City Charmer near Historic OldTown Winchester.

Photo gallery for City Charmer near Historic OldTown Winchester.

A porch with a red door, white chairs, and a welcome sign.
A dining area with a wooden table and chairs, a chandelier, a Christmas tree, and a television in the background.
A living room with a Christmas tree, a black leather chair, a coffee table, and a dining area with a table and chairs.
A two-story house with a red door, a porch with white chairs, and a number '414' on the front.
A kitchen with white cabinets, a black countertop, a ceiling fan, a window with blinds, and a sign above the window that reads "MARKET".

Reviews

10 out of 10
Exceptional

Highlights

  • Fun for everyone
    Enjoy a variety of top-rated games for endless fun and relaxation.
  • Private garden
    A rare find — relax in the peaceful, private garden space.
  • At the centre of it all
    Stay in a top rated central location, steps from the best attractions, dining, and entertainment.
  • Discover nearby landmarks
    Near Bright Box Theater

Popular amenities

  • Patio
  • Barbecue
  • Air-conditioning
  • Refrigerator
  • Internet
  • Washing machine

Explore the area

View map
Winchester, VA
  • Place, Shenandoah Valley Discovery Museum
    ‪19 min walk‬
  • Place, Patsy Cline Historic House
    ‪4 min drive‬
  • Place, Shenandoah University
    ‪4 min drive‬
  • Airport, Martinsburg, WV (MRB-Eastern West Virginia Regional)
    ‪22 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 Double Bed

Bedroom 1

1 Queen Bed

1 bathroom

Bathroom 1

Bathtub or shower · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Garden
Dining area

Add dates for prices

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About the area

Winchester

Winchester is home to this holiday home. Shenandoah Valley Discovery Museum and Rock Harbor Golf Course are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Nalls Farm Market and Frederick County Fairgrounds. Appleland Sports Center and Dinosaur Land are also worth visiting.
View more Holiday homes in WinchesterOpens in a new window
Map
Winchester, VA

What's nearby

  • Jim Barnett Park - 12 min walk - 1.1 km
  • Bright Box Theater - 17 min walk - 1.5 km
  • Shenandoah Valley Discovery Museum - 19 min walk - 1.6 km
  • Patsy Cline Historic House - 4 min drive - 1.8 km
  • Shenandoah University - 4 min drive - 3.1 km

Getting around

  • Martinsburg, WV (MRB-Eastern West Virginia Regional) - 23 min drive

Restaurants

  • ‪McDonald's - ‬15 min walk
  • ‪Hideaway Café - ‬17 min walk
  • ‪Wendy's - ‬14 min walk
  • ‪Arby's - ‬13 min walk
  • ‪Violino Ristorante Italiano - ‬16 min walk

Frequently asked questions

Is City Charmer near Historic OldTown Winchester. pet-friendly?

No, pets are not allowed at this property.

How much is parking at City Charmer near Historic OldTown Winchester. ?

On-site parking is available at the property.

What time is check-in at City Charmer near Historic OldTown Winchester. ?

Check-in begins at 3:00 PM.

What time is check-out at City Charmer near Historic OldTown Winchester. ?

Checkout is at 10:00 AM.

Where is City Charmer near Historic OldTown Winchester. located?

Situated in Winchester, this holiday home is within a 10-minute walk of Friendship Park and Apple Valley Square Shopping Center. Nalls Farm Market and Northpark Shopping Center are also within 15 minutes.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 59 out of 61 reviews
Rating 8 - Good. 2 out of 61 reviews
Rating 6 - Okay. 0 out of 61 reviews
Rating 4 - Poor. 0 out of 61 reviews
Rating 2 - Terrible. 0 out of 61 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very easy to find. Very comfortable stay.
Stayed 2 nights in Nov 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was fantastic. Everything was as advertised and the neighborhood is extremely quiet. Only 1 mile from Old town Winchester too.
Stayed 2 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful

Great stay. Host was amazing and easy to communicate with. House was perfect! Close to all the sights and restaurants.
Stayed 2 nights in Apr 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cozy and Quaint

What a great cozy space. The location was great as it was central and close to college campus that we were visiting. It had everything we needed and communication with the host was very easy.
Stayed 2 nights in Feb 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quiet and cozy

Very well kept two-bedroom house on a quiet street across from the local elementary school. Lacks a dishwasher, but that wasn't really an issue. This was a perfect spot for a quiet retreat. Hosts were very welcoming and responsive.
Stayed 5 nights in Mar 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place in Winchester!

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
Stayed 2 nights in May 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect "City Charmer"

This house is lovely. Spotlessly clean and well cared for. We had just stayed at a Ritz Carlton the previous week and I swear the beds were just as comfortable. Location was great, the view off of the front porch is so welcoming. Walk to town was convenient and we loved all of the recommendations from the owner. Would have loved to stay longer. Highly recommend.
Stayed 2 nights in Sep 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Back again!

This was our second visit to the CityCharmer and it was as cozy as we remembered!!! The front porch is beyond amazing and the house is comfortable, extremely clean and well appointed. Crystal continues to be an amazing hostess and provides many thoughtful touches. CityCharmer is convenient to the Winchester pedestrian mall, the interstates and all the wonderful things to do in the area. I think you will be happy if you choose to stay here!
Stayed 2 nights in Oct 2019
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cute cozy place

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.
Stayed 3 nights in Oct 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Getaway

A friend and I had a very nice visit to Winchester and found this rental to be comfortable and convenient. It’s several blocks from the Historic District, but we walked there and back with no problem. Everywhere we went we found people to be pleasant and friendly. We enjoyed lunch at El Centro in the Historic District and a delicious dinner at Everest Indian Restaurant on Berryville Ave. The owner, Crystal, is very helpful and responsive. This is a place I would definitely return to at another time.
Stayed 3 nights in May 2023
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Exceptional historical home.

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.
Stayed 2 nights in Sep 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Winchester Winter Vacation 2022

We had a great time in Winchester visiting family for the start of the Christmas season! This charming little house was perfect for my husband and I and so close to family and Old Town Winchester. Crystal even set up a Christmas tree and outdoor decorations to give the home that extra charm for the holidays. The rooms were roomy enough. The kitchen had ample space to cook when we didn’t feel like going out for dinner. Very tidy, clean, and comfortable during our 10-day. Thank you again, Crystal, for your hospitality. We hope to come back again!
Stayed 9 nights in Dec 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect for girls' getaway

Those front porch rockers are what drew me in and we were not disappointed! The City Charmer did indeed charm us and was the perfect location for a girlfriends' weekend getaway. Cozy, easy access to town, an owner who made sure everything was just right ... we couldn't have asked for more. Would definitely return here next time we venture to Winchester!
Stayed 2 nights in Oct 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

National Park trip

Great place to stay and relax after a great day on a National Park adventure This house is close to Shenandoah National Park, Caverns and Harpers Ferry.
Stayed 4 nights in Sep 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Charming and comfortable

Fantastic experience, clean and quiet. Close to old town and walking mall. Would come back without hesitation!
Stayed 4 nights in Sep 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Good Weekend Stay

Enjoyed a pleasant weekend with my husband at City Charmer. I had not visited Winchester in many years and was delighted to find this clean, quiet home in a peaceful neighborhood within easy walking distance of Old Town. Crystal was kind enough to turn the excellent AC on before our arrival, & we were delighted to sit on the roomy front porch each evening, relaxing and enjoying the Mayberry-like neighborhood. While the rooms are small, the home has been updated nicely. We especially appreciated the good water pressure in the tub/shower combo. Overall, a quiet, convenient little cottage with a home town feel. Nice stay.
Stayed 2 nights in Aug 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relaxing Time

The property was wonderful and met all our needs for a chilled vacation in Virginia and had easy access to Winchester Old Town. The host (Crystal) helped us greatly in addition to the facilities available. Her responses were always quick and just overall a really good person to deal with. This is an ideal place if you are visiting Winchester.
Stayed 10 nights in Jun 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful home and close to downtown Winchester

Great location. Quick walk or Uber drive to downtown Winchester. Perfect little getaway. Home is cute and very inviting.
Stayed 4 nights in Feb 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Super

Any complaints I had were very minor. Overall I could hardly ask for a more convenient and restful week.
Stayed 7 nights in Apr 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Book launch Event

The property is walking distance from Old town Winchester. The bed was comfortable, the house is nice and cozy. I have one suggestion, it would be nice if there was another mirror in the house. Maybe over the dressers in the bedrooms. We will definitely be back.
Stayed 3 nights in Apr 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great little places, near town

Quiet and close to town. Property owner checked in and was very informative about everything. It was decorated for Christmas. I felt very at home here and will definitely be coming back!!
Stayed 12 nights in Dec 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family wedding

Was the perfect location for our event . Close to all and very nice quiet neighborhood
Stayed 4 nights in Nov 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Girl’s Getaway

Everything about renting this cottage was perfect. Crystal was very accommodating and communicative during the rental process. The cottage is exactly as pictured. Perfect for a small group to enjoy exploring Winchester’s battlefields, wineries, breweries, restaurants, and black box theatre. About a twenty minute walk to Old Town. Plenty of parking on streets and in a parking garage if walking isn’t for you. The cottage has a beautiful front porch with four rocking chairs. Perfect for enjoying an afternoon cocktail or morning coffee. The cottage is on a quiet part of the street across from a school. Very comfortable beds, sofa and linens. Very good water pressure in the shower! A compact cottage that is very well appointed for a short vacation. If you are looking for a perfect getaway - this cottage is for you!
Stayed 2 nights in Oct 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Small Cute Cottage

We stayed in this small home while visiting my daughter and her family. This is home s located in a quite neighborhood. Very well kept older home. Very comfortable beds. I highly recommend this home.
Stayed 4 nights in Jul 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Convenience

Easy from start to finish. Great location to take day trips from and convenient to shopping and restaurants. Nice place to come home to and relax. There were only three of us which was the right amount of people to be comfortable.
Stayed 5 nights in Aug 2021
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