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, 134 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, 118 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!

Top Guest favourite

Home in Bardstown

4.83 out of 5 average rating, 114 reviews

Upscale 1 Story Bourbon Trail XLBeds King 2 Single

UPSCALE 1 STORY HOUSE * 3 BDRM (4 Beds), 2 BATH, OPEN FLOOR PLAN, provides a Great Space to Enjoy time with your FAMILY AND/OR FRIENDS while visiting BARDSTOWN & THE BOURBON TRAIL. Primary Bedroom Suite has XL K/S Sterns & Foster Bed, ensuite Bathroom & walk-in Closet. Large Guest Room Q/S Bed and Dedicated Workspace 3rd Bedroom 2 XL Single Beds, Brand New Top of the Line Beauty Rest Cooks kitchen has all Appliances, cookware & dishware etc. F/S Washer and Dryer. CENTRAL HVAC & HEATING

Top Guest favourite

Cabin in Louisville

4.95 out of 5 average rating, 336 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.

Guest favourite

Home in Louisville

4.96 out of 5 average rating, 137 reviews

Highlands Hangout - Restaurant Row, WALK TO ALL

Located in the HEART of it all! Welcome to The Highlands Hangout! 50 steps from Restaurant Row, park your car in your 2-car garage & walk to everything! Situated in the hip Highlands, the safest and most walkable neighborhood close to downtown Louisville, this home boasts 12 beds! 4 bedrooms & 3 full baths await you & your family & friends - plus an extra large outdoor deck that overlooks restaurant row and the best game room in Louisville Kentucky!!! We look forward to your arrival!

Guest favourite

Home in Bardstown

4.92 out of 5 average rating, 291 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, 278 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, 391 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, 109 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, 154 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, 125 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.