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View PropertiesAs of Apr, 27 2026
Rabbu ROI Score
Cutchogue appears higher risk based on current data and may require deeper, property-specific diligence to find compelling opportunities.
Cutchogue is a hyper-seasonal North Fork hamlet on Long Island where short-term rental revenue is heavily concentrated in the summer months. With an average daily rate of $603—well above the $381 New York state average—and average annual revenue of $74,751, the market commands premium nightly rates but contends with just 15% average occupancy, far below the 40% state benchmark. The combination of high property values (averaging roughly $1.9M) and limited year-round demand means investors need to scrutinize deal-level economics carefully before committing capital.
According to Rabbu market data, the Cutchogue short-term rental market shows:
| Metric | Context | Value |
|---|---|---|
| Active Airbnb Listings | As of Apr, 27 2026 | 29 |
| Average Daily Rate (ADR) | vs. $381 state avg. | $603 |
| Average Occupancy Rate | vs. 40% state avg. | 15% |
| RevPAN | ADR * Occupancy Rate | $90 |
| Average Monthly Revenue | Historical 12-month average | $6,229 |
| Average Annual Revenue | Historical 12-month average | $74,751 |
Data sources: Rabbu proprietary analytics as of Apr, 27 2026 and Zillow Home Value Index (ZHVI) as of Apr, 27 2026.
Investors are drawn to Cutchogue for its premium nightly rates and North Fork wine-country appeal, though the market's deep seasonality and elevated home prices require careful property-level analysis.
Key investment factors
"Cutchogue presents limited overall investment potential, reflected in a Rabbu ROI Score of 32 out of 100. Revenue is starkly seasonal: August peaks at $21,661 average monthly revenue while January dips to just $964, meaning roughly 75% of annual income arrives between May and September. For investors who can secure a well-positioned 4-bedroom property at a favorable basis—or who already own in the area—the summer earning power is genuinely impressive, but the math gets challenging against $1.9M average home values and sub-15% annualized occupancy."
— Rabbu Market Analysis Team
Cutchogue displays extreme seasonality, with August ($21,661) and July ($18,220) generating more than 20 times the revenue of the slowest months like January ($964) and February ($1,003). Investors should plan for a compressed earning window from roughly June through September, which accounts for the vast majority of annual income.
| Month | Trend | Revenue |
|---|---|---|
| January |
|
$964 |
| February |
|
$1,003 |
| March |
|
$1,323 |
| April |
|
$2,387 |
| May |
|
$5,813 |
| June |
|
$9,632 |
| July |
|
$18,220 |
| August |
|
$21,661 |
| September |
|
$7,145 |
| October |
|
$2,949 |
| November |
|
$1,924 |
| December |
|
$1,722 |
Four-bedroom properties dominate the supply with 13 of the market's 29 listings, while 2-bedroom and 3-bedroom units are evenly split at 5 each. The concentration toward larger homes reflects the family and group-oriented nature of North Fork vacation demand, and the relatively thin supply of smaller units could represent either limited demand or an underserved niche.
| Size | Trend | Value |
|---|---|---|
| 2 bedrooms |
|
5 |
| 3 bedrooms |
|
5 |
| 4 bedrooms |
|
13 |
ADR increases meaningfully with property size, from $474 for 2-bedroom units to $776 for 4-bedroom homes—a 64% premium. The step up from 3-bedroom ($517) to 4-bedroom pricing is especially steep, suggesting that the additional bedroom and capacity commands a disproportionate rate increase in this market.
| Size | Trend | Value |
|---|---|---|
| 2 bedrooms |
|
$474 |
| 3 bedrooms |
|
$517 |
| 4 bedrooms |
|
$776 |
Revenue per available night varies dramatically by size: 4-bedroom properties lead at $128, while 2-bedroom and 3-bedroom units lag significantly at $25 and $22 respectively. This wide gap underscores that only larger properties are generating enough occupancy-adjusted revenue to potentially justify Cutchogue's high acquisition costs.
| Size | Trend | Value |
|---|---|---|
| 2 bedrooms |
|
$25 |
| 3 bedrooms |
|
$22 |
| 4 bedrooms |
|
$128 |
Occupancy rates are uniformly low, but 4-bedroom properties stand out at 17% versus just 5% for 2-bedrooms and 4% for 3-bedrooms. The substantially higher fill rate for larger homes suggests that groups seeking spacious vacation rentals are the primary demand driver, while smaller units struggle to attract consistent bookings.
| Size | Trend | Value |
|---|---|---|
| 2 bedrooms |
|
5% |
| 3 bedrooms |
|
4% |
| 4 bedrooms |
|
17% |
Four-bedroom properties generate average monthly revenue of $11,641—roughly three times the $3,618 and $3,845 earned by 2- and 3-bedroom units respectively. This sharp revenue differential makes 4-bedroom homes the clear focus for investors seeking cash-flow viability in a market where smaller configurations produce modest returns.
| Size | Trend | Value |
|---|---|---|
| 2 bedrooms |
|
$3,618 |
| 3 bedrooms |
|
$3,845 |
| 4 bedrooms |
|
$11,641 |
On an annual basis, 4-bedroom homes average $139,697 in revenue, compared to $43,424 for 2-bedroom and $46,142 for 3-bedroom properties. While $140K in annual revenue is notable, it must be weighed against the market's average home value of nearly $1.9M to determine whether the yield justifies the capital outlay.
| Size | Trend | Value |
|---|---|---|
| 2 bedrooms |
|
$43,424 |
| 3 bedrooms |
|
$46,142 |
| 4 bedrooms |
|
$139,697 |
Parking is offered by 100% of listings, followed closely by kitchens (93%), backyards (90%), and BBQ grills (90%)—signaling that guests expect a full home experience oriented around outdoor living. Beach access (45%) and pools (35%) appear in a meaningful share of listings and likely serve as competitive differentiators during peak summer months.
| Amenity | Trend | Value |
|---|---|---|
| Parking |
|
100% |
| Kitchen |
|
93% |
| Backyard |
|
90% |
| BBQ Grill |
|
90% |
| Dryer |
|
83% |
| Washer |
|
79% |
| Patio or Balcony |
|
79% |
| Outdoor Furniture |
|
79% |
| Self Check-in |
|
66% |
| Workspace |
|
59% |
| Beach Access |
|
45% |
| Pets |
|
35% |
| Pool |
|
35% |
| Waterfront |
|
28% |
Rabbu's ROI Score is a proprietary metric that evaluates short-term rental investment potential based on multiple factors.
| Factor | Cutchogue Performance | Weight |
|---|---|---|
| Revenue-to-Price Ratio | Average | 40% |
| Occupancy Stability | Below average | 30% |
| Market Growth Trend | Below average | 15% |
| Supply/Demand Balance | Average | 15% |
Cutchogue's ROI Score of 32 out of 100 places it in the "Limited investment potential" band, flagging it as a higher-risk market that warrants thorough property-level analysis. The score reflects an average revenue-to-price ratio weighed down by below-average occupancy stability and a below-average market growth trend, while supply/demand balance registers as average. Investors exploring this market should pair these data points with on-the-ground regulatory research and a conservative underwriting approach given the seasonal concentration of income.
Understanding local STR regulations is essential before investing in Cutchogue. Here's the current regulatory landscape:
Short-term rental operators in Cutchogue and the broader Town of Southold, New York, may be required to obtain a rental permit or register their property with the town. Investors should verify current permit requirements directly with the Town of Southold and Suffolk County before listing a property.
Common restrictions that may apply include occupancy limits based on bedroom count, minimum-stay requirements, noise and nuisance ordinances, parking mandates, and potential HOA or community association rules. Some jurisdictions on the North Fork have also considered or enacted caps on the number of STR permits issued, so confirming availability is an important early step.
Short-term rental hosts in New York are typically subject to state and county occupancy taxes, as well as applicable sales taxes. Platforms like Airbnb often collect and remit certain taxes on the host's behalf, but operators should confirm their full obligations with a local tax professional.
Regulations subject to change. Always verify with local authorities before purchasing. A Rabbu partner agent specializing in Cutchogue can provide current regulatory guidance.
Financing an Airbnb investment in Cutchogue requires lenders who understand STR income. Rabbu partner lenders offer:
"Over the next 12–18 months, Cutchogue's extreme seasonality is unlikely to shift meaningfully—July and August will continue to drive the lion's share of revenue, with winter months generating under $1,100. Active listings have grown significantly year over year (up 200%), which could put downward pressure on occupancy and rates if demand doesn't keep pace. ADR may hold relatively steady given the area's appeal to affluent summer travelers, though investors should plan for occupancy rates that remain in the 12–18% range annually and budget accordingly for the long off-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. Data reflects trailing 12-month averages and may not capture very recent market shifts or regulatory changes. Individual property results will vary based on location, condition, pricing strategy, and management quality.
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