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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, (33)
"Lovely space close to campus. Great for parents visiting students. "
The price is SAR 372
SAR 1,018 total
includes taxes & fees
20 Apr - 21 Apr
Luxurious 1-bedroom with Free Parking

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

9.8 out of 10, Exceptional, (19)
"This place was extremely nice and worked perfectly for our family in town for a funeral. It was a great gathering place. We will go back if the need arises. "
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, (14)
"Very nice house with everything you need for a night away"
The price is SAR 681
SAR 1,499 total
includes taxes & fees
29 Apr - 30 Apr
Hot Tub/Playground/12 min to Horse Park/30min Ark

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

10.0 out of 10, Exceptional, (29)
"The house was exactly as listed. It was comfortable and fit all our needs. "
Welcome to “The Spot” - North Limestone/Downtown!

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

9.8 out of 10, Exceptional, (9)
"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, (92)
"We really enjoyed our stay here. The beds are so comfortable, slept like a baby. Plenty of space in the home for a big family. Everything was in great working order. Communication with owner was fast and friendly. I would highly recommend staying here. My kids loved it too. owner s"
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, (69)
"This was our second stay at this location. I highly recommend it as it's a great place to call home when you're away from home. "
The price is SAR 447
SAR 844 total
includes taxes & fees
21 Apr - 22 Apr
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, (138)
"Martin Manor's description didn't do it justice. We six were overwhelmed with the character, peacefulness, and warmth of the home. Weather did not permit enjoying the paddle boats or pond, but we loved the grounds and found the house to more than meet our needs for a fellowship gathering of friends from five states. We enjoyed visiting with another friend in nearby Versailles, a bourbon tasting, and two wineries during our stay. We would definitely recommend a stay at the Martin Manor."
Authentic, Rustic, Historic Log Cabin

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

10.0 out of 10, Exceptional, (165)
"Our family stayed at Seth's property during our spring break. The house was beautiful and spacious. There was plenty of room for our family to spread out. The furniture was very comfy and the hot tub was a nice bonus. The location was perfect. We walked to a couple dinner locations and the grocery store. Seth was a fantastic communicator and checked in to make sure we had everything that we needed. We would definitely stay here again for our next trip to Lexington. "
The price is SAR 987
SAR 2,381 total
includes taxes & fees
27 Apr - 28 Apr
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, (54)
"Everything you need is in this house. Cute neighborhood. "
The price is SAR 544
SAR 999 total
includes taxes & fees
12 May - 13 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, (105)
"We enjoyed our stay while visiting UK. The location to the university was perfect. Our host gave us wonderful suggestions for places to eat. We had a great stay!"
Newly renovated Historic House within walking distance to UK.

Isla's Landing - Charming Historic 1940s Home

10.0 out of 10, Exceptional, (39)
"Great property nicely located for the University and all that Lexington has to offer. Everything was clean and the property is well maintained and well equipped. Recommended and would stay again!"
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)
"This house has all the character that I love and all the functionality that I love. The kitchen and bathrooms are updated and the rest of the house is charming! Neighbors have horses. Nice quiet neighborhood. Hard to find a house with a king size bed which is must for my husband and they had extra blankets. Just needed an extra fan to make some background noise. "
15 Mi to Dtwn Lexington: Serene Wilmore Home!

Newly remodeled beautiful home in a nice neighborhood!

9.8 out of 10, Exceptional, (58)
"Excellent stay. Very comfortable clean house. Super convienient to anyplace in Lexington. As advertised. 100% would stay again. Great communication. "
Newly remodeled beautiful home in a nice neighborhood!

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

9.6 out of 10, Exceptional, (5)
"This is a wonderfully equipped and comfortable cottage with a great location to explore Lexington and surrounding areas. Close to attractions and also has many basic amenities right nearby. "
The price is SAR 747
SAR 1,630 total
includes taxes & fees
20 Apr - 21 Apr
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, (72)
"House was great. Location is perfect, in the middle of town. Holly was great to work with. "
The price is SAR 619
SAR 1,051 total
includes taxes & fees
20 Apr - 21 Apr
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)
"Great place to stay for a larger group. Would have been nice to see the fence fully enclose the backyard but you could live without that for a few days."
Spacious 5-bedroom House, Garage/Hot Tub/Bar, Close to RRG, Fiber WiFi

Horse Show on Sherman

9.8 out of 10, Exceptional, (87)
"100% will stay again. Great price great communication "
The price is SAR 296
SAR 715 total
includes taxes & fees
21 Apr - 22 Apr
Horse Show on Sherman

Golf Simulator | Hot Tub | Game Room | Pool Table

10.0 out of 10, Exceptional, (49)
"We had 4 couples, siblings and spouses. This home offered each couple a private bedroom and bathroom. Plenty of common area space to gather, share meals, and visit. The game room provided a lot of fun. We also enjoyed the hot tub and outdoor seating area. Location was near attractions, but in a quiet neighborhood. Would definitely recommend!"
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, (1526)
"We stayed in a cottage. The cottage needs a lot of repairs. We had to climb 36 stairs in rainy conditions to reach our cabin. The complimentary breakfast was nice. The staff were all friendly and helpful. The walk to the restaurant from the cottages was outstanding and fun. Despite the state of disrepair to our cabin, we would still recommend this location as a must-do family adventure and destination."
The price is SAR 435
SAR 480 total
includes taxes & fees
29 Apr - 30 Apr
Natural Bridge State Resort Park

Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!

9.6 out of 10, Exceptional, (141)
"Cozy, clean and comfortable cabin!"
The price is SAR 425
SAR 864 total
includes taxes & fees
11 May - 12 May
Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!

Tranquil Getaway in the Woods ~ Sunset Ridge

9.8 out of 10, Exceptional, (53)
"My girlfriends and I loved the quaint cabin. The firepit was great! Beds are comfortable and comes with plenty of kitchen amenities! I would recommend adding a curtain option for the bed by the window.. Though it's off the beaten path, we were removed enough from others and no issue of safety."
The price is SAR 394
SAR 559 total
includes taxes & fees
21 Apr - 22 Apr
Tranquil Getaway in the Woods ~ Sunset Ridge
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.