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

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, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Gather by the fire
    One of the few properties with a dedicated outdoor firepit.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
3 bedrooms2 bathroomsSleeps 7

Popular amenities

  • Garage parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue
  • Deck or patio

Explore the area

View map
Midway, KY
  • Place, Equus Run Vineyard & Winery
    ‪4 min drive‬
  • Place, Old Friends Thouroughbred Retirement Farm
    ‪9 min drive‬
  • Place, Kearney Hills Golf Links
    ‪11 min drive‬
  • Airport, Lexington, KY (LEX-Blue Grass)
    ‪21 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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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

Property # 804211vb
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

About the area

Midway

Midway is home to this holiday home. Kentucky Horse Park and Headley-Whitney Museum 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. Relax and indulge in the area's winery tours and health/beauty spas, or seek out an adventure with hiking and cycling nearby.
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Map
Midway, KY

What's nearby

  • Equus Run Vineyard & Winery - 4 min drive - 7.8 km
  • Old Friends Thouroughbred Retirement Farm - 9 min drive - 15.2 km
  • Kearney Hills Golf Links - 11 min drive - 21.2 km
  • Masterson Station Park - 12 min drive - 17.5 km
  • Kentucky Horse Park - 14 min drive - 22.7 km

Getting around

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

Restaurants

  • ‪Dairy Queen - ‬10 min drive
  • ‪McDonald's - ‬3 min drive
  • ‪Rocky’s Pub - ‬11 min drive
  • ‪Circle K - ‬10 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.

How much is parking at Charming Cottage Conveniently Located In The Heart Of Horse And Bourbon Country?

On-site parking is available at the 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 within 9 miles (15 km) of Equus Run Vineyard & Winery, Headley-Whitney Museum and Nostalgia Station Toy Train Museum. Old Friends Thouroughbred Retirement Farm and Raintree Gallery and Framing are also within 9 miles (15 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 128 out of 131 reviews
Rating 8 - Good. 2 out of 131 reviews
Rating 6 - Okay. 1 out of 131 reviews
Rating 4 - Poor. 0 out of 131 reviews
Rating 2 - Terrible. 0 out of 131 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Barbara N.

Liked: Cleanliness, check-in, communication, location, listing accuracy
our Cottage was so lovely. perfect!
Stayed 5 nights in Apr 2026
Verified

10/10 Excellent

Taylor G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was a very comfortable turn-of-the-century home that's well-maintained with many modern features. The lot is small but cozy and well-maintained, and within walking distance to a really nice bakery and basketball court, and a 2-minute drive to several really nice food options in the "downtown" Midway area.
Stayed 4 nights in Mar 2026
Verified

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
Verified

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
Verified

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
Verified

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
Response from VrboOwner on 7 September 2024
5 ⭐️ guests
Verified

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
Verified

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
Response from VrboOwner on 24 October 2022
5 ⭐️⭐️⭐️⭐️⭐️Guest, fun& enjoyable!
Verified

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
Verified

10/10 Excellent

Amy M.

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
Verified

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
Verified

10/10 Excellent

Patrick B.

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

Getaway

Great stay and spot! Look forward to returning!
Stayed 4 nights in May 2024
Verified

10/10 Excellent

Terry M.

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
Response from VrboOwner on 24 March 2020
Would love to have you back and thanks for taking such good care of the cottage. Happy you enjoyed your stay
Verified

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
Verified

10/10 Excellent

Molly R.

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
Verified

10/10 Excellent

Nancy V.

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
Response from VrboOwner on 24 March 2020
Wonderful guest and do hope they return for another stay. Left the cottage in immaculate condition, a five star group
Verified

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
Verified

10/10 Excellent

Floyd D.

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
Verified

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
Verified

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
Verified

10/10 Excellent

Ann B.

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
Verified

10/10 Excellent

Kimberly E.

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
Response from VrboOwner on 17 May 2022
You are welcome back any time
Verified

10/10 Excellent

Debbie K.

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
Response from VrboOwner on 24 March 2020
What a wonderful happy group, and Debbie and her family of friends are welcome back anytime. Home was left like they had not even been there, much appreciated! #5 stars
Verified

10/10 Excellent

Teddy D.

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
Verified

10/10 Excellent

Darcy S.

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
Response from VrboOwner on 13 May 2021
Five Star guest, the kind you will remember in a very good way! Just say yes if Darcy ask to stay with you.

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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