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Holiday Rentals in Jessamine County

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Featured Holiday Rentals in Jessamine County

Our top choices for Jessamine County holiday rentals

Spacious family Lodge with solar heated pool, hot tub, fire pit and EV charger.
Outdoor dining

Spacious family Lodge with solar heated pool, hot tub, fire pit and EV charger.

10.0 out of 10, Exceptional, (91)
"Sam was an awesome host. He stopped by several time to ensure we could get the bonfire going and once to drop off some beverages for us to try. The lodge is very spacious, there were four couples and with five bedrooms we all had plenty of room. There were multiple different activities we could do including bags, hot tub and patio tables to play cards and hang out! If ever in this area I would highly recommend staying. The neighborhood is quiet and friendly.We will be back soon! "
Spacious family Lodge with solar heated pool, hot tub, fire pit and EV charger.
Stay in a newly renovated home in the heart of Dtown Lexington
Exterior

Stay in a newly renovated home in the heart of Dtown Lexington

9.0 out of 10, Wonderful, (6)
"This home was adequately set up and clean. I thought the pillows could have been nicer. The internet was fine once we got the correct name. "
The price is €179
includes taxes & fees
29 Sept - 30 Sept
Stay in a newly renovated home in the heart of Dtown Lexington
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, (68)
"We gambled n we won"
The price is €226
includes taxes & fees
29 Sept - 30 Sept
This house is a 3 bedroom(s), 2 bathrooms, located in Lexington, KY.
Location, Location, Location
Fridge, microwave, oven, stovetop

Location, Location, Location

9.2 out of 10, Wonderful, (59)
"House was cute and great location in downtown Lexington! "
The price is €188
includes taxes & fees
28 Sept - 29 Sept
Location, Location, Location
Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena
Property grounds

Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena

9.8 out of 10, Exceptional, (96)
"Clean, comfortable apartment in the heart of Lexington. Communication with hosts was excellent. Great value for money."
The price is €180
includes taxes & fees
14 Sept - 15 Sept
Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena
This house is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
Fridge, microwave, oven, stovetop

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

9.4 out of 10, Exceptional, (58)
"Super location, amenities, very clean, fenced yard for our dog was a definite bonus. Would rent again for sure!"
The price is €193
includes taxes & fees
24 Sept - 25 Sept
This house is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
The Luxe/Hot Tub/10 Min Keenland/12 Min Downtown/Fenced In Yard/ Pet Friendly
Terrace/patio

The Luxe/Hot Tub/10 Min Keenland/12 Min Downtown/Fenced In Yard/ Pet Friendly

10.0 out of 10, Exceptional, (13)
"We truly enjoyed our stay here. The large kitchen is impressive. The hot tub worked well and the outdoor space was delightful."
The price is €383
includes taxes & fees
29 Sept - 30 Sept
The Luxe/Hot Tub/10 Min Keenland/12 Min Downtown/Fenced In Yard/ Pet Friendly
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, (33)
"Just a few days in Lexington "
The price is €175
includes taxes & fees
14 Sept - 15 Sept
This bungalow is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!
Property grounds

Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!

10.0 out of 10, Exceptional, (279)
"Peaceful, relaxing, really enjoyed it"
The price is €217
includes taxes & fees
6 Oct - 7 Oct
Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!
ONE OF A KIND Sanctuary with POOL. Keeneland, Bourbon Trail
Dining

ONE OF A KIND Sanctuary with POOL. Keeneland, Bourbon Trail

10.0 out of 10, Exceptional, (23)
"We really loved the house and especially the beautiful views from the house!"
ONE OF A KIND Sanctuary with POOL. Keeneland, Bourbon Trail
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, (77)
"This was a wonderful property with plenty of room. Very clean and beds were so comfortable. Will definitely stay here again. "
The price is €331
includes taxes & fees
10 Sept - 11 Sept
This house is a 4 bedroom(s), 3 bathrooms, located in Lexington, KY.
Lakefront Home Close to Bourbon Trail--Dog friendly!
Property grounds

Lakefront Home Close to Bourbon Trail--Dog friendly!

9.8 out of 10, Exceptional, (78)
"Fantastic house and location! Close to the bourbon trail and cannot beat a morning coffee over looking the lake!"
Lakefront Home Close to Bourbon Trail--Dog friendly!
Treetops Solar Sanctuary
Property grounds

Treetops Solar Sanctuary

9.8 out of 10, Exceptional, (80)
"Such a fun and homey place! Perfect location to get all around Lexington. Very clean and well equipped!"
The price is €146
includes taxes & fees
6 Oct - 7 Oct
Treetops Solar Sanctuary
Historic 1850 Towering Italianate Villa, Hobby Horse Farm
Exterior

Historic 1850 Towering Italianate Villa, Hobby Horse Farm

10.0 out of 10, Exceptional, (1)
"After long days at a local Lexington event, it was a perfect place to come back to and relax. The house was large enough for the entire family to have some space to relax, whether it was inside or taking in the beautiful scenery on the deck.The large family dining area was also perfect for meals, and the kitchen allowed us to have some family time around preparing and eating meals.Would stay at this location again"
The price is €1,115
includes taxes & fees
10 Sept - 11 Sept
Historic 1850 Towering Italianate Villa, Hobby Horse Farm
Pool | Hot Tub | Covered Porch | Patio | Game Room
Fridge, microwave, oven, stovetop

Pool | Hot Tub | Covered Porch | Patio | Game Room

9.8 out of 10, Exceptional, (116)
"Enjoyed the trip to the city and the surrounding area"
The price is €759
includes taxes & fees
14 Sept - 15 Sept
Pool | Hot Tub | Covered Porch | Patio | Game Room
This apartment is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
Fridge, microwave, oven, stovetop

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

2.0 star property
9.4 out of 10, Exceptional, (10)
"Great location and huge place. Gorg windows and high ceilings. I stayed here for a friends wedding and loved it. Will stay again next time I’m in town! "
The price is €189
includes taxes & fees
10 Sept - 11 Sept
This apartment is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
It's rare to find a place that's both historic & one-of-a-kind
Interior

It's rare to find a place that's both historic & one-of-a-kind

10.0 out of 10, Exceptional, (45)
"We really enjoyed staying here! We had a swim meet in Danville and commuted back and forth. Check in and out was easy! "
The price is €137
includes taxes & fees
23 Sept - 24 Sept
It's rare to find a place that's both historic & one-of-a-kind
This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.
Exterior

This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.

8.6 out of 10, Excellent, (33)
"We’ve enjoyed our stay. Great people to work with. "
The price is €151
includes taxes & fees
24 Sept - 25 Sept
This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.
KY Bourbon Trail FUN! Double Shot on Main 2 Bed/2 Bath
Exterior detail

KY Bourbon Trail FUN! Double Shot on Main 2 Bed/2 Bath

10.0 out of 10, Exceptional, (112)
"House was very clean and central to everything we were visiting."
The price is €192
includes taxes & fees
23 Sept - 24 Sept
KY Bourbon Trail FUN! Double Shot on Main 2 Bed/2 Bath
Cozy cabin in the heart of horse country
Terrace/patio

Cozy cabin in the heart of horse country

10.0 out of 10, Exceptional, (22)
"Host was very responsive and accommodating, cabin was in a great location, close to everything we were in town to do. It was clean and well stocked for our 5 night stay. "
Cozy cabin in the heart of horse country
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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Top Jessamine County Hotel Reviews

Find out more about Jessamine County

Find out more about Jessamine County

Holiday Homes in Jessamine County

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