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Check prices for these dates

Next weekend
6 Jum. II - 8 Jum. II
In two weeks
13 Jum. II - 15 Jum. II
In one month
27 Jum. II - 29 Jum. II
In two months
25 Raj. - 27 Raj.

Compare 440 Vacation Homes in Winchester with updated reviews, rates, and availability.

Authentic, Rustic, Historic Log Cabin
Exterior

Authentic, Rustic, Historic Log Cabin

10.0 out of 10, Exceptional, (143)
"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
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, (6)
"Will definitely be back. "
Spacious 5-bedroom House, Garage/Hot Tub/Bar, Close to RRG, Fiber WiFi
Location, Location, Location
Exterior

Location, Location, Location

9.4 out of 10, Exceptional, (48)
"Would definitely stay again!"
The price is SAR 413
SAR 804 total
includes taxes & fees
2 Jun - 3 Jun
Location, Location, Location
Keeneland- LEX Airport Darling
Fridge, microwave, oven, stovetop

Keeneland- LEX Airport Darling

9.8 out of 10, Exceptional, (12)
"We are repeat customers, will definitely try to rent again. "
Keeneland- LEX Airport Darling
Adorable 3 bedroom home - virtually everything new in historic Georgetown
3 bedrooms, desk, iron/ironing board, free WiFi

Adorable 3 bedroom home - virtually everything new in historic Georgetown

10.0 out of 10, Exceptional, (5)
Adorable 3 bedroom home - virtually everything new in historic Georgetown
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, (73)
"Definitely recommend staying here. Not too far from 75, and tons of places in Richmond and nearby for shopping/restaurants. Place was very clean, comfortable furniture and beds. Quiet neighborhood, just a cozy place to stay."
The price is SAR 446
SAR 827 total
includes taxes & fees
2 Jun - 3 Jun
Modern 2bd 2ba- Near I-75, Free WiFi, No Steps
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, (166)
"We really enjoyed our stay. Was very comfortable and welcoming home. "
The price is SAR 668
SAR 1,939 total
includes taxes & fees
15 Jun - 16 Jun
Hot Tub | Walk to Downtown | Patio | Fire Pit | Game Room
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, (10)
"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!
Lexington Home ~ 2 Mi to University of Kentucky!
Fridge, microwave, stovetop, dishwasher

Lexington Home ~ 2 Mi to University of Kentucky!

10.0 out of 10, Exceptional, (62)
"Another great stay; perfect for our Family!!"
Lexington Home ~ 2 Mi to University of Kentucky!
Spacious King Suite / Game Room / Patio / Firepit
Exterior

Spacious King Suite / Game Room / Patio / Firepit

10.0 out of 10, Exceptional, (3)
"This house was perfect accommodations for our group of 3 couples. It was very clean and well stocked. The neighborhood is quiet. The location in Georgetown was convenient to Lexington attractions as well as to restaurants in downtown Georgetown. We recommend this VRBO highly. "
The price is SAR 435
SAR 1,170 total
includes taxes & fees
30 Jun - 1 Jul
Spacious King Suite / Game Room / Patio / Firepit
Bigfoot Bungalow / RRG / Hot Tub!
Terrace/patio

Bigfoot Bungalow / RRG / Hot Tub!

9.6 out of 10, Exceptional, (7)
"The cabin is very nice and it was in a nice quiet area, which is exactly what I was looking for. Convenient location to great hiking spots. I would gladly stay here again, it was great. "
Bigfoot Bungalow / RRG / Hot Tub!
Delightfully secluded 1 bed and a loft for extra space. TV and DVD player.
Property grounds

Delightfully secluded 1 bed and a loft for extra space. TV and DVD player.

9.0 out of 10, Wonderful, (19)
"Great place to stay if you aren't looking to get to fancy and just need a place to lay your head down between hikes"
Delightfully secluded 1 bed and a loft for extra space. TV and DVD player.
This house is a 4 bedroom(s), 3 bathrooms, located in Lexington, KY.
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (70)
"We stayed here for a night and attended an event at the Greyline station for the weekend! Wish we could of stayed long ! Next time! Amazing property!"
The price is SAR 611
SAR 1,478 total
includes taxes & fees
3 Jun - 4 Jun
This house is a 4 bedroom(s), 3 bathrooms, located in Lexington, KY.
Hot tub! Fire pit! Picnic area! Grill! Dog friendly! Hardwicks Creek Haven @RRG
Property grounds

Hot tub! Fire pit! Picnic area! Grill! Dog friendly! Hardwicks Creek Haven @RRG

10.0 out of 10, Exceptional, (17)
"We enjoyed it very much! Beautiful home and peaceful atmosphere!"
Hot tub! Fire pit! Picnic area! Grill! Dog friendly! Hardwicks Creek Haven @RRG
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.

9.4 out of 10, Exceptional, (58)
"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 SAR 544
SAR 993 total
includes taxes & fees
23 Jun - 24 Jun
This house is a 3 bedroom(s), 2 bathrooms, located in Lexington, KY.
Isla's Landing - Charming Historic 1940s Home
TV

Isla's Landing - Charming Historic 1940s Home

10.0 out of 10, Exceptional, (41)
"Convenient to downtown, hospitals and campus. "
Isla's Landing - Charming Historic 1940s Home
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, (74)
"Super nice and clean "
The price is SAR 619
SAR 1,050 total
includes taxes & fees
25 Jun - 26 Jun
Spacious Home - Sleeps 8 Fire-pit 1 Block to EKU & Downtown, 2 Miles to I-75
New-Keeneland-Airport Honey!
Smart TV

New-Keeneland-Airport Honey!

10.0 out of 10, Exceptional, (21)
"The house is very comfortable, clean and well stocked. And the location is so convenient to the airport, Keeneland, UK, shopping and dining. And the host is great! We visit Lexington a couple times a year and this is one we’ll definitely want to stay in again. "
New-Keeneland-Airport Honey!
Firepit | Outdoor Deck | Great Location
TV, fireplace, offices

Firepit | Outdoor Deck | Great Location

10.0 out of 10, Exceptional, (74)
"Great house in a perfect location. "
The price is SAR 743
SAR 2,035 total
includes taxes & fees
15 Jun - 16 Jun
Firepit | Outdoor Deck | Great Location
This bungalow is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
Exterior

This bungalow is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.

8.8 out of 10, Excellent, (23)
"Great location. Comfy house. "
The price is SAR 390
SAR 804 total
includes taxes & fees
30 Jun - 1 Jul
This bungalow is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
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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