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Check prices for these dates

Next weekend
11 Rab. II - 13 Rab. II
In two weeks
18 Rab. II - 20 Rab. II
In one month
2 Jum. I - 4 Jum. I
In two months
30 Jum. I - 1 Jum. II

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

Luxurious 1-bedroom with Free Parking
Exterior

Luxurious 1-bedroom with Free Parking

9.8 out of 10, Exceptional, (31)
"We were in town for a sporting event on campus and discovered the apartment was very conveniently located...not only to the University of Kentucky campus but to other popular sites in town. The apartment included a very modern kitchen and a very nice Kroger grocery within easy walking distance with which to stock that kitchen. We missed a more defined living room area, but the comfy king size bed, large shower, and off street parking made up for it. We would definitely stay here again."
The price is SAR 300
SAR 905 total
includes taxes & fees
16 Apr - 17 Apr
Luxurious 1-bedroom with Free Parking
Bluegrass Oasis - Entire house,12 guests, 5mi to KHP
Smart TV

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
Exterior

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

10.0 out of 10, Exceptional, (13)
"Literally perfect and exactly like the listing"
The price is SAR 689
SAR 1,512 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!
Exterior

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

10.0 out of 10, Exceptional, (28)
"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
Fridge, microwave, oven, stovetop

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
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (91)
"The place served our purposes very well. It was very nice and clean. The owners were very helpful and accommodating. We need to stay at this place in the summer so we can enjoy the enclosed porch. "
Cali king beds. Best of Nicholasville! Koi pond relaxing backyard. 3 bed 2 bath
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, (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 371
SAR 740 total
includes taxes & fees
2 Apr - 3 Apr
Modern 2bd 2ba- Near I-75, Free WiFi, No Steps
Spacious house minutes from the Horse Park
Fridge, microwave, oven, stovetop

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
Exterior

Authentic, Rustic, Historic Log Cabin

10.0 out of 10, Exceptional, (136)
"Overall, the property is wonderful and we had a great two days celebrating our dad’s birthday! 11 adults were there in total. I was satisfied and would stay again— just posting here for others who may be considering and would like details. Of course it was January when we stayed— so summer may make a diff but the temperature was inconsistent in different rooms— particularly the room off the downstairs master. There are only 2 tvs— one in the fireplace room downstairs (which we never found the...
Authentic, Rustic, Historic Log Cabin
Hot Tub | Walk to Downtown | Patio | Fire Pit | Game Room
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (163)
"Nice Time!"
Hot Tub | Walk to Downtown | Patio | Fire Pit | Game Room
This house is a 3 bedroom(s), 2 bathrooms, located in Lexington, KY.
Fridge, coffee/tea maker, cookware/dishes/utensils

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

9.2 out of 10, Wonderful, (52)
"Clean and pretty good for the price "
The price is SAR 544
SAR 971 total
includes taxes & fees
15 Apr - 16 Apr
This house is a 3 bedroom(s), 2 bathrooms, located in Lexington, KY.
Newly renovated Historic House within walking distance to UK.
Property grounds

Newly renovated Historic House within walking distance to UK.

10.0 out of 10, Exceptional, (102)
"It was big enough for my family "
Newly renovated Historic House within walking distance to UK.
Isla's Landing - Charming Historic 1940s Home
TV

Isla's Landing - Charming Historic 1940s Home

10.0 out of 10, Exceptional, (36)
"Upon arrival, entered this cozy and inviting home which met all of our needs! Loved the location, amenities, and the backyard was a bonus for our pup! Alllen communicated well too! Thank you! "
Isla's Landing - Charming Historic 1940s Home
15 Mi to Dtwn Lexington: Serene Wilmore Home!
Fridge, microwave, stovetop, dishwasher

15 Mi to Dtwn Lexington: Serene Wilmore Home!

3.0 star property
9.6 out of 10, Exceptional, (8)
"It worked great for us "
15 Mi to Dtwn Lexington: Serene Wilmore Home!
Newly remodeled beautiful home in a nice neighborhood!
Fridge, microwave, oven, stovetop

Newly remodeled beautiful home in a nice neighborhood!

9.8 out of 10, Exceptional, (56)
" There were just some minor electrical issue, but overall very nice home."
Newly remodeled beautiful home in a nice neighborhood!
Remodeled gorgeous cottage overlooking horse farm. Family and work friendly.
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (4)
"We spent a quick weekend to go see the rodeo, The house was the perfect location and very easy to check into. It had all the amenities you would want and the horses in the field were beautiful. We would defiantly return. "
The price is SAR 746
SAR 1,629 total
includes taxes & fees
29 Apr - 30 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
Exterior

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

9.8 out of 10, Exceptional, (70)
"House was great. Location is perfect, in the middle of town. Holly was great to work with. "
The price is SAR 563
SAR 959 total
includes taxes & fees
16 Apr - 17 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
Outdoor spa tub

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

3.0 star property
10.0 out of 10, Exceptional, (5)
"We needed a place equal distance for our family to celebrate an early Christmas. We were very pleased with the property. It was clean and had enough room for all our activities. We had a great time."
Spacious 5-bedroom House, Garage/Hot Tub/Bar, Close to RRG, Fiber WiFi
Horse Show on Sherman
Exterior

Horse Show on Sherman

9.8 out of 10, Exceptional, (85)
"Eccentric, cool decor with great host communication and very convenient location! "
The price is SAR 296
SAR 715 total
includes taxes & fees
7 Apr - 8 Apr
Horse Show on Sherman
Golf Simulator | Hot Tub | Game Room | Pool Table
Terrace/patio

Golf Simulator | Hot Tub | Game Room | Pool Table

10.0 out of 10, Exceptional, (47)
"The property was very clean, nice, and modern, perfect location, and easy access to the distilleries and downtown!"
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
Seasonal outdoor pool

Natural Bridge State Resort Park

3.5 star property
8.6 out of 10, Excellent, (1510)
"Property very clean. Excellent breakfast. Close to Natural Bridge. "
The price is SAR 454
SAR 500 total
includes taxes & fees
8 Apr - 9 Apr
Natural Bridge State Resort Park
Hot Tub & WiFi - Romantic Hideaway - Wooded Retreat near Red River Gorge, Kentucky!
Terrace/patio

Hot Tub & WiFi - Romantic Hideaway - Wooded Retreat near Red River Gorge, Kentucky!

9.2 out of 10, Wonderful, (75)
"They helped us out ASAP before we drove out due to inclimate weather conditions. Offered us multiple other safe locations or cancellation/rescheduling and communicated consistently.Our cabin was clean as a whistle with every little thing we may have forgotten accomodated. It's super cute,comfortable and perfect for a getaway in the trees!!"
The price is SAR 577
SAR 999 total
includes taxes & fees
14 Apr - 15 Apr
Hot Tub & WiFi - Romantic Hideaway - Wooded Retreat near Red River Gorge, Kentucky!
Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!
Outdoor spa tub

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

9.6 out of 10, Exceptional, (138)
"Loved the cabin. I wish we had planned to stay longer. There are a lot of beautiful things to enjoy in the area."
The price is SAR 425
SAR 864 total
includes taxes & fees
13 Apr - 14 Apr
Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - 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.