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Sperryville, VA
Challenging To Investors
Local STR Agent
Local STR Agent

Bottom line: Short‑term rentals are allowed in Sperryville only with a Special Use Permit issued by Rappahannock County. Do not proceed without one.
Sperryville hosts earn a median $37,502/year with $299 ADR and 40% occupancy.
Top performers pull in $49,020+ per year.
See the full Sperryville market breakdownOperational planning specific to Sperryville:
Rappahannock County
State of Virginia (High‑Level Requirements)
Enforcement
Note: Rappahannock County has explicitly moved to require SUPs and has approved tourist homes with conditions in recent years, underscoring the need to secure county approval prior to listing.
Rappahannock County (general)
Planning & Zoning Department (for zoning confirmation, SUP procedures, submittals)
Treasurer’s Office (Transient Occupancy Tax registration/filings)
Rappahannock News (local media)
Note: Emails and extensions may change; verify current contacts on the county website before filing.
Compliance Notice: Virginia localities can change STR rules quickly. Confirm zoning district, current application checklists, hearing calendars, and tax procedures directly with the county before purchasing or filing.
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Sperryville is a small unincorporated village in Rappahannock County, Virginia, nestled in the foothills of the Blue Ridge Mountains in the northern part of the state. With a population of just a few hundred residents, the community has a quiet, rural character shaped by rolling farmland, country roads, and its proximity to some of Virginia's most scenic wilderness. Sperryville is best known as a gateway to Shenandoah National Park and Old Rag Mountain, and it sits at the heart of a region celebrated for its wineries, art galleries, and small-farm food scene. The village lies approximately 60 to 70 miles southwest of Washington, D.C., and roughly 20 miles northwest of Culpeper, making it a convenient rural escape from the mid-Atlantic's largest metropolitan area.
Just a few miles to the west of Sperryville, Shenandoah National Park stretches along the crest of the Blue Ridge, with the Thornton Gap entrance only a short drive from the village. The park's famous Skyline Drive winds for more than 100 miles through hardwood forests and over mountain gaps, offering overlooks, picnic areas, campgrounds, and trailheads that connect to hundreds of miles of hiking routes. From Sperryville, visitors can typically reach the Thornton Gap entrance in about 10 to 15 minutes, putting the broader park within easy reach for a long day of sightseeing or a week of backcountry exploration.
A short drive west of Sperryville, Old Rag Mountain is one of the most iconic hiking destinations in the mid-Atlantic. The roughly 9-mile loop to the rocky summit includes a famous rock scramble near the top and rewards hikers with panoramic views of the Piedmont and Shenandoah Valley. The trailhead parking area is generally about 15 to 20 minutes from Sperryville, and because of the mountain's popularity, hikers are encouraged to arrive early, especially on fall weekends when foliage season draws crowds from across the region.
Rappahannock County itself is one of Virginia's quieter but increasingly well-known wine and food destinations, with a cluster of small family-run vineyards and farm-to-table restaurants scattered along the country roads surrounding Sperryville. The county seat, the small town of Washington, Virginia, sits only about 5 miles to the north and adds a handful of historic inns, galleries, and shops to the mix. Together, these nearby stops give visitors a reason to slow down, sample local wines, and explore back roads that feel a world away from urban Northern Virginia.
Sperryville's appeal as a short-term rental base comes from the way it combines genuine small-town character with direct access to Shenandoah National Park, the Old Rag wilderness, and a broader rural landscape of vineyards, farms, and artist studios. Travelers who want a peaceful Blue Ridge retreat with hiking, wine tasting, and scenic drives all within a short drive will find Sperryville an unusually well-positioned home base.
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