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Entire home

City Charmer near Historic OldTown Winchester.

Vacation home in Winchester with kitchen and patio

Photo gallery for City Charmer near Historic OldTown Winchester.

Exterior
2 bedrooms, iron/ironing board, free WiFi, bed sheets
Property grounds
Dining
Exterior detail
Nestled in the heart of Historic Old Town Winchester, this charming 1950's cottage style home offers a peaceful retreat with a large backyard and patio. Take advantage of the fully-equipped kitchen, charcoal grill, and laundry facilities or explore nearby restaurants, bars, shopping venues.

Reviews

10 out of 10
Exceptional

Entire home

2 bedrooms1 bathroomSleeps 4800 sq ft

Popular amenities

  • Parking available
  • Dryer
  • Barbecue grill
  • Washer
  • Outdoor Space

Add dates for prices

About this property

Entire place

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

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.

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Bathtub or shower
  • Hair dryer
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • DVD player
  • TV

Outdoor areas

  • Charcoal grill
  • Garden
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Cobblestone flooring in public areas
  • Hardwood flooring in public areas
  • Smoking not allowed
  • Note from host: Smoking/Vaping is permitted outdoors only.

Services and conveniences

  • Iron/ironing board

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Garden
  • Unit size: 800 square feet

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Fridge, microwave, oven, stovetop

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

  • Kitchen
  • Free WiFi
  • Air conditioning
  • Laundry
8.0 out of 10, Very Good, 3 reviews
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

Policies

Check-in

Check-in time starts at 3:00 PM
Contactless check-in available

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Rules

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

Pets

Pets not allowed

Children and extra beds

Children are welcome
Note from host: Do not allow children to lock doors without adult.

Events

No events allowed

Smoking

Smoking is not permitted
Smoking/Vaping is permitted outdoors only.

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 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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

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
City Charmer near Historic OldTown Winchester.
City Charmer near Historic OldTown Winchester. Winchester

About the neighborhood

Winchester is home to this vacation home. Stonewall Jackson's Headquarters and George Washington's Office are local landmarks, and travelers looking to shop may want to visit Apple Valley Square Shopping Center and Northpark Shopping Center. Nalls Farm Market and Shenandoah Valley Discovery Museum are also worth visiting.
Visit our Winchester travel guideOpens in a new window
View more Vacation Homes in WinchesterOpens in a new window
Map
Winchester, VA

What's nearby

  • Shenandoah Valley Discovery Museum - 19 min walk - 1.0 mile
  • Shenandoah University - 2 min drive - 1.3 miles
  • Apple Blossom Mall - 3 min drive - 2.2 miles
  • Museum of the Shenandoah Valley - 4 min drive - 2.2 miles
  • Winchester Medical Center - 6 min drive - 3.5 miles

Getting around

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

Restaurants

  • ‪McDonald's - ‬15 min walk
  • ‪Arby's - ‬13 min walk
  • ‪Pizzoco Pizza Parlor - ‬19 min walk
  • ‪Wendy's - ‬14 min walk
  • ‪Piccadilly's Public House & Restaurant - ‬13 min walk

Frequently asked questions

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

No, pets are not allowed at this 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. ?

Check-out is at 10:00 AM.

Where is City Charmer near Historic OldTown Winchester. located?

Situated in Winchester, this vacation 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.

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City Charmer near Historic OldTown Winchester. Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 58 out of 60 reviews
Rating 8 - Good. 2 out of 60 reviews
Rating 6 - Okay. 0 out of 60 reviews
Rating 4 - Poor. 0 out of 60 reviews
Rating 2 - Terrible. 0 out of 60 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Kelly S.

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

10/10 Excellent

Dawn V.

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

10/10 Excellent

Edward V., Sterling, VA

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

10/10 Excellent

Eve B., Pittsburgh PA

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

10/10 Excellent

Karen W.

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

10/10 Excellent

Kathy S.

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

8/10 Good

Dawn W.

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

10/10 Excellent

Jerry H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 4 nights in Oct 2024

10/10 Excellent

natalie s.

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

10/10 Excellent

Seth M.

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

10/10 Excellent

Francine R., Santa Clarita, CA

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

10/10 Excellent

Elizabeth W.

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

10/10 Excellent

Kathryn V.

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

10/10 Excellent

Ellen B.

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

10/10 Excellent

Jennifer S.

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

10/10 Excellent

Grant T., Alloa Scotland UK

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

10/10 Excellent

Michelle L., PALM HARBOR

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

10/10 Excellent

Bruce S.

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

10/10 Excellent

Sheilah C.

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

10/10 Excellent

Cami J.

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

10/10 Excellent

Mary S.

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

10/10 Excellent

Laureen M., Richmond, VA

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

10/10 Excellent

Scott S., Henderson, NV

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

10/10 Excellent

Jeffrey C.

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

10/10 Excellent

valerie c.

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

Great cozy little house.

This house was just what we needed for our stay in Winchester! We especially enjoyed its proximity to Old Town. Will stay here again!
Stayed 3 nights in Jun 2021

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