Holiday rentals with breakfast in Shelby County

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Top-rated Holiday Accommodation with Breakfast in Shelby County

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Top Guest favourite

Guest suite in Louisville

4.97 out of 5 average rating, 136 reviews

Action City! Extravaganza at Bardstown Rd!

In the HEART of the Highlands, this spot sits near the corner of the main strip- just steps to Bardstown Rd. A few minutes drive to anywhere in city limits! And exactly where YOU want to be! Action Packed: Restaurants, Shopping, Bars, Parks, and Church- all walkable. A surprise local GIFT CARD given with each stay! This place is stylish, chic, cozy, and extremely quiet, as double pane windows have been installed. Recently renovated, it houses all the essentials for a weekend or week long stay.

Guest favourite

Home in Louisville

4.87 out of 5 average rating, 124 reviews

Parkside Retreat

Situated off of a parkway with mature trees lining the street, this parkside retreat is close to most everything. We are a short drive to Churchill Downs, Downtown, the Airport. Our home sits on one of the most beautiful streets in the entire neighborhood. We are 7 houses from Iroquois Park. It is terrific for walking, hiking, or just having a picnic. We have a privacy fence with a jacuzi tub on the deck. Many updates make this home the perfect choice to relax after a day of fun activities

Top Guest favourite

Home in Midway

4.99 out of 5 average rating, 120 reviews

Country Cottage in Horse and Bourbon Country

This completely updated cottage is located on a scenic byway voted one of the ten best scenic drives in the United States, on which you will see thoroughbred farms for which Kentucky is famous. Keeneland and the Kentucky Horse Park are within 20 minutes. There are 4 distilleries within 10 miles, 11 within 30 miles, and 23 within an hour’s drive. Two bedrooms, new kitchen, new bathroom, washer and dryer, covered porch, deck, air conditioning, wifi, cable TV, and ample parking. Relax and enjoy!

Guest favourite

Cabin in Louisville

4.95 out of 5 average rating, 337 reviews

Captain's Cabin: Bourbon Trail, History & Romance

Your own log cabin on a wooded hillside with gourmet breakfast served to your door (on weekends)! It's been the location for 4 movies, including Lifetime! Period furnishings and modern conveniences make this an unforgettable retreat. A massive stone fireplace creates a quiet ambiance. Watch wildlife by the lake, creek or from back porch swings. Comfy bed, luxury sheets, high-speed internet, bluetooth stereo and special touches make your stay magical! Ask for Cooking With Bourbon Experience.

Top Guest favourite

Loft in Louisville

5 out of 5 average rating, 133 reviews

Urban Bourbon Loft - hip Germantown, downtown

LOCATION !!! Good vibes abound in this Germantown Loft - located in the heart of it all - close to the Highlands, KY Expo, and Downtown. Welcome to HAPPYSPACE LLC's latest creation, a 7 BR, 3.5 full bath designer decorated luxury loft! Walk to restaurants & bars! This home exudes tons of comfort and good vibes & was created exclusively as a vacation rental. 3 kitchens and 3.5 baths allow for plenty of privacy & convenience. Relax in style at the Ultra chic URBAN BOURBON Loft!!

Guest favourite

Home in Bardstown

4.92 out of 5 average rating, 295 reviews

The Nicholson Guest House

Stay in a historic cottage, dating back to the 1830's. Conveniently located in the heart of downtown Bardstown, within walking distance to restaurants, shopping, markets, events, and nightlife. Bardstown is the Bourbon Capital of the World! Don’t hesitate to visit some local distilleries to experience some truly amazing Bourbon. Farm fresh eggs, homemade pancake mix, snacks, and water are provided to all guests. We also offer Electric Bicycles. Contact me directly for info.

Top Guest favourite

Guesthouse in Louisville

4.98 out of 5 average rating, 283 reviews

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.

Guest favourite

Apartment in Louisville

4.95 out of 5 average rating, 393 reviews

Sunny Clifton Loft

Recently renovated studio apartment with loads of natural light, steps from award-winning local restaurants, bakeries, bars, and housed above our independent record store. We do our best to AirBnB ethically & responsibly.. Revenue from this unit helps to 1) keep on-site residential rents affordable & increase-free 2) maintain the historic building & protect it from outside development while 3) help us steer our future as a brick and mortar independent business.

Guest favourite

Apartment in Midway

4.91 out of 5 average rating, 111 reviews

Downtown Midway Loft--Walk Everywhere!

Located in the heart of downtown Historic Midway, this renovated studio apartment makes for the perfect retreat. The bedroom features a queen sized Tempur-Pedic mattress, ROKU TV, and desk. Plan your day with a morning coffee in the full kitchen that's equipped with basic cookware for prepping light meals. The apartment is located on the third floor, so pack light as it is accessed only by stairs. We are delighted to host your stay in beautiful Kentucky!

Top Guest favourite

Tiny home in Louisville

4.97 out of 5 average rating, 159 reviews

Trendy Tiny Home w/ King Bed Loft

Unique experience in style! Enjoy a weekend or an extended stay at this charming carriage house just walking distance to popular restaurants, breweries and local shops. The location is perfect! Inside you'll find a fully equipped kitchen, bathroom, living room with a 55" smart tv, a dedicated work space/desk and a king sized bed in the loft. Guests will have privacy with self-check in smart locks and a dedicated parking space. We can't wait to host you!

Top Guest favourite

Home in Louisville

4.98 out of 5 average rating, 127 reviews

Yellow Bird - Best Nest on Frankfort - Sleeps 4-6

One fantastic location right on "The Avenue", walkable to restaurants, bars & shops, minutes from Downtown. Our 2nd place here can host guests who need more space than our "Front Porch on Frankfort" just a couple blocks away (See our 5 Star Reviews!). With the most comfy Queen beds in each bedroom, a full size sofa bed in the back den, a well-stocked kitchen, we can host long term guests. There's a dedicated dining area plus a patio table out back too.

Top Guest favourite

Guest suite in Louisville

4.95 out of 5 average rating, 320 reviews

Highlands Lower Level Studio Guest Suite

Private, well-lit, entrance is in rear of home. The space is approx. 600sq. ft. There is a gas fireplace, 42" HD TV w/Netflix & Amazon Prime. Kitchen has Keurig coffee maker, convection oven, inferred glass top burner, microwave, refrigerator/freezer w/ice, washer/dryer& a large marble shower, with heated floors in the shower room. Also space equipped w/ Medify air purifier w/H13 true Hepa medical grade filter.