City Charmer near Historic OldTown Winchester.

Top rated by guests
Exterior detail
Dining
Dining
Private kitchen
Private kitchen
review stars
10Outstanding
(59 Ratings)
"The house was fantastic. Everything was as advertised and the neighborhood is extremely quiet. Only 1 mile from Old town Winchester too."
Marc H.
Don't miss out! Price and availability may change
10 / 10
Outstanding(59 Ratings)

House in Winchester, VA

4 guests · 2 bedrooms · 1 bath

Reasons to book

Guests love it hereGuests give this property a top rating
Great price for your budgetOne of the lowest cost properties in the area
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About this house rental

Renovated 1950's cottage style home. Enjoy a small house with a great front porch and a large backyard with patio. Just minutes to drive and about 10-15 minutes to walk to Historic Old Town Winchester which includes numerous restaurants, bars, shopping, and often some kind of event like the Shenandoah Apple Blossom Festival! Our house is located about 65 miles West of Washington D.C. if you're looking for a day trip to the big city or just sit back and relax right here in our small town.

This home was my grandma's home so even with a fresh new look, it will always be special to me. I visited my grandma in this home for over thirty years and always admired the character of it. While renovating, it was so important to me to keep some of that original charm--from the custom-made cabinets to the original hardwood floors; It's all there just spruced up a bit!

Our home has two bedrooms--a queen size bed, full bed, and a pull out sofa with queen size mattress. We also have a pack & play for infants. The kitchen has all the cooking essentials, microwave and a Keurig machine for coffee. There is also a charcoal grill out back. Laundry is available in the basement. The steps are steep so please be careful.

Amenities at City Charmer near Historic OldTown Winchester.

Non-smoking
No pets allowed

Map of Winchester, VA


Ratings and reviews

10 / 10
Outstanding(59 Ratings)
10 / 10Outstanding·Oct 2025
The house was fantastic. Everything was as advertised and the neighborhood is extremely quiet. Only 1 mile from Old town Winchester too.
10 / 10Outstanding·May 2024
I was looking for a nice home base, with a washer and dryer during a hiking trip to Shenandoah and came across Crystal’s place. The home was just as the listing described and more. The welcome sign was a nice touch, as was the jug of water, coffee machine and the cork board of suggested restaurants. Such a cute home too in the middle of a nice neighborhood! Highly recommend
10 / 10Outstanding·Oct 2023
Me and a buddy stayed a few days in Winchester to tour the nearby battlefields and attractions in town. House was in a nice neighborhood that is a five minute drive or 15-20 minute walk to Old Town. Bedrooms were clean and comfortable. The host was super responsive and helped us out with multiple suggestions. Thanks so much, Crystal! I would like to revisit Winchester at some point (didn’t quite get to see everything we wanted) and would definitely stay here again.
8 / 10Excellent·Oct 2023
We were treated like gold by the owner and loved being there. The only things I can see needs improvement are due to the beautiful shiny old hardwood floors a large area rug in the dining room and hallway. The sound level is very high. One or two comfy chairs as well. And a nightlight suggestion for travelers overall because the bathroom entry is very dark without it. But it's truly a gem and we are grateful to have found it and this meticulous caring owner.

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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at City Charmer near Historic OldTown Winchester.. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is City Charmer near Historic OldTown Winchester. pet friendly?

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at City Charmer near Historic OldTown Winchester.?

We found 2 amenities for this rental. This includes non-smoking, and no pets allowed.