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Midway Holiday Rentals

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Holiday Rentals in Midway

Terrace/patio
Cozy cabin in the heart of horse country
10.0 out of 10, Exceptional, (4)
"Very close to several distilleries. Was perfect for our guys weekend."
Cozy cabin in the heart of horse country
Outdoor dining
Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!
10.0 out of 10, Exceptional, (233)
"Fantastic property. Owner is responsive and friendly without being too much. Top notch. Will stay again!"
The price is NZ$413
includes taxes & fees
3 Jun - 4 Jun
Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!
Exterior
Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location
10.0 out of 10, Exceptional, (115)
"This historic home is in the best neighborhood in Lexington, right in the middle of other historic homes and walking distance to many great restaurants. It is nicely appointed, very clean, and very comfortable. The listing photos depict it very well. My family and I would stay here again."
The price is NZ$842
includes taxes & fees
28 May - 29 May
Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location
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Fridge, microwave, oven, stovetop
Stay in a 1953 Gunnison Home is within walking distance to St Joe Hospital
9.2 out of 10, Wonderful, (18)
"I stayed in Lexington for a week for my son’s surgery. This house had everything I needed. A nice back yard for my dog to romp and play. Close proximity to food and medical center Will definitely be back"
The price is NZ$350
includes taxes & fees
17 Jun - 18 Jun
Stay in a 1953 Gunnison Home is within walking distance to St Joe Hospital
Property grounds
Spacious family Lodge with solar heated pool, hot tub, fire pit and EV charger.
10.0 out of 10, Exceptional, (58)
"There is something for everyone here! It was the perfect home for our family get together!"
Spacious family Lodge with solar heated pool, hot tub, fire pit and EV charger.
Property grounds
Treetops on Garden
10.0 out of 10, Exceptional, (58)
"I stayed several days and was able to check out both rooms rented by the host. The room I stayed in was quiet and well maintained. Nice neighborhood for walking. The host was friendly and accommodating. Highly recommended!"
Treetops on Garden
Exterior
Bourbon Trail, Ark Encounter, Family Gatherings, WiFi, Cabin
9.8 out of 10, Exceptional, (187)
"We had gathered friends and family from around the country to play some golf and attend the PGA Championship at Valhalla. The cabin was everything Mary said it was. It was clean and had enough beds and space for our party of 12. It was quiet, had plenty of pots, pans and glasses. Everything worked. The pool table was great. We recommend this property for a large group"
The price is NZ$1,089
includes taxes & fees
28 May - 29 May
Bourbon Trail, Ark Encounter, Family Gatherings, WiFi, Cabin
TV
This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.
9.0 out of 10, Wonderful, (22)
"The code was showing on the wall next to the door which made us feel less than safe. I tried to contact the owner and he never responded. The sofa smelt like someone peed in it. The bedroom close to the kitchen had a mold smell. But the most worrying issue was the shower that was in the bathtub was on a platform with no rail to hold on to in order to get out safely. Otherwise we enjoyed the house."
The price is NZ$263
includes taxes & fees
3 Jun - 4 Jun
This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.
2 bedrooms, desk, iron/ironing board, travel cot
175 LEX - Spacious Two Bedroom Downtown Lexington
9.8 out of 10, Exceptional, (8)
"Perfect spot for our family group (five adults) to stay while attending graduations of our niece and nephew from University of Kentucky."
The price is NZ$377
includes taxes & fees
9 Jun - 10 Jun
175 LEX - Spacious Two Bedroom Downtown Lexington
Property grounds
NEW!!! 6 BR + 5 Bath Penthouse Overlooking Downtown. 1 mile from Buffalo Trace
9.8 out of 10, Exceptional, (6)
"We had an amazing time. The property is gorgeous and the decor exquisitely done. The location was close to restaurants and shops. Would highly recommend this property!"
NEW!!! 6 BR + 5 Bath Penthouse Overlooking Downtown. 1 mile from Buffalo Trace
Exterior
Capital City Cottage
9.8 out of 10, Exceptional, (8)
"We loved our quick stay here. We were in Frankfort to visit the State Capitol, so it was super convenient. Everything about the house was as described in the listing, all very clean and comfortable."
The price is NZ$384
includes taxes & fees
28 May - 29 May
Capital City Cottage
Smart TV, books
Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.
9.0 out of 10, Wonderful, (69)
"Clean & Cute! "
The price is NZ$250
includes taxes & fees
3 Jun - 4 Jun
Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.
Exterior
"Centrally Located to Many Distilleries" House on the Kentucky Bourbon Trail
9.8 out of 10, Exceptional, (88)
"Good size for two couples and maybe a child or smaller sized single guest. Two full updated bathrooms are a key feature. Comfy living room furniture and nice tv. Pet friendly (not a gated yard) and great location for kayaking. It is close to the road so it can be noisy. There is ample parking but be aware that the adjacent church lot is very busy with kayakers. Owners are very easy to work with."
"Centrally Located to Many Distilleries" House on the Kentucky Bourbon Trail
Exterior
KY Bourbon Trail FUN! Double Shot on Main 2 Bed/2 Bath
10.0 out of 10, Exceptional, (57)
"Nice location, exactly as represented, made for a great trip!"
KY Bourbon Trail FUN! Double Shot on Main 2 Bed/2 Bath
Fridge, microwave, oven, stovetop
Totally renovated downtown home walk to all
9.6 out of 10, Exceptional, (42)
"The location was perfect for the Kentucky theater, and there were nice dining options in walking distance. The home was easy to access, and the cookies were AMAZING. The biggest drawback was that we couldn’t get the wi fi to work (although the antenna did mostly). "
The price is NZ$506
includes taxes & fees
28 May - 29 May
Totally renovated downtown home walk to all
Exterior
3 Bdr/3 Bath House in Andover Convenient to All of Lexington
10.0 out of 10, Exceptional, (263)
"This house is always clean and welcoming on arrival. The location is great with lots of restaurants and shopping nearby. We golfed every day of our stay and the area courses are in great shape and reasonably priced. We love it here and hope to return."
3 Bdr/3 Bath House in Andover Convenient to All of Lexington
Property grounds
RockinC Cabin. Private cabin in the tall trees. On a120 acre farm.
10.0 out of 10, Exceptional, (73)
"The absolute perfect place to stay! If there were more than 5 stars, I’d give those out too!"
RockinC Cabin. Private cabin in the tall trees. On a120 acre farm.
Fridge, microwave, stovetop, dishwasher
Gorgeous Lexington Retreat ~ 2 Mi From UK!
9.8 out of 10, Exceptional, (15)
"Beautiful property in a quiet neighborhood"
Gorgeous Lexington Retreat ~ 2 Mi From UK!
Interior
The Havilah House! Country living with amazing views!
10.0 out of 10, Exceptional, (30)
"I met my 8 girlfriends from college in central Kentucky. The Havilah House was the perfect location for keeneland and bourbon tours and halfway between the bluegrass and Louisville airports. The house is comfortable and well stocked. The host was very responsive and answered our questions quickly. I would highly recommend it."
The Havilah House! Country living with amazing views!
Exterior
Lexington Apt. with parking & private entrance Preview listing
10.0 out of 10, Exceptional, (105)
"Everytime my wife and I come to Lexington to watch the races at Keenland we try to stay here. Place is peaceful, quiet, and joyce is an the best host."
The price is NZ$233
includes taxes & fees
28 May - 29 May
Lexington Apt. with parking & private entrance Preview listing
Don't see what you're looking for?
See all available properties in Midway
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Midway you may be interested in

Lobby
GLō Best Western Lexington
3.0 star property
9.4 out of 10, Exceptional, (2264)
"The Hotel was so unique. The style and decor is amazing! The Breakfast bar wonderful! So many great options and clean! Friendly and kind staff. "
The price is NZ$193
includes taxes & fees
3 Jun - 4 Jun
GLō Best Western Lexington
Interior
Embassy Suites by Hilton Lexington Green
3.5 star property
9.2 out of 10, Wonderful, (1003)
"Lexington is a beautiful city to visit and this hotel made the stay even better! We had been on our trip for two weeks when we got to the Embassy Suites. This is a beautiful hotel with an excellent staff, complimentary cocktails during happy hour and a great breakfast. This was our best stay over the two weeks!"
The price is NZ$242
includes taxes & fees
20 Jun - 21 Jun
Embassy Suites by Hilton Lexington Green
Lobby
GuestHouse Lexington
2.5 star property
8.2 out of 10, Very good, (1008)
"stayed there before will stay there again when in lexington ky"
The price is NZ$127
includes taxes & fees
9 Jun - 10 Jun
GuestHouse Lexington
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Midway holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Midway. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Midway. Seeing all the best attractions is bound to make you fall in love with Midway. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Midway short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Midway?

Yes, there are holiday rentals close to the most popular sights in Midway, or you can select a more secluded option if you're looking for a relaxing stay. Midway is known for its wineries and local tours. Make sure you have time to check out the art while you're in the area.

How many holiday rentals are there in Midway?

With 9 Expedia holiday rentals, you're guaranteed to find just the right place for your Midway stay.

What’s there to see and do in Midway?

While exploring the area, visit family-friendly sights like Explorium, or get outside and enjoy nature at Masterson Station Park. Equus Run Vineyard & Winery and Damselfly Gallery are other places to visit while you're in town.

What’s a holiday rental in Midway like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Midway. Holiday rentals provide amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for a family getaway.

Recent reviews of Midway properties
Expedia verified reviews