Performance indicators for the Woodstock short-term rental market based on reliable data.
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The highest-performing listings in Woodstock.
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Generally Investor friendly
STRs are explicitly allowed in Shenandoah County (covering areas outside Woodstock town), with a clear by-right permitting pathway for properties with 4 or fewer bedrooms requiring a simple online application and a moderate $225 annual fee. However, larger properties or non-dwelling structures require a more complex Special Use Permit process with public hearings, and mandatory inspections add a moderate burden. The lack of overall caps and supportive tone from local authorities help mitigate investor risk, but the uncertainty for properties within Woodstock town limits reduces friendliness.
Local STR Agent
STR specialist · Woodstock, VA
Woodstock is a town and the county seat of Shenandoah County, Virginia, United States. It has a population of 5,212 according to the 2017 census. Woodstock comprises 3.2 square miles of incorporated area of the town, and is located along the "Seven Bends" of the North Fork of the Shenandoah River. While some tourism references list Woodstock as the fourth oldest town in Virginia, the area was sparsely settled and perhaps platted in 1752 or shortly thereafter, but the town was actually established by charter in 1761. While there are a number of Virginia towns closer to the eastern seaboard that claim earlier founding dates, Woodstock was one of the first towns west of the Blue Ridge Mountains. The Massanutten Military Academy is located in Woodstock, as is it the former location of the national headquarters of Sigma Sigma Sigma sorority. Woodstock is also home to the River Bandits of the Valley Baseball League, the Shenandoah County Public School's Central campus, and the Shenandoah County Fairgrounds.