Vacation rentals in Jessamine County

4.98 out of 5 average rating, 248 reviews

Cottage in Wilmore

River House - Cottage with KY River View & Access

Come relax at the peaceful river house. It feels like a retreat right on the Kentucky River with a party-sized dock for easy river access. It’s a cozy cottage on stilts with a breakfast bar on the porch and swing on the patio. Be surrounded by nature and beautiful views of the river and palisades. Tuck away in seclusion just minutes away from downtown Wilmore, Asbury University & Seminary. 35 minutes or less from LEX Bluegrass Airport, Keeneland and Shaker Village. See guidebook for more info.

4.97 out of 5 average rating, 317 reviews

Apartment in Wilmore

Basement apt. w/private entrance & kitchenette

Our full basement apartment with private entrance is modest but comfortable. Located within one mile of Asbury Seminary and University, our space is ideally suited for commuting students, out-of-town guests, or folks visiting the beautiful Bluegrass region. Our home is a 15-minute walk from the campuses and business district. We are a family of six and you will occasionally hear our boys upstairs, but as a Christian family, we strive to treat our guests as we would want to be treated. Reg. 9485

4.99 out of 5 average rating, 109 reviews

Newly renovated upscale house with high ceilings

Get away and cozy in at this clean and comfortable two bed, two bath private home centrally located in a convenient, quiet neighborhood less than a five-minute walk to Kroger, restaurants, coffee, and a yoga studio. Easily accessible to Fayette Mall and UK by car. Fully equipped kitchen for cooking meals, reclining sofa for relaxing, 65" TV, books and games. One new Sealy king bed and a bunk bed with one double and two twin mattresses (one trundle). Washer and dryer available for your use.

Guesthouse in Nicholasville

4.98 out of 5 average rating, 347 reviews

Cottage Retreat - Wine, Horses, Convenient

Just south of Lexington KY. Cottage Retreat - nestled between horse farms & open land this 25 acre farm is a unique & convenient location to relax and spend time unwinding. 7.8 miles from the Bluegrass Airport, 10.8 miles from Rupp Arena, 8.4 miles from Keeneland - you're close to numerous items of interest. Enjoy the fully remodeled private cottage, stroll down the lane, enjoy the close proximity of horses, and perhaps buy a bottle of wine on site. No pets and no smoking. Thank you.

5 out of 5 average rating, 188 reviews

Farm stay in Lancaster

Serene barn loft in the heart of the Bluegrass

Relax and unwind in this charming barn loft nestled amidst 13 rolling acres on Honey & Vine Farm. This loft is the ideal honeymoon and anniversary space! Enjoy coffee in the morning from Adirondack chairs overlooking the pond, spectacular sunsets from the deck, and absolute serenity in this peaceful setting. Queen bed, private entrance, and beautiful sunsets. The goats and two horses love meeting new friends! 20 minutes to Danville and near hiking, lake Herrington, and Shaker Village.

4.93 out of 5 average rating, 287 reviews

Apartment in Wilmore

Travelers Loft - Asbury & Lexington area apartment

You deserve a unique and simple guest experience! This full apartment with an upstairs sleeping loft is located in Wilmore for you. ► A short walk from Asbury University and Seminary ► 25 minutes from Lexington, Keeneland, UK, and the airport ► A quiet neighborhood with green space ► Upstairs loft bedroom with low, pitched ceilings ► Secure keyless entry ► Hi Speed Internet ► Roku TV ► Peaceful & secure ► Keurig coffee maker ► One set of towels and sheets for stays less than a week

4.89 out of 5 average rating, 169 reviews

Perfect for Traveling Professionals & Vacation!

Traveling professionals, relocation guests, vacation guests, this is the perfect house for you! This 3 bedroom 2 bath ranch-style home w/ a garage has a gourmet kitchen and an open floor plan. Perfectly located in the heart of Lexington in a family-friendly neighborhood near Trader Joes, hospitals, restaurants, the Summit Shopping Center, Fayette Mall and a short trip to Keeneland or downtown Lexington. This is the perfect home away from home. All are welcome! Pet Friendly, per request!

4.94 out of 5 average rating, 160 reviews

Southern Hospitality! Best location close to UK!

This home has been completely renovated with truly flawless finishes. Approximately 1 mile from all hospitals; UK, Central Baptist, St.Joseph. New kitchen and appliances. Very convenient location to Keeneland, Shopping, and Restaurants. Extremely clean and comfortable living spaces. The living and bed rooms have been equiped with Tv’s. WiFi is included. The shower even has a Bluetooth fan for playing music in the shower. I’ve provided everything to make your trip as enjoyable as possible.

4.92 out of 5 average rating, 296 reviews

Cabin in Nicholasville

National Historic O'neal Cabin

Originally built during the late 1700’s, this two-story log cabin was restored in 1995. The O'neal Cabin is listed on the National Register of Historic Places. Located in central Kentucky, six miles from historic downtown Lexington, the O’Neal Log Cabin is in the heart of horse country and the bourbon trail. Whether you are looking for a getaway, a place to stay during the horse sales or a retreat while you visit Lexington’s sites, the O'Neal Log Cabin is perfect retreat.

4.91 out of 5 average rating, 258 reviews

Guesthouse in Lexington

Cozy studio with private pool and firepit

Welcome to our charming studio apartment located above our detached garage with a private pool. Whether you're looking for a relaxing getaway or a convenient base to explore the city, our cozy studio has everything you need. Close to the following locations: Fayette mall 1.9 miles Bluegrass airport 4.5 miles University of Kentucky 4.6 miles Keeneland 5.1 miles Manchester Music Hall 5.7 miles Rupp Arena 6.4 miles Lexington Opera House 6.5 Please no smoking in the room.

4.96 out of 5 average rating, 114 reviews

Summer Bliss! Pool&FunZone Oasis! Hottub! GameRm!

Your friends and family will be centrally located in a peaceful Cul-de-sac in Lexington with all the perks! Whether you are going to Keeneland, a sporting event, or just looking for a fun getaway, we have all the entertainment you need! Featuring a pool, hot tub, arcade machine, pool table, ping pong, air hockey, and shuffleboard table! Looking to just relax? Help yourself to our complimentary coffee bar and take in the cozy sounds by our fire pit in the back yard!

4.93 out of 5 average rating, 267 reviews

Home in Nicholasville

Cali King beds w/ Koi pond Oasis. 15 min from LEX

Nicholasville's finest short term rental! We recently finished remodeling this spacious ranch home in Nicholasville Ky and are extremely excited to share it with future guests. It looks brand new on the inside and has an awesome oasis in the backyard with water effects/ koi pond. It is close to all the great things to do in Lexington including Keeneland and the University of Kentucky. Mattresses are top of the line and will ensure you have a very comfortable stay.

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Popular amenities for Jessamine County vacation rentals

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Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Jessamine County

4.84 out of 5 average rating, 87 reviews

Home in Versailles

Woodford Stables / Walk to Eckert's Orchard

MasonRating, 5 stars1 day ago

great place and very nice host will definetly stay again

4.83 out of 5 average rating, 60 reviews

Home in Lancaster

Lakefront property - Higher Ground

SonyaRating, 5 stars3 weeks ago

I must say that I was extremely impressed with the accommodations. Everything was exactly as listed. The home was spacious and felt like home. It made the weekend even more special. Would highly recommend this location. The host Katrina was very responsive. Thank you for sharing your home with me and my family.

5 out of 5 average rating, 11 reviews

2 bedroom Cozy & Welcoming Condo

JadenRating, 5 stars2 months ago

Very great home, was very clean and perfect all around for our stay!

5 out of 5 average rating, 13 reviews

Whitfield Manor

RyanRating, 5 stars7 months ago

Chris saved our vacation! We had a not so great experience when first arriving in Lexington due to our original host not responding to us and basically leaving me and my family stranded without a place to stay. Chris is a wonderful host. Thanks to him we didn’t have to drive 2+ hours back home. We actually got to enjoy ourselves. Definitely recommend Chris’s house to anyone coming into Lexington.

4.91 out of 5 average rating, 141 reviews

Chalet in Wilmore

Timberframe on Farm Lexington, KY Solar Power

MistyRating, 5 stars3 days ago

This was our second stay and we will def be back. The property is beautiful and peaceful and has gorgeous porch views. The house was cozy and kitchen fully stocked.

5 out of 5 average rating, 21 reviews

Home in Harrodsburg

The Blue Heron Lakeside Chalet

LizRating, 5 stars3 weeks ago

We really enjoyed our stay! It was unique in that it offers a main house and a guest house, and it turned out that this was the perfect arrangement for us (2 moms who are close friends, and our two sons, who are also close friends). When we weren't out and about, we all hung out in the A-frame main house. At bedtime, we parted ways.The A-frame has everything you might need during your stay. Then you also have the boathouse, which is beyond cute and very cozy. Both structures overlook the lake, and the outdoor deck spaces are very comfortable and inviting. I especially appreciated the propane fire pit one evening when it got a little chilly. Also, having a Keurig and pods in each house was awesome! Shelly sent detailed directions in advance of our travels, which was very helpful, and she made some local recommendations re: food and groceries. We followed up on those, and were not disappointed! She was also very responsive to us when we asked for assistance or recommendations. <3

4.89 out of 5 average rating, 151 reviews

Fully Renovated | Finished Basement | Luxury Beds

KrisRating, 5 stars4 days ago

The house was very clean, private and comfortable. The beds were super comfy and we all slept great! It was in a safe location.