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Holiday Homes in Winchester

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Winchester

Modern 2bd 2ba- Near I-75, Free WiFi, No Steps
Fridge, microwave, oven, stovetop

Modern 2bd 2ba- Near I-75, Free WiFi, No Steps

9.8 out of 10, Exceptional, (80)
"Had a great time "
The price is AU$342
includes taxes & fees
25 Aug - 26 Aug
Modern 2bd 2ba- Near I-75, Free WiFi, No Steps
Cozy, Bright Home in Historic Downtown
Fridge, microwave, stovetop, coffee/tea maker

Cozy, Bright Home in Historic Downtown

9.0 out of 10, Wonderful, (16)
"We loved it you are in downtown it a nice place to stay"
The price is AU$206
includes taxes & fees
18 Aug - 19 Aug
Cozy, Bright Home in Historic Downtown
Cozy 1-bedroom in Lexington
Exterior

Cozy 1-bedroom in Lexington

9.6 out of 10, Exceptional, (9)
"Lots of things nearby to do. Came to town for a show at Rupp and it was an easy walk to there. Property is nice. Comfy couch, bed.. Funky selection of coffees for the keurig but not a biggie."
Cozy 1-bedroom in Lexington
Peregrine Cabin - Off the Grid, hike-in cabin
Terrace/patio

Peregrine Cabin - Off the Grid, hike-in cabin

10.0 out of 10, Exceptional, (12)
"We absolutely loved being tucked into the woods. We had a great experience and it was the perfect trip for our anniversary. "
The price is AU$278
includes taxes & fees
18 Aug - 19 Aug
Peregrine Cabin - Off the Grid, hike-in cabin
Skyridge Woodland Cabin @ tranquil High Rock - Wi-Fi, Hot tub, Pet friendly
Outdoor dining

Skyridge Woodland Cabin @ tranquil High Rock - Wi-Fi, Hot tub, Pet friendly

9.2 out of 10, Wonderful, (5)
"We absolutely loved the cabin. The bed was exceptionally comfortable, cute little fully equipped kitchen was awesome, we loved the robes as well, loved that we were able to find such a cute little cabin that was pet friendly and had all the amenities that we wanted. Thank you very much for this great experience, though our car isnt the happiest with it, we definitely enjoyed our stay lol. "
The price is AU$339
includes taxes & fees
18 Aug - 19 Aug
Skyridge Woodland Cabin @ tranquil High Rock - Wi-Fi, Hot tub, Pet friendly
This house is a 2 bedroom(s), 1 bathrooms, located in Georgetown, KY.
Coffee/tea maker, cookware/dishes/utensils

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

8.4 out of 10, Very good, (30)
"This home was welcoming, meticulously kept, and a complete joy to stay in!"
The price is AU$275
includes taxes & fees
22 Aug - 23 Aug
This house is a 2 bedroom(s), 1 bathrooms, located in Georgetown, KY.
Hot Tub & Fire Pit: Romantic Getaway in Frenchburg
Fridge, microwave, stovetop, dishwasher

Hot Tub & Fire Pit: Romantic Getaway in Frenchburg

9.4 out of 10, Exceptional, (3)
"Better than expected. My only issue was the blanket, but I could just be a picky sleeper. Can't wait to visit again!"
The price is AU$428
includes taxes & fees
18 Aug - 19 Aug
Hot Tub & Fire Pit: Romantic Getaway in Frenchburg
‘Clara’ Just Off I-75! 2 Full Bedrooms!
Terrace/patio

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

8.4 out of 10, Very good, (19)
"Great location"
The price is AU$267
includes taxes & fees
24 Aug - 25 Aug
‘Clara’ Just Off I-75! 2 Full Bedrooms!
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
Fridge, microwave, stovetop, dishwasher

Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre

9.0 out of 10, Wonderful, (4)
"This was the perfect little cabin for our anniversary getaway. Had everything we needed for cooking at the cabin on the days we didn't want to venture out to eat. Houae was super clean and exactly like the listing! Would definitely stay again if we revisit the area."
The price is AU$428
includes taxes & fees
21 Aug - 22 Aug
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
"Hickory Heights" - Overlook Dome 006 in RRG
1 bedroom, iron/ironing board, WiFi, bed sheets

"Hickory Heights" - Overlook Dome 006 in RRG

10.0 out of 10, Exceptional, (3)
"Such a fun and unique property! It was great for a birthday/date getaway weekend!! "
The price is AU$363
includes taxes & fees
19 Aug - 20 Aug
"Hickory Heights" - Overlook Dome 006 in RRG
East Suite-Bleubird Studio- 5miles to KY Horse Park, 30min The Ark,Bourbon Trail
Exterior

East Suite-Bleubird Studio- 5miles to KY Horse Park, 30min The Ark,Bourbon Trail

10.0 out of 10, Exceptional, (54)
"2nd time staying here,the location is perfect.property is amazing,secluded yet just a few blocks to town.Jane makes you feel very much at home with the added touch.will be back soo."
The price is AU$349
includes taxes & fees
24 Aug - 25 Aug
East Suite-Bleubird Studio- 5miles to KY Horse Park, 30min The Ark,Bourbon Trail
Hot Tub! The Glow Hill - Ark 30 min - Horse Prk 13 min - Rupp - 20 min
Exterior

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. "
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 Lexington, KY.
Interior

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

9.4 out of 10, Exceptional, (58)
"Super location, amenities, very clean, fenced yard for our dog was a definite bonus. Would rent again for sure!"
The price is AU$340
includes taxes & fees
19 Aug - 20 Aug
This house is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
GameRoom, Hammock, FirePit, Patio&Grill, Downtown-Hickory Plaid
Property grounds

GameRoom, Hammock, FirePit, Patio&Grill, Downtown-Hickory Plaid

8.4 out of 10, Very good, (9)
"Super cute home with everything we needed. Loved the upstairs room and the backyard. Perfect location for getting to town or for the KY Horse Park, plus supermarkets just 2 miles away. Lots of towels, beds were very comfortable, and the kitchen was very well stocked."
The price is AU$360
includes taxes & fees
20 Aug - 21 Aug
GameRoom, Hammock, FirePit, Patio&Grill, Downtown-Hickory Plaid
Ursa Major Cabin - 10 mins from Natural Bridge State Park, Red River Gorge
Interior

Ursa Major Cabin - 10 mins from Natural Bridge State Park, Red River Gorge

9.4 out of 10, Exceptional, (51)
"Wonderful cabin! Great communication with the owner. The interior is up to date and well appointed. I would stay there again."
The price is AU$402
includes taxes & fees
19 Aug - 20 Aug
Ursa Major Cabin - 10 mins from Natural Bridge State Park, Red River Gorge
ESCAPE!-In The Woods of Red River Gorge!-Hot Tub-High Speed WIFI!-Outdoor Shower
Outdoor spa tub

ESCAPE!-In The Woods of Red River Gorge!-Hot Tub-High Speed WIFI!-Outdoor Shower

10.0 out of 10, Exceptional, (2)
"This place was different than any other place I’ve stayed at; so cool! It was very comfortable and super clean. The setting is perfect for a quiet getaway, but the location is close to everything. We had a great stay! "
The price is AU$374
includes taxes & fees
18 Aug - 19 Aug
ESCAPE!-In The Woods of Red River Gorge!-Hot Tub-High Speed WIFI!-Outdoor Shower
175 LEX - Bon Voyage Condo
Smart TV, fireplace

175 LEX - Bon Voyage Condo

10.0 out of 10, Exceptional, (2)
"Clean, convenient place to stay! Would stay again in future. Parking under building is a huge bonus!!"
The price is AU$329
includes taxes & fees
24 Aug - 25 Aug
175 LEX - Bon Voyage Condo
Bluegrass Retreat
Private kitchen

Bluegrass Retreat

9.4 out of 10, Exceptional, (22)
"Our family really enjoyed our stay. Good area and the house was perfect for our family of 4."
The price is AU$381
includes taxes & fees
24 Aug - 25 Aug
Bluegrass Retreat
Hot Tub, Fire Pit, WiFi, EV Charger | Biggie cabin near Red River Gorge, KY!
Fridge, microwave, oven, stovetop

Hot Tub, Fire Pit, WiFi, EV Charger | Biggie cabin near Red River Gorge, KY!

10.0 out of 10, Exceptional, (12)
"Biggie cabin was perfect, and great location! Would absolutely stay there again! "
The price is AU$558
includes taxes & fees
19 Aug - 20 Aug
Hot Tub, Fire Pit, WiFi, EV Charger | Biggie cabin near Red River Gorge, KY!
The Luxe/Hot Tub/Private Bar/ 12 Min to Horse Park
Outdoor spa tub

The Luxe/Hot Tub/Private Bar/ 12 Min to Horse Park

2.0 star property
10.0 out of 10, Exceptional, (5)
"We enjoyed our stay so much! Great location and fabulous house for 8 adults. Extra gathering space in back building was A! "
The price is AU$802
includes taxes & fees
18 Aug - 19 Aug
The Luxe/Hot Tub/Private Bar/ 12 Min to Horse Park
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

GLō Best Western Lexington

GLō Best Western Lexington

10/10 Excellent
"Pet friendly and staff was so nice! Love the decor and the funky color accents. "
Lea 1-night trip
Posted 15 hours ago
GLō Best Western Lexington