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Compare 424 Vacation Homes in Winchester with updated reviews, rates, and availability.

Luxurious 1-bedroom with Free Parking

9.8 out of 10, Exceptional, (35)
"We had an awesome stay in Lexington! The house was very clean. Communication was clear and responses to any questions that we had were very timely. The house was very close to the UK campus and about a mile to downtown. We would absolutely stay here again!"
The price is AED 364
AED 955 total
includes taxes & fees
8 Jun - 9 Jun
Luxurious 1-bedroom with Free Parking

Bluegrass Oasis - Entire house,12 guests, 5mi to KHP

9.8 out of 10, Exceptional, (19)
"Overall, was a great place to stay with a few other families. Was conveniently located to the events we had going on and the check in/out process was very simple."
Bluegrass Oasis - Entire house,12 guests, 5mi to KHP

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

10.0 out of 10, Exceptional, (17)
"This place was perfect for our one night stay in Kentucky. Beautifully decorated, and was equipped with anything you need!! Hot tub was our favorite! "
The price is AED 595
AED 1,425 total
includes taxes & fees
13 May - 14 May
Hot Tub/Playground/12 min to Horse Park/30min Ark

Welcome to “The Spot” - North Limestone/Downtown!

10.0 out of 10, Exceptional, (30)
"Wonderful accommodations: clever and attractive decor, very clean and well appointed. Definitely a great place to stay. "
Welcome to “The Spot” - North Limestone/Downtown!

3 BR 2 bath 5 beds! sleeps 8. Pool, hot tub oasis in LEX

9.4 out of 10, Exceptional, (10)
"Great house. Clean. Well-appointed. All the little things you need like basic condiments, coffee filters, dishwasher pods, etc. Nice beds…great parking…and a HUGE table for family meals."
3 BR 2 bath 5 beds! sleeps 8. Pool, hot tub oasis in LEX

Cali king beds. Best of Nicholasville! Koi pond relaxing backyard. 3 bed 2 bath

10.0 out of 10, Exceptional, (94)
"Well-appointed home in a safe neighborhood with easy access to Lexington. The owner was quick to respond to any questions. Had a great stay & can highly recommend."
Cali king beds. Best of Nicholasville! Koi pond relaxing backyard. 3 bed 2 bath

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

9.8 out of 10, Exceptional, (71)
"Understated, quiet, clean... loved our stay"
The price is AED 437
AED 806 total
includes taxes & fees
13 May - 14 May
Modern 2bd 2ba- Near I-75, Free WiFi, No Steps

Spacious house minutes from the Horse Park

9.2 out of 10, Wonderful, (23)
"Everything went very smoothly for our stay - easy self check-in and checkout. House was clean and well main and it was great being able to use the garage."
Spacious house minutes from the Horse Park

Authentic, Rustic, Historic Log Cabin

10.0 out of 10, Exceptional, (141)
"Beautiful property and amazing host!Communication is top notch!This was our third time staying at this homey cabin and hope to visit again in the future!"
Authentic, Rustic, Historic Log Cabin

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

10.0 out of 10, Exceptional, (166)
"We really enjoyed our stay. Was very comfortable and welcoming home. "
Hot Tub | Walk to Downtown | Patio | Fire Pit | Game Room

This house is a 3 bedroom(s), 2 bathrooms, located in Lexington, KY.

9.4 out of 10, Exceptional, (57)
"A terrific area! Convenient to restaurants, shopping, and the New Circle exit. There's a neighborhood park behind the home and ducks have been through the yard. Neighbors are nice and it's safe for families and groups. We love it here! House was clean and well appointed. Highly Recommended!"
The price is AED 533
AED 960 total
includes taxes & fees
13 May - 14 May
This house is a 3 bedroom(s), 2 bathrooms, located in Lexington, KY.

Newly renovated Historic House within walking distance to UK.

10.0 out of 10, Exceptional, (107)
"Clean, spacious, and conveniently located. "
Newly renovated Historic House within walking distance to UK.

Isla's Landing - Charming Historic 1940s Home

10.0 out of 10, Exceptional, (39)
"We had a short weekend stay and enjoyed the home and location. The host was great to communicate with "
Isla's Landing - Charming Historic 1940s Home

15 Mi to Dtwn Lexington: Serene Wilmore Home!

3.0 star property
9.6 out of 10, Exceptional, (9)
"The front porch is absolutely amazing! There is a good bit of traffic going by but we spent hours out there visiting and just relaxing."
15 Mi to Dtwn Lexington: Serene Wilmore Home!

Newly remodeled beautiful home in a nice neighborhood!

9.8 out of 10, Exceptional, (60)
"Clean property with thoughtful touches. Would recommend to others! "
Newly remodeled beautiful home in a nice neighborhood!

Remodeled gorgeous cottage overlooking horse farm. Family and work friendly.

9.8 out of 10, Exceptional, (7)
"Property was clean comfortable and very enjoyable! Easy access to Georgetown Lexington and area points of interest. Would definitely stay here again."
The price is AED 731
AED 1,608 total
includes taxes & fees
15 May - 16 May
Remodeled gorgeous cottage overlooking horse farm. Family and work friendly.

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

9.8 out of 10, Exceptional, (74)
"Super nice and clean "
The price is AED 606
AED 1,028 total
includes taxes & fees
2 Jun - 3 Jun
Spacious Home - Sleeps 8 Fire-pit 1 Block to EKU & Downtown, 2 Miles to I-75

Spacious 5-bedroom House, Garage/Hot Tub/Bar, Close to RRG, Fiber WiFi

3.0 star property
10.0 out of 10, Exceptional, (6)
"Will definitely be back. "
Spacious 5-bedroom House, Garage/Hot Tub/Bar, Close to RRG, Fiber WiFi

Horse Show on Sherman

9.8 out of 10, Exceptional, (88)
"Nice little gem of a property located close to everything in Lexington."
The price is AED 290
AED 674 total
includes taxes & fees
19 May - 20 May
Horse Show on Sherman

Golf Simulator | Hot Tub | Game Room | Pool Table

10.0 out of 10, Exceptional, (50)
"We had a great time in Lexington. The house was lovely and met our expectations."
Golf Simulator | Hot Tub | Game Room | Pool Table
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

3.5 star property
8.6 out of 10, Excellent, (1552)
"Wonderful area"
The price is AED 463
AED 510 total
includes taxes & fees
13 May - 14 May
Natural Bridge State Resort Park

Tranquil Getaway in the Woods ~ Sunset Ridge

9.8 out of 10, Exceptional, (55)
"The cabin was beautiful and the scenery was great. Everything you need for a great getaway "
The price is AED 386
AED 547 total
includes taxes & fees
13 May - 14 May
Tranquil Getaway in the Woods ~ Sunset Ridge

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

9.4 out of 10, Exceptional, (68)
"We needed a short convenient layover in the middle of a trip and this worked perfectly. "
The price is AED 397
AED 813 total
includes taxes & fees
14 May - 15 May
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.