8 Best Airbnb Vacation Rentals In Winchester, Kentucky

airbnb winchester

Located in Kentucky and serves as the county seat of Clark County, the city of Winchester lies halfway between Ashland and Louisville. It is well-known as the birthplace of beer cheese. In fact, the city hosts the annual Kentucky Beer Cheese Festival every year in June which attracts a large influx of tourists. Winchester also boasts a good number of historic buildings that are worth exploring. Be it a fun vacation with kids, an adventurous getaway, or a romantic holiday with loads of shopping and dining sprees, this city will never let you down. No matter what kind of holiday you are planning to spend in Winchester, it is vital to find a good place to stay that is warm, cozy, and feels just like home. Read on to know about the best Airbnb vacation rentals in Winchester, Kentucky, which will make your holiday pleasant and blissful.

1. Comfortable bungalow with state-of-the-art amenities (from USD 88)

This impressive bungalow offers one bedroom and two bathrooms that can accommodate up to four guests at a time. Natural Bridge State Park is just 35 minutes away from this property and downtown Lexington is just 30 minutes away. The master bathroom is equipped with a hot tub where you can take a relaxing dip after a tiring sightseeing or shopping spree. There is a massive backyard for families as well. Free Wi-Fi is available for guests and there is a smart TV in the living room. The kitchen is fully stocked with utensils and basic needs such as salt, oil, and pepper. Two free parking spaces are available on the premises. Pets are allowed but smoking and parties are not permitted on the property.

Ale-8 Bungalow-Winchester, KY near Natural Bridge
Winchester, Kentucky, United States
98 reviews Superhost  Wifi Available
Entire residential home 1 Bed 4 Guests 1 Bedroom 2 Bathrooms

Accommodates: 4

Top guest reviews
Amenities & Room:
we did put a couple of books under the bedroom tv to see it better
communication was easy and the space was clean
darian’s place is clean and spacious
host is very nice and responsive
but stay was good for some minor details host is aware of
the space was amazing and close to a lot of things
a great place to stay
Read more reviews

2. Pet-friendly escape with a country vibe (from USD 75)

This amazing house is ideal for three guests with its one bedroom and one bathroom. If you are looking for an escape hatch where you can relax and unwind, this is the perfect place for you. Pets are allowed on this property but it is advised to keep them attended at all times. Moreover, additional charges are applicable if you want to clean your pets within the premises. A kitchen, a washing machine, air conditioning, a coffee-maker, and more are some of the essential facilities available in the house. This open guest house is equipped with all the basic necessities for an ideal holiday. Security cameras have been installed on the property, guaranteeing security. If you’re on an extended holiday and want to finish some work, there is also a dedicated workspace available.

Escape and unwind in the country
Winchester, Kentucky, United States
80 reviews Superhost
Entire guesthouse 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
the bed was super comfy
full kitchen was great for cooking when we didn’t eat out
super clean and had everything needed + more we loved eating breakfast outside on the patio
the kitchen has basic cookware - we easily were able to make full dinners
very clean
the house was spotless and comfortable
very clean we would definitely stay again
very secluded clean and just all around amazing
the guest house was extremely clean
jamie is a great host
the host has thought of every little detail to make your stay perfect
jamie was so helpful with any questions i had and accommodating with any needs that arose
jamie’s place is the perfect location for a relaxing getaway
plus there's a great dog park in lexington (jacobson park)
it's an easy drive to red river gorge and natural bridge state park
very quiet perfect for a secluded get away
great place to get away and enjoy a quiet atmosphere
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3. Tranquil guesthouse near downtown Winchester (from USD 45)

This wonderful guest house is located opposite Winchester’s College Park. If you are a fitness freak, facilities such as a public gym and a recreational center are located right in the vicinity of this property. The house has amenities such as heated floor tiles, a TV, a sink, and many more. Electronic combination locks are fitted both on the inside and outside of the doors. The house contains a single bedroom with a queen-size bed. Wi-Fi, bathroom essentials, air conditioning, free parking on the premises and on the street are also available. Guests are also served a complimentary breakfast every morning. Long-term stays up to 28 days or more are allowed at this property. However, pets and children below the age of 12 are not permitted in the house.

Carriage House on the Park
Winchester, Kentucky, United States
73 reviews Superhost  Wifi Available
Entire guesthouse 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the apartment is perfectly sized and is set up with a convenient coffee area
bed was super comfy
we loved the shower beautiful bathroom and extra vanity the most
it was very clean comfortable and quite
sparkling clean apartment perfect for my husband and i
it was very clean and perfect my me and my husband
the space was so clean it has such a cozy feel
the place was as depicted and very clean
great host in a wonderful neighborhood
fantastic place and hosts with attention to every detail
great space located in wonderful quiet neighborhood
the neighborhood is beautiful and quiet
this is an amazingly beautiful place to stay with easy access and location
highly recommend for a stay in central ky area
robin's place was fantastic for our trip
Read more reviews

4. Sweet couples’ getaway (from USD 50)

A convenient walking distance from downtown Winchester, this snug cottage is the perfect place to spend a laid-back romantic vacation with its 500 sq ft (46.5 sq m) of coziness. It includes a single bedroom with a double bed, a well-equipped kitchen, a fully furnished living room, and a pleasant dining space. If you’re curious how it feels like to live on a farm, this place has that kind of feel. There is an organic vegetable garden, sheep, chicken, cats, and a dog in the backyard. Moreover, it is surrounded by Kentucky Horse Park, Fort Boonesboro, Red River Gorge, and Kentucky Bourbon Trail amongst other landmarks. So, if you’re an adventure seeker and you are up for some sightseeing, this is a great place for you.

Cozy Cottage
Winchester, Kentucky, United States
397 reviews Superhost  Wifi Available
Entire guesthouse 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
cozy cabin is quiet & comfortable with many kitchen amenities and farm views of chickens & sheep
cozy cottage very sweet set up
molly’s cottage is cozy and comfortable
tranquil little cottage with all the amenities you could want for a comfortable stay in the area
very warm heater and the claw foot tub was incredible hospitable hosts with sweet dogs too
the linens and towels were clean and nice
the house was very clean and the bed was comfortable
quiet clean rural stay right in town
the bed though seemed clean and was comfy
it's clean lovely and very relaxing
host was friendly and welcoming
the hosts were very friendly and helpful
great place and friendly hospital hosts
we especially enjoyed the owner’s talkative cat
friendly people and well built comfortable cabin
but such a cute place
not far from downtown that has several great places to eat
molly has cute place right in winchester
cute and cozy great location wonderful host
we really enjoyed our stay at molly's place
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5. Perfect campervan for adventurers (from USD 46)

Enjoy your holiday in a campervan for an ideal stay. Guests can cook their meals on the grill by the fire. Heating or air conditioning, whatever you need, is available inside the camper. Cooking utensils are also available along with plates, cups, pans, indoor coffee pots, blankets, and much more. You can purchase firewood once you arrive. The camper can host up to four guests. It has one bedroom with two beds and one bathroom. Fresh farm eggs and soft drinks can be purchased nearby. All kinds of games such as volleyball, mini-golf, badminton, and basketball can be played in the front yard. Hosts will be glad to help you with the technicalities of the switches in the camper. Experience the unique stay in this amazing camper called ‘Lucy’.

I Love Lucy (Low cleaning fee)
Winchester, Kentucky, United States
70 reviews Superhost
Camper/RV 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
the heater worked well so we were comfortable even though it got pretty cold overnight (below freezing)
it is a small space but cozy lovely and comfortable
the camper was very clean and very charming
the place was clean and unique
the stationary camper was clean and inviting
the grounds are clean and offer so much to do
the hosts were very helpful and friendly
natalie and jason were exceptional hosts; very responsive
natalie and her husband were very helpful and quick to respond with any questions we had
these hosts are amazing so sweet and they respond quickly to any questions
natalie and her husband were very cool and kind
exactly as pictured great location for exploring red river gorge and the natural bridge area about 40 minute drive
we had a relaxing weekend and really enjoyed walking around the beautiful property
it was even better than we expected the rv is adorable and the location is beautiful and private
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6. Private hideout for small families (from USD 95)

This private basement guest suite is perfectly suited for small families or a group of friends. It has two bedrooms that can accommodate up to five people at a time. The house is located in the vicinity of many attractions which are all a 30 to 45 minutes’ drive away. These include famous places such as Keeneland, Woodford Reserve, Natural Bridge, Kentucky Horse Park, Kentucky Artisan Center, and others. Facilities offered here include free parking on premises, fully equipped kitchen, Wi-Fi, TV, washing machine, etc. They also have a lovely outdoor seating, cozy bedding, and a relaxing massage chair. The place is very easily accessible from Interstate 64 and 75, so if you are up for a road trip to Winchester, Kentucky, do check this place out.

Hideaway Haven
Winchester, Kentucky, United States
69 reviews Superhost  Wifi Available
Entire guest suite 2 Beds 5 Guests 2 Bedrooms 1 Bathroom

Accommodates: 5

Top guest reviews
Amenities & Room:
the couch and chairs were also comfortable
the beds were super comfortable
the queen bed in a separate bedroom was so comfortable
my daughter slept on that and said it was quite comfortable
the apartment was lovely and in a beautiful secluded country setting
great communication and very clean place
place was very clean and organized
great place very clean and spacious
the place is very cozy and very clean
everything was clean and we had all we needed for a great long weekend
laurie & her husband david were very welcoming hosts
amazing host super quick responses very lovely place thank you so much
laurie and david are super nice and wonderful hosts
laurie was very friendly and helpful
laurie and david are great hosts and have a beautiful house
the location of this place was amazing
the location was perfect for us
must visit place if you are near natural bridge and red river gorge area
it was an easy drive to natural bridge state park
very clean and close to red river gorge
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7. Camping retreat with spellbinding scenic views (from USD 20)

If you are an adventurer and love overnight camping, then this retreat is the ideal location for you. It is a simple and enjoyable camping retreat in Winchester, Kentucky. Apart from unlimited access to the fields and creeks behind the barn, there is also plenty of wildlife and natural beauty around. If you like exploring nature, there is a walking trail that you will love. Table, chairs, charcoal grill, and cooler are provided to guests. Fresh country eggs and soft drinks are also offered at additional charges. This place is located 40 mi (64 km) from Red River Gorge and 7 mi (11 km) from Fort Boonesborough State Park. Drinking alcohol and smoking are not allowed inside and guests are advised to bring their own tent, drinking water, lighters, and other necessities along.

Camp Coca Cola (bring your own tent)
Winchester, Kentucky, United States
14 reviews Superhost
Campsite 1 Bed 4 Guests 1 Bathroom

Accommodates: 4

Top guest reviews
natalie and jason were amazing hosts very friendly and hospitable
over all it was a nice experience and the owners were nice
Read more reviews

8. Cozy haven in a historic neighborhood

This cozy room is certainly going to make you fall in love with this place. The house is located on Winchester’s main street with a coffee house nearby. It is approximately 45 minutes away from Keeneland and it is easily accessible from the Interstate. Only one bedroom is available to guests and it can accommodate two at a time. However, an additional bedroom can also be arranged for an additional charge. All the basic facilities such as a kitchen, a TV, Wi-Fi, a washing machine, air conditioning, a smoke alarm, free on-street parking, fire extinguisher, and more are readily available for all guests. Pets are not allowed on this property.

Historic Downtown Winchester Home
Winchester, Kentucky, United States
101 reviews
Private room in house 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
her place is comfortable and has great wifi
shanda and andy are wonderful very nice bedroom towels and fan were set out for me
i was comfortable with the family the space and the neighborhood
great stay most comfortable pillows ever fit my needs completely
beautiful home with a very comfortable guest room
clean and ambient as advertised
the place is neat and clean
outstanding comfortable clean and excellent hosting
the house was very easy to find super clean and very cozy
the bathroom across the hallway was clean too and equipped with a lot of fluffy towels
very kind and communicative host
she was kind and very welcoming
shanda was a gracious host
this was a wonderful couple they were very accommodating they helped with directions and made us feel at home
shanda is an amazing host
great location walking distance to downtown
great location and super cute house
a nice short walk to anything downtown has to offer
main st had cute shops to visit as well
parking is very close and easily accessible right on the street by the side of the house
Read more reviews

Enjoy your stay in Winchester at these Airbnb vacation rentals

Winchester, Kentucky, provides some of the finest locations for cultural tourism. These vacation rentals hosted in the city by Airbnb will definitely make your stay comfortable and enjoyable. With your accommodation close to nature, you will feel more at home despite being far away from it. So what are you waiting for? Start packing your stuff and choose your favorite rental now.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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