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Entire apartment

2nd Story Historic Downtown 2BR with Modern Amenities

Photo gallery for 2nd Story Historic Downtown 2BR with Modern Amenities

Fridge, microwave, oven, stovetop
2 bedrooms, iron/ironing board, free WiFi, bed sheets
Onsite parking
Onsite parking
Exterior

Reviews

9.0 out of 10
Wonderful

Entire apartment

2 bedrooms1 bathroomSleeps 5

Popular amenities

  • Kitchen
  • Parking available
  • Pet-friendly
  • Free WiFi
  • Air conditioning

Add dates for prices

About this property

Entire place

You'll have the entire apartment to yourself and will only share it with other guests in your party.

2nd Story Historic Downtown 2BR with Modern Amenities

Experience this unique and historic two bedroom apartment in the heart of downtown Winchester Kentucky. This building is over 150 years old and rich in history in the community, however, features modern amenities to ensure an amazing stay. This building is immediately across the street from the historic clocktower courthouse.

You'll feel right at home in the fully remodeled bathroom (European Wet Room), kitchen and bedrooms. You'll also feel plenty of old world charm. Walking distance to all!

Property amenities

Internet

  • Available in the apartment: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Stovetop

Bedrooms

  • 2 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 1 bathroom
  • Hair dryer
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Entertainment

  • TV

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • One pet total (up to 50 lbs per pet)

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center
  • In the mountains
  • On a lake

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

Policies

Check-in

Check-in time starts at 1:00 PM

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
1 total (up to 50 lbs per pet)
Restrictions apply; for more information contact the property at the number on the booking confirmation
Note from host: We love our animal guests.

Children and extra beds

Children are welcome
Note from host: All ages welcome.

Events

No events 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
Onsite parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

Property is also known as

2nd Story Historic Downtown 2BR With Modern Amenities Apartment
2nd Story Historic Downtown 2BR With Modern Amenities Winchester

About the area

Located in Winchester, this apartment is in the city center and on a lake. Bluegrass Heritage Museum and Fort Boonesborough State Park are local landmarks, and some of the area's activities can be experienced at Southwind Golf Course and Cassell Creek Golf Course.
Visit our Winchester travel guideOpens in a new window
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Map
Winchester, KY

What's nearby

  • Bluegrass Heritage Museum - 6 min walk - 0.6 km
  • Clark Regional Medical Center - 2 min drive - 2.4 km
  • Lykins Park - 4 min drive - 3.4 km
  • Southwind Golf Course - 5 min drive - 5.1 km
  • Fort Boonesborough State Park - 13 min drive - 14.7 km

Getting around

  • Blue Grass Airport (LEX) - 31 min drive

Restaurants

  • ‪Taco Bell - ‬3 min drive
  • Dairy Queen
  • ‪Rally's - ‬3 min drive
  • Hardee's
  • ‪DJ's Bar & Grill - ‬4 min drive

Frequently asked questions

Is 2nd Story Historic Downtown 2BR with Modern Amenities pet-friendly?

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 50 lbs per pet.

How much does it cost to stay at 2nd Story Historic Downtown 2BR with Modern Amenities?

As of Aug 13, 2025, prices found for a 1-night stay for 2 adults at 2nd Story Historic Downtown 2BR with Modern Amenities on Aug 18, 2025 start from CA $121.43, excluding taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

What time is check-in at 2nd Story Historic Downtown 2BR with Modern Amenities?

Check-in begins at 1:00 PM.

What time is check-out at 2nd Story Historic Downtown 2BR with Modern Amenities?

Check-out is at 10:00 AM.

Where is 2nd Story Historic Downtown 2BR with Modern Amenities located?

Located in the heart of Winchester, this apartment building is steps from Clark County Courthouse and Winchester Opera House. Bluegrass Heritage Museum and College Park are also within 15 minutes.

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2nd Story Historic Downtown 2BR with Modern Amenities Reviews

Reviews

9.0

Wonderful

Rating 10 - Excellent. 9 out of 13 reviews
Rating 8 - Good. 3 out of 13 reviews
Rating 6 - Okay. 0 out of 13 reviews
Rating 4 - Poor. 0 out of 13 reviews
Rating 2 - Terrible. 1 out of 13 reviews

9.4/10

Cleanliness

Reviews

10/10 Excellent

RADENE B.

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

Great little place

My daughter and I had a wonderful stay. The rental had everything we needed. The location was close to everything.
Stayed 3 nights in Aug 2024

10/10 Excellent

Irvin C.

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

Very nice

Love the place
Stayed 4 nights in Jul 2024

10/10 Excellent

Elizabeth W.

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

Nice little apartment conveniently located

Great spot. Easy drive to outdoor activities. Several places to eat and drink nearby. Host very responsive. Hope to stay here again!
Stayed 3 nights in Apr 2024

8/10 Good

John J.

Liked: Cleanliness, communication, location, listing accuracy

Well worth the money

Great place to stay... i feel like it wasnt advertised as well as it could have been. We loved the gas fireplace. Was concerned about check-in as i hadnt heard from the owner, but within a day of our arrival i reached out and the owner was always fast and responsive at that point. Any concerns vanished. What a great location!
Stayed 2 nights in Nov 2024

10/10 Excellent

Linda P.

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

Interesting and unique- very clean!

Fantastic
Stayed 2 nights in May 2024

10/10 Excellent

Angelique D.

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

Historic charm.

Charming historic building. The floors creak and have a slight lean, as would be expected in a 150 yr old building. Modern comforts all located in historic downtown Winchester. Walking distance to boutique shopping, cafes and activities. Beds were comfy too.
Stayed 3 nights in Mar 2023

2/10 Terrible

Brad H.

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

Never got in!

Never had a bad VRBO experience until this one. We booked this property 2 weeks in advance of our trip but never heard from property owner until we reached out to personal number. By the time they got back with us about how to enter the property, it was too late for us to reasonably make our trip. We communicated as such and asked for a partial refund to which there was no reply. Enjoy your free pay day!! Disappointing and frustrating. Would not recommend
Stayed 1 night in Jun 2024

8/10 Good

Kyile M.

Liked: Cleanliness, location, listing accuracy
Disliked: Check-in
Stayed 2 nights in Apr 2024

10/10 Excellent

Brian M.

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

Great location

We had a great stay, the unit has lots of charm and is very cozy. We enjoyed the walkability to great local shops and restaurants. It's within a short driving distance to other great areas to check out!
Stayed 3 nights in Oct 2023

10/10 Excellent

Brandon

Stayed 1 night in Feb 2023

8/10 Good

Susan F.

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

Awesome historic property

The host is most helpful. The staircase is a bit daunting. The historic building has charm with wifi convenience.
Stayed 5 nights in Oct 2022

10/10 Excellent

Mallory M.

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

GREAT Experience

Susan and Joel were AMAZING to work with. They are responsive, kind and the apartment was amazing. The location was great, we were there during the summer concert series and we were right in the middle of it. Live music, food, drinks. We could walk everywhere we needed to go. It was perfect. I would definitely stay there again.
Stayed 2 nights in May 2022

10/10 Excellent

Max I.

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

Lovely stay

This spot was great! Right in the middle of cute downtown Winchester! I would definitely recommend this spot to anyone!
Stayed 2 nights in Nov 2021