Guesthouse vacation rentals in Jefferson County

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Top-rated guesthouse rentals in Jefferson County

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

Guest favorite
Guesthouse in Georgetown
Indian Creek Barn Cottage w/ EV & RV Charger
Private barn cottage in the knobs of Kentuckiana located on a 12 acre horse farm, recently renovated into a cozy comfortable space. The barn cottage is private space with 500 sqft, fully furnished 1 bedroom, 1 bath with living area, kitchenette equipped with a microwave, toaster, coffee maker, and mini refrigerator. Located just outside of New Albany, IN and less than 15 minutes to Louisville, KY allowing for the relaxation of the countryside, while also enjoying the city attractions!
Aug 8 – 15
$80 per night
4.92 out of 5 average rating, 182 reviews
Guest favorite
Guesthouse in Louisville
Highlands Carriage House
Secluded Retreat in the Heart of the Highlands! Perfect for DERBY! Our carriage house is perfectly located in the heart of all Louisville has to offer. We are only steps from the finest dining, entertainment, pubs, shopping, parks, and coffee in Louisville. Bustling and eccentric Bardstown Road is only half a block away, yet the Carriage House feels secluded and very private. It is located 5 miles from Churchill Downs, 7 miles from the airport, and 2 miles from downtown.
Jun 14 – 21
$93 per night
4.99 out of 5 average rating, 233 reviews
Guest favorite
Guesthouse in Louisville
Cute Carriage House off Frankfort Avenue
Welcome to "The Cute Carriage House at Frankfort Avenue". Experience serenity in a genuine "tiny house” that comfortably accommodates two people. There are several sleeping options that I will mention below. We are located a short block from premier restaurants and shops on Frankfort Avenue in the classy Clifton Neighborhood...and close to Cherokee Park and the cool Bardstown Road. FYI https://www.leoweekly.com/2020/10/the-winners-of-the-2020-readers-choice-awards/
Jun 19 – 26
$60 per night
4.91 out of 5 average rating, 442 reviews

Popular amenities for Jefferson County guesthouse rentals

Family-friendly guest house rentals

Guest favorite
Guesthouse in Louisville
Highlands - Elegant Calm Clean & Green - Walkable
Aug 13 – 20
$109 per night
4.99 out of 5 average rating, 356 reviews
Guest favorite
Guesthouse in Louisville
Germantown Carriage House w/garage
Aug 23 – 30
$76 per night
4.96 out of 5 average rating, 640 reviews
Guest favorite
Guesthouse in Louisville
Charming Carriage House with 2 private baths.
May 27 – Jun 3
$96 per night
4.93 out of 5 average rating, 281 reviews
Superhost
Guesthouse in Louisville
Park Carriage House. Rest & Explore with Hollyhock
Feb 25 – Mar 4
$175 per night
4.88 out of 5 average rating, 106 reviews
Guest favorite
Guesthouse in Louisville
Yoga Barn with 90’s Loft Bedroom
May 21 – 28
$100 per night
4.94 out of 5 average rating, 47 reviews
Guest favorite
Guesthouse in Pendleton
The Waterfall Place, Suite and Walkout!
Aug 13 – 20
$353 per night
4.89 out of 5 average rating, 45 reviews
Guest favorite
Guesthouse in Shepherdsville
Bourbon Country/ Derby Guest House
Apr 19 – 26
$195 per night
4.96 out of 5 average rating, 47 reviews
Guest favorite
Guesthouse in Louisville
Retro Chic Private Getaway in the Highlands.
Jul 3 – 10
$86 per night
4.95 out of 5 average rating, 57 reviews

Guest house rentals with a patio

Guest favorite
Guesthouse in Louisville
*BRAND NEW* Gem of Germantown Private Derby Suite
May 18 – 25
$163 per night
5.0 out of 5 average rating, 144 reviews
Guest favorite
Guesthouse in Shelbyville
Spacious suite, country views, pool table, firepit
Jul 6 – 13
$114 per night
4.97 out of 5 average rating, 33 reviews
Guest favorite
Guesthouse in Jeffersonville
Modern Guesthouse overlooking Ohio River
Jun 21 – 28
$85 per night
4.9 out of 5 average rating, 51 reviews
Guest favorite
Guesthouse in Louisville
The tiny Walnut in Beechmont
Jan 14 – 21
$57 per night
4.89 out of 5 average rating, 9 reviews
Guest favorite
Guesthouse in Louisville
Modern & Chic stay in Louisville
Mar 30 – Apr 6
$93 per night
4.9 out of 5 average rating, 59 reviews
Guest favorite
Guesthouse in Lanesville
Escape to JUST add ICE Resort and Retreat!
Mar 8 – 15
$200 per night
5.0 out of 5 average rating, 11 reviews
Guest favorite
Guesthouse in Louisville
Charming Carriage House in Old Louisville
Nov 2 – 9
$213 per night
4.98 out of 5 average rating, 89 reviews
Superhost
Guesthouse in Louisville
Modern & Restful Suite 1 BR
Mar 7 – 14
$80 per night
New place to stay
Guest favorite
Guesthouse in Bloomfield
Country 1 bedroom guesthouse with heated pool
Oct 8 – 15
$225 per night
5.0 out of 5 average rating, 5 reviews
Guesthouse in Jeffersonville
Mother-in-law suite-KY Derby
Dec 6 – 13
$550 per night
New place to stay

Guest house rentals with a washer and dryer

Guest favorite
Guesthouse in Louisville
The City Cottage…quiet, peaceful, and convenient!
Aug 1 – 8
$109 per night
4.97 out of 5 average rating, 111 reviews
Guest favorite
Guesthouse in Louisville
New custom guesthouse | Free parking | Sleeps 4
Dec 25 – Jan 1
$118 per night
5.0 out of 5 average rating, 32 reviews
Guest favorite
Guesthouse in Louisville
Lavish church suite with choir loft
Oct 20 – 27
$198 per night
5.0 out of 5 average rating, 30 reviews
Guest favorite
Guesthouse in Louisville
Highlands Carriage House - Deer Park
Mar 10 – 17
$136 per night
4.97 out of 5 average rating, 76 reviews
Guest favorite
Guesthouse in Louisville
Walk to Everything! *IDEAL DERBY*
Aug 16 – 23
$110 per night
4.88 out of 5 average rating, 49 reviews
Guest favorite
Guesthouse in Louisville
Carriage House - Crescent Hill (Frankfort Avenue)
Apr 3 – 10
$175 per night
4.93 out of 5 average rating, 88 reviews
Guest favorite
Guesthouse in Louisville
Lavish Flat near DT, Paristown & Food/Shops
Jun 17 – 24
$129 per night
4.85 out of 5 average rating, 59 reviews
Guest favorite
Guesthouse in Jeffersonville
The Cottage Next Door
Jun 4 – 11
$94 per night
4.89 out of 5 average rating, 175 reviews
Guesthouse in Louisville
Private 3BR luxury apartment
Mar 14 – 21
$180 per night
5.0 out of 5 average rating, 3 reviews
Superhost
Guesthouse in Prospect
Lewis & Clark Trail Guest Suite
Dec 11 – 18
$113 per night
New place to stay
Guesthouse in Louisville
A private suite near downtown Louisville, KY
May 5 – 12
$193 per night
4.75 out of 5 average rating, 4 reviews
Guesthouse in Louisville
A private suite near downtown Louisville, KY
May 5 – 12
$215 per night
4.25 out of 5 average rating, 4 reviews

Destinations to explore