Holiday rentals in Lexington

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Top-rated holiday rentals in Lexington

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Train in Lawrenceburg

4.98 out of 5 average rating, 250 reviews

Bourbon Trail: Caboose on the Farm

Nestled under the shadows of elm trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunk-beds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

30 Aug – 6 Sep

$199 SGD per night
Guest favourite

Loft in Lexington

4.97 out of 5 average rating, 142 reviews

Spring Street Loft by Rupp-Covered Parking + Deck

Brand new 2nd-level loft with free covered parking spot beneath, a huge deck and outdoor dining option. Directly across Maxwell St. from Rupp Arena's parking lot-you can't get any closer! This single unit building was built on stilts to maximize outdoor space and downtown views. Your perfect oasis in the middle of the action includes a full kitchen, laundry room, bathroom, living area and Smart TV. Come for a concert or stay awhile, you'll have everything you need during your trip to Lexington!

2–9 Dec

$143 SGD per night
Guest favourite

Cottage in Lexington

4.94 out of 5 average rating, 644 reviews

Little House Dwntwn - Close to Rupp & Restaurants

1 BR, 1 bath, restored house on quiet street in downtown. Patio (with umbrella), & front porch - each with table & chairs, Off-street parking, TV in Living Room and in Bedroom, Broadband Internet, Cntl A/C, Complete kitchen w/microwave, refrigerator - freezer, toaster oven, regular oven and stove, flatware, dishes and cooking utensils, dishwasher, and washer-dryer. 15 min. to Keeneland or Horse Park. 1.5 miles to UK. 1/2 mile to Rupp (10 minute walk.) Walk to many restaurants and attractions.

12–19 Feb

$112 SGD per night

Popular amenities for Lexington holiday rentals

Stay near Lexington's top sights

Rupp Arena140 locals recommend
Keeneland164 locals recommend
Hamburg Pavilion46 locals recommend
Fayette Mall38 locals recommend
Kroger Field34 locals recommend
University of Kentucky66 locals recommend

Other great holiday rentals in Lexington

Guest favourite

Flat in Lexington

4.99 out of 5 average rating, 172 reviews

City Chic Loft - Downtown

13–20 Jan

$164 SGD per night
Guest favourite

Home in Lexington

4.98 out of 5 average rating, 281 reviews

Distillery District Diamond-pet friendly

29 Jun – 6 Jul

$166 SGD per night
Guest favourite

Guest house in Nicholasville

4.95 out of 5 average rating, 168 reviews

The Grain House

12–19 Aug

$136 SGD per night
Guest favourite

Guest suite in Lexington

5.0 out of 5 average rating, 102 reviews

The Gainesway Suite-Near UK/Hospitals/Keeneland

20–27 May

$130 SGD per night
Guest favourite

Home in Lexington

4.96 out of 5 average rating, 319 reviews

Horse Farm Creekside Cabin- 6 min to KY Horse Park

22–29 Nov

$247 SGD per night
Guest favourite

Guest house in Winchester

4.95 out of 5 average rating, 155 reviews

Carriage House on the Park

14–21 Aug

$109 SGD per night
Guest favourite

Guest house in Winchester

4.98 out of 5 average rating, 171 reviews

Escape and unwind in the country

9–16 Jan

$103 SGD per night
Superhost

Apartment in Lexington

4.88 out of 5 average rating, 224 reviews

*New Downtown Apartment*

10–17 Sep

$114 SGD per night
Guest favourite

Home in Lexington

4.92 out of 5 average rating, 158 reviews

My Old Kentucky Home

11–18 Jun

$130 SGD per night
Guest favourite

Apartment in Lexington

4.9 out of 5 average rating, 114 reviews

Across From UK Hospital-Weekly/Monthly Discounts!

5–12 Jun

$131 SGD per night
Guest favourite

Guest house in Lexington

5.0 out of 5 average rating, 48 reviews

West meets South in this Garden Cottage Retreat

23–30 Jul

$141 SGD per night
Guest favourite

Treehouse in Georgetown

4.98 out of 5 average rating, 86 reviews

Treehouse with TWO outdoor tubs by the creek!

25 Sep – 2 Oct

$236 SGD per night

Quick stats about holiday rentals in Lexington

Total rentals

1.6K properties

Rentals with dedicated workspaces

890 properties have a dedicated workspace

Rentals with a pool

110 properties have a pool

Pet-friendly rentals

660 properties allow pets

Family-friendly rentals

1.1K properties are a good fit for families

Total number of reviews

89K reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Kentucky
  4. Fayette County
  5. Lexington