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View PropertiesAs of Apr, 27 2026
Rabbu ROI Score
Middleburg presents a competitive opportunity: investor interest and demand are strong, but higher prices or tighter competition may require more selective deal sourcing.
Middleburg, VA is a boutique short-term rental market nestled in Virginia's horse and wine country, where just 26 active Airbnb listings command an impressive average daily rate of $465—well above the $339 state average. While the market's high home values ($2,263,199 average) and 24% occupancy rate create a challenging revenue-to-price dynamic, the 77% year-over-year growth in listings signals rising investor interest and strengthening demand. With average annual revenue of $53,488 per listing and pronounced summer seasonality, Middleburg rewards operators who can capture premium weekend and seasonal bookings from the affluent DC-area traveler base.
According to Rabbu market data, the Middleburg short-term rental market shows:
| Metric | Context | Value |
|---|---|---|
| Active Airbnb Listings | As of Apr, 27 2026 | 26 |
| Average Daily Rate (ADR) | vs. $339 state avg. | $465 |
| Average Occupancy Rate | vs. 34% state avg. | 24% |
| RevPAN | ADR * Occupancy Rate | $110 |
| Average Monthly Revenue | Historical 12-month average | $4,457 |
| Average Annual Revenue | Historical 12-month average | $53,488 |
Data sources: Rabbu proprietary analytics as of Apr, 27 2026 and Zillow Home Value Index (ZHVI) as of Apr, 27 2026.
Middleburg attracts STR investors because its luxury-rural positioning near Washington, DC delivers premium nightly rates in a market with very limited competition.
Key investment factors
"Middleburg presents a competitive but selective opportunity for STR investors comfortable with luxury-tier entry prices and lower occupancy rates. The market's strength lies in its pricing power—$465 ADR and $110 RevPAN reflect genuine demand from travelers seeking upscale countryside escapes—rather than volume-driven returns. Seasonality is pronounced, with August peaking at $6,682 in average monthly revenue and the winter trough in February dipping to $2,371, creating a nearly 3:1 spread that investors must plan around. For operators who secure the right property at a reasonable basis and execute a premium guest experience, Middleburg can deliver meaningful supplemental income, but the below-average revenue-to-price ratio means deal sourcing discipline is essential."
— Rabbu Market Analysis Team
Middleburg exhibits strong seasonality, with August topping out at $6,682 in average monthly revenue and February bottoming at $2,371—a spread of nearly $4,300. Investors should expect roughly 60% of annual revenue to come from the May–October window, making pricing optimization during peak months critical to overall returns.
| Month | Trend | Revenue |
|---|---|---|
| January |
|
$2,411 |
| February |
|
$2,371 |
| March |
|
$3,232 |
| April |
|
$3,909 |
| May |
|
$5,100 |
| June |
|
$5,872 |
| July |
|
$5,804 |
| August |
|
$6,682 |
| September |
|
$4,833 |
| October |
|
$5,068 |
| November |
|
$3,997 |
| December |
|
$4,201 |
The 26 active listings are concentrated in 1-bedroom properties (9 listings), followed by 2-bedrooms (7) and 3-bedrooms (5), with the remaining units in other configurations. The small total supply and relatively even distribution across sizes suggest that there isn't a single dominant property type, and larger homes (3+ bedrooms) remain underrepresented—potentially an opportunity for investors targeting group and family travelers.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
9 |
| 2 bedrooms |
|
7 |
| 3 bedrooms |
|
5 |
ADR scales from $267 for 1-bedroom listings up to $426 for 3-bedrooms, with the biggest jump occurring between 1- and 2-bedroom units ($132 premium). The relatively modest $27 gap between 2- and 3-bedroom ADRs suggests that the added bedroom at the larger end may not justify significantly higher nightly pricing, though it does contribute to higher total revenue.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
$267 |
| 2 bedrooms |
|
$399 |
| 3 bedrooms |
|
$426 |
Revenue per available night increases steadily from $60 for 1-bedroom listings to $101 for 3-bedrooms, indicating that larger properties generate meaningfully more revenue on a per-night basis even after accounting for occupancy. Three-bedroom units deliver nearly 70% more RevPAN than 1-bedrooms, making them the strongest performers on this efficiency metric.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
$60 |
| 2 bedrooms |
|
$87 |
| 3 bedrooms |
|
$101 |
Occupancy rates are remarkably flat across property sizes, ranging from 22% for 2-bedroom listings to 24% for 3-bedrooms. This consistency suggests that demand in Middleburg is more event- and season-driven than size-dependent, and that cash-flow stability hinges more on capturing high ADR during booked nights than on filling the calendar.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
23% |
| 2 bedrooms |
|
22% |
| 3 bedrooms |
|
24% |
Three-bedroom properties lead monthly revenue at $4,734, followed closely by 2-bedrooms at $4,454, while 1-bedroom units trail at $3,304. The $1,430 monthly gap between the smallest and largest units adds up to over $17,000 annually, underscoring the revenue advantage of larger configurations in this market.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
$3,304 |
| 2 bedrooms |
|
$4,454 |
| 3 bedrooms |
|
$4,734 |
Annual revenue ranges from $39,651 for 1-bedroom listings to $56,808 for 3-bedroom properties—a 43% premium for adding two bedrooms. Given Middleburg's high average home values, investors should weigh whether the incremental $17,000 in annual revenue from a larger property justifies the likely higher acquisition cost.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
$39,651 |
| 2 bedrooms |
|
$53,455 |
| 3 bedrooms |
|
$56,808 |
Parking is universal at 100% of listings—essential for a rural destination—while kitchens (89%), backyards (81%), and in-unit laundry (81%) round out the top tier. The prevalence of outdoor amenities like patios (65%), outdoor furniture (62%), and BBQ grills (42%) signals that guests expect a countryside retreat experience, and notably 19% of listings already offer EV chargers, reflecting the affluent DC-area guest profile.
| Amenity | Trend | Value |
|---|---|---|
| Parking |
|
100% |
| Kitchen |
|
89% |
| Backyard |
|
81% |
| Dryer |
|
81% |
| Washer |
|
81% |
| Self Check-in |
|
77% |
| Patio or Balcony |
|
65% |
| Outdoor Furniture |
|
62% |
| Workspace |
|
62% |
| Pets |
|
46% |
| BBQ Grill |
|
42% |
| EV Charger |
|
19% |
| Pool |
|
4% |
| Waterfront |
|
4% |
Rabbu's ROI Score is a proprietary metric that evaluates short-term rental investment potential based on multiple factors.
| Factor | Middleburg Performance | Weight |
|---|---|---|
| Revenue-to-Price Ratio | Below average | 40% |
| Occupancy Stability | Average | 30% |
| Market Growth Trend | Above average | 15% |
| Supply/Demand Balance | Average | 15% |
Middleburg's ROI score of 44 out of 100 places it in the "Competitive Opportunity" band, meaning the market offers genuine appeal but demands selective deal sourcing. The below-average revenue-to-price ratio—driven by home values averaging over $2.2 million against $53,488 in annual revenue—is the primary drag, while average occupancy stability and above-average market growth partially offset that challenge. Investors should pair this data with thorough local regulatory research and focus on properties where acquisition cost allows the market's premium ADR and growing demand to translate into acceptable returns.
Understanding local STR regulations is essential before investing in Middleburg. Here's the current regulatory landscape:
Operators looking to run a short-term rental in Middleburg, Virginia should verify whether a local business license, zoning approval, or STR-specific permit is required by the Town of Middleburg or Loudoun County. Virginia does not impose a statewide STR permit, so requirements vary—investors should confirm current rules with local planning and zoning offices before listing.
Common restrictions in Virginia's small-town and rural STR markets can include occupancy caps tied to septic or well capacity, minimum stay requirements, noise ordinances, and off-street parking mandates. HOA covenants and deed restrictions in certain Middleburg-area developments may further limit or prohibit short-term rentals, so reviewing property-level restrictions is essential before purchasing.
Virginia requires short-term rental operators to collect and remit the state's transient occupancy tax, and Loudoun County may levy an additional local lodging tax. Many booking platforms handle tax collection automatically, but hosts should confirm compliance with both state and local tax authorities to avoid penalties.
Regulations subject to change. Always verify with local authorities before purchasing. A Rabbu partner agent specializing in Middleburg can provide current regulatory guidance.
Financing an Airbnb investment in Middleburg requires lenders who understand STR income. Rabbu partner lenders offer:
"Over the next 12–18 months, Middleburg's short-term rental market is likely to see continued supply growth as investors respond to the area's above-average market growth trend, though the pace may moderate from the 77% surge observed this past year. ADR could hold steady or inch up 1–3% given the luxury positioning and limited inventory, while occupancy may settle in the 22–26% range—typical for a high-rate, low-density leisure destination. Summer months from June through August should remain the strongest booking window, with shoulder-season events like fall wine and equestrian weekends continuing to support October revenue near $5,000. Investors should plan for softer January and February months where revenue dips below $2,500 and budget accordingly."
— Rabbu Market Analysis Team
Rabbu provides Airbnb and short-term rental market data and statistics across the United States. Our mission is to empower investors with accurate insights and easy-to-use tools, so they can confidently identify and act on the best opportunities in the Airbnb market.
Rabbu proprietary analytics as of Apr, 27 2026 and Zillow Home Value Index (ZHVI) as of Apr, 27 2026. Revenue projections are estimates based on comparable properties and do not guarantee future performance. Data reflects trailing 12-month averages as of April 2026 and may not capture very recent market shifts. Local regulations, HOA restrictions, and tax obligations vary and should be independently verified before investing.
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