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.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 09, 2024.
1. Pet-friendly escape with a country vibe (from USD 85)
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.
Top guest reviews
Amenities & Room:
the bed was super comfyfull kitchen was great for cooking when we didn’t eat outsuper clean and had everything needed + more we loved eating breakfast outside on the patiothe kitchen has basic cookware - we easily were able to make full dinnersCleanliness:
very cleanthe house was spotless and comfortablevery clean we would definitely stay againvery secluded clean and just all around amazingthe guest house was extremely cleanHost:
jamie is a great hostthe host has thought of every little detail to make your stay perfectjamie was so helpful with any questions i had and accommodating with any needs that aroseRead more reviewsLocation:
jamie’s place is the perfect location for a relaxing getawayplus there's a great dog park in lexington (jacobson park)it's an easy drive to red river gorge and natural bridge state parkvery quiet perfect for a secluded get awaygreat place to get away and enjoy a quiet atmosphere
2. Tranquil guesthouse near downtown Winchester (from USD 60)
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.
Top guest reviews
Amenities & Room:
the apartment is perfectly sized and is set up with a convenient coffee areabed was super comfywe loved the shower beautiful bathroom and extra vanity the mostCleanliness:
it was very clean comfortable and quitesparkling clean apartment perfect for my husband and iit was very clean and perfect my me and my husbandthe space was so clean it has such a cozy feelthe place was as depicted and very cleanHost:
great host in a wonderful neighborhoodfantastic place and hosts with attention to every detailRead more reviewsLocation:
great space located in wonderful quiet neighborhoodthe neighborhood is beautiful and quietthis is an amazingly beautiful place to stay with easy access and locationhighly recommend for a stay in central ky arearobin's place was fantastic for our trip
3. Sweet couples’ getaway (from USD 60)
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.
Top guest reviews
Amenities & Room:
cozy cabin is quiet & comfortable with many kitchen amenities and farm views of chickens & sheepcozy cottage very sweet set upmolly’s cottage is cozy and comfortabletranquil little cottage with all the amenities you could want for a comfortable stay in the areavery warm heater and the claw foot tub was incredible hospitable hosts with sweet dogs tooCleanliness:
the linens and towels were clean and nicethe house was very clean and the bed was comfortablequiet clean rural stay right in townthe bed though seemed clean and was comfyit's clean lovely and very relaxingHost:
host was friendly and welcomingthe hosts were very friendly and helpfulgreat place and friendly hospital hostswe especially enjoyed the owner’s talkative catfriendly people and well built comfortable cabinRead more reviewsLocation:
but such a cute placenot far from downtown that has several great places to eatmolly has cute place right in winchestercute and cozy great location wonderful hostwe really enjoyed our stay at molly's place
4. Perfect campervan for adventurers (from USD 36)
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’.
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 comfortableCleanliness:
the camper was very clean and very charmingthe place was clean and uniquethe stationary camper was clean and invitingthe grounds are clean and offer so much to doHost:
the hosts were very helpful and friendlynatalie and jason were exceptional hosts; very responsivenatalie and her husband were very helpful and quick to respond with any questions we hadthese hosts are amazing so sweet and they respond quickly to any questionsnatalie and her husband were very cool and kindRead more reviewsLocation:
exactly as pictured great location for exploring red river gorge and the natural bridge area about 40 minute drivewe had a relaxing weekend and really enjoyed walking around the beautiful propertyit was even better than we expected the rv is adorable and the location is beautiful and private
5. Private hideout for small families
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.
Winchester, Kentucky, United States
9.09 km (5.7 mi) from Fort Boonesborough State ParkSuperhost
Accommodates: 5
Top guest reviews
Amenities & Room:
the couch and chairs were also comfortablethe beds were super comfortablethe queen bed in a separate bedroom was so comfortablemy daughter slept on that and said it was quite comfortablethe apartment was lovely and in a beautiful secluded country settingCleanliness:
great communication and very clean placeplace was very clean and organizedgreat place very clean and spaciousthe place is very cozy and very cleaneverything was clean and we had all we needed for a great long weekendHost:
laurie & her husband david were very welcoming hostsamazing host super quick responses very lovely place thank you so muchlaurie and david are super nice and wonderful hostslaurie was very friendly and helpfullaurie and david are great hosts and have a beautiful houseRead more reviewsLocation:
the location of this place was amazingthe location was perfect for usmust visit place if you are near natural bridge and red river gorge areait was an easy drive to natural bridge state parkvery clean and close to red river gorge
6. Camping retreat with spellbinding scenic views (from USD 12)
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.
Top guest reviews
Read more reviewsHost:
natalie and jason were amazing hosts very friendly and hospitableover all it was a nice experience and the owners were nice
7. 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.
Winchester, Kentucky, United States
12.22 km (7.6 mi) from Fort Boonesborough State ParkTop guest reviews
Amenities & Room:
her place is comfortable and has great wifishanda and andy are wonderful very nice bedroom towels and fan were set out for mei was comfortable with the family the space and the neighborhoodgreat stay most comfortable pillows ever fit my needs completelybeautiful home with a very comfortable guest roomCleanliness:
clean and ambient as advertisedthe place is neat and cleanoutstanding comfortable clean and excellent hostingthe house was very easy to find super clean and very cozythe bathroom across the hallway was clean too and equipped with a lot of fluffy towelsHost:
very kind and communicative hostshe was kind and very welcomingshanda was a gracious hostthis was a wonderful couple they were very accommodating they helped with directions and made us feel at homeshanda is an amazing hostRead more reviewsLocation:
great location walking distance to downtowngreat location and super cute housea nice short walk to anything downtown has to offermain st had cute shops to visit as wellparking is very close and easily accessible right on the street by the side of the house
8. Comfortable bungalow with state-of-the-art amenities
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.
Winchester, Kentucky, United States
14.3 km (8.9 mi) from Fort Boonesborough State ParkAccommodates: 4
Top guest reviews
Read more reviewsAmenities & Room:
we did put a couple of books under the bedroom tv to see it better
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.
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