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Compare 349 Vacation Homes in Winchester with updated reviews, rates, and availability.

This house is a 4 bedroom(s), 3 bathrooms, located in Lexington, KY.
Exterior

This house is a 4 bedroom(s), 3 bathrooms, located in Lexington, KY.

9.6 out of 10, Exceptional, (58)
"This house set up was perfect for four good friends from out of town going to see a performance at the Lexington Opera House. The kitchen was nice and updated, the living room was great and comfy for socializing and we each had our own bedroom for privacy. Would definitely come back again if we're in the area."
The price is SAR 563
SAR 1,420 total
includes taxes & fees
24 Feb - 25 Feb
This house is a 4 bedroom(s), 3 bathrooms, located in Lexington, KY.
Isla's Landing - Charming Historic 1940s Home
Living Room

Isla's Landing - Charming Historic 1940s Home

10.0 out of 10, Exceptional, (34)
"A very comfortable little house, and situated with drivable distance from many great Lexington areas. Owner is very helpful and communicative. Thank you very much."
Isla's Landing - Charming Historic 1940s Home
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, (40)
"We just returned from spending 9 nights at this wonderful home. Everything from the communication with the owner to the location and property updates were perfect. The beds were very comfortable and the closets nicely sized. We had everything we needed during our stay and were located near tons of shopping, restaurants and even the interstate. The property is located in a quiet neighborhood even though it’s so close to everything. We were in town to visit our son at UK, which was only a 15...
2 Bed/2 Bath Home in Andover area. Premier Host with 250+ 5-Star Reviews!
My Old Kentucky Home
Private kitchen

My Old Kentucky Home

10.0 out of 10, Exceptional, (16)
"House is pretty small but perfect for a few days to catch a UK basketball game"
The price is SAR 319
SAR 914 total
includes taxes & fees
2 Mar - 3 Mar
My Old Kentucky Home
Westwood Luxury Ranch Home includes washer/dryer
Private kitchen

Westwood Luxury Ranch Home includes washer/dryer

10.0 out of 10, Exceptional, (24)
"This house is as advertised. Super clean and spacious. Pretty toddler friendly. Communication was great. Would recommend! "
The price is SAR 638
SAR 1,315 total
includes taxes & fees
3 Mar - 4 Mar
Westwood Luxury Ranch Home includes washer/dryer
‘Clara’ Just Off I-75! 2 Full Bedrooms!
Living area

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

8.4 out of 10, Very Good, (16)
"The propery was VERY clean, located optimally, and accomodated our needs. "
The price is SAR 236
SAR 609 total
includes taxes & fees
24 Feb - 25 Feb
‘Clara’ Just Off I-75! 2 Full Bedrooms!
Golf Simulator | Hot Tub | Game Room | Pool Table
Indulge in a fully stocked, high-end kitchen oasis. Impeccable design, top-of-the-line appliances, and all the culinary essentials create a haven for extraordinary culinary experiences.

Golf Simulator | Hot Tub | Game Room | Pool Table

10.0 out of 10, Exceptional, (43)
"The house was great, even better than pictures. Game room was fantastic and everything worked properly, was a very fun place to hang out and get a little friendly competition going between friends. The hot tub was in the best condition I’ve ever seen from a bnb rental. Water was clear all the jets worked the lid was easy to operate not broken and waterlogged. In my experience the hot tubs at rentals are always in some sort of disarray so this was a very pleasent change from the norm. House was...
Golf Simulator | Hot Tub | Game Room | Pool Table
Your Home Away From Home
Exterior

Your Home Away From Home

9.8 out of 10, Exceptional, (202)
"The house was very cozy and comfortable. However, If you like a softer mattress the room next to the master bedroom has the most comfortable mattress in the house, and is really low to the ground The rest are a little on the firm side. The queen bed in the master is softer than the king bed. That was really the only downfall. I would stay again. "
Your Home Away From Home
Few and Proud
Living area

Few and Proud

9.6 out of 10, Exceptional, (4)
"Nice location. The house was clean. You have plenty of TV's. Enough off-street parking for 3 cars in the driveway. The house was nice and quiet at night. Tips: bring your own hairdryer, shampoo and soap. Kitchen is decently stocked. Improvements: Could use a larger coffee pot. Master bath mirror is too high to use if you are under 5'-8" Still a nice place to stay. "
The price is SAR 844
SAR 1,715 total
includes taxes & fees
24 Feb - 25 Feb
Few and Proud
The House On Main-Sleeps 16/ Historic Home/ KHP 11min/ Ark 30min/ Walk Downtown
Downstairs Foyer

The House On Main-Sleeps 16/ Historic Home/ KHP 11min/ Ark 30min/ Walk Downtown

10.0 out of 10, Exceptional, (6)
"This house was set up well for multiple families traveling together. Lots of gathering places. Multiple kitchens and updated bathrooms for people to utilize.Would highly recommend!"
The House On Main-Sleeps 16/ Historic Home/ KHP 11min/ Ark 30min/ Walk Downtown
Hot Tub/Playground/12 min to Horse Park/30min Ark
Terrace/patio

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

10.0 out of 10, Exceptional, (10)
"Very convenient and cozy "
The price is SAR 405
SAR 1,153 total
includes taxes & fees
24 Feb - 25 Feb
Hot Tub/Playground/12 min to Horse Park/30min Ark
Firepit | Outdoor Deck | Great Location
Family Room

Firepit | Outdoor Deck | Great Location

10.0 out of 10, Exceptional, (67)
"We needed a big place to stay to accommodate our family, and this place was excellent. Bigger in person than the pictures show. The game room was a fantastic bonus we could use without disturbing sleeping family."
Firepit | Outdoor Deck | Great Location
Celebrate the best of Kentucky while staying at Kentucky's Best on Berry
Living area

Celebrate the best of Kentucky while staying at Kentucky's Best on Berry

10.0 out of 10, Exceptional, (7)
"House was clean and exactly as described. Great location. Will definitely book again!"
The price is SAR 825
SAR 1,634 total
includes taxes & fees
24 Feb - 25 Feb
Celebrate the best of Kentucky while staying at Kentucky's Best on Berry
Totally renovated downtown home walk to all
Exterior

Totally renovated downtown home walk to all

9.6 out of 10, Exceptional, (61)
"Very nice place and an awesome location! "
The price is SAR 844
SAR 1,175 total
includes taxes & fees
24 Feb - 25 Feb
Totally renovated downtown home walk to all
Hot Tub | Close to Downtown | Game Room | Fire Pit |
Front of our newly constructed farmhouse.

Hot Tub | Close to Downtown | Game Room | Fire Pit |

10.0 out of 10, Exceptional, (54)
"This home is perfect for families! It's also in a location that is very convenient to downtown and the university area. The beds are very comfortable, and the home layout is very functional. Our whole family enjoyed the stay!"
The price is SAR 1,793
SAR 3,677 total
includes taxes & fees
19 Mar - 20 Mar
Hot Tub | Close to Downtown | Game Room | Fire Pit |
4 Bedroom House with Game Room
Combination game room and 4th bedroom

4 Bedroom House with Game Room

10.0 out of 10, Exceptional, (11)
"We enjoyed our stay tremendously! The house was spacious, clean and had everything we needed! Will definitely be coming back! "
4 Bedroom House with Game Room
Stylish Richmond Home. Near EKU and Downtown
Living area

Stylish Richmond Home. Near EKU and Downtown

9.4 out of 10, Exceptional, (16)
"Six friends having a girls weekend. The house was excellent and very clean. Could have use a few more towels a wash cloths. We would definitely stay here again. "
Stylish Richmond Home. Near EKU and Downtown
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!
Location, Location, Location
Living area

Location, Location, Location

9.2 out of 10, Wonderful, (43)
"The only thing we needed that we did not find is soap for the showers. Otherwise, all was great!"
The price is SAR 413
SAR 800 total
includes taxes & fees
24 Feb - 25 Feb
Location, Location, Location
Horse Show on Sherman
View from the living room looking past the bar area to the kitchen and hallway

Horse Show on Sherman

9.8 out of 10, Exceptional, (83)
"Was in town for business. With lots of busyness during the day, this place was perfect for me to return after work. I could cook a little food then take a walk around the Neiborhood that was friendly and safe. Place was quiet in the evening and close to plenty of shops and eating places if that's your thing. Hostess Dru was the best with "
The price is SAR 296
SAR 688 total
includes taxes & fees
24 Feb - 25 Feb
Horse Show on Sherman
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, (1496)
"Hiking trail was nice"
The price is SAR 322
SAR 355 total
includes taxes & fees
24 Feb - 25 Feb
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, (279)
"Loved the location but 4 wheel drive is highly recommend. Very steep driveway."
The price is SAR 347
SAR 744 total
includes taxes & fees
24 Feb - 25 Feb
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!

Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!

9.4 out of 10, Exceptional, (62)
"We needed a short convenient layover in the middle of a trip and this worked perfectly. "
The price is SAR 386
SAR 817 total
includes taxes & fees
24 Feb - 25 Feb
Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!
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.