City Charmer near Historic OldTown Winchester.
5.0
Outstanding(59 Reviews)House in Winchester, VA
4 guests · 2 bedrooms · 1 bath
Reasons to book
Guests love it hereGuests give this property a top rating
Free cancellationFull refund if you change your mind
Includes essentialsGarden, Kitchen or Kitchenette, Air conditioner and more
About this house rental
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.
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.
Amenities
Air conditioner
Kitchen or Kitchenette
Internet / Wifi
Parking
Laundry
Balcony or Patio
TV
Garden
Map of Winchester, VA
Reviews
5.0
Outstanding(59 Reviews)5.0
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
5.0
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.
5.0
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.
5.0
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.
5.0
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.
5.0
Great stay. Host was amazing and easy to communicate with. House was perfect! Close to all the sights and restaurants.
5.0
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.
5.0
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.
5.0
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!
5.0
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!
5.0
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.
5.0
Fantastic experience, clean and quiet. Close to old town and walking mall. Would come back without hesitation!
5.0
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.
5.0
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.
5.0
Great location. Quick walk or Uber drive to downtown Winchester. Perfect little getaway. Home is cute and very inviting.
5.0
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.
5.0
Super
Any complaints I had were very minor. Overall I could hardly ask for a more convenient and restful week.
5.0
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.
5.0
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!!
5.0
Family wedding
Was the perfect location for our event . Close to all and very nice quiet neighborhood
5.0
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!
5.0
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.
5.0
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.
5.0
This house was just what we needed for our stay in Winchester! We especially enjoyed its proximity to Old Town. Will stay here again!
5.0
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!
5.0
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.
5.0
Wonderful cottage
The cottage was exceptionally clean and very well equipped for what you will need. The location is within walking distance to old town Winchester, as well as close driving distance to many good wineries. We highly recommend this home!
5.0
Quaint and Cozy
Nice little getaway place near vineyards, breweries, a historic downtown, and just far enough away from it all. The big stores are close by in case you forgot anything on your trip. It was well kept & well stocked. We would definitely stay again!
5.0
City Charmer definitely charmed
My adult daughter and I stayed here during her spring break. The decor was delightful and so welcoming. The beds were extremely comfortable. We enjoyed many walks in the neighborhood. The location was very accessible. A few things I especially appreciated: plenty of toilet paper, lots of dishes/cooking items, and a wonderful front porch with rocking chairs! We would definitely return to this little gem.
5.0
This was the perfect place to stay while seeing the sights of Winchester Va!
5.0
Felt like home away from home!
This was the perfect place to stay while seeing the sights of Winchester Va!
5.0
A "home away from home"
We have stayed at "The Charmer" many times over the past few years because we have family in the area. The little house was perfect for us and has everything we needed. It is cozy, comfortable, well located and has both a wonderful wrap around front porch and a small patio with table and chairs. Crystal is a wonderful hostess, dedicated to making sure your stay is a great one! We definitely recommend "The Charmer"!
5.0
"The City Charmer" is the perfect place for your Winchester stay! It is centrally located and convenient to interstates and the downtown pedestrian mall.The house is clean, cozy and has everything you need whether you want to use it as a "home base'" to explore the area or just relax on the amazing porch. Crystal is a wonderful host and most responsive to any questions you might have. We have stayed here many times and never been disappointed!
5.0
You'll be "Charmed"
"The City Charmer" is the perfect place for your Winchester stay! It is centrally located and convenient to interstates and the downtown pedestrian mall.
The house is clean, cozy and has everything you need whether you want to use it as a "home base'" to explore the area or just relax on the amazing porch. Crystal is a wonderful host and most responsive to any questions you might have. We have stayed here many times and never been disappointed!
5.0
Winchester Adventure
Our "Cottage" was well appointed and comfortable and the owners were very responsive to all our inquiries and questions!! We had a great time exploring the Winchester area including the MUESEUM OF THE SHENNANDOAH VALLEY and will definitely return when it's warmer !!
5.0
City Charmer
This was exactly the getaway we needed! Easy walk to old town!
5.0
Great house
Crystal 's house is a great house to stay to explore the Winchester area.
5.0
Will be back
Very cozy house, walkable to downtown
5.0
Great little property
Really enjoyed the stay. Plenty of space, nice atmosphere. Really appreciated some of the little touches, like the kerig machine and grill, and the fully functional kitchen. Will definitely stay again when I'm in town.
5.0
Comfortable and perfect for our stay
Clean and very well equipped with all the essentials needed during our time.
Nice short walk to Olde Town Winchester.
FAQs
How much does this house cost compared to others in Winchester?
The average price for a rental in Winchester is $121 per night. This rental is $10 above the average.
Is parking included with this house?
Yes, parking is listed as an amenity at City Charmer near Historic OldTown Winchester. . For more information, we encourage you to contact the property about where to park.
Is there a pool at this house?
We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.
Is City Charmer near Historic OldTown Winchester. pet friendly?
Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"
What amenities are available at City Charmer near Historic OldTown Winchester. ?
We found 8 amenities for this rental. This includes air conditioner, kitchen or kitchenette, internet / wifi, parking, and laundry.
Explore similar vacation rentals in Winchester
Explore all rentals in Winchester
Sleep Inn & Suites
Hotel
in Winchester4star
1 king bed, 1 sofa bed
Pool · Kitchen or Kitchenette · Air conditioner
Experience the best of Winchester with this Hotel available for $106. This property is equipped with amenities including Air conditioner, Internet / Wifi and Laundry, and more.
$$$$
The George Washington Hotel, A Wyndham Grand Hotel
Hotel
in Winchester3star
2 full beds
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Looking for the perfect place to call home during your trip to Winchester? This Hotel offers a comfort and style with top-notch amenities, including Air conditioner, Internet / Wifi and Laundry, and more.
$$$$
Spark by Hilton Winchester
Vacation rental
in WinchesterPool · Kitchen or Kitchenette · Internet / Wifi
Experience vacation in Winchester with our Vacation rental, Spark by Hilton Winchester. Enjoy amenities such as Internet / Wifi, Laundry and Kitchen or Kitchenette, and more.
$$$$
Fairfield Inn & Suites Winchester
Hotel
in Winchester2star
Pool · Kitchen or Kitchenette · Air conditioner
Hotel in Winchester, for $133 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)
$$$$
Yellow Submarine trendy basement apt and courtyard
Apartment
in Winchester4 guests · 2 bedrooms · 1 bath
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Experience vacation in Winchester with our Apartment, Yellow Submarine trendy basement apt and courtyard. Enjoy amenities such as Air conditioner, Internet / Wifi and Balcony or Patio, and more.
$$$$
2018 Forest River R pod
Towable trailer
in Winchester4 guests
Pets allowed · Kitchen or Kitchenette · Air conditioner
This inviting Towable trailer in Winchester can fit your needs for many types of vacations, at $105 per night.
$$$$
'23 Jayco Jay Flight SLX Baja
Towable trailer
in Winchester5 guests
Pets allowed · Kitchen or Kitchenette · Air conditioner
Towable trailer in Winchester, for $125 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)
$$$$
Hilton Garden Inn Winchester
Vacation rental
in WinchesterPool · Kitchen or Kitchenette · Internet / Wifi
When traveling to Winchester, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $122 per night.
$$$$
Hampton Inn Winchester-University/Mall Area
Hotel
in Winchester2star
1 king bed
Pool · Kitchen or Kitchenette · Air conditioner
Looking for a memorable stay in Winchester? Our Hotel might just be what you're looking for. Enjoy amenities including Air conditioner, Internet / Wifi and Laundry, and more during your stay.
$$$$
Hampton Inn By Hilton Winchester-North
Vacation rental
in WinchesterGarden · Pool · Kitchen or Kitchenette
Looking to create some memories in Winchester? Look no further than our Vacation rental, Hampton Inn By Hilton Winchester-North. Enjoy top-rated amenities including Air conditioner, Internet / Wifi and Laundry, and more.
$$$$
Charming 3-bedroom townhome with AC and WiFi in lovely Winchester
House
in Winchester6 guests · 3 bedrooms · 1 bath
Pets allowed · Kitchen or Kitchenette · Air conditioner
This inviting House in Winchester can fit your needs for many types of vacations, at $126 per night.
$$$$
Hampton Inn By Hilton Winchester-University/Mall Area
Vacation rental
in WinchesterPool · Kitchen or Kitchenette · Air conditioner
Vacation rental in Winchester, for $111 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)
$$$$
Courtyard by Marriott Winchester Medical Center
Hotel
in Winchester3star
1 king bed, 1 sofa bed
Pool · Kitchen or Kitchenette · Air conditioner
Experience the best of Winchester with this Hotel available for $108. This property is equipped with amenities including Air conditioner, Internet / Wifi and Laundry, and more.
$$$$
Hampton Inn Winchester N/Conference Center, VA
Hotel
in Winchester2star
1 king bed
Garden · Pool · Kitchen or Kitchenette
Looking for a Hotel in Winchester, this Hotel for $121 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.
$$$$
Fairfield Inn & Suites by Marriott Winchester
Vacation rental
in WinchesterGarden · Pool · Kitchen or Kitchenette
Looking for a memorable stay in Winchester? Our Vacation rental might just be what you're looking for. Enjoy amenities including Air conditioner, Fireplace and Internet / Wifi, and more during your stay.
$$$$
Candlewood Suites Winchester
Hotel
in Shawnee2star
Kitchen or Kitchenette · Air conditioner · Parking
This Hotel in Winchester, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!
$$$$
Candlewood Suites Winchester
Vacation rental
in WinchesterKitchen or Kitchenette · Air conditioner · Internet / Wifi
Looking for a memorable stay in Winchester? Our Vacation rental might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more during your stay.
$$$$
Charming 1-bedroom apartment with AC, WiFi in pleasant Winchester pet-friendly
Apartment
in Winchester4 guests · 1 bedroom · 1 bath
Pets allowed · Air conditioner · Internet / Wifi
Indulge in a peaceful retreat at Charming 1-bedroom apartment with AC, WiFi in pleasant Winchester pet-friendly , our elegant Apartment in Winchester. Enjoy amenities including Air conditioner, Internet / Wifi and Laundry, and more.
$$$$
Courtyard by Marriott Winchester
Hotel
in Winchester3star
1 king bed, 1 sofa bed
Garden · Pool · Kitchen or Kitchenette
Experience the best of Winchester with this Hotel available for $122. This property is equipped with amenities including Air conditioner, Internet / Wifi and Laundry, and more.
$$$$
Courtyard by Marriott Winchester Medical Center
Vacation rental
in WinchesterPool · Air conditioner · Internet / Wifi
Business stays, family stays, couples stay, getaway vacation, and rental in Winchester at Courtyard by Marriott Winchester Medical Center for $126 for your next trip.
$$$$
La Quinta Inn & Suites by Wyndham Winchester
Vacation rental
in WinchesterPool · Kitchen or Kitchenette · Internet / Wifi
This attractive Vacation rental in Winchester, $120 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Winchester travel inspiration
Read our blogGuides
Top Things to Do in Oahu and Honolulu
Guides
Top Things to Do in Fort Lauderdale, Florida
Guides
Top Things to Do in Miami: From Beaches to Culture
Guides
The Best Things to Do in Orlando: Attractions, Food, and Family Fun
Guides
Things to Do in Galveston, Texas
Guides
Top Things to Do in Myrtle Beach
Guides
Ski Trip Packing List: What to Bring Skiing or Snowboarding
Trends
VacationRenter Holiday Travel Trends 2023
Keep exploring
- Lake Tahoe Cabins
- Ruidoso Cabins
- Blue Ridge Cabins
- Estes Park Cabins
- Lake George Cabins
- Eureka Springs Cabins
- Branson Cabins
- Lake of the Ozarks Cabins
- Lake Arrowhead Cabins
- Lake Texoma Cabins
- Canyon Lake Cabins
- Sevierville Cabins
- Flagstaff Cabins
- Colorado Springs Cabins
- Hot Springs Cabins
- Bass Lake Cabins
- Buffalo River Cabins
- Possum Kingdom Lake Cabins
- Chattanooga Cabins
- Nashville Cabins
- Wears Valley Cabins
- Cloudcroft Cabins
- Deep Creek Lake Cabins
- Mammoth Lakes Cabins
- Anna Maria Islands Rentals
- Outer Banks Vacation Rentals
- Rosemary Beach Rentals
- Holden Beach Rentals
- Hilton Head Vacation Rentals
- Topsail Beach Rentals
- Kiawah Island Rentals
- Panama City Beach Rentals
- Ocean Isle Beach Rentals
- Folly Beach Rentals
- Dauphin Island Rentals
- Rehoboth Beach Rentals
- Bethany Beach Rentals
- Cape Cod Rentals
- 30A Rentals
- Seaside Florida Rentals
- Edisto Beach Rentals
- Fort Myers Beach Rentals
- Miramar Beach Rentals
- Port Aransas Rentals
- Emerald Isle Rentals
- Orange Beach Rentals
- Surfside Beach Rentals
- Hampton Beach Rentals
- Assateague Island Rentals
- Jacksonville Beach Vacation Rentals
- North Shore Vacation Rentals
- Ogunquit Vacation Rentals
- North Redington Beach Rentals
- Lido Key Vacation Rentals
- Sea Colony Rentals
- Pass A Grille Vacation Rentals
- Blue Ridge Mountain Rentals
- Vail Lodging
- Jackson Hole Lodging
- Winter Park Lodging
- Telluride Lodging
- Big Sky Rentals
- Aspen Lodging
- Park City Rentals
- Steamboat Springs Lodging
- Breckenridge Rentals
- Lake Tahoe Rentals
- Copper Mountain Lodging
- Mammoth Mountain Lodging
- Beech Mountain Rentals
- Crested Butte Rentals
- Sun Valley Lodging
- Keystone Lodging
- Taos Lodging
- Sugar Mountain Cabins
- Beaver Creek Lodging
- Deep Creek Lake Rentals
- Smith Mountain Lake Rentals
- Ocean Lakes Rentals
- Lake Anna Rentals
- Torch Lake Rentals
- Lake Winnipesaukee Rentals
- Norris Lake Rentals
- Lake Gaston Rentals
- Canyon Lake Rentals
- Lake Oconee Rentals
- Lake Wallenpaupack Rentals
- Lake Martin Rentals
- Lake Havasu Rentals
- Lake of the Ozarks Rentals
- Lake Michigan Vacation Rentals
- Lake Chelan Rentals
- Finger Lakes Rentals
- Lake Keowee Vacation Rentals
- Lake Conroe Rentals
- Lake Erie Vacation Rentals
- Lake Austin Vacation Rentals
- Sebago Lake Rentals
- Lake Tillery Rentals
- Keuka Lake Rentals