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The highest-performing listings in Monterey.
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Challenging to Investors
Monterey allows some STRs but imposes strict 31‑day minimums, caps (e.g., 4% in sensitive coastal areas), a complete ban on commercial STRs in the Big Sur coastal plan, and heavy discretionary permitting (CDP/design review) with 7‑year terms and renewals, all backed by severe fines for violations (400–800% of advertised rate) and an advertising ban for unpermitted rentals.
Local STR Agent
STR specialist · Monterey, VA
Monterey, Virginia is a small town serving as the county seat of Highland County, the least populous county in the Commonwealth of Virginia. With a population of only a couple hundred residents, Monterey exudes the quiet, unhurried character of an Appalachian mountain community, surrounded by rolling pastures, forested ridges, and wide open skies. The town sits in the heart of the Allegheny Highlands and is often considered a gateway to an outdoor region sometimes called "Virginia's Switzerland" for its high-elevation meadows, working dairy and cattle farms, and reliable winter snowfall. Monterey is roughly a two-hour drive northwest of Staunton, the nearest mid-sized city, and about four hours from Washington, D.C.
One of the most famous events in the region is the annual Highland County Maple Festival, held in Monterey and surrounding communities each March. The festival celebrates the area's long tradition of maple syrup production, with sugar camps open for tours, pancake breakfasts, and craft vendors drawing visitors from across the mid-Atlantic. Because Highland County is one of the top maple-syrup-producing counties in Virginia, the festival has become a marquee draw for travelers interested in rural food traditions and small-town Americana, and it also marks the unofficial start of the spring tourism season in the mountains.
Just beyond Monterey, the vast George Washington and Jefferson National Forests spread across the Allegheny Mountains, offering hiking, fishing, camping, and backcountry drives. Forest roads and trailheads along routes such as State Route 84 and the winding back roads of Highland County are favorites for cyclists, motorcyclists, and leaf-peepers in autumn, when the hardwood slopes turn vivid shades of red, orange, and gold. A particularly well-known scenic corridor loops through the surrounding ridges and is regularly cited as one of the more memorable drives in western Virginia.
A short drive to the south, Bath County offers the Warm Springs and Hot Springs communities, where natural thermal springs and historic inns have welcomed travelers for generations. The same mountain landscape continues across the county line, with national forest land, trout streams, and quiet country roads that complement the slower pace of Highland County.
Monterey's combination of small-town charm, dramatic mountain scenery, and access to both cultural events like the Maple Festival and the outdoor expanse of the national forest makes it a quietly compelling base for a short-term rental. Visitors seeking cool summer nights, vibrant fall foliage, snowy winter weekends, and a genuine escape from crowded tourist corridors find here a place where Appalachian rhythms still set the pace, and where a mountain cabin or cottage can serve as a year-round retreat.