HouseStay has supported families seeking flexible, temporary housing solutions. For job relocations, snowbirds, and military reassignments, Winchester has been a reliable destination for those needing a comfortable place to land.
In recent months, we’ve listed 3 fully furnished rentals, including 2 apartments and 1 house. These properties were equipped with amenities like No Smoking Allowed, Indoor Fireplace, and Deck—perfect for creating a space that truly felt like home. Many rentals also included convenient utilities such as Trash Pick Up, WiFi, and Cable TV.
The average monthly rent for a 1 bedroom / 1 bath Apartment in Winchester has hovered around $1,890 but have ranged between $1,523 and $2,573, giving future renters a helpful benchmark as they plan ahead. If you like Winchester, consider checking out nearby properties in Sterling, Herndon, Boston, and Reston, where similar family friendly monthly housing options may be available. Our listings are always being updated, so be sure to check back soon for new opportunities in Winchester!
HouseStay has offered a wide selection of Winchester, VA properties that met the evolving needs of digital nomads, remote workers, consultants, and other location-flexible professionals. These past rentals were in popular Winchester neighborhoods, and included 2 apartments.
Each property was thoughtfully equipped with amenities that support a productive remote lifestyle—like No Smoking Allowed, Full Kitchen, and Smoke Detector—creating an environment that balances work and relaxation. Utilities such as Trash Pick Up, WiFi, and Cable TV were commonly included to make extended stays seamless and stress-free.
The average availability of 3 fully furnished properties in the past reflects Winchester’s popularity among traveling professionals seeking temporary housing. Rental pricing for a 1 bedroom / 1 bath Apartment has averaged around $1,549 per month, with prices ranging from $1,523 to $1,575, depending on the property, location, and included features. HouseStay’s transparent pricing has catered to a wide range of budgets, offering flexible rental terms and detailed cost breakdowns to support the needs of digital nomads on the move.
You can explore cities nearby Winchester, like Sterling, Herndon, Boston, and Reston where similar monthly furnished rentals may be available. Check back soon—our listings are updated regularly, and Winchester continues to be a go-to city for remote work and temporary stays.
HouseStay has featured a variety of homes that offered the perfect blend of comfort, style, and relaxation. From houses, these properties were thoughtfully curated to feel like a true vacation retreat.
Vacationers have enjoyed 3 unique properties located in the Winchester neighborhoods, close to popular attractions and entertainment options. Each home was equipped with amenities designed to elevate the leisure experience—like No Smoking Allowed, Indoor Fireplace, and Deck for added comfort.
Utility packages often included essentials like Trash Pick Up, WiFi, and Heat, ensuring a smooth and enjoyable extended stay for travelers. With average monthly pricing for a 3 bedroom / 1 bath rental around $2,573, guests were able to plan memorable getaways that fit a variety of group sizes and budgets.
Nearby cities like Sterling, Herndon, Boston, and Reston may offer similar monthly vacation housing options. Our inventory updates regularly, so check back soon for a stylish and stress-free extended stay in Winchester.
HouseStay Guarantee
We perform in-depth background checks on Host and Tenants to create a community everyone can trust.
Roommate Free
HouseStay only offers entire accommodations. We don’t offer spare rooms or shared spaces.
Fully Furnished
All accommodations listed on HouseStay are fully furnished and include all utilities in the monthly rate.
Month-to-Month Flexibility
Not sure how long you’ll be staying? All listings are available for a minimum of 30 nights with no maximum.
Winchester, Virginia is a hidden gem in the Shenandoah Valley that offers a variety of monthly short-term rentals perfect for families looking to relocate to a charming, historic town. The neighborhoods of Old Town Winchester and Historic District offer unique, fully furnished rental options with easy access to local schools such as Shenandoah University and John Handley High School. Families can enjoy visiting the Museum of the Shenandoah Valley, taking a stroll through Jim Barnett Park, or shopping at the Apple Blossom Mall during their stay. With Winchester’s close proximity to cities like Washington D.C., Baltimore, and Richmond, families can easily explore the surrounding area and take weekend trips to nearby beaches or parks.
Digital nomads looking for month-to-month fully furnished rentals will appreciate Winchester’s affordable cost of living, reliable high-speed internet, and coworking spaces such as EESCO Workspaces and The Alton. Winchester offers a peaceful and picturesque backdrop for remote work, with outdoor activities like hiking in the Shenandoah National Park or kayaking on the Shenandoah River just a short drive away. Additionally, Winchester Medical Center provides excellent healthcare services for digital nomads in need of medical care during their stay.
Vacationers seeking a relaxing getaway will love staying in one of Winchester’s extended stay furnished rentals, where they can experience the city’s rich history at landmarks like the George Washington’s Office Museum and Belle Grove Plantation. Outdoor enthusiasts can explore the nearby Sky Meadows State Park or go wine tasting along the Shenandoah Valley Wine Trail. Winchester’s proximity to Dulles International Airport makes it a convenient destination for travelers looking to escape the hustle and bustle of the city for a peaceful retreat.
Business travelers and interns will find Winchester to be a convenient and comfortable city to book an extended stay furnished rental. With close proximity to major corporations like Trex, GEICO, and Mercury Paper, Winchester offers a prime location for short-term housing. The city’s hospitals, including Winchester Medical Center and Valley Health, provide top-notch medical care for business travelers in need of healthcare services. Additionally, Winchester’s vibrant downtown area offers a variety of restaurants, shops, and entertainment venues for professionals to unwind after a long day of work.