10 Best Airbnb Vacation Rentals In Winchester, Virginia - Updated 2024

| 4 min read

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 February 06, 2024.

1. Charming loft in a historic building (from USD 70)

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.

Stayed at this property?
Winchester, Virginia, United States
1.67 km (1.1 mi) from Jim Barnett Park
557 reviews   Wifi Available
Entire loft 1 Bed 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
ac and ceiling fan kept it cool
check in easy good ac and wifi
ac was ice cold in the apartment which was amazing
lovely little apartment with plenty of space and comforts
down a quaint little alley the space is large and inviting quiet and comfortable
it was clean and comfy
bedding and towels are clean
the space was clean and well stocked
quiet clean fully equipped
very spacious clean and comfortable
host was extremely cordial and helpful
very responsive host who was always ready and willing to help
the owners are great as well
charlie was very responsive to any questions we had
charlie was a friendly host who helped us feel welcome
great location on the old town walking mall
loved the location steps away from the walking mall
great location and a very cute apartment
the location was excellent
great location if you want to be on the walking mall
Read more reviews

2. Simple and clean room with a patio (from USD 71)

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.

Stayed at this property?
Winchester, Virginia, United States
1.88 km (1.2 mi) from Jim Barnett Park
125 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the mattress was very comfortable and there was good water pressure in the shower
very clean and lots of helpful tips
clean and adequate unit with everything needed
place very clean and in a nice residential area
kim's place was clean and had everything i needed
kim’s place is very clean comfortable and charming
kim was very responsive
host is quick to communicate and had great local tips
kim has a great place and is a very helpful host
kim is a wonderful communicative and hardworking host
kim is a great host she communicated well with us and was accommodating to our needs
great location - just a few blocks from walking mall
perfect location for any downtown shopping
excellent location super close to downtown
this stay is in a historic building near the heart of town within walking distance of great breakfast
a super cozy place in a great location
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3. Stylish vintage home (from USD 126)

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.

Stayed at this property?
Winchester, Virginia, United States
1.58 km (1.0 mi) from Jim Barnett Park
285 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
comfortable furniture for hanging out
lots of comfortable space and amenities
it has very comfortable furniture and was stylishly decorated
super cozy live music across the street was awesome
enjoyed staying at michelle’s place and pleasantly surprised at the eclectic style décor of the apartment and its roominess
this place was super clean the clean smell was for sure there
beautiful decor and clean
the apartment is clean well appointed and spacious
the space itself is clean and cozy i’d absolutely stay there again
super cute place very clean and tidy
host was great
fantastic host that is very prompt if you need to message her any questions
host michelle is the greatest
host is amazing and so responsive
michelle is a nice host and her suggestions for the area were helpful
really cute place very close to the old town walking mall
great location and value
perfect location to walk to everything
tone of cute shops and restaurants within walking distance
great space with a location just two blocks from the walking mall
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4. Sweet home away from home (from USD 116)

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.

Stayed at this property?
Winchester, Virginia, United States
1.39 km (0.9 mi) from Jim Barnett Park
207 reviews   Superhost Wifi Available
ENTIRE HOME 2 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
nice kitchen and the coffee bar was great everything we needed
inviting porch with comfortable rocking chairs
our kids enjoyed playing in the backyard the beds were super comfortable with extra soft sheets
the beds linens and pillows were very comfortable
beds were very comfortable
very clean with everything you would need
house is clean and well done
we especially appreciated how clean it was
so nice and clean
everything was sparkling clean
hosts were easily reachable and accommodating
crystal is a fantastic host
the host was exceptional in communicating and it making every effort to make sure we were pleased
crystal was a wonderful host very accommodating and prompt with any questions we had
hosts are more than responsive
nice convenient location
the location was safe and convenient
great house in a great location in winchester
wonderful house and location daily walked to historic downtown
cozy and comfortable home in a great location close to old town and major business districts
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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.

Stayed at this property?
Winchester, Virginia, United States
894 meters (0.6 ft) from Jim Barnett Park
53 reviews   Wifi Available
ENTIRE RENTAL UNIT 1 Bed 1 Guest 1 Bedroom 1 Bathroom

Accommodates: 1

Top guest reviews
Amenities & Room:
i loved the balcony and the other touched that he had in the apartment
it was quaint and comfortable and had a cool little balcony
this is a funny little apartment but is definitely comfortable
the apartment was very clean and inviting
the apartment was clean and met all my needs
super clean and close to downtown
great host with immediate response to questions or concerns
host if very responsive
alexander is a great host
alexander is a great host
it was great and i thank my host for his gracious hospitality
good for location and value
great restaurants within walking distance
a great spot off the square within walking distance
well worth the cost fantastic location near shenandoah
the apartment was well stocked and the location ideal to get around to downtown
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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.

Stayed at this property?
Winchester, Virginia, United States
1.57 km (1.0 mi) from Jim Barnett Park
59 reviews  
Entire house 3 Beds 3 Bedrooms 1 Bathrooms
Top guest reviews
it was extremely clean and comfortable
a very clean well appointed sweet house
the house was clean and beautiful
the place was spotless and very welcoming
very clean and functional space for multiple guests
sulma is an excellent host
sulma is an outstanding host and truly has the gift of hospitality
the host communicated really well
she was super responsive
wilma was very responsive and a wonderful host
but the location for being close to the university was perfect too
great location - walking distance to all attractions in town
nice place good location to downtown
fantastic place in walking distance to the oldtown centre
we loved being able to walk to old town
Read more reviews

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.

Stayed at this property?

618 meters (0.4 ft) from Jim Barnett Park
19 reviews  
Entire house 3 Beds 6 Guests

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.

Stayed at this property?
Winchester, Virginia, United States
1.75 km (1.1 mi) from Jim Barnett Park
118 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
pro-tip: best wifi coverage is laying in bed
i especially appreciated the a/c system that was easily adjustable
eat breakfast at amherst diner around the corner it’s awesome
the bed is super comfy
we had an awesome stay very cozy place :)
the space was very clean and cozy
wonderful stay very responsive very clean and very flexible
the place itself was clean comfortable and spacious for what i needed
the apartment was clean and fully stocked with everything you would need
the space is comfortable clean and charming in a neighborhood full of beautiful old homes
kim was a great host
:) kim was a great host and very helpful with any questions i had
kim was an amazing host
kim was a helpful host and quick to respond
kim was a very responsive host
nice basement apartment close to town
good location with a short walk to downtown
perfect place near old town
great location within a walkable distance
location is great to downtown area
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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.

Stayed at this property?
Winchester, Virginia, United States
1.61 km (1.0 mi) from Jim Barnett Park
123 reviews   Wifi Available
ENTIRE RENTAL UNIT 1 Bed 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
the little deck off the kitchen was a nice touch as well
the kitchen is sunny and well-equipped complete with tea and coffee upon our arrival
the apt is lovely
the space was immaculate and comfortable
you won't be disappointed with this apartment
lots of charm and very clean
it's clean and well kept
the place is clean and comfortable
the room was very clean and private
otherwise a clean and warm place
cindy & mel are good hosts
they were kind and gracious and made us feel like we were at home
cindy and mel were great hosts
cindy and mel are perfect hosts
hosts were very helpful and quick to respond
the location is amazing
the location was ideal only a few blocks from the main pedestrian walking mall
wonderful location in the heart of old town
it was a central location in a cute town
terrific location - walked around the village which is just beautiful
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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.

Stayed at this property?
Winchester, Virginia, United States
929 meters (0.6 ft) from Jim Barnett Park
152 reviews   Wifi Available
ENTIRE HOME 3 Beds 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
super comfortable with a lot of daylight
tv was great and the living room comfortable
check-in instructions were very clear and the beds were super comfy
the stock kitchen was the best
the house is so cozy and the beds were very comfortable
her place was very clean and organized
house was super clean and the sheets were so soft
a great spot in winchester clean and cozy house and easy communication with hosts
clean and more than enough room for our family
beautifully decorated & very clean
having laundry facilities was so helpful & convenient
jenn is a great host
hosts are responsive and thoughtful
jenn was really kind to respond to my questions so quickly
jenn was very responsive to questions i had about check in
cute old house close to shenandoah university
great house in a great location
location is optimal and close to so many historical sites
great location just a 2 minute uber ride to old town
this house is in a good location
Read more reviews

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!

Stayed at this property?
Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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