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Townhouse holiday rentals in Jessamine County

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Top-rated townhouse rentals in Jessamine County

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Townhouse in Lexington

4.78 out of 5 average rating, 181 reviews

Bellaire Suite at Legacy Trail

Be our guest in downtown Lexington’s premier Airbnb experience, the Bellaire Suite! Nestled in the burgeoning West Sixth area, the chic and spacious ground-floor suite is located directly on the beautiful 12-mile Legacy Trail and a minute’s walk to local hot spots such as the West Sixth Brewery, County Club restaurant, and Coolalvin Park. You’ll find solace and inspiration under the 10 foot ceilings with plenty of natural light and fresh, contemporary design throughout. A plush, king-size bed welcomes your retreat, while a fully equipped kitchen tempts your best culinary endeavors. Movie nights are un-matched with a massive 84” theater and sound system with Roku streaming. Also included for exclusive guest use are a full-size washer/dryer, high speed internet, complimentary welcome snacks, and much more. Come enjoy this newly opened gem in downtown Lexington!

Guest favourite

Townhouse in Lexington

4.97 out of 5 average rating, 160 reviews

Quiet, comfy & near dining, UK, attractions, shop.

This nice, comfy townhome is big enough for the whole family with kids or multiple couples....3 Bedrooms (all upstairs), 2.5 baths, full kitchen, washer/dryer. One King, 1 Q, and 1 full bed. Large sofa for sleeping if needed (not sleeper sofa). Living room and 2 bedrooms have TV's & commercial grade wireless internet throughout. Only 1.5 miles to Fayette Mall and 2.5 from the new Summit at Fritz Farm for your shopping, dining, and entertainment needs. Close to UK, hospitals, and Keeneland.

Guest favourite

Townhouse in Lexington

4.95 out of 5 average rating, 431 reviews

LUXURY Downtown Retreat 💙 w/ King Tempur-Pedic Bed

* STR Reg #15062369-5 - Maximum occupants 4 - Guests are prohibited from allowing more than maximum occupancy * This beautifully remodeled historic property is located in Downtown Lexington. Walk to Rupp Arena, several cool bars/breweries and upscale restaurants. 15 minute car ride to Keeneland Racetrack, Kentucky Horse Park & Kroger Field. King Tempur-pedic mattress with sleeper sofa. 2 smart TV's and high speed internet service. Beautiful kitchen with gas range and stainless steel appliances.

Guest favourite

Townhouse in Lexington

4.9 out of 5 average rating, 408 reviews

Cozy, cute 2BR townhouse near downtown, businesses

Registration#15019537-1 Comfy, cozy Five Squared is tucked in a quiet neighborhood near downtown's restaurants, bars and arts; Rupp Arena and UK basketball games and concerts; the hip Distillery District's restaurants; and Meadowthorpe's antique shops. For business travelers, it's also convenient to New Circle Road and local industry. Our place is great for couples, solo travelers, families with kids, and anyone who likes cotton sheets, exposed brick and the gentle rumble of passing trains.

Guest favourite

Townhouse in Lexington

4.93 out of 5 average rating, 192 reviews

Mulberry Hill

Mulberry Hill, in the heart of Lexington's historic district, is steps away from nightlife, restaurants, shopping, events, and culture. This sunny townhome is the perfect blend of cozy and modern - its clean, bright and newer construction is paired with historic details like reclaimed heart of pine floors. This is a great spot if you’re in town to visit a Transy or UK student, attend a concert or basketball game at Rupp Arena, visit breweries and distilleries, or enjoy a day at Keeneland.

Guest favourite

Townhouse in Lexington

4.99 out of 5 average rating, 151 reviews

Bourbon Trail for couples. Downtown & Free Parking

Cozy townhome in downtown Historic Mulberry Hill on Limestone. We can see Transylvania University campus... it's one block walk. An easy flat walk to Rupp Arena, restaurants & bars, craft breweries, downtown events, opera house, farmers market & more. Or a $7 Uber if the weather is bad. Just 8 miles drive to Keeneland Horse Racetrack and 9 miles to the Kentucky Horse Park. Check out our adjacent property with an identical floorplan. Our home is not suitable for kids.

Guest favourite

Townhouse in Lexington

4.79 out of 5 average rating, 189 reviews

Luxury Stay at Kentucky Horse park-Newtown Springs

✥ Luxury townhouse in Lexington, KY ✥ ONLY 6 miles from the famous Kentucky Horse Park, this beautiful townhome is fully equipped with all the essentials you need *If traveling with a family/large group we offer discounted rates on our listings directly next to each other* ✦ 5 miles from Rupp Arena and Kroger Field ✦ Right next to Amazon center! ✦ 5 minutes from the interstate I-75 / I-64 ✦ 2 minutes away from Lexington Downtown ✦ 8 miles from Keenland

Townhouse in Lexington

4.79 out of 5 average rating, 337 reviews

3 Bedroom Downtown Townhouse, Close to All!

Our homey 3 bedroom, 2 bath townhouse is walking distance to the city center, Rupp Arena, and plenty of restaurant and dining options. It includes a large master bedroom with ensuite bathroom and two other small bedrooms - all with new queen beds. The kitchen has new stainless appliances and the living/dining room is a perfect place to gather with family and friends. It is perfect for families with kids, couples or friends traveling.

Guest favourite

Townhouse in Lexington

4.96 out of 5 average rating, 26 reviews

L in Lexington

Welcome friends! Need a comfortable retreat from a busy day exploring all that Lexington has to offer? Whether here for the races at Keeneland, touring The Bourbon Trail, taking in a football game at Kroger Field or a basketball game at Rupp Arena, this cozy 2 bedroom, 1.5 bath townhouse is the perfect solution! Located in the heart of Lexington, Lochdale in Lexington is only minutes from adventure in "The Horse Capital of the World".

Guest favourite

Townhouse in Frankfort

4.89 out of 5 average rating, 127 reviews

Bourbon Trail Lakehouse - Pet Friendly!

Lake house? ✔️ 🛶 Bourbon Trail? ✔️ 🥃 Horse country? ✔️ 🐎 You’re sure to fall in 💗 with lake views, cozy bedding, modern decor & a well-stocked kitchen. Located in the capital on the Ky Bourbon Trail, this peaceful Lakehouse is sure to be the perfect getaway for couples, friends & families alike! Minutes to several distilleries, 10 mins to the Capitol, 30 mins to Lexington. Pets are allowed for $150 per stay.

Townhouse in Wilmore

4.94 out of 5 average rating, 18 reviews

“Old Forester” at The Glover House

The Old Forrester is a spacious one bedroom condo in the heart of the bluegrass that will exceed your expectations! It is furnished with a plush king sized bed, two smart TV’s, high speed WiFi and a kitchen with full amenities. This is located minutes from Keeneland, Rupp Arena, Kentucky’s Bourbon trail, and Blue Grass Airport. The perfect place to relax after a long day on the town.

Townhouse in Lexington

4.76 out of 5 average rating, 121 reviews

Cozy Lexington Townhouse

BRAND NEW TEMPUR-PEDIC MATTRESSES (September 2023) Now offering a King bed master! This is a recently renovated 2 bedroom, 1 1/2 bath townhouse with an ideal location near downtown, bordering Lexington’s Mount Tabor park. You will enjoy 55” Smart TVs in the living room and both bedrooms, high speed WiFi and many other amenities.

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Popular amenities for Jessamine County townhouses

Free parking on premises

Air conditioning

Family-Friendly townhouses

Townhouse in Lexington

4.95 out of 5 average rating, 92 reviews

Town home with private garage and backyard

Townhouse in Lexington

4.71 out of 5 average rating, 118 reviews

Conveniently Located in the Heart of Lexington

Guest favourite

Townhouse in Lexington

4.82 out of 5 average rating, 307 reviews

LEXINGTON, KY's Ultimate Chill Spot

Townhouse in Lexington

4.86 out of 5 average rating, 189 reviews

*Bourbon, Bourbon, Bourbon*

Guest favourite

Townhouse in Chevy Chase

4.93 out of 5 average rating, 30 reviews

Chevy Chase / Cooper Condo

Townhouse in Lexington

4.46 out of 5 average rating, 28 reviews

Ollie’s little Cove

Townhouse in Lexington

4.84 out of 5 average rating, 253 reviews

Downtown Townhome Near Rupp Arena

Townhouse in Lexington

4.74 out of 5 average rating, 258 reviews

Renovated Downtown Townhouse

Townhouse rentals with a washing machine and dryer

Guest favourite

Townhouse in Versailles

4.98 out of 5 average rating, 56 reviews

Charming Historic Home in Downtown Versailles

Guest favourite

Townhouse in Lexington

5.0 out of 5 average rating, 49 reviews

Southern Charm

Townhouse in Lexington

4.82 out of 5 average rating, 22 reviews

Modern Boho Airbnb

Guest favourite

Townhouse in Lexington

4.96 out of 5 average rating, 52 reviews

Distillery Luxury - 3 bedroom Townhome (2)

Guest favourite

Townhouse in Lexington

5.0 out of 5 average rating, 30 reviews

2 bd Downtown Townhome. Private Deck & Garage.

Townhouse in Lexington

4.9 out of 5 average rating, 40 reviews

The Midland- Walk to brewery/shops

Townhouse in Lexington

4.8 out of 5 average rating, 95 reviews

Authentic Bluegrass Historic Home- 1 mi to dwntwn!

Townhouse in Lexington

4.97 out of 5 average rating, 29 reviews

JW's LOFT - Pet Fee Additional Charge

Townhouses with a patio

Guest favourite

Townhouse in Lexington

4.91 out of 5 average rating, 33 reviews

Bounce to Hamburg/I-75/St. Joe E

Guest favourite

Townhouse in Lexington

5.0 out of 5 average rating, 27 reviews

Southern Charm - Spacious Townhome close to UK

Townhouse in Lexington

4.73 out of 5 average rating, 26 reviews

Cheerful 2 bed/ 2 bath ranch near NCR with garage.

Guest favourite

Townhouse in Lexington

4.99 out of 5 average rating, 72 reviews

*Two Bed Luxury Townhome| Privacy Fenced in Yard*

Townhouse in Lexington

4.74 out of 5 average rating, 27 reviews

Historic Haven, Spacious 4BR Townhouse Oasis

Townhouse in Lexington

5.0 out of 5 average rating, 3 reviews

Luxurious Getaway

Townhouse in Lexington

5.0 out of 5 average rating, 5 reviews

Luxury Distillery District Townhouse

Guest favourite

Townhouse in Lexington

5.0 out of 5 average rating, 5 reviews

Keeneland- LEX Airport Darling

Destinations to explore