gorge
Cecil's Cozy Cottage
9.4 out of 10, Exceptional, (66)
"Property was describe very well and was very clean and comfortable. It was perfect for a visit with my daughter. Owners were super responsive and very easy to work with. Would definitely stay again when in the area."
United States
Christine W.
$215 nightly
The price is $219
Nov 11 - Nov 12
Total with taxes and fees
Cecil's Cozy Cottage
Great Locatoin- Mins to Rupp-Kroger Field-Downtown Lexington- Modern Retro 70's
10.0 out of 10, Exceptional, (7)
"Awesome stay for a football game"
United States
Cohen M.
$277 nightly
The price is $322
Nov 9 - Nov 10
Total with taxes and fees
Great Locatoin- Mins to Rupp-Kroger Field-Downtown Lexington- Modern Retro 70's
Red River Gorge, High Speed Wi-Fi, KY Dragway, Hollerwood Stay
10.0 out of 10, Exceptional, (7)
"More bathroom paper "
United States
Cassady J.
Red River Gorge, High Speed Wi-Fi, KY Dragway, Hollerwood Stay
This house is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
10.0 out of 10, Exceptional, (12)
"Home was exactly as pictured. Very convenient for our needs. Home was very pet friendly including fenced back yard. Would highly recommend."
United States
John C.
$295 nightly
The price is $316
Nov 10 - Nov 11
Total with taxes and fees
This house is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
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
318
Accommodation
420 Vacation Homes
Lowest Price
$125
Highest Price
$327

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