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View PropertiesAs of Apr, 27 2026
Rabbu ROI Score
Middletown presents a competitive opportunity: investor interest and demand are strong, but higher prices or tighter competition may require more selective deal sourcing.
Middletown, NY is a compact short-term rental market with just 23 active Airbnb listings and an average annual revenue of $20,236 per property. The market's ADR of $310 sits below the $381 state average, and occupancy clocks in at 28% — well under the 40% state benchmark — signaling that hosts here need to be strategic about pricing and guest acquisition. Still, a 109% year-over-year growth in active listings suggests rising investor interest, and a favorable supply/demand balance indicates demand hasn't been fully tapped.
According to Rabbu market data, the Middletown short-term rental market shows:
| Metric | Context | Value |
|---|---|---|
| Active Airbnb Listings | As of Apr, 27 2026 | 23 |
| Average Daily Rate (ADR) | vs. $381 state avg. | $310 |
| Average Occupancy Rate | vs. 40% state avg. | 28% |
| RevPAN | ADR * Occupancy Rate | $87 |
| Average Monthly Revenue | Historical 12-month average | $1,686 |
| Average Annual Revenue | Historical 12-month average | $20,236 |
Data sources: Rabbu proprietary analytics as of Apr, 27 2026 and Zillow Home Value Index (ZHVI) as of Apr, 27 2026.
Investors look at Middletown for its favorable supply/demand dynamics and proximity to the broader New York metro area, though selectivity in deal sourcing is essential given compressed margins.
Key investment factors
"Middletown presents a competitive but narrow opportunity for STR investors. With only 23 active listings — virtually all studios — and occupancy sitting at 28%, the market is early-stage and best suited for operators who can capitalize on strong summer and fall demand while managing leaner winter months. August leads the revenue calendar at $2,872, while January bottoms out at just $890, creating a significant seasonal swing that investors need to plan around. The ROI score of 37 out of 100 reflects average revenue-to-price dynamics and below-average occupancy stability, meaning careful deal selection and operational efficiency will be critical to generating solid returns."
— Rabbu Market Analysis Team
Middletown's revenue curve is heavily seasonal, peaking in August at $2,872 and bottoming out in January at just $890 — a spread of nearly $2,000. Investors should expect roughly 60–70% of annual revenue to come from the May through October window, making cash flow management during winter months a key operational consideration.
| Month | Trend | Revenue |
|---|---|---|
| January |
|
$890 |
| February |
|
$1,011 |
| March |
|
$984 |
| April |
|
$1,154 |
| May |
|
$1,746 |
| June |
|
$1,902 |
| July |
|
$2,555 |
| August |
|
$2,872 |
| September |
|
$2,065 |
| October |
|
$2,137 |
| November |
|
$1,598 |
| December |
|
$1,316 |
The entire active supply in Middletown consists of studio-type listings, with all 11 reported properties falling into this category. This extremely concentrated supply mix could represent an opportunity for investors willing to introduce larger property formats — such as 1- or 2-bedroom units — into an underserved market.
| Size | Trend | Value |
|---|---|---|
| Studio |
|
11 |
Studios in Middletown command an ADR of $85, which is the only property size currently represented in the market. Without larger units for comparison, the ADR picture is limited, but the gap between the market-wide $310 ADR and the studio-specific $85 suggests significant variation in nightly rates across individual listings.
| Size | Trend | Value |
|---|---|---|
| Studio |
|
$85 |
Studios deliver a RevPAN of just $25 in Middletown, reflecting the combination of a modest $85 ADR and 30% occupancy. This relatively low revenue per available night underscores the importance of maximizing both rate and occupancy to make studio investments pencil out.
| Size | Trend | Value |
|---|---|---|
| Studio |
|
$25 |
Studio listings in Middletown average 30% occupancy, which is slightly above the market-wide 28% but still well below the state average of 40%. Investors targeting this property size should anticipate significant vacancy and plan pricing and marketing strategies accordingly.
| Size | Trend | Value |
|---|---|---|
| Studio |
|
30% |
Studios generate an average of $912 per month in Middletown, which falls meaningfully below the overall market average of $1,686. This gap suggests that other non-studio or unique listings in the market are pulling in substantially higher revenues, and property differentiation could be a path to outperformance.
| Size | Trend | Value |
|---|---|---|
| Studio |
|
$912 |
At $10,946 annually, studio units in Middletown earn roughly half of the market's overall $20,236 average. Investors considering studios should weigh this modest income potential against acquisition and operating costs carefully, as the return profile is constrained at current occupancy and rate levels.
| Size | Trend | Value |
|---|---|---|
| Studio |
|
$10,946 |
Parking (100%), kitchen (96%), and self check-in (96%) are essentially table stakes for Middletown listings, while workspace (74%) and backyard access (48%) round out the top five. The high prevalence of practical amenities signals a guest base that values convenience and self-sufficiency, and listings without these basics may struggle to compete.
| Amenity | Trend | Value |
|---|---|---|
| Parking |
|
100% |
| Kitchen |
|
96% |
| Self Check-in |
|
96% |
| Workspace |
|
74% |
| Backyard |
|
48% |
| Outdoor Furniture |
|
44% |
| Dryer |
|
39% |
| Patio or Balcony |
|
39% |
| Washer |
|
35% |
| BBQ Grill |
|
30% |
| Pets |
|
30% |
| Pool |
|
17% |
| Sauna |
|
4% |
Rabbu's ROI Score is a proprietary metric that evaluates short-term rental investment potential based on multiple factors.
| Factor | Middletown Performance | Weight |
|---|---|---|
| Revenue-to-Price Ratio | Average | 40% |
| Occupancy Stability | Below average | 30% |
| Market Growth Trend | Average | 15% |
| Supply/Demand Balance | Above average | 15% |
Middletown's ROI score of 37 out of 100 places it in the competitive opportunity band, where investor interest is present but margins require careful deal selection. The revenue-to-price ratio is average and occupancy stability sits below average, which together limit the upside for passive or under-managed investments — though a favorable supply/demand balance offers a potential edge for operators who can differentiate. Pairing this data with thorough local regulatory research and a clear operational plan will be essential to unlocking value in this market.
Understanding local STR regulations is essential before investing in Middletown. Here's the current regulatory landscape:
Short-term rental operators in Middletown, NY may need to obtain permits or register with local authorities before listing a property. Investors should verify current requirements directly with the City of Middletown and check for any New York State-level STR regulations that may apply.
Common STR restrictions in similar New York markets include occupancy limits, minimum stay requirements, noise ordinances, parking regulations, and HOA rules that may restrict or prohibit short-term rentals. Some jurisdictions also impose caps on the number of permits issued, so early research into local zoning and building codes is advisable.
Short-term rental hosts in New York are typically subject to state and local occupancy taxes, sales tax, and potentially tourism-related levies. Platforms like Airbnb often collect and remit certain taxes on behalf of hosts, but operators should confirm their full tax obligations with a local tax professional.
Regulations subject to change. Always verify with local authorities before purchasing. A Rabbu partner agent specializing in Middletown can provide current regulatory guidance.
Financing an Airbnb investment in Middletown requires lenders who understand STR income. Rabbu partner lenders offer:
"Over the next 12–18 months, Middletown's STR market is likely to remain seasonal, with the strongest performance concentrated between May and October when monthly revenues can exceed $2,000. ADR growth may stay modest at 1–3% given current occupancy levels, so investors should focus on maximizing summer and fall bookings rather than expecting dramatic year-round gains. The rapid growth in listing counts could put additional pressure on occupancy unless demand keeps pace — something to watch closely heading into the next peak season."
— 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. Local regulations, permit requirements, and tax obligations may change; always verify current rules with municipal and state authorities before investing. Individual property results will vary based on location, condition, pricing strategy, and management quality.
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