City Charmer near Historic OldTown Winchester.

Winchester, Virginia
$138 avg/night Minimum Stay 2 Nights
Bed 2

Bed

Bath 1

Bath

Home Private Vacation Home

Property Type

Sleep 4

Max Sleeps

Night 2 nights

Min Stay

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.
<br>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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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    2 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 800 Sq Ft (74 Sq M)
  • KITCHEN

    Blender Coffee/tea Maker Cookware/dishes/utensils Microwave Oven Paper Towels Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Charcoal Grill Garden Outdoor Furniture Patio
  • BATHROOMS

    1 Bathroom Bathtub Or Shower Hair Dryer Soap Toilet Paper Towels Provided
  • ENTERTAINMENT

    DVD Player TV
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Cobblestone Flooring In Public Areas Hardwood Flooring In Public Areas If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. Note From Host: Smoking/Vaping Is Permitted Outdoors Only. Smoke-free Property

CheckIn Check-in : 03:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 4

Map Map

School District Rates & Availability

Review Review

  • Marc H.

    Submitted Oct 6, 2025

    Stayed Oct 3, 2025

    The house was fantastic. Everything was as advertised and the neighborhood is extremely quiet. Only 1 mile from Old town Winchester too.

  • natalie s.

    Submitted May 17, 2024

    Stayed May 11, 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

  • Seth M.

    Submitted Oct 31, 2023

    Stayed Oct 24, 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.

  • Dawn W.

    Submitted Oct 9, 2023

    Stayed Sep 26, 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.

  • Eve B.

    Submitted Sep 11, 2023

    Stayed Sep 8, 2023

    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.

  • Kathy S.

    Submitted May 19, 2023

    Stayed May 13, 2023

    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.

  • Kelly S.

    Submitted Apr 7, 2023

    Stayed Apr 5, 2023

    Great stay. Host was amazing and easy to communicate with. House was perfect! Close to all the sights and restaurants.

  • Edward V.

    Submitted Mar 24, 2023

    Stayed Mar 19, 2023

    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.

  • Dawn V.

    Submitted Feb 26, 2023

    Stayed Feb 24, 2023

    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.

  • Francine R.

    Submitted Dec 11, 2022

    Stayed Dec 1, 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!

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Total

Includes taxes and fees
$138+
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