Winchester, Virginia, has earned the nickname “the Apple Capital” as it’s one of the most well-known and largest apple export markets in the US and for its abundant apple orchards. The city even celebrates the Shenandoah Apple Blossom Festival every year in May, and this is an event that attracts hundreds of thousands of people. Besides this, visitors will find many attractions, including Old Town Winchester, Stonewall Jackson’s Headquarters, Patsy Cline Historic House, and Museum of the Shenandoah Valley. There are plenty of places to visit and things to do in Winchester. If you’re planning your trip to this fascinating city, keep reading to discover the best Airbnbs in Winchester, Virginia, listed below.
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 October 24, 2024.
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1. Charming loft in a historic building (from USD 65)
The area of Old Town Winchester is practically an open mall so there are a lot of restaurants and shops within walking distance. This is where this charming accommodation is located. The place is lined with historic buildings, including the one where this loft is at. The interiors of the loft are quite rustic in style but the red walls give it a cosy ambience. There is a queen-sized bed and a sofa bed which is perfect for small groups of up to four people. The kitchen and bathroom are well-equipped with basic necessities as well.
Winchester, Virginia, United States
1.67 km (1.1 mi) from Jim Barnett ParkAccommodates: 3
Top guest reviews
Host:
host was extremely cordial and helpfulvery responsive host who was always ready and willing to helpthe owners are great as wellcharlie was very responsive to any questions we hadcharlie was a friendly host who helped us feel welcomeLocation:
great location and a very cute apartmentloved the location steps away from the walking mallgreat location on the old town walking mallthe location was excellentgreat location if you want to be on the walking mallCleanliness:
it was clean and comfybedding and towels are cleanthe space was clean and well stockedquiet clean fully equippedvery spacious clean and comfortableRead more reviewsAmenities & Room:
ac and ceiling fan kept it coolcheck in easy good ac and wifiac was ice cold in the apartment which was amazinglovely little apartment with plenty of space and comfortsdown a quaint little alley the space is large and inviting quiet and comfortable
2. Simple and clean room with a patio (from USD 2003)
This lovely room is also located in the historic 1870s building that’s just a few blocks away from the main downtown area. Its location is ideal for those who want to tour the area easily. Many of the historic sights are nearby as well. Meanwhile, the interiors of the room are quite simple yet charming in style with the majority of the color scheme being white and having wooden accents. There is also a private screened patio for you to enjoy a lovely breakfast or a wonderful dinner.
Winchester, Virginia, United States
1.88 km (1.2 mi) from Jim Barnett ParkSuperhost
Accommodates: 2
Top guest reviews
Host:
kim was very responsivehost is quick to communicate and had great local tipskim has a great place and is a very helpful hostkim is a wonderful communicative and hardworking hostkim is a great host she communicated well with us and was accommodating to our needsLocation:
excellent location super close to downtownperfect location for any downtown shoppinggreat location - just a few blocks from walking mallthis stay is in a historic building near the heart of town within walking distance of great breakfasta super cozy place in a great locationCleanliness:
very clean and lots of helpful tipsclean and adequate unit with everything neededplace very clean and in a nice residential areakim's place was clean and had everything i neededkim’s place is very clean comfortable and charmingRead more reviewsAmenities & Room:
the mattress was very comfortable and there was good water pressure in the shower
3. Stylish vintage home (from USD 204)
You’ll feel like you were transported into a period drama with this lovely little apartment. The design of the apartment is entirely vintage and it’s even located above a vintage shop. The location is also surrounded by several coffee shops, restaurants, and shopping hubs. The host is very accommodating and is even happy to give their recommendations for the area. For guests who are bringing their cars, there is free parking on-site too.
Winchester, Virginia, United States
1.58 km (1.0 mi) from Jim Barnett ParkAccommodates: 2
Top guest reviews
Host:
host was greatfantastic host that is very prompt if you need to message her any questionshost michelle is the greatesthost is amazing and so responsivemichelle is a nice host and her suggestions for the area were helpfulLocation:
really cute place very close to the old town walking mallgreat location and valueperfect location to walk to everythingtone of cute shops and restaurants within walking distancegreat space with a location just two blocks from the walking mallCleanliness:
this place was super clean the clean smell was for sure therebeautiful decor and cleanthe apartment is clean well appointed and spaciousthe space itself is clean and cozy i’d absolutely stay there againsuper cute place very clean and tidyRead more reviewsAmenities & Room:
comfortable furniture for hanging outlots of comfortable space and amenitiesit has very comfortable furniture and was stylishly decoratedsuper cozy live music across the street was awesomeenjoyed staying at michelle’s place and pleasantly surprised at the eclectic style décor of the apartment and its roominess
4. Sweet home away from home (from USD 277)
This lovely 1950s house is a few minutes away from the Historic Old Town of Winchester. Located in a charming and quiet neighborhood, the host takes pride in the fact that this used to be her grandmother’s home so there is some sweet sentimental value to the place. There were renovations but the old charm remains. It’s a perfect holiday home for families who are traveling to see the city. Many restaurants and tourist spots are within the vicinity as well.
Winchester, Virginia, United States
1.39 km (0.9 mi) from Jim Barnett ParkAccommodates: 4
Top guest reviews
Host:
hosts were easily reachable and accommodatingcrystal is a fantastic hostthe host was exceptional in communicating and it making every effort to make sure we were pleasedcrystal was a wonderful host very accommodating and prompt with any questions we hadhosts are more than responsiveLocation:
nice convenient locationthe location was safe and convenientgreat house in a great location in winchesterwonderful house and location daily walked to historic downtowncozy and comfortable home in a great location close to old town and major business districtsCleanliness:
very clean with everything you would needhouse is clean and well donewe especially appreciated how clean it wasso nice and cleaneverything was sparkling cleanRead more reviewsAmenities & Room:
nice kitchen and the coffee bar was great everything we neededinviting porch with comfortable rocking chairsour kids enjoyed playing in the backyard the beds were super comfortable with extra soft sheetsthe beds linens and pillows were very comfortablebeds were very comfortable
5. Cozy but modern apartment fit for couples
Though housed in an old building, this one-bedroom apartment located in downtown Winchester is a modern and ideal option for couples traveling together or even a solo traveler. The size is just right yet it has all the comforts of a modern apartment. It even has a washer and dryer and the host is willing to provide some additional needs should you request them. Many restaurants and shops are within walking distance so the location is perfect as well.
Winchester, Virginia, United States
894 meters (0.6 ft) from Jim Barnett ParkAccommodates: 1
Top guest reviews
Host:
great host with immediate response to questions or concernshost if very responsivealexander is a great hostalexander is a great hostit was great and i thank my host for his gracious hospitalityLocation:
good for location and valuegreat restaurants within walking distancea great spot off the square within walking distancewell worth the cost fantastic location near shenandoahthe apartment was well stocked and the location ideal to get around to downtownCleanliness:
the apartment was very clean and invitingthe apartment was clean and met all my needssuper clean and close to downtownRead more reviewsAmenities & Room:
i loved the balcony and the other touched that he had in the apartmentit was quaint and comfortable and had a cool little balconythis is a funny little apartment but is definitely comfortable
6. Spacious house with great accessibility
This lovely downtown house is a spacious place perfect for families and big groups. There are three bedrooms, a vast living area, and a well-equipped kitchen and bathrooms. The ambiance is also well-light and clean. Traveling for business? This house has a room for private office space should you need one. The location is very accessible to a number of restaurants, breweries, and shops for your needs. You can also explore the museums nearby or visit Shenandoah University or Winchester Medical Center.
Winchester, Virginia, United States
1.57 km (1.0 mi) from Jim Barnett ParkTop guest reviews
Host:
sulma is an excellent hostsulma is an outstanding host and truly has the gift of hospitalityshe was super responsivethe host communicated really wellwilma was very responsive and a wonderful hostLocation:
but the location for being close to the university was perfect toogreat location - walking distance to all attractions in townnice place good location to downtownfantastic place in walking distance to the oldtown centrewe loved being able to walk to old townRead more reviewsCleanliness:
it was extremely clean and comfortablea very clean well appointed sweet housethe house was clean and beautifulthe place was spotless and very welcomingvery clean and functional space for multiple guests
7. Humble family home in a quiet neighborhood
If you’re traveling with your family to Winchester and you’re looking for a quiet neighborhood but not too far from the main attractions, this property is for you. It’s like staying at your own home except you’re on a vacation. The house has all the basic necessities even with a laundry area, exercise area, and a gas grill for some barbecue. Aside from that, pets are very welcome to come along as well provided the guest cleans up properly after them. The backyard is fenced so you need not worry if they would try to escape. Indeed it is the perfect family weekend getaway.
618 meters (0.4 ft) from Jim Barnett Park
8. Snug little room in a 19th-century house
This accommodation is one of eight rooms located in a house built in the 1870s. You will get to enjoy your own privacy as the room is located in the basement. Because of its size however, this property is ideal for couples or solo travelers. Despite that, the apartment is complete with basic amenities including a full-sized refrigerator and an automatic dishwasher. The downtown area is also walkable from the quiet neighborhood this property is located in. The hospitable host will gladly be of assistance to your needs as well.
Winchester, Virginia, United States
1.75 km (1.1 mi) from Jim Barnett ParkAccommodates: 2
Top guest reviews
Host:
kim was a great host:) kim was a great host and very helpful with any questions i hadkim was an amazing hostkim was a helpful host and quick to respondkim was a very responsive hostLocation:
great location within a walkable distanceperfect place near old towngood location with a short walk to downtownnice basement apartment close to townlocation is great to downtown areaCleanliness:
the space was very clean and cozywonderful stay very responsive very clean and very flexiblethe place itself was clean comfortable and spacious for what i neededthe apartment was clean and fully stocked with everything you would needthe space is comfortable clean and charming in a neighborhood full of beautiful old homesRead more reviewsAmenities & Room:
pro-tip: best wifi coverage is laying in bedi especially appreciated the a/c system that was easily adjustableeat breakfast at amherst diner around the corner it’s awesomethe bed is super comfywe had an awesome stay very cozy place :)
9. Newly renovated apartment in a great location
This newly renovated one-bedroom apartment is ideal for couples or pairs. The unit is located inside the Historic Seymour House in Old Town Winchester. It’s within the vicinity of many restaurants and shops as well as a couple of minutes’ drive to many of Winchester’s historic landmarks. Don’t be fooled by the old-looking exteriors, the design of the apartment is very much modern and stylish without completely shattering the authentic feel of the historic building. Aside from the usual amenities, there is also free parking nearby and metered parking on certain timeslots.
Winchester, Virginia, United States
1.61 km (1.0 mi) from Jim Barnett ParkAccommodates: 3
Top guest reviews
Host:
cindy & mel are good hoststhey were kind and gracious and made us feel like we were at homecindy and mel were great hostscindy and mel are perfect hostshosts were very helpful and quick to respondLocation:
the location is amazingthe location was ideal only a few blocks from the main pedestrian walking mallwonderful location in the heart of old townit was a central location in a cute townterrific location - walked around the village which is just beautifulCleanliness:
lots of charm and very cleanit's clean and well keptthe place is clean and comfortablethe room was very clean and privateotherwise a clean and warm placeRead more reviewsAmenities & Room:
the little deck off the kitchen was a nice touch as wellthe kitchen is sunny and well-equipped complete with tea and coffee upon our arrivalthe apt is lovelythe space was immaculate and comfortableyou won't be disappointed with this apartment
10. Lovely cottage fit for the family
If you’re vacationing as a family or a somewhat large group and prefer to stay in a charming neighborhood, then Millwood House might just be the perfect fit for you. The charming cottage has three bedrooms and two bathrooms and can comfortably sleep at least six people. The house is just a stone’s throw away from Shenandoah University, so this is also ideal for visitors who have business at the university. Apart from that, there’s a Starbucks and a couple of great restaurants within walking distance too. Old Town Winchester and other historic landmarks are also just a mile away via car.
Winchester, Virginia, United States
929 meters (0.6 ft) from Jim Barnett ParkAccommodates: 6
Top guest reviews
Host:
having laundry facilities was so helpful & convenientjenn is a great hosthosts are responsive and thoughtfuljenn was really kind to respond to my questions so quicklyjenn was very responsive to questions i had about check inLocation:
cute old house close to shenandoah universitygreat house in a great locationlocation is optimal and close to so many historical sitesgreat location just a 2 minute uber ride to old townthis house is in a good locationCleanliness:
her place was very clean and organizedhouse was super clean and the sheets were so softa great spot in winchester clean and cozy house and easy communication with hostsclean and more than enough room for our familybeautifully decorated & very cleanRead more reviewsAmenities & Room:
super comfortable with a lot of daylighttv was great and the living room comfortablecheck-in instructions were very clear and the beds were super comfythe stock kitchen was the bestthe house is so cozy and the beds were very comfortable
Relive the past when staying at Winchester, Virginia
With such history behind it, even the houses and buildings at Winchester are historic in look, feel, and design. Most of them were built as far back as the 18th and 19th centuries. Book your stay soon and learn about the history of the Apple Capital!
History
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