Vacation Rentals By Owner In Winchester, VA

Nestled within the City of Winchester, Va., in the Shenandoah Valley, 30 Minutes from the Blue Ridge Mountains, sits a charming and quaint Tiny Home on 2+ Acres, known as the “Secret Gardens Tiny Home.” It has a loft with a queen size bed and laundry facilities within for your comfort. In addition, there is a private patio that looks out over one of our beautiful zen gardens. The patio is enclosed for your full privacy should you want it. All of the environments inside and out are over seen with no chemicals used. This being the case we ask that you not use chemical cleaners or scented products that may impact the space. brbr Secret Gardens Tiny House is accessed from a long driveway with private parking for guests right outside the gate leading directly to the patio and front door. brbrThe private residence of the owners of the estate is just across the driveway as they live on site. brbrLoads of outdoor activity nearby! brbrNumerous restaurants, pubs, shops, and Historic sights and sounds of the beautiful Shenandoah Valley are all within easy driving distance. History enthusiasts will love exploring Historic Downtown Winchester or the many nearby Civil War Battlefields.brbrGuests have access to the entirety of the tranquil and peaceful grounds and may readily enjoy our organic vegetable and herbs; winding through paths that showcase Gardens and Multiple Varieties of Stunning Ornamental Flowers and Shrubs.br brYou can experience a restful & peaceful time sitting by our fire pit with a warm mug of organic coffee or tea.brbrbrAutumn is particularly beautiful at the Tiny Home! Nature's paintbrush touches leaves from trees that throughout our landscape!brbrAll designed to make your stay here to be truly just like heaven!

Guest House

Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed

Winchester, Virginia, United States

Bed

Bath

Sleeps

$64.26

When staying at APM Inn and Suites you will have a choice of a comfy couch, and/or a spacious desk. You will have a bathtub/shower. We have in some rooms a coffee maker, microwave and fridge. We offer free Wi-Fi to all guest and for guest convince we have laundry facilities on site. APM Inn and Suites is located right off of Interstate 81 and route 7. If you feel the need to venture out you are close to hiking, fishing, sight seeing, fine dining and a casino.

Hotel

Clean, neat, peace and quiet

Winchester, Virginia, United States

Bed

Bath

Sleeps

$192.61

Come enjoy to this fabulous 3rd floor one room studio apt with kitchen and bath( with tub) & comfortable queen sized mattress. This apt is open and airy with lots of windows and desk and nice closet space. You are just a couple of blocks from downtown walking mall. Free parking and coin operated laundry on site. You will LOVE it !

Rosamond nice downtown studio apt

Winchester, Virginia, United States

Bed

Bath

Sleeps

$218.67

Welcome to Morocco Loft ~ this is a large loft on the third floor of a vintage tudor style building high up overlooking the downtown cityscape with lots of character and charm. You will love the trendy decor and unique layout just steps from the downtown walking mall, discovery museum and the many unique shops and restaurants of Winchester.

Morocco Loft 2BR overlooking city walking mall

Winchester, Virginia, United States

Bed

Bath

Sleeps

$112.01

Welcome!brNestled within the city of Winchester, Va. in the Shenandoah Valley, 30 minutes from the Blue Ridge Mountains and a 5 minute drive to the Old Town Walking Mall by car, sits this charming and quaint carriage/guesthouse on 2+ secluded acres known as 'The Secret Gardens Guest House'. brbrThe Carriage House dates from the 1920’s and features a bedroom with an antique double four-poster bed, full bathroom with old-fashioned pedestal tub with safety bar and shower, beautifully updated kitchen, a private cafe style screened-in porch overlooking a gorgeous view of Zen Gardens and much more!brbrThe charm and grace of this intimate cottage is lovely. The vibrant décor blends past and present with unique elegance. You can easily imagine a tasseled buggy pulling up as you enjoy the pleasure of modern conveniences. brbrThe year round natural beauty framing our adorable Carriage House is unparalleled in Winchester. More than two acres of exquisite Zen Gardens are just a few steps away. Guests love spending time on our screened in porch, taking in a view that brings the blooms of the season to your doorstep as you sip your morning Organic coffee or tea in fresh robes that we provide for every guest. All of the environments inside and out are over seen with no chemicals used. This being the case we ask that you not use chemical cleaners or scented products that may impact the space. brbr In truth, the photographs of the Gardens on this site, simply don’t do it justice. It is a one-of-a-kind experience.brbrOur Organic herbal and veggie garden – where guests are welcome to choose fresh herbs/veggies for their dining pleasure – offers another special treat. brbrWe have an outdoor fire pit area, ideal for star gazing that just can’t be appreciated in the downtown lights. Or you could take the time to sit by our fire pit with a warm mug of Organic coffee or Organic tea while listening to the soft sounds of the season, lifetime memories with that special someone are created.brbrWe also welcome business travelers wanting more than an efficiency apartment as well as lone adventurers. Every time of the year is special in this sanctuary from the busy world.brbrAs the Carriage House is a delicately crafted setting, guests must be at least 21 years old.brbrThe guest house offers the simplicy of living. While Wifi may be available, there is no TV on site. You are more than welcome to bring your own devices and stream what you like if you need more stimulation. brThe kitchen is fully equiped other than a microwave. Again, simplicity of living. brbrShort stays or long, you will be embraced by the quiet space and open gardens.

Guest House

Secret Gardens Carriage House

Winchester, Virginia, United States

Bed

Bath

Sleeps

$171.69

Renovated colonial style home. Enjoy a spacious home with large living room, dining room, kitchen, 3 bedrooms with 4 beds and 2.5 bathrooms. Perfect for a larger group or a longer stay. Just a few miles drive to Old Town Winchester which includes numerous restaurants, bars, shopping and some kind of event, like-- the Shenandoah Apple Blossom Festival! Our house is located about 65 miles West of Washington D.C. Near by to other scenic attractions as well -Skyline Drive, Luray Caverns, and Harper's Ferry! brbrThis house has been a long term rental for 12 years but it was our first home and the start of our family so it will always be special. We enjoy this experience so much with our other property that we decided to renovate it and do another vacation rental! brbrThe house is fully equipped with everything you need to cook with and all the linens you could need. Full size appliances--fridge, stove & dishwasher. Washer and dryer on the main level. Upstairs is a King bed in the master and three Full beds. A shower in the Master bedroom and shower/tub on the 2nd level as well. All bedrooms are upstairs. A pack and play portable crib and dining booster seat is available for babies. Living room has a 50 inch tv with large sectional sofa. Kuerig machine for coffee drinkers.brbrPlease only park in the driveway. No street or yard parking is permitted. Please remove shoes before walking on upstairs carpet. Smoking outside only. br

Private Vacation Home

Colonial Getaway near Old Town Historic Winchester

Winchester, Virginia, United States

Bed

Bath

6

Sleeps

$353.5

Your 2026 Apple Blossom begins at this 2-bedroom apartment, located directly next to Handley Library on the Parade Route! The cozy space is equipped with all the essentials like a hair dryer, heating, iron, and AC. Kickback, relax, and enjoy everything Winchester and our apartment has to offer during this special weekend! Thursday, April 29 - Sunday, May 3 booking only.

Available for 2026 Apple Blossom Only! 2 Bedroom on Parade Route!

Winchester, Virginia, United States

Bed

Bath

Sleeps

$230.46

This bright 3BR house (2 queens, 1 full, 1 twin) is ideal for families, travel nurses, business travelers or vacationers in the area. Enjoy a full kitchen, fast WiFi, Smart TV, washer/dryer, very large yard and driveway parking for 3-4 cars. Located just 15 mins from Winchester Medical Center and 8 mins to Old Town or Shenandoah University, 7 mins to Costco and 10 min to Walmart or Target. Close to I-81, wineries, and hiking trails. Clean and quiet.

Private Vacation Home

Charming 3-bedroom house with porch and yard in Winchester

Winchester, Virginia, United States

Bed

Bath

Sleeps

$172.26

Get ready to relax in this 1-bedroom apartment (walk-out cabin basement) at the top of a mountain with gorgeous views of the Shenandoah Valley! This lovely space features a cozy queen bed in the spacious bedroom and a nice sofa bed in the living room, to include an extra seating area, kitchenette, and dining space. Guests can enjoy outdoor amenities like a fire pit, gas fire table, propane grill, and more.

Stunning Mountain Top 1 Bedroom Apartment - Walk-out Basement

Winchester, Virginia, United States

Bed

Bath

Sleeps

$217.11

Welcome to our Winchester Retreat! brbrCome relax at our 3-bedroom home offering a perfect escape with breathtaking views of the Shenandoah Valley. Relax in the living area, featuring two big picture windows that frame the Shenandoah Mountains. Located just a short drive from Washington, DC, and about 30 min from the Shenandoah park entrance, our home is an ideal getaway for both relaxation and exploration.brbrWith breathtaking panoramic views, charming exterior and modern interior design. This three bedroom cottage located in the heart of the Shenandoah Mountains is the perfect retreat to spend time with family or simply get away and relax. Whether you are an outdoor enthusiast, nature admirer, or beer lover, you’ll enjoy three modernly furnished bedrooms and stunning sunrises.brbr- 20 min to Eagle Rock & Tuscarora Trail in the George Washington & Jefferson National Forestbr- 20 min to Star in the Valley Vinyard and many othersbr- 20 min to Vibrissa & Box Office Breweriesbr- 35 min to Shenandoah Park Entrance

Cabin

Dog Friendly Mountain Retreat with Stunning Views

Winchester, Virginia, United States

Bed

Bath

Sleeps

$136.01

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.brbrThis 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! brbrOur 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.br

Private Vacation Home

City Charmer near Historic OldTown Winchester.

Winchester, Virginia, United States

Bed

Bath

4

Sleeps

$230.34

Apartment in Winchester, pet friendly! We live on 5 acres nestled in our own little piece of heaven, located in Shenandoah Valley. We raise chickens and bees. This is a beautiful country getaway perfect for relaxing with a nice drive to old town Winchester.brbrThis peaceful apartment is very clean, clutter free and almost everything is fairly new. It is super cozy and comfy with a private entrance and a secure electronic lock. You can enjoy the deer passing through the property from time to time. We also take the time to follow CDC guidelines to ensure your safety and ours.brbrPlease feel free to walk any area of our property outside of the fenced in area. Keep a comfortable distance from the beehives especially if you have allergies.brWe do sell our raw honey and fresh eggs let us know if you're interested. Payable in cash.

Cozy Apartment located on our 5-acre property

Winchester, Virginia, United States

Bed

Bath

Sleeps

$203.75

You will love this new updated downtown apt ! Come stay @ the Dragonfly Inn full of light and whimsy …it’s just one block from the walking mall in downtown Winchester, Virginia. Short/Mid/Long Term stays are welcome. Park for free (2 spaces) and be close to everything downtown. Awesome fully furnished newly updated 1BR 1BA 2nd floor Apt. Washer Dryer in the unit. brALL utilities included /WiFi -600/ SMART TV in Living Rm and Bedroom Streaming ROKU /Nice tiled bathroom w/glass shower/Fully equipped eat in kitchen w/gas stove/spacious fridge! brThis apartment is within walking distance from almost everything downtown Winchester. brTwo designated free parking spots. brCome park your car —check in and relax and enjoy ! brDo not miss:br*the iconic John Handley Library - br*George Washington Hotel’s Half Note Lounge /live entertainment br*Bright Box - music venue on walking mall. br*Museum of the Shenandoah Valley- 15 min walkbr*Discovery Museum - 5 min walk br*Knead Bread / Bakery on Piccadilly St. br*Expresso Bar great coffee on walking mall br*Violinos Restaurant (Italian~ fancy ) br*Macados -huge deli sandwiches br*Romas -fab pizza and pasta br*Vibrasa - beer garden/ food on Kent St.br*El Centro ( Mexican ) Walking mall br*Chopsticks (Thai) on Kent St. br*Hopscotch Coffee on Millwood Ave ( vinyl and great coffee) br*Amherst Diner br*Bonnie Blue incredible food on Amherst st br*Handiworks Gallery -unique gifts brKimberly’s Gifts & Ice Cream on Braddock brbr— you’ll love these spots !brbrAlso if you are interested in moving to the area I have been a licensed Realtor in Virginia and West Virginia for over 20 years and I would be happy to help you find your perfect house ! br***Please be respectful of your neighbors .brQuiet hours are 10 pm to 7 ambrImportant Please NOTE: brWe do not raise our nightly prices over MAJOR HOLIDAYS and over our local APPLE BLOSSOM instead we charge a flat $100 holiday fee — please understand this is in addition to your initial payment and the request for it will be sent out the week before your arrival thru your VRBO account. brHOUSE RULES : brNo Smoking or Vaping brNo pets w/o prior approval brNo parties of any kind brNo drama please … brWe love being able to host our guests !!brPlease leave the apt as you found it when you depart.

Dragonfly Inn Modern 1 BR 1BA downtown apt. Great walking location !

Winchester, Virginia, United States

Bed

Bath

Sleeps

$121.42

Welcome to your cozy 1-bedroom apartment at Brookfield Corporate Apartments in Winchester, VA! This fully furnished unit offers a comfortable living space with all utilities, internet, and cable included. Located in a quiet, convenient area, you'll have easy access to local shops, restaurants, and historic downtown Winchester. Perfect for short or long stays. Enjoy a hassle-free experience with all the comforts of home.

Charming 1-bedroom apartment with AC, WiFi in pleasant Winchester pet-friendly

Winchester, Virginia, United States

Bed

Bath

Sleeps

$217.6

Cozy up and get away to our tranquil A framed Cabin we affectionately call The Overlook; where you'll enjoy a 360-degree view of the Shenandoah Mountains. Soak in our breathtaking views no matter the season and escape to the peace and quiet our cabin provides.brRelax by the fire at night, hike the beautiful trails nearby, enjoy our famous wineries/breweries, and rest easy in our fully stocked home equipped with everything you could need to get the vacation you deserve!brThe spacebrOur cabin is fully stocked home with everything you'll need for a comfortable stay. Enjoy our fast wifi speed and spacious living room and porch to enjoy the breathtaking scenery around you. Wake up in the morning to a stunning sunrise view of the mountains and feel free to bring lots of friends and family with you as our home has not only three bedrooms upstairs, but a fully finished basement with sleeping arrangements for up to 5 guests!brDon't worry about bringing your supplies from home because we provide it all! Our kitchen is equipped with all cooking supplies, dinnerware, spices, a coffee maker, and more! Enjoy a hot bath or shower fully stocked with soaps and bathroom necessities. Cozy up at night and sit by the fire pit with a glass of wine or lounge inside with reading materials or board games we provide!brGuest accessbrThe Overlook is nestled on the mountain overlooking the Shenandoah Valley with 100+ mile views. Guests have access to the whole home with no shared spaces. This is the only house on that section of the road. The top of the driveway can be a little tricky, but there is plenty of parking for guests. In winter conditions you may need AWD or 4WD. When you book you will receive a personal door code that you can enter on your arrival.brOther things to notebrOur stay allows you to be removed from the hustle and bustle, but be close to enjoying the local wineries, and breweries. You are 20min from historic downtown Winchester VA. Please make sure you keep your trash picked up outside and the trash can locked as we have been known to be visited by bears on several occasions. Please also do not use the fire pits if it is windy as you could start a forest fire.

Cabin

The Overlook

Winchester, Virginia, United States

4

Bed

Bath

11

Sleeps

$185.83

Separate back entrance. Spacious fully finished walk out basement with fully furnished. It has two bed room . 1st bedroom has 1 queen bed and 2nd bedroom has two full bed . Air mattress is also available for extra person . Full kitchen with dining area. Big Living room has big screen and Projector.

Very charming & spacious 2 bedrm

Winchester, Virginia, United States

Bed

Bath

Exceptional(2)

$389.76

If you are coming to Winchester and you want to stay in an elegant renovated loft just steps from the iconic John Handley library and the downtown walking mall… then this is the spot. Hardwood floors, floor to ceiling windows all the charm that a building built in the 1900’s exudes. brGuests will enjoy the fully stocked kitchen, comfortable king size bed, as well as a queen bed room with desk /a sleeping porch with two twins /and pull out sofa bed in the loft for extra guests. You will love it !

Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown

Winchester, Virginia, United States

Bed

Bath

Exceptional(7)

$145.03

Nestled in the picturesque city of Winchester, the Queen of Winchester offers a tranquil escape in a prime location that perfectly blends convenience and comfort. This beautifully renovated three-bedroom apartment is situated on the upper level with a terrace deck, promising privacy and views of the surrounding area. Whether you're visiting for a relaxing retreat or a business trip, this property is designed to ensure a memorable and luxurious stay.brUpon entering the Queen of Winchester, you are greeted by a modern and stylish interior. The apartment features three spacious bedrooms, each thoughtfully designed with contemporary decor and cozy bedding to provide the perfect setting for a restful night's sleep. Large windows allow natural light to flood the rooms, enhancing the airy and welcoming atmosphere.brThe living area is the heart of the apartment, where guests can unwind and relax. It's equipped with comfortable seating, a state-of-the-art entertainment system, and tasteful art that adds a touch of elegance. The space opens up to an upper-level terrace deck, an idyllic spot for morning coffees or evening drinks while taking in the serene views of Winchester's landscape.brThe kitchen in the Queen of Winchester is a chef's dream. It is fully equipped with modern appliances, including a refrigerator, stove, microwave, and dishwasher. Ample counter space and a variety of cooking utensils make it easy to prepare meals, from quick breakfasts to elaborate dinners. Adjacent to the kitchen is a charming dining area that seats six, ideal for enjoying home-cooked meals or hosting dinner parties.brOne of the apartment's highlights is its location. Conveniently located off Interstate 81 and close to downtown Old Town Winchester, guests have easy access to a range of attractions and amenities. Explore the historic streets of Old Town, where you can visit unique shops, local eateries, and cultural landmarks. Winchester Hospital is also nearby, making the apartment a perfect choice for medical professionals or families visiting patients.brSafety is a priority at the Queen of Winchester. The apartment is a separate unit above the Juliana MedSpa, ensuring privacy and security. The area is well-lit, and ample parking is available, making it easy for guests to come and go as they please. Additionally, being next to FoodMaxx, an international grocery store, means that everything from exotic spices to daily necessities is just a stone's throw away.brFor those who appreciate the convenience of location without compromising on tranquility, the Queen of Winchester is an ideal choice. Its proximity to major highways and downtown, coupled with the privacy of an upper-level apartment, offers the best of both worlds. Whether it's exploring the historical charm of Winchester, conducting business, or seeking a peaceful retreat, this property caters to all needs.brMoreover, staying above a MedSpa has its perks. Guests can book appointments for relaxing treatments just downstairs, adding an element of luxury and convenience to the stay. From soothing facials to therapeutic massages, the spa offers a range of services to rejuvenate both body and mind.brIn summary, the Queen of Winchester is more than just a place to stay; it's a destination that offers a unique and enriching experience. From its chic, comfortable interiors and stunning terrace views to its unbeatable location and safety features, every aspect of the apartment is designed to provide an exceptional stay. Discover the charm of Winchester and indulge in the luxury and convenience of this exquisite rental property. Whether for a short visit or an extended stay, the Queen of Winchester welcomes you to enjoy all that it and the city have to offer.

The Queen of Winchester Three Bedroom with Upper Level Deck

Winchester, Virginia, United States

Bed

Bath

5

Sleeps

$161.77

Condo

Modern Mid-Century Townhome w/Deck near festivals

Winchester, Virginia, United States