Entire home

City Charmer near Historic OldTown Winchester.

Photo gallery for City Charmer near Historic OldTown Winchester.

A two-story house with a red door, a porch with white chairs, and a number '414' on the front.
A living room with a Christmas tree, a black leather chair, a coffee table, and a dining area with a table and chairs.
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 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 center of it all
    Stay in a top rated central location, steps from the best attractions, dining, and entertainment.
2 bedrooms1 bathroomSleeps 4

Popular amenities

  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue grill
  • Deck or patio

Explore the area

View in a 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)
    ‪25 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

About this property

City Charmer near Historic OldTown Winchester.

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.

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House Rules

Check in after 3:00 PM
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
Do not allow children to lock doors without adult.
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
Smoking/Vaping is permitted outdoors only.
If more than one vehicle, please park any additional cars across the street.
No additional guests are allowed at the home that are not on reservation without approval from host.
Please be respectful of neighbors. No loud music or noise. Thank you

Important information

You need to know

Property # 1309433vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

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.
Map
Winchester, VA

What's nearby

  • Stonewall Jackson's Headquarters - 17 min walk - 1.5 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 - 2.1 km

Getting around

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

Restaurants

  • ‪Chick-fil-A - ‬5 min drive
  • ‪McDonald's - ‬7 min drive
  • ‪Cook Out - ‬4 min drive
  • ‪Starbucks - ‬4 min drive
  • ‪Taco Bell - ‬4 min drive

Frequently asked questions

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

No, pets are not allowed at this property.

How much does it cost to stay at City Charmer near Historic OldTown Winchester. ?

As of 21 Aug, 2026, prices found for a 1-night stay for 2 adults at City Charmer near Historic OldTown Winchester. on 21 Dec, 2026 start from S$360, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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.

About the host

Hosted by Crystal Ford

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