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Charming Cottage Conveniently Located In The Heart Of Horse And Bourbon Country

Holiday home in Midway with kitchen and patio

Photo gallery for Charming Cottage Conveniently Located In The Heart Of Horse And Bourbon Country

Exterior
Exterior
Terrace/patio
Terrace/patio
Interior

Reviews

10 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 71900 sq ft

Popular amenities

  • Parking available
  • Barbecue grill
  • Washer
  • Dryer
  • Kitchen
  • Outdoor space

Explore the area

View in a map
Midway, KY
  • Place, Kentucky Horse Park
    ‪14 min drive‬
  • Place, The Kentucky Castle
    ‪17 min drive‬
  • Place, Keeneland Racing Course
    ‪21 min drive‬
  • Airport, Lexington, KY (LEX-Blue Grass)
    ‪23 min drive‬

Rooms & beds

3 bedrooms (sleeps 7)

Bedroom 1

1 Queen Bed

Bedroom 2

2 Single Beds

Bedroom 3

1 Single Bed and 1 Queen Bed

2 bathrooms

Bathroom 2

Toilet · Shower only

Upstairs Bath

Bathtub or shower · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Office
Outdoor play area
Garden
Dining area

About this property

Charming Cottage Conveniently Located In The Heart Of Horse And Bourbon Country

This newly renovated and furnished home is only 3 1/2 blocks from historic Midway's downtown shops and restaurants. Clean, allergy & scent-free space. Hardwood & tile floors throughout. There are two bedrooms upstairs, one w/ a Queen and twin, one w/ two twin that can convert to a King and the Master Bedroom downstairs has a Queen bed. It can sleep seven. There are three flat screen TV's, one in the Living room and one in each bedroom upstairs w/HBO & SEC channels.Wifi Internet Access is provided. The Kitchen/Breakfast room is spacious w/ microwave, coffeemaker & toaster oven. There is equestrian and local art throughout. The porch is charming, relaxing and private with a ceiling fan and infrared grill. On site off street parking with a two car garage. There is a Bakery two doors down and a playground behind. The cottage is located in the heart of Thoroughbred and Bourbon country. Midway is off of I-64, just 20 minutes from Lexington and and hour from Louisville- you can hit every destination on your vacation easily.
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Air conditioning
Outdoor space
Parking available

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House Rules

Check in after 4:00 PM
Minimum age to rent: 18
Check out before 10:30 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit

We should mention

A car is required for transport to and from this property

About the area

Midway

Midway is home to this holiday home. Buffalo Trace Distillery and Equus Run Vineyard & Winery are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Old Friends Thouroughbred Retirement Farm and Blue Grass Railroad Museum. Looking to enjoy an event or a game? See what's going on at Keeneland Racing Course or Rupp Arena. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
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Map
Midway, KY

What's nearby

  • Equus Run Vineyard & Winery - 4 min drive - 7.5 km
  • Kentucky Horse Park - 14 min drive - 29.6 km
  • Woodford Reserve Distillery - 15 min drive - 19.1 km
  • The Kentucky Castle - 17 min drive - 18.3 km
  • Keeneland Racing Course - 21 min drive - 24.1 km

Getting around

  • Lexington, KY (LEX-Blue Grass) - 21 min drive

Restaurants

  • ‪Dairy Queen - ‬10 min drive
  • ‪McDonald's - ‬3 min drive
  • ‪Circle K - ‬10 min drive
  • ‪Rocky’s Pub - ‬11 min drive
  • ‪Wallace Station Deli and Bakery - ‬3 min drive

Frequently asked questions

Is Charming Cottage Conveniently Located In The Heart Of Horse And Bourbon Country pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Charming Cottage Conveniently Located In The Heart Of Horse And Bourbon Country?

Check-in begins at 4:00 PM.

What time is check-out at Charming Cottage Conveniently Located In The Heart Of Horse And Bourbon Country?

Checkout is at 10:30 AM.

Where is Charming Cottage Conveniently Located In The Heart Of Horse And Bourbon Country located?

Situated in Midway, this holiday home is 0.6 mi (1 km) from Damselfly Gallery and within 9 miles (15 km) of Equus Run Vineyard & Winery and Headley-Whitney Museum. Nostalgia Station Toy Train Museum and Old Friends Thouroughbred Retirement Farm are also within 9 miles (15 km).

Reviews

10

Exceptional

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy
Rating 10 - Excellent. 124 out of 127 reviews
Rating 8 - Good. 2 out of 127 reviews
Rating 6 - Okay. 1 out of 127 reviews
Rating 4 - Poor. 0 out of 127 reviews
Rating 2 - Terrible. 0 out of 127 reviews

Reviews

10/10 Excellent

Laura M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Best location in Midway!

Close to the charming downtown of Midway, right outside of Lexington. So cozy and clean. Great host and a great stay!
Stayed 2 nights in Mar 2025

10/10 Excellent

Kathy w.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location

We couldn't have a better stay or host.
Stayed 4 nights in Oct 2022

10/10 Excellent

Debbie S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This home was a perfect location! Also very comfy, cozy & quaint! Plenty of room. The beds were very comfortable. The owner was very attentive and helpful in all ways! The bakery, just a few steps away, is fantastic. The deck is great for sitting out in the evening or morning coffee. We would stay here again. And I would highly recommend.
Front porch
Back deck
Stayed 2 nights in Jun 2025

10/10 Excellent

Holly W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent choice to stay, relax, laugh and renew. This cottage was perfect for our long weekend. The rooms inside were comfortable and cozy. The artwork and decor were an added plus. The outside deck was so relaxing for our morning coffee and pastries from the bakery 2 doors down. Steve is the host with the most. We love what Midway has to offer and will be back. Thank you Steve! Holly, Sue, Patty and Roxann
Stayed 3 nights in Jul 2025

10/10 Excellent

Horseencore J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Midway Retreat

Very convenient . Really nice property. Very much enjoyed our stay. We definitely plan to be back.
Stayed 2 nights in Jun 2023

10/10 Excellent

Kenneth D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect !!

We really enjoyed the home and the town of Midway ! Steve was great and very accommodating ! We loved the back porch and the coziness of the home. We will be returning in the future !!!
Stayed 2 nights in Aug 2022

10/10 Excellent

Kevin T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quaint cottage in beautiful horse country

Absolutely perfect little cottage in horse country. Close to Keeneland for a perfect weekend trip with the family. Beautiful porch and fire pit in the yard. Would 100% recommend. Steve was incredibly helpful with not only the home but recommendations in the area and keeneland tips.
Stayed 2 nights in Oct 2023

10/10 Excellent

Alexandrea L., Michigan City, Indiana

Liked: Cleanliness, check-in, communication, location, listing accuracy

Unique & charming cottage!

The house was incredible! So unique with very interesting decor that I LOVED! Very warm and inviting. Host Steve was wonderful and we really enjoyed talking with him - he had excellent and helpful suggestions. A+
Stayed 2 nights in Oct 2022

10/10 Excellent

Kyle K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect quick getaway

It literally took Steve 5 minutes to call me after I first booked his property. He was very helpful and had great suggestions for what to do while we were there. The house was perfect for 3 couples and the proximity to midway and their restaurants was perfect! We will for sure be back.
Stayed 2 nights in Aug 2020

10/10 Excellent

Gail C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Bourbon Trail Newbies

My brother, myself and our spouses combined bourbon and a family gathering. I looked at The Charming cottage location and the pictures plus glowing reviews. I decided right away that this was the place for us. I don’t like to brag, but I picked us a winner! Steve is a wonderful host.
Stayed 3 nights in Jun 2024

10/10 Excellent

Beth H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect location!

This is a charming cottage with lots of character & creature comforts. The breezy covered deck behind the house is ideal for hangin’ out. Owner is gracious & helpful. Location was perfect for our girls’ trip. Enjoyed gorgeous fall foliage, Kentucky Bluegrass Rail Explorers (so much fun!), walked to quaint downtown Midway for shopping & lunch, visited the champion thoroughbreds of Claiborne Farm (home of Secretariat), Race Day at Keeneland, toured the decks of Noah’s life-sized ark, and roamed beautiful Kentucky Horse Park. ♥️🐎
Stayed 4 nights in Oct 2024

10/10 Excellent

Rhonda P., Breese, IL

Relaxation

The cottage was warm and inviting. Steve is the best. Was there to greet us and show us around. His suggestions of where to eat and visit were to the tee. The people in Midway are so friendly. The cottage had anything you could possibly need. Would like to visit again when you could set on the deck. Even with the snow and rain, we had an awesome time.
Stayed 2 nights in Mar 2018
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Cindi K.

Awesome experience. Would definitely rent again.

Perfect location for Keeneland and Bourbon Tours. The pictures of the home are good, but it is so much better in person. The home is full of little details that make it wonderful. We visited with two other couples and our only regret is that we didn't spend more time at the house especially on the wonderful deck. Steve is awesome and went out of his way to make sure we were comfortable. In Midway (walking distance) don't miss the School Bakery or the Heirloom Restaurant.
Stayed 2 nights in Apr 2016

10/10 Excellent

Ryan S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great outdoor space to unwind and catch up

We had a men's family golf outing for a few days and several of us wanted an alternative to the hotel most were staying at. This location was perfect as it was closer to both golf courses. We weren't at the property a ton of time but really enjoyed the evenings after golfing talking on the back porch and around the large fire pit. Steve was attentive and a great guy. Chatted with us a bit but left us alone unless we needed something etc. The bakery director next door was a nice place to get a breakfast sandwich and soak up the remainder of the bourbon from the previous night 😉
Stayed 3 nights in May 2023

10/10 Excellent

Christine J.

Perfect for a relaxing long weekend.

What we really loved was the privacy. The back covered patio is just awesome. We had our Echo out there and listened to music, played cards and even slow danced. The decor is something along the lines of Joanna Gaines. We found ourselves walking around looking at it all. There were no corners cut when the owner remodeled. Which is something I really appreciate. We ate in town at Heirloom for lunch on Saturday and it was really great. Our visit was to go to the distilleries. We visited Four Roses, Wild Turkey, Woodford Reserve and Maker's Mark. All were great but our favorites were: Wild Turkey and Maker's Mark. We loved the horse farms along the way! Just beautiful. We plan to come back. Christine
Stayed 3 nights in Aug 2018

10/10 Excellent

Jay W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Just like HOME. wonderful getaway in the Kentucky Bluegrass.
Stayed 5 nights in Oct 2025

10/10 Excellent

cameron s.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything about this cottage was terrific!
Stayed 5 nights in Oct 2025

10/10 Excellent

Connor A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was great. Cottage was very clean, well stocked, and cozy.
Stayed 2 nights in Oct 2025

10/10 Excellent

Jana K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Charming community and lovely home. Close to shopping and restaurants. Host is helpful and responsive, yet non-intrusive. It was a quiet and peaceful stay. Just what I needed to unwind and relax.
Stayed 4 nights in Sep 2025

10/10 Excellent

Jamil F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and access to main Street Midway. Also logistically accessible to many Bourbon distilleries in the area. Very spacious house with capability to house larger parties. The deck was awesome to relax and enjoy bourbon.
Stayed 2 nights in Aug 2025

10/10 Excellent

Linsley H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Kentucky charm

We came down for a 70th birthday party nearby and this cute cottage was perfect for 3 friends over the weekend. Spacious inside and out. Loved the rocking chairs on porch! Plenty of places to chat and kitchen was the most well-stocked kitchen we've ever seen in a rental. Thank you so much! Would absolutely stay again and may do so for the fall races!
Stayed 2 nights in Apr 2025

10/10 Excellent

Lou U.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect get away

This wonderful cottage is everything it says it is. Charming and well appointed and walking distance to town.
Stayed 2 nights in Sep 2024

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

eclectic Fun and great location

Wonderful property!! Looking forward to our next stay
Stayed 3 nights in Aug 2024

6/10 Okay

Jason N.

Liked: Communication

Great Location but Odd Experience

Overall the experience was fine, not great or good. The kitchen had random left over alcohol in the pantry, random condiments and various food in the fridge. Needs a refresh of pots and pans to cook with. There was an odd odor that we could not determine to be skunk or weed that was kept in the home. Upstairs air conditioner units did not function well. Interaction with the owner were awkward, invited himself into the home for a drink and cigar, lit a bonfire in the backyard with his grandson, after we were gone all day he came then to mow the grass when we wanted to just unwind. Overall, the place was fine but not somewhere I am returning to anytime in the future.
Stayed 2 nights in Jul 2024

10/10 Excellent

Darci C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wedding party

Perfect place for bride and bridesmaids. We had the best time!
Stayed 2 nights in Jul 2024

About the host

Hosted by STEVE SIMOFF

Host profile image
I am a high energy, people kinda person! I enjoy my family, friends, horses, being outdoors, gardening & yard work, doing things for others, and giving back to my community. This year (2016) I am running for a seat on the City Council in Midway, my hometown.

Originally from a small farming community in Iowa, I grew up with thoroughbred horses. I earned a degree in commercial advertising and graphic design and started working in the travel industry. I went on to own and manage several successful travel agencies which I eventually sold.

I moved to the midwest and had a successful thoroughbred training operation in Ky for 18 years before retiring. I am now a (ROAP) certified Racing Official in the industry.

Why they chose this property

This was my home for over 10 years and we wanted to renovate it and give it a new purpose but keep it in the family. I was a thoroughbred trainer for 18 years and currently a certified racing official.

What makes this property unique

Beautiful sunrises & sunsets. Pastures with horses and cattle nearby and the occasional hawk or deer. Off-street parking, city park w/ basketball courts & swings for the kids. Intriguing landscape makes it very private in summer especially.

It's a short walk to downtown shops and restaurants. Fun to walk around town and see the different styles of houses.

There's a walking trail being developed at the Walter Bradley Park that meanders in and around the creek to add to the walking experience. We'd be happy to tell you how to find it!

Languages:

English

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