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Compare 352 Vacation Homes in Winchester with updated reviews, rates, and availability.

Horse Country 2 - Sleeping For 12 - Beautiful Outdoor Space - 3 Bedrooms + Loft
Living area

Horse Country 2 - Sleeping For 12 - Beautiful Outdoor Space - 3 Bedrooms + Loft

9.0 out of 10, Wonderful, (29)
"Property was all that it was advertised to be. Multiple rooms and sleeping areas. Very responsive owner. Close to several bourbon tasting venues and to Keeneland horse racing park."
The price is AED 973
AED 1,769 total
includes taxes & fees
30 Nov - 1 Dec
Horse Country 2 - Sleeping For 12 - Beautiful Outdoor Space - 3 Bedrooms + Loft
2 Bed/2 Bath Home in Andover area. Premier Host with 250+ 5-Star Reviews!
Exterior detail

2 Bed/2 Bath Home in Andover area. Premier Host with 250+ 5-Star Reviews!

10.0 out of 10, Exceptional, (31)
"My wife worked at UK as a travel nurse and we booked very last minute. While she was at work I was in charge of watching the 4 month old and check in wasn’t till 1pm. We were able to call the house a home around 9:30am! Absolutely amazing service and PERFECT location for everyone! Definitely will be coming back "
2 Bed/2 Bath Home in Andover area. Premier Host with 250+ 5-Star Reviews!
Newly renovated Historic House within walking distance to UK.
Living area

Newly renovated Historic House within walking distance to UK.

10.0 out of 10, Exceptional, (92)
"This house was perfect for a mom’s getaway weekend. Plenty of space, comfortable beds, and close to lots of restaurant options. Easy checking. Highly recommend. "
Newly renovated Historic House within walking distance to UK.
Lexington’s Premier Cul De Sac Townhome 2BR, 2.5BA, 1100 sqft
Master Bedroom with Queen Size Tempur Pedic Mattress

Lexington’s Premier Cul De Sac Townhome 2BR, 2.5BA, 1100 sqft

9.6 out of 10, Exceptional, (125)
"Perfect location to visit the horse farms. Super clean and the owner goes above and beyond to make sure you have everything you need. Also gave us good ideas where to eat and visit."
The price is AED 312
AED 576 total
includes taxes & fees
24 Nov - 25 Nov
Lexington’s Premier Cul De Sac Townhome 2BR, 2.5BA, 1100 sqft
Robin's Nest luxury cabin, Red River Gorge
Interior

Robin's Nest luxury cabin, Red River Gorge

9.8 out of 10, Exceptional, (139)
"Easy trip to the park. All of the trails were fabulous. Property was really easy w the kids and teens. The teens stayed ip top and we took the smll bedroom across frkm the bunkned roo. "
Robin's Nest luxury cabin, Red River Gorge
Hamburg Haven / Garage /🔥 Pit / 7mi to Rupp / WiFi
Fire Pit & Hot Tub

Hamburg Haven / Garage /🔥 Pit / 7mi to Rupp / WiFi

9.4 out of 10, Exceptional, (34)
"My daughters and I were stopping for the night on our way into Knoxville and the house was perfect for a girls spa night! Dalton was great and very friendly. One of the cleanest houses we’ve ever stayed in. My only wish was that we stayed for more than one night. Would highly recommend. "
The price is AED 327
AED 870 total
includes taxes & fees
1 Dec - 2 Dec
Hamburg Haven / Garage /🔥 Pit / 7mi to Rupp / WiFi
Experience the Grand Getaway: Centrally Located Luxury
Interior

Experience the Grand Getaway: Centrally Located Luxury

4.0 out of 10, (2)
"When we pulled up to the property we were quick to notice there was nothing "luxurious" awaiting us. The property was overgrown with weeds and an old car in the driveway (when we first called host confirmed it was a relative's that was left in driveway). Upon entering the home we faced with the smell of terrible cigarette smoke (not good when we had a daughter with asthma). After our 7 hour drive we all needed to use the bathroom. We were unable to find a single towel in any of them...
The price is AED 1,377
AED 2,174 total
includes taxes & fees
24 Nov - 25 Nov
Experience the Grand Getaway: Centrally Located Luxury
Barn! 2-Hole Golf Course, BBall, Wiffleball, Soccer, Theater, Arcade, 2 Hot Tubs
Exterior

Barn! 2-Hole Golf Course, BBall, Wiffleball, Soccer, Theater, Arcade, 2 Hot Tubs

2.0 star property
10.0 out of 10, Exceptional, (1)
"The Barn and the grounds were out of this world! We had a blast and highly recommend! "
Barn! 2-Hole Golf Course, BBall, Wiffleball, Soccer, Theater, Arcade, 2 Hot Tubs
Spacious Home - Sleeps 8 Fire-pit 1 Block to EKU & Downtown, 2 Miles to I-75
The Wellington in Richmond, KY

Spacious Home - Sleeps 8 Fire-pit 1 Block to EKU & Downtown, 2 Miles to I-75

9.8 out of 10, Exceptional, (68)
"Super nice and clean "
The price is AED 551
AED 960 total
includes taxes & fees
27 Nov - 28 Nov
Spacious Home - Sleeps 8 Fire-pit 1 Block to EKU & Downtown, 2 Miles to I-75
Hot Tub | Walk to Downtown | Patio | Fire Pit | Game Room
Escape to our charming bungalow in the Chevy Chase neighborhood, located just minutes away from some of the city's best restaurants. Book your stay now and experience the perfect combination of comfort and convenience!

Hot Tub | Walk to Downtown | Patio | Fire Pit | Game Room

10.0 out of 10, Exceptional, (155)
"Appreciated the K-cups! Nice layout and Great Location. "
Hot Tub | Walk to Downtown | Patio | Fire Pit | Game Room
WiFi, Hot Tub, Pets, Prime Location in Red River Gorge!

WiFi, Hot Tub, Pets, Prime Location in Red River Gorge!

9.6 out of 10, Exceptional, (14)
"Needed some time away and we like the nature. "
The price is AED 458
AED 913 total
includes taxes & fees
24 Nov - 25 Nov
WiFi, Hot Tub, Pets, Prime Location in Red River Gorge!
NEW! East Suite- Southern Charm in Georgetown Kentucky-Bleubird Studio + Suites
East Suite. Queen. French doors to balcony. Ceiling fan. Original paintings/art.

NEW! East Suite- Southern Charm in Georgetown Kentucky-Bleubird Studio + Suites

10.0 out of 10, Exceptional, (46)
"Always a wonderful stay! Jane is a delight!"
NEW! East Suite- Southern Charm in Georgetown Kentucky-Bleubird Studio + Suites
Kentucky's Finest - Pet Friendly
Living area

Kentucky's Finest - Pet Friendly

9.6 out of 10, Exceptional, (13)
"Quick and easy "
The price is AED 331
AED 822 total
includes taxes & fees
24 Nov - 25 Nov
Kentucky's Finest - Pet Friendly
3 Bdr/3 Bath House in Andover Convenient to All of Lexington
Front of Home

3 Bdr/3 Bath House in Andover Convenient to All of Lexington

10.0 out of 10, Exceptional, (279)
"Can not say enough good things. Prperty is in a great area. We stayed 3 nights and we covered everything we could fit in. Great restaurants, the ARK, winery, distillery, casino, Horse Park... and much more. The management group/ owner was first class along with his support crew. They took geat care of us!!!thetotresponded"
3 Bdr/3 Bath House in Andover Convenient to All of Lexington
Cozy Lexington Townhome ~ 3 Mi to UK Campus!
Lexington Vacation Rental | 2BR | 1.5BA | 1,041 Sq Ft | Stairs Required

Cozy Lexington Townhome ~ 3 Mi to UK Campus!

9.2 out of 10, Wonderful, (5)
"Overall this place is great. Very clean which is important to my husband and I. Felt very safe as well. A week before arriving I emailed to find out what kind of coffeemaker was in unit. Four days later, the response was both a Mr. Coffee and a Keurig. I packed plenty of K cups but there wasn’t a Keurig, only a Mr. Coffee. No big deal I guess as regular coffee was on counter. Check-in info said dishwasher pods, extra toilet paper and garbage bags were in unit. They were not. I did text property...
Cozy Lexington Townhome ~ 3 Mi to UK Campus!
Ursa Major Cabin - 10 mins from Natural Bridge State Park, Red River Gorge
Dining Area

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

9.6 out of 10, Exceptional, (39)
"We loved our stay at Ursa Major. The cabin is in a great location and a lovely setting, especially for autumn colors. The design and decor are thoughtful and the cabin is well-appointed for guest comfort and convenience. The large side patio with sliding door access to both bedrooms is a nice design. The large outdoor table even expands for large groups. We made use of the barbecue grill, fire pit, and hot tub. We slept like babies in the peaceful setting and comfortable bed. We enjoyed...
The price is AED 398
AED 951 total
includes taxes & fees
24 Nov - 25 Nov
Ursa Major Cabin - 10 mins from Natural Bridge State Park, Red River Gorge
NEW! Freshly Furnished 4 Bedroom Sweet Kentucky Home in the heart of Lexington.
Interior

NEW! Freshly Furnished 4 Bedroom Sweet Kentucky Home in the heart of Lexington.

10.0 out of 10, Exceptional, (12)
"Had a great time going to Keeneland and Woodford Distillery"
NEW! Freshly Furnished 4 Bedroom Sweet Kentucky Home in the heart of Lexington.
Isla's Landing - Charming Historic 1940s Home
Living Room

Isla's Landing - Charming Historic 1940s Home

10.0 out of 10, Exceptional, (31)
"👍"
Isla's Landing - Charming Historic 1940s Home
Lexington Home ~ 5 Mi to University of Kentucky!
Lexington Vacation Rental | 3BR | 2.5BA | 2,806 Sq Ft | Stairs Required

Lexington Home ~ 5 Mi to University of Kentucky!

10.0 out of 10, Exceptional, (4)
"This property was located in a very nice area near the outer belt so it was easy to get around Lexington. House was tastefully decorated and very clean. We travel a lot and this might have had the best amenities of any house we have stayed at. "
Lexington Home ~ 5 Mi to University of Kentucky!
Casa Alegre Summary:

Casa Alegre Summary:

8.0 out of 10, Very Good, (3)
"We basically use this house to layer heads and have a good dinner with family and friends after a long hikes at Red River gorge all weekend long beautiful spots in Kentucky"
Casa Alegre Summary:
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
Hiking

Natural Bridge State Resort Park

3.5 star property
8.6 out of 10, Excellent, (1460)
"best "
The price is AED 334
AED 368 total
includes taxes & fees
25 Nov - 26 Nov
Natural Bridge State Resort Park
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!

Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!

9.8 out of 10, Exceptional, (265)
"The Cozy Cabin was a great set up for our annual hiking trip. The cabin was very clean, had everything we needed and was very comfortable. All instructions were accurate and the listing was exactly as described. The hot tub was key after long days out on the trails. The host was very helpful and able to send over replacement propane tanks for the fire pit, which was much appreciated. We had a wonderful trip and would absolutely stay here again. "
The price is AED 340
AED 756 total
includes taxes & fees
5 Dec - 6 Dec
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB
Property grounds

Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB

10.0 out of 10, Exceptional, (121)
"Very clean and well taken care of! The owner was very flexible after we had to reschedule"
The price is AED 547
AED 907 total
includes taxes & fees
3 Dec - 4 Dec
Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB
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.