Midway holiday rentals

We found 219 holiday rentals — enter your dates for availability
Discover a selection of 11 homes and other holiday rentals in Midway that are perfect for your trip. Whether you're staying in a holiday rental with a group or just with your pet, you'll find the amenities that you need and want, which might include cable TV and a washer and dryer. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Midway

Showing deals for:25 Dec - 1 Jan

Room
Dining
Interior
Pool
Exceptional
(63 reviews)

Raven Fox Farm-Country Charm! 5 BR Only 8 miles from Keeneland and BG Airport

Versailles

8% off
AU$7,706
for 7 nights, 1 room
AU$1,101 per night
includes taxes & fees
Raven Fox Farm-Country Charm! 5 BR Only 8 miles from Keeneland and BG Airport
Room
Interior
Private kitchen
Private kitchen
Exceptional
(8 reviews)

2-bedroom farmhouse, Lexington. Marimac Farm. 9 minutes to KHP

Lexington

8% off
AU$2,799
for 7 nights, 1 room
AU$400 per night
includes taxes & fees
2-bedroom farmhouse, Lexington. Marimac Farm. 9 minutes to KHP
Original steep & narrow staircase. Guests must OK this before booking accepted.
15 minutes to Woodford Reserve
Built in early 1800,s
Parlor/Exit
Exceptional
(52 reviews)

Railway Guest House in Charming Midway KY Horse Park,Bourbon Trail,Keeneland.

Midway

16% off
AU$1,597
for 7 nights, 1 home
AU$228 per night
includes taxes & fees
Railway Guest House in Charming Midway KY Horse Park,Bourbon Trail,Keeneland.
Interior
Private kitchen
Outdoor dining
game, exercise, flex space
Exceptional
(37 reviews)

Cozy, Fun, Relaxing 4Bd, 2Bth Home near Keeneland.

Lexington

8% off
AU$3,350
for 7 nights, 1 home
AU$479 per night
includes taxes & fees
Cozy, Fun, Relaxing 4Bd, 2Bth Home near Keeneland.
Property grounds
Living area
Exterior
Living area
Exceptional
(49 reviews)

Loft above Beautiful Horse Barn on Bourbon Trail

Georgetown

8% off
AU$2,859
for 7 nights, 1 room
AU$408 per night
includes taxes & fees
Loft above Beautiful Horse Barn on Bourbon Trail
Room
Living area
Outdoor dining
Dining
Wonderful
(35 reviews)

Your Kentucky Home

Georgetown

8% off
AU$2,790
for 7 nights, 1 home
AU$399 per night
includes taxes & fees
Your Kentucky Home
Interior
Terrace/patio
Exterior
Living area
Wonderful
(40 reviews)

Pet-Friendly Bluegrass Retreat w/ Fenced Yard

Georgetown

8% off
AU$2,754
for 7 nights, 1 home
AU$393 per night
includes taxes & fees
Pet-Friendly Bluegrass Retreat w/ Fenced Yard
Interior
Private kitchen
Room
Living area
Exceptional
(9 reviews)

"The Dawning House" - Peaceful Modern Stay w/ Yard

Georgetown

8% off
AU$3,402
for 7 nights, 1 home
AU$486 per night
includes taxes & fees
"The Dawning House" - Peaceful Modern Stay w/ Yard
Terrace/patio
Room
Exterior
Interior
Exceptional
(59 reviews)

Stunning Horse Farm Experience on Bourbon Trail!

Georgetown

9% off
AU$3,607
for 7 nights, 1 home
AU$515 per night
includes taxes & fees
Stunning Horse Farm Experience on Bourbon Trail!
Dining
Open dining area perfect for meals or gathering together
Exterior
Ideal for families or group stays
Exceptional
(10 reviews)

Georgetown Getaway, Sleeps 6, Fenced Yard (Pet-Friendly), Near Lexington & I-75

Georgetown

8% off
AU$6,310
for 7 nights, 1 home
AU$901 per night
includes taxes & fees
Georgetown Getaway, Sleeps 6, Fenced Yard (Pet-Friendly), Near Lexington & I-75
Dining
Property grounds
Private kitchen
Living area
Exceptional
(24 reviews)

The Stagg House on the Ky River

Frankfort

7% off
AU$2,502
for 7 nights, 1 home
AU$357 per night
includes taxes & fees
The Stagg House on the Ky River
Cozy bedroom with a queen bed dressed in crisp white bedding, soft rug underfoot, and warm natural light streaming through the window. Simple décor and calming tones make it a restful spot for a good night’s sleep. 32 In small tv.
Relax on a private turf patio with a hot tub, grill, outdoor dining table, and string lights for a cozy evening vibe. Perfect spot to unwind, cook out, or enjoy a peaceful night under the lights.
Modern kitchen with white cabinets, black appliances, microwave, and full fridge—fully stocked with pots/pans and ready for your stay.
Clean full bathroom with a shower-tub combo, white sink vanity, warm wood floors, and a toilet upgraded with a bidet for added comfort. Bright, simple space perfect for getting ready or winding down.
Exceptional
(11 reviews)

Hot Tub Tiny Home Hideaway Near Horse Park and Ark

Georgetown

8% off
AU$2,456
for 7 nights, 1 home
AU$351 per night
includes taxes & fees
Hot Tub Tiny Home Hideaway Near Horse Park and Ark
Room
Private kitchen
Interior
Exterior
Exceptional
(39 reviews)

The Bourbon Sanctuary

Frankfort

8% off
AU$1,730
for 7 nights, 1 home
AU$247 per night
includes taxes & fees
The Bourbon Sanctuary
Room
Private kitchen
Interior
Dining
Exceptional
(12 reviews)

Game Room | King Suite | Firepit | Patio | Grill

Georgetown

8% off
AU$4,186
for 7 nights, 1 home
AU$598 per night
includes taxes & fees
Game Room | King Suite | Firepit | Patio | Grill
Exterior
Private kitchen
Interior
Interior
Exceptional
(26 reviews)

Horse and Bourbon Lover’s Farm Cabin - 2 bed/2 bath in Versailles, KY

Versailles

8% off
AU$2,046
for 7 nights, 1 cabin
AU$292 per night
includes taxes & fees
Horse and Bourbon Lover’s Farm Cabin - 2 bed/2 bath in Versailles, KY

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Why people love visiting arty Midway

The area's wineries and art galleries are just some of the reasons to come on holiday to Midway. This walkable city attracts visitors thanks to its horse riding and local tours. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Midway

Do you want to discover things to do while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Midway a one-of-a-kind holiday spot. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • The Kentucky Castle (7.4 mi / 11.9 km)
  • Keeneland Racing Course (8.3 mi / 13.3 km)
  • Cherry Blossom Golf and Country Club (10.4 mi / 16.7 km)
  • Equus Run Vineyard & Winery (2.2 mi / 3.5 km)
  • Prodigy Vineyards & Winery (6.4 mi / 10.3 km)
  • Kearney Hills Golf Links (8.4 mi / 13.5 km)

Exploring the natural landscape of Midway

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Midway. Here are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Masterson Station Park (7.9 mi / 12.8 km)
  • Yuko-En on the Elkhorn Garden (8 mi / 12.9 km)
  • Cove Spring Park (10.2 mi / 16.4 km)
  • Old Governor’s Mansion (10.8 mi / 17.4 km)
  • The Arboretum State Botanical Garden of Kentucky (13.5 mi / 21.7 km)
  • Jacobson Park (18.1 mi / 29.1 km)

Transport options to and around Midway

Fly into Lexington, KY (LEX-Blue Grass), the closest airport, located 9.1 mi (14.6 km) from the city centre.

Frequently asked questions

What is the best area to stay in Midway when booking a holiday rental?
When considering a holiday rental in Midway, Kentucky, the charming downtown area is an excellent choice. This picturesque neighbourhood is known for its historic buildings and a vibrant setting, making it an inviting spot for visitors. Here, you'll find several properties ranging from quaint cottages to modern homes, providing a variety of options to suit different tastes and budgets.Staying in downtown Midway places you within walking distance of delightful attractions such as the Midway Museum, which offers insights into the local history and culture, and the beautiful Midway City Park, superb for leisurely strolls or picnics. Additionally, the area boasts delightful local shops and eateries, showcasing the region's unique flavours.Another appealing option is to explore the outskirts of Midway, where you can enjoy a more rural setting while still being close to the town's amenities. This area often features larger properties with expansive gardens, ideal for families or groups looking for a peaceful retreat.
What is the most popular type of holiday rental accomodation in Midway?
In Midway, holiday houses are the most popular type of holiday rental, with around 30 available throughout the area. These houses typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces for relaxing after a day of exploring the charming town or nearby attractions. Additionally, there are several cabins, apartments, and cottages available, providing a variety of options for travellers seeking a different experience. Cabins often offer a rustic feel, while apartments and cottages are great for those wanting a more compact home-like atmosphere.
Are there any family house rentals in Midway?
In Midway, Kentucky, there are several family-friendly holiday rentals available, providing a charming base for exploring the area. The town itself boasts a picturesque, small-town atmosphere, ideal for families looking for a relaxing getaway. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces great for children to play in.Visitors can also enjoy nearby attractions such as the beautiful Midway Park, which offers playgrounds and picnic spots, as well as the scenic horse farms that define the region. These properties often come with amenities like Wi-Fi and air conditioning, ensuring a comfortable stay for all.
Can I rent a holiday home with a pool or hot tub in Midway?
In Midway, Kentucky, there are several holiday homes available for rent that feature pools and hot tubs. This charming town, known for its picturesque landscapes and proximity to the Kentucky horse country, offers a tranquil setting for those seeking a relaxing getaway. Many of these properties come with amenities such as private pools, hot tubs, spacious patios, and well-equipped kitchens, allowing guests to enjoy both comfort and leisure.Visitors can explore the scenic beauty of the area, including local parks and nature trails, making it an ideal destination for families or groups looking to unwind and enjoy outdoor activities.
Are there pet-friendly house rentals in Midway?
In Midway, Kentucky, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with pets. Many of these properties come equipped with essential amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces where pets can roam freely.The quaint town of Midway is known for its charming atmosphere and proximity to scenic spots. Visitors can explore local parks that offer walking paths and open spaces, great for enjoying leisurely strolls with pets. Additionally, the nearby Kentucky Horse Park is a fantastic destination for animal lovers, featuring beautiful trails and opportunities for interaction with horses, making it an ideal outing for those with furry companions.
Are there any remote work holiday rentals in Midway?
In Midway, Kentucky, there are numerous remote work holiday rentals available, with around 36 options to choose from. The town is known for its picturesque setting and charming atmosphere, making it an excellent choice for those looking to work remotely while enjoying a peaceful environment. Many of these properties come equipped with essential amenities such as dedicated work desks and reliable Wi-Fi, ensuring a comfortable and productive workspace.Additionally, Midway offers a pleasant small-town experience, with local cafés and parks nearby for breaks and leisurely strolls. The area is also rich in equestrian culture, with opportunities to explore the beautiful countryside through horseback riding or scenic walks. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Midway?
In Midway, popular rental amenities include kitchens, which allow guests to prepare their own meals, and onsite parking for convenient access. Many properties also feature a coffee and tea maker, superb for starting the day with a warm beverage. Outdoor spaces such as decks or patios offer a lovely setting for relaxation, while blenders are available for those looking to make smoothies or other blended drinks.
When is the best time to visit Midway for a holiday rental?
April is an ideal time to visit Midway, Kentucky, as the spring season brings mild temperatures and the vibrant colours of blooming flowers, making it great for outdoor exploration. During this month, you can enjoy comfortable daytime temperatures averaging 15 to 20 degrees Celsius, allowing for pleasant strolls through the charming town and its picturesque surroundings.As summer approaches, the peak season from July to September draws in many tourists eager to experience the lively option of local events and outdoor activities. This is when Midway truly comes alive, with activities such as horse racing and various festivals creating a bustling environment. However, if you prefer a more tranquil experience, early spring is a fantastic time to visit, as you'll encounter fewer crowds while still enjoying the beauty of Kentucky in bloom.For those looking to save on their holiday rental, December represents a quieter time to visit. While the temperatures dip to around freezing (0 to 5 degrees Celsius), the festive spirit and holiday decorations create a unique charm in Midway, making it a delightful option for those who enjoy a slower pace.Ultimately, the best time to book a holiday rental in Midway depends on your preferences for crowd levels and activities.
What are the top attractions in Midway?
In Midway, Kentucky, visitors can enjoy a quaint small-town atmosphere with several charming attractions. The town is known for its historic Main Street, where you can find unique shops, local restaurants, and the Midway University campus which adds a collegiate vibe to the area.One of the highlights is the Midway Depot, a restored train station that serves as a reminder of the town's railway history. Nearby, the picturesque Woodford Reserve Distillery offers tours and tastings, showcasing the art of bourbon production in the heart of horse country.Outdoor enthusiasts can explore the scenic beauty surrounding Midway, with options for hiking and enjoying nature in the nearby parks.
Are all fees included in the Midway holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Midway holiday homes with parking?
Stayz offers a wide selection of holiday homes in Midway with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Midway holiday homes?
You can find great discounts on holiday homes in Midway on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Midway holiday home booking on Stayz?
To find Midway holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Midway?
A long-stay holiday home in Midway is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Midway holiday home?
Book your Midway holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Midway?
Prices for holiday homes in Midway vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Midway to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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