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5.0 / 5Exceptional
8 reviews


  • Kitchen
  • Air Conditioning
  • Washer
  • Dryer


What's nearby

  • Popular Location
    Mt Hebron Cemetery
    13 min walk
  • Popular Location
    Bright Box Theater
    17 min walk
  • Popular Location
    Stonewall Jackson's Headquarters
    19 min walk
  • Airport
    Martinsburg, WV (MRB-Eastern West Virginia Regional)
    25 min drive

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Book online or call:

  • City Charmer Near Historic Oldtown Winchester

    Room Amenities

    • 800 sq ft
    • 2 bedrooms
    • 1 bathroom
    • Sleeps 6
    More details

About this area


This vacation home is located in Winchester. Mt Hebron Cemetery and Stonewall Jackson's Headquarters are local landmarks, and some of the area's activities can be experienced at Rock Harbor Golf Course and Valerie Hill Winery. Looking to enjoy an event or a game while in town? See what's going on at Summit Point Raceway, or consider a night out at Barns of Rose Hill. Our guests love the property's quiet location.

Popular Location

What's nearby

  • Mt Hebron Cemetery - 13 min walk
  • Handley Regional Library - 17 min walk
  • Bright Box Theater - 17 min walk
  • Stonewall Jackson's Headquarters - 19 min walk
  • Jim Barnett Park - 5 min drive

Getting around

  • Washington, DC (DCA-Ronald Reagan Washington National) - 93 min drive

About this property

City Charmer Near Historic Oldtown Winchester

Vacation home in Winchester with kitchen and patio
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. Perfect for 3 to 4 people but can sleep 6 if you don't mind the sofa. 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.
Air-conditioned accommodations at this vacation home offer DVD players and coffee/tea makers. Rooms open to patios. Kitchens offer refrigerators, stovetops, microwaves, and separate dining areas. Additionally, rooms include hair dryers and irons/ironing boards.

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Property amenities


Internet access

Parking and transportation

Onsite parking


Coffee/tea maker


2 bedrooms
Bed sheets provided


1 bathroom
Towels provided
Hair dryer

Living spaces

Dining room


TV with cable/satellite service
DVD player

Outdoor areas



Washing machine and dryer


Air conditioning


No pets allowed


Smoke-free property

Services and conveniences

Iron/ironing board


Sleeps 6
Unit size: 800 sq ft (74 sq m)



Check-in time starts at 3:00 PM


Check-out before 11:00 AM

Special check-in instructions

  • Guests will receive an email from the property manager with check-in and check-out instructions.


  • Pets not allowed

Children and extra beds

  • Children are welcome.

Property payment types


Important information

You need to know

Extra-person charges may apply and vary depending on property policy.
Government-issued photo identification and a credit card, debit card, or cash deposit are 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.
    Onsite parties or group events are strictly prohibited.

Property is also known as

  • City Charmer Historic Oldtown Winchester House
  • City Charmer Historic Oldtown House
  • City Charmer Historic Oldtown Winchester
  • City Charmer Historic Oldtown
  • City Charmer Near Historic Oldtown Winchester Winchester


5 - Excellent
4 - Good
3 - Okay
2 - Mediocre
1 - Poor

5/5 Excellent

    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!

    5/5 Excellent

      Very good...

      Excellent for a short stay...

      5/5 Excellent

        City Charmer is the perfect description!

        It is a great location and I can't wait to stay there, again!

        5/5 Excellent

          It’s a very charming home in a great neighborhood.

          This house was perfect for our sisters weekend. It’s a very charming home in a quiet neighborhood, the home had everything we needed.

          5/5 Excellent

            Cute, cozy, and best front porch ever!

            We had a wonderful time with family here! Great location...everything you need is nearby, convenient to the interstates and an easy walk to the pedestrian mall with shops, restaurants and museums. The house was very clean and comfortable and even decorated for Christmas. There were many thoughtful touches, and Crystal (the hostess) was very helpful. We hope to return.

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