Entire home

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

Overview
Amenities
Policies
Location
Host

Exceptional

3 bedrooms2 bathroomsSleeps 71900 sq ft

Popular amenities

Parking available
Barbecue grill
Washer
Dryer
Kitchen
Outdoor space

Explore the area

Midway, KY

Kentucky Horse Park
‪19 min drive‬
The Kentucky Castle
‪20 min drive‬
Keeneland Racing Course
‪25 min drive‬
Lexington, KY (LEX-Blue Grass)
‪26 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.

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Amenities

Kitchen

Washing machine

Dryer

Air conditioning

Outdoor space

Parking available

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Kitchen
Washer
Dryer
Air conditioning

House Rules

Check in after 4:00 PM

Minimum age to rent: 18

Check out before 10:30 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

No pets allowed

Smoking

Smoking is not permitted

Important information

You need to know

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. Kentucky Horse Park and Damselfly Gallery are cultural highlights, and some of the area's landmarks include Buffalo Trace Distillery 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.

View more Holiday homes in Lexington

Midway, KY

What's nearby

Equus Run Vineyard & Winery - 5 min drive - 7.5 km
Kentucky Horse Park - 19 min drive - 29.6 km
The Kentucky Castle - 20 min drive - 18.3 km
Buffalo Trace Distillery - 21 min drive - 28.0 km
Keeneland Racing Course - 25 min drive - 27.9 km

Getting around

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

Restaurants

‪Dairy Queen - ‬10 min drive
‪Circle K - ‬10 min drive
‪The Midway Bakery - ‬1 min walk
‪Subway - ‬3 min drive
‪Heirloom Restaurant - ‬10 min walk

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).

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

10/10 Excellent

Holly W.

25 Jul, 2025

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

Debbie S.

10 Jun, 2025

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.

Stayed 2 nights in Jun 2025

10/10 Excellent

Laura M.

22 Mar, 2025

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

Verified traveller

6 Sept, 2024

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

10/10 Excellent

Amy M.

20 May, 2024

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

Relaxing family getaway

The cottage was perfect for our trip! Comfortable, cozy, and homey!

Stayed 3 nights in May 2024

10/10 Excellent

Lou U.

23 Sept, 2024

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

Patrick B.

5 May, 2024

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

Getaway

Great stay and spot! Look forward to returning!

Stayed 4 nights in May 2024

10/10 Excellent

Kathy w.

17 Oct, 2022

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

Molly R.

2 Jan, 2024

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

Nice getaway

We stayed for 3 nights to relax after the holidays. The area was wonderful for us to spend time together.

Stayed 3 nights in Dec 2023

10/10 Excellent

Terry M., Dallas, TX

1 May, 2019

The cabin was great. Very comfortable.

Steve, the owner, very nice and helpful on information. We would certainly stay here the next time we visit this area.

Stayed 3 nights in Apr 2019

10/10 Excellent

Floyd D.

5 Jul, 2024

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

Golf & Bourbon Trail Trip

Steve is a great host and the property is exactly as described. Our trip went smoothly with no issues at all! Looking forward to a return trip in the very near future!

Stayed 4 nights in Jul 2024

10/10 Excellent

Darci C.

12 Jul, 2024

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

10/10 Excellent

Nancy V.

19 May, 2019

Great Location!

Great location with a relaxing patio! Steve is very knowledgeable about the area and provided excellent recommendations and assistance in seeing the highlights of the area!

Stayed 2 nights in May 2019

10/10 Excellent

Horseencore J.

7 Jun, 2023

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

Ann B.

13 Oct, 2023

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

Girl trip

We had a great time seeing so many horses.

Stayed 4 nights in Oct 2023

10/10 Excellent

Kimberly E., Franklin

24 Apr, 2022

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

Horse Country Stay

We loved our stay in Midway at this charming property! Steve was wonderful at providing us with recommendations for the area! We walked in and there were fresh flowers in every room —what a special touch. When coming back to the area, we will definitely stay here again!!

Stayed 3 nights in Apr 2022

10/10 Excellent

Debbie K.

23 Oct, 2018

Great location, plenty room

Enjoyed our stay. The house was comfortable & great for relaxing at the end of the day. Location was central to our planned activities in the area. Steve was easy to work with & gave us some good tips about the area in advance of our trip. The Midway Bakery 2 doors down was excellent!

Stayed 3 nights in Oct 2018

10/10 Excellent

Linda P.

29 Sept, 2023

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

Golden Girls Princesses

We had a great time ! Steve was great to work with.

Stayed 3 nights in Sep 2023

10/10 Excellent

Teddy D.

5 Jun, 2023

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

Great place to stay!

My friends and I spent 2 nights in this marvelous cottage. The town is quite unique with delicious places to eat, where you can sit outside, if you want to watch those passing by. We sat around the firepit in the evening-great place to sip bourbon :). Location has easy access to the many bourbon sites and tours. I highly recommend staying here, Stephen was a great host, we hope to return..

Stayed 2 nights in May 2023

10/10 Excellent

Darcy S., Edmond, OK

28 Apr, 2021

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

Amazing cottage and host

This amazing cottage is very clean, has everything you could possibly need, and is conveniently located. The back yard is so peaceful. Steve is a terrific host who went above and beyond to make our stay so very special and memorable. I would definitely book this property again!

Stayed 3 nights in Apr 2021

10/10 Excellent

Trent M.

6 Aug, 2023

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

Golfing and bourbon

Between the bourbon distilleries and the golf courses that we chose to play the location was ideal. The property was everything that we needed and Steve was great. He was there for anything if we needed it.

Stayed 4 nights in Jul 2023

10/10 Excellent

Tyler P.

9 Apr, 2023

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

Fun and convenient

This is a fun and fascinating property. Within a short walk of attractions in Midway you’ll enjoy peace and quiet with a beautiful view of the sunset.

Stayed 2 nights in Apr 2023

10/10 Excellent

Beth H.

28 Oct, 2024

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

Kenneth D.

27 Aug, 2022

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.

20 Oct, 2023

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

About the host

Hosted by STEVE SIMOFF

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!