Holiday rentals with breakfast in Saint Matthews

Find and book unique Holiday Accommodation with Breakfast on Airbnb

Top-rated Holiday Accommodation with Breakfast in Saint Matthews

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Guest favourite

Guest suite in Louisville

4.97 out of 5 average rating, 106 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.

25 Jul – 1 Aug

$185 NZD per night

Guest favourite

Cabin in Louisville

4.95 out of 5 average rating, 304 reviews

Captain's Cabin:Historic Romantic by Bourbon Trail

Your own log cabin on a wooded hillside overlooking a private lake with gourmet breakfast served to your door (on weekends)! It's been the location for Lifetime and Hallmark movies! Period furnishings and modern conveniences make this an unforgettable retreat. A massive stone fireplace creates a quiet ambiance. Watch wildlife 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

31 Oct – 7 Nov

$530 NZD per night

Guest favourite

Home in Louisville

4.99 out of 5 average rating, 238 reviews

★WorldlyHighlands★LARGE Kitchen, FASTWifi, Parking

Upper Highlands home in privileged location w/ keyless entry. A block from Bardstown Road, close to I-264 for fast commutes and all the HIGHLANDS excitement. Harmony of convenience & quiet allows for perfect stays for families, couples, business/vacation travelers alike. •4 bedrooms (includes basement), ALL WITH SMART TVs •Large kitchen w/new appliances, 2019-23 •PARKING up to 4 cars •Back porch GAS GRILL •NEW Patio furniture, 2021 •Super Fast fiber-optic WiFi •NEW Samsung Washer&Dryer, 2020

12–19 Sep

$376 NZD per night

Guest favourite

Apartment in Simpsonville

4.98 out of 5 average rating, 130 reviews

Ridgecrest Estate. Comfort and convenience.

A newly renovated 650-sq-ft. upstairs apartment with private entrance. Property sits on 5 acres in the heart of the Saddlebred Capital of the world. Just 9 miles east of the Watterson Expressway, Ridgecrest estate is an ideal location for enjoying the best of Kentucky in a quiet and peaceful environment. Quick access to I-64 (1/4 mile); 45 min. to Keeneland, 30 min to Churchill Downs, and 2 min to the Outlet Shoppes. No children under 13. Additional guests more than 2, $20 extra per night.

12–19 Oct

$201 NZD per night

Superhost

Condo in Louisville

4.91 out of 5 average rating, 214 reviews

Downtown Condo | Private 1 CAR Garage & Balcony

Beautiful Downtown Loft Condo with private balcony overlooking 4th Street. Walking distance to fantastic eateries, bars, concerts, ball games, and much more. Steps to the Palace Theater and 4th Street Live and next door to the Seelbach Hotel. Private 1 CAR, connected to the building for easy downtown parking. Building has secure entry and an elevator. The building is an old clothing department store, BYCKS. This 4th floor unit boasts exposed ceilings, brick walls, and hardwood flooring.

10–17 Dec

$458 NZD per night

Guest favourite

Home in Louisville

4.97 out of 5 average rating, 129 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 10 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!

23–30 Aug

$1,929 NZD per night

Guest favourite

Loft in Louisville

4.97 out of 5 average rating, 696 reviews

Bourbon City Loft - Free downtown parking!

If this loft is booked, please check out my other listings... https://www.airbnb.com/h/derby-city-loft https://www.airbnb.com/h/river-city-loft Spacious 950 sq. ft. loft located in the heart of downtown Louisville. Walking distance to shops, restaurants, bars and 1 block from 4th Street Live! You'll be 4 blocks from the YUM! Center, 2 blocks from the Kentucky International Convention Center, and less than 10 minutes from Churchill Downs! Free parking in a secured parking garage!

21–28 Nov

$275 NZD per night

Superhost

Guesthouse in Louisville

4.87 out of 5 average rating, 109 reviews

Park Carriage House. Rest & Explore with Hollyhock

The Carriage house is located behind a historic mansion in beautiful Crescent Hill. Situated next to a park, this ideal location is still one block away from Frankfort Ave. shopping & dining, conveniently located near downtown, Churchill Downs, & four blocks from the Largest park in downtown Louisville. Newly designed and renovated-includes two separate bedrooms, office area, full kitchen, bathroom, & laundry. Free wifi, & parking. Refresh and relax in this satisfying getaway!

17–24 Dec

$651 NZD per night

Guest favourite

Guesthouse in Louisville

4.98 out of 5 average rating, 243 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.

16–23 Oct

$222 NZD per night

Guest favourite

Guesthouse in Louisville

4.91 out of 5 average rating, 452 reviews

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/

8–15 Jul

$207 NZD per night

Guest favourite

Apartment in Louisville

4.95 out of 5 average rating, 355 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.

30 Sep – 7 Oct

$185 NZD per night

Guest favourite

Tiny home in Louisville

4.94 out of 5 average rating, 93 reviews

Trendy Tiny Home w/ King 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!

5–12 Oct

$231 NZD per night