Entire home

City Charmer near Historic OldTown Winchester.

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Where to?

Dates

July 2025

August 2025

Welcome to a charming two-story home with a cozy porch and a beautiful garden.

Relax in this serene bedroom with a large bed, a dresser, and a plant.

Enjoy a serene atmosphere surrounded by lush trees and a lawn area with a charming gazebo.

Enjoy meals in the dining area with a dark table and four chairs, a coffee station, and a kitchen in the background.

Relax on the inviting porch with a pair of white rocking chairs and enjoy the beautiful garden surroundings.

Overview
Amenities
Policies
Location
Host

Entire home

2 bedrooms1 bathroomSleeps 4800 sq ft

Popular amenities

Parking available
Barbecue grill
Dryer
Washer
Kitchen

Explore the area

Winchester, VA

Shenandoah University
‪2 min drive‬
Museum of the Shenandoah Valley
‪4 min drive‬
Winchester Medical Center
‪6 min drive‬
Martinsburg, WV (MRB-Eastern West Virginia Regional)
‪25 min drive‬

Room options

About the neighborhood

Winchester

Located within a 5-minute walk of Friendship Park, this vacation home is within a 15-minute stroll of Apple Valley Square Shopping Center. The vacation home includes a kitchen, a patio, and a refrigerator.

View more Vacation Homes in Winchester

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

‪Arby's - ‬13 min walk
‪McDonald's - ‬15 min walk
‪Pizzoco Pizza Parlor - ‬20 min walk
‪Wendy's - ‬14 min walk
‪Subway - ‬16 min walk

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.

The vacation home is air-conditioned and features a kitchen and a patio, and there's space to spread out with 2 bedrooms. Guests can expect to find free WiFi and a TV with a DVD player. Other standard amenities include a washing machine, a coffee maker, and an ironing board.

Property manager

Crystal Ford

Similar properties

Kitchen
Washer
Dryer
Pet friendly

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

Barbecue 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
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

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

Pets

This property doesn't allow pets

Children and extra beds

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

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

Check-in: 3:00 PM
Check-out: 10:00 AM

We should mention

Details about charges, deposits, or other important information:

This property is managed by a private host, not a professional engaged in trade or business.
Charges for extra guests may apply and vary depending on the property's policy.
A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
Onsite parties or group events are strictly prohibited.
Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock.

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

Frequently asked questions

What is there to do near this vacation home?

This vacation home in Winchester is within a 10-minute walk of Friendship Park and Apple Valley Square Shopping Center. You'll also find Jim Barnett Park and Bright Box Theater less than a mile away.

Will I be able to park at this vacation home?

No, this vacation home doesn't offer parking.

Is this vacation home associated with a casino?

No, this vacation home is not connected to a casino.

Is there an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home.

What will couples enjoy most about a stay at City Charmer near Historic OldTown Winchester. ?

Couples staying at this vacation home will value amenities like a kitchen, kitchens in some accommodations, as well as a garden.

Are there hot tubs at City Charmer near Historic OldTown Winchester. ?

No, there isn't a spa tub at this vacation home.

Does this vacation home offer breakfast?

No, this vacation home doesn't offer breakfast.

Does this vacation home allow pets to stay for free?

No, pets aren't allowed at this vacation home.

Does this vacation home have connecting rooms?

No, this vacation home doesn't feature connecting guestrooms.

How close is the airport from this vacation home?

The closest major airport to this vacation home is Martinsburg, WV (MRB-Eastern West Virginia Regional), which is 19.5 mi away (23 minutes by car).

Are there rooms with balconies at City Charmer near Historic OldTown Winchester. ?

Yes, every accommodation at City Charmer near Historic OldTown Winchester. comes with a deck.

City Charmer near Historic OldTown Winchester. Reviews

Exceptional

10/10

Cleanliness

10/10 Excellent

Jerry H.

Oct 29, 2024

Liked: Cleanliness

Stayed 4 nights in Oct 2024

10/10 Excellent

natalie s.

May 17, 2024

Liked: Cleanliness

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.

Oct 31, 2023

Liked: Cleanliness

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

8/10 Good

Dawn W.

Oct 9, 2023

Liked: Cleanliness

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

Eve B., Pittsburgh PA

Sep 11, 2023

Liked: Cleanliness

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

Kathy S.

May 19, 2023

Liked: Cleanliness

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

10/10 Excellent

Kelly S.

Apr 7, 2023

Liked: Cleanliness

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

Edward V., Sterling, VA

Mar 24, 2023

Liked: Cleanliness

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

Dawn V.

Feb 26, 2023

Liked: Cleanliness

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

Francine R., Santa Clarita, CA

Dec 11, 2022

Liked: Cleanliness

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.

Nov 11, 2022

Liked: Cleanliness

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.

Sep 16, 2022

Liked: Cleanliness

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.

Sep 9, 2022

Liked: Cleanliness

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.

Aug 21, 2022

Liked: Cleanliness

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

Jul 6, 2022

Liked: Cleanliness

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

May 17, 2022

Liked: Cleanliness

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.

Apr 30, 2022

Liked: Cleanliness

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.

Apr 28, 2022

Liked: Cleanliness

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.

Jan 5, 2022

Liked: Cleanliness

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.

Nov 15, 2021

Liked: Cleanliness

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

Oct 15, 2021

Liked: Cleanliness

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

Aug 7, 2021

Liked: Cleanliness

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.

Aug 7, 2021

Liked: Cleanliness

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.

Jun 6, 2021

Liked: Cleanliness

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

10/10 Excellent

robin b.

May 14, 2021

Liked: Cleanliness

Virginia getaway

House was very nice and clean and close to Old Town in Winchester. Everything was right there for us in the house and very convenient. We would definitely stay again.

Stayed 4 nights in May 2021