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Jessamine County Holiday Rentals

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Top Holiday Rentals Destinations in Jessamine County

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.
Private One Bedroom Apartment in Downtown Lexington near Rupp Arena
Property grounds

Private One Bedroom Apartment in Downtown Lexington near Rupp Arena

10.0 out of 10, Exceptional, (142)
"This is our third time staying here! We love the location, the quaintness of the place and the ease of check in and check out! Looking forward to staying here again! "
The price is AU$259
includes taxes & fees
14 Sept - 15 Sept
Private One Bedroom Apartment in Downtown Lexington near Rupp Arena
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 AU$319
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 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 AU$268
includes taxes & fees
9 Sept - 10 Sept
This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, 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 AU$378
includes taxes & fees
7 Sept - 8 Sept
Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!
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, (4)
"Cute, fully renovated house in what seemed to be in an up and coming neighborhood. The street itself seemed a bit sketchy, but we felt safe and comfortable to walk to the restaurants nearby. Super close to downtown Lexington, which was a huge plus! Beds and couch were very comfy. It worked for our 2 night stopover on our way up north. Thank you!"
The price is AU$314
includes taxes & fees
29 Sept - 30 Sept
Stay in a newly renovated home in the heart of Dtown Lexington
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!
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, (67)
"We gambled n we won"
The price is AU$413
includes taxes & fees
7 Sept - 8 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, (58)
"House was cute and great location in downtown Lexington! "
The price is AU$341
includes taxes & fees
7 Sept - 8 Sept
Location, Location, Location
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 AU$636
includes taxes & fees
7 Sept - 8 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.

9.0 out of 10, Wonderful, (31)
"Just a few days in Lexington "
The price is AU$289
includes taxes & fees
9 Sept - 10 Sept
This bungalow is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
Treetops Solar Sanctuary
Property grounds

Treetops Solar Sanctuary

9.8 out of 10, Exceptional, (80)
"Very easy to find and check in. I was by myself so I usually stay in hotels but felt very safe here. All details were taken care of and it was a fabulous place to stay!"
The price is AU$282
includes taxes & fees
10 Sept - 11 Sept
Treetops Solar Sanctuary
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 AU$243
includes taxes & fees
7 Sept - 8 Sept
It's rare to find a place that's both historic & one-of-a-kind
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)
"We had a great stay. Perfect for multigenerational families."
The price is AU$593
includes taxes & fees
8 Sept - 9 Sept
This house is a 4 bedroom(s), 3 bathrooms, located in Lexington, KY.
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!"
The price is AU$1,870
includes taxes & fees
8 Sept - 9 Sept
ONE OF A KIND Sanctuary with POOL. Keeneland, Bourbon Trail
Carriage on Petticoat
Terrace/patio

Carriage on Petticoat

2.0 star property
10.0 out of 10, Exceptional, (22)
"Very nice house. Conveniently located and the host was very responsive."
The price is AU$608
includes taxes & fees
10 Sept - 11 Sept
Carriage on Petticoat
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
High Spirits Estate - Pool, Hot Tub, Game Room, EV charger, Sleeps 20
Exterior

High Spirits Estate - Pool, Hot Tub, Game Room, EV charger, Sleeps 20

10.0 out of 10, Exceptional, (4)
"Excellent and well-appointed home which made our family get-together wonderful. The property itself is large and spacious, so there is lots to do--rain or shine!Close to several bourbon distilleries, horse stables, and parks. Highly recommend!"
High Spirits Estate - Pool, Hot Tub, Game Room, EV charger, Sleeps 20
Bourbon on Broadway
Smart TV

Bourbon on Broadway

2.0 star property
10.0 out of 10, Exceptional, (14)
"Very nice place, clean, great design and location"
The price is AU$389
includes taxes & fees
7 Sept - 8 Sept
Bourbon on Broadway
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 AU$1,776
includes taxes & fees
14 Sept - 15 Sept
Pool | Hot Tub | Covered Porch | Patio | Game Room
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

Everything you need to know about Jessamine County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Jessamine County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Jessamine County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Jessamine County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Jessamine County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Jessamine County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Jessamine County holiday rentals we have chosen for you start as low as AU$243 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Jessamine County rentals

At Expedia, we put the best Jessamine County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Jessamine County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Jessamine County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Jessamine County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.