Winthrop, MA Airbnb Market Data, Statistics, and Occupancy Rates

Winthrop Short-Term Rental Market Overview

Winthrop, MA is a compact coastal community just minutes from Boston that offers short-term rental investors a niche opportunity with above-average occupancy stability. With only 31 active Airbnb listings and average annual revenue of $31,918, the market is small but shows clear seasonal demand driven by its beach access and proximity to the city. An ROI score of 61 out of 100 places Winthrop in the "Attractive Opportunity" range, suggesting a healthy balance between revenue potential and property values averaging $880,803.

Key Market Statistics

According to Rabbu market data, the Winthrop short-term rental market shows:

Data sources: Rabbu proprietary analytics as of Apr, 27 2026 and Zillow Home Value Index (ZHVI) as of Apr, 27 2026.

Why Investors Consider Winthrop

Winthrop attracts STR investors because of its coastal appeal, proximity to Boston, above-average occupancy stability, and a still-limited supply of short-term rentals.

Expert Market Assessment

"Winthrop presents a moderate-to-attractive opportunity for STR investors willing to navigate a clearly seasonal market. Revenue peaks from May through October — with October's $3,654 average actually edging out the summer months — while January and February dip to roughly $1,065–$1,102. The 2-bedroom segment stands out as a sweet spot, combining the highest occupancy rate (34%) with a RevPAN of $71 that far exceeds both 1- and 3-bedroom configurations. The market's small scale is both a strength and a limitation: low competition today, but fast-growing supply (59% YoY listing growth) warrants monitoring."

— Rabbu Market Analysis Team

Key Airbnb Metrics & Trends in Winthrop

Average revenue by month in Winthrop

Winthrop displays pronounced seasonality, with October ($3,654) narrowly leading all months and peak-season revenues (May–October) running 3–3.5× higher than the winter trough of $1,065 in January. Investors should expect roughly six strong months and plan reserves for the November-through-February slowdown.

Active Airbnb listings by property size in Winthrop

One-bedroom units dominate the supply landscape at 16 of 31 listings, while 2-bedroom (6) and 3-bedroom (5) properties are comparatively scarce. The limited supply of larger units, combined with their stronger revenue metrics, may signal an opportunity for investors willing to acquire multi-bedroom properties.

Average daily rate (ADR) by property size in Winthrop

ADR climbs from $135 for 1-bedroom units to $209 for 2-bedrooms and $232 for 3-bedrooms, though the jump from 2 to 3 bedrooms is relatively modest at just $23. This suggests the premium guests will pay for an extra bedroom tapers off, making 2-bedroom units an efficient middle ground for rate versus acquisition cost.

Average RevPAN by property size in Winthrop

Two-bedroom listings deliver the strongest RevPAN at $71, more than triple the $22 earned by 1-bedrooms and more than double the $33 for 3-bedrooms. This gap is driven by 2-bedrooms' significantly higher occupancy rate, making them the most productive configuration on a per-available-night basis.

Average occupancy rates by property size in Winthrop

Occupancy rates vary sharply by size: 2-bedroom listings lead at 34%, while 1-bedrooms (16%) and 3-bedrooms (15%) hover near or below the market average. For investors focused on consistent booking volume and cash-flow predictability, 2-bedroom properties clearly outperform in this market.

Average monthly revenue by property size in Winthrop

Three-bedroom listings top monthly revenue at $4,056, followed closely by 2-bedrooms at $3,874, while 1-bedrooms trail at $1,858. The narrow $182 gap between 2- and 3-bedroom monthly earnings — combined with the occupancy advantage of 2-bedrooms — makes the mid-size segment particularly compelling.

Average annual revenue by property size in Winthrop

Annual revenue ranges from $22,299 for 1-bedroom listings to $48,681 for 3-bedrooms, with 2-bedrooms close behind at $46,493. Given that 2-bedroom properties likely come with lower acquisition costs than 3-bedrooms yet generate nearly identical annual income, they may offer the best return on invested capital.

Most common amenities for Airbnb listings in Winthrop

Parking leads the amenity list at 97% prevalence — essentially a market requirement — followed by kitchen (90%), washer (90%), and dryer (87%). Beach access (45%) and waterfront positioning (26%) highlight the coastal character of Winthrop's listings and signal that guests expect convenient outdoor and seaside amenities alongside home-like essentials.

Understanding Winthrop's ROI Score: 61/100

Rabbu's ROI Score is a proprietary metric that evaluates short-term rental investment potential based on multiple factors.

How the ROI Score is Calculated

What This Means for Investors

Winthrop's ROI score of 61 out of 100 places it in the "Attractive Opportunity" band, reflecting a market where above-average occupancy stability helps offset an average revenue-to-price ratio driven by home values near $881K. Market growth trend and supply/demand balance both rate as average, suggesting steady but not explosive conditions. Investors should pair these metrics with up-to-date local regulatory research to build a complete picture before committing capital.

Short-Term Rental Regulations in Winthrop

Understanding local STR regulations is essential before investing in Winthrop. Here's the current regulatory landscape:

Permit Requirements

Short-term rental operators in Winthrop, MA may be required to register with the town and obtain a permit or license before listing their property. Massachusetts requires STR operators to register with the state as well, so investors should verify current requirements with both Winthrop's local government and the Commonwealth.

Key Restrictions

Common restrictions that may apply include occupancy limits, minimum stay requirements, noise and nuisance ordinances, and parking standards. HOA rules can further limit STR activity in certain buildings or neighborhoods, and some municipalities in Massachusetts impose caps on the number of permits issued. Investors should confirm which restrictions are in effect before purchasing.

Tax Obligations

Massachusetts imposes a state room occupancy excise tax on short-term rentals, and municipalities like Winthrop may add a local option tax as well. Platforms such as Airbnb often collect and remit these taxes automatically, but hosts should verify their filing obligations to ensure full compliance.

Regulations subject to change. Always verify with local authorities before purchasing. A Rabbu partner agent specializing in Winthrop can provide current regulatory guidance.

Future Outlook & Long-Term Forecast

"Over the next 12–18 months, Winthrop's STR market is likely to see continued seasonal swings, with peak-month revenues in the $3,400–$3,700 range and winter lows dipping below $1,200. The 59% year-over-year growth in active listings signals rising investor interest, though the market's small scale means supply could approach saturation if that pace continues. Occupancy rates, currently at 19% overall, may face pressure from new supply, though well-positioned 2-bedroom units — which already achieve 34% occupancy — should hold up best. Investors entering now should plan conservatively around ADR in the $240–$260 range and budget for meaningful off-season softness."

— Rabbu Market Analysis Team

Frequently asked questions about Airbnb in Winthrop, MA

What is the average Airbnb occupancy rate in Winthrop?

The average occupancy rate for Airbnb listings in Winthrop is currently 19%, which sits below the Massachusetts state average of 44%. That said, occupancy varies significantly by property size — 2-bedroom listings lead at 34%, while 1-bedroom and 3-bedroom units average 16% and 15% respectively. Seasonality plays a large role, with the warmer months driving the bulk of bookings.

How much do Airbnb hosts make in Winthrop?

On average, Airbnb hosts in Winthrop earn approximately $2,659 per month and $31,918 per year based on trailing 12-month performance. Revenue varies considerably by property size: 3-bedroom listings average $4,056 per month ($48,681 annually), 2-bedrooms average $3,874 per month ($46,493 annually), and 1-bedrooms come in at $1,858 per month ($22,299 annually). Peak months like October and June can push monthly revenue above $3,600.

Is Winthrop a good market for Airbnb investment?

Winthrop scores 61 out of 100 on Rabbu's ROI Score, placing it in the "Attractive Opportunity" tier. The market benefits from above-average occupancy stability and a balanced supply/demand environment, though the revenue-to-price ratio is average given home values near $880,803. Investors targeting 2-bedroom properties may find the best combination of occupancy and revenue, but should plan for meaningful seasonal variation in income.

What is the average daily rate (ADR) for Airbnb in Winthrop?

The average daily rate across all active Airbnb listings in Winthrop is $252, which is well below the Massachusetts state average of $582. ADR scales with property size: 1-bedroom listings average $135, 2-bedrooms $209, and 3-bedrooms $232. The lower ADR compared to the state average reflects Winthrop's positioning as a more affordable coastal alternative near Boston.

Are short-term rentals legal in Winthrop?

Short-term rentals are generally permitted in Massachusetts, but operators in Winthrop should verify local licensing or permit requirements with the town government. Massachusetts has a statewide registration requirement and room occupancy tax framework for STRs. Regulations can change, so it's advisable to consult local authorities and review any HOA restrictions before purchasing an investment property.

When is peak season for Airbnb in Winthrop?

Peak season in Winthrop runs roughly from May through October, with average monthly revenues ranging from $3,377 to $3,654 during that stretch. Interestingly, October ($3,654) slightly outperforms the traditional summer months of June ($3,624) and July ($3,623). The off-season from January through February sees the lowest revenue, dipping to around $1,065–$1,102 per month.

How many Airbnbs are there in Winthrop?

As of April 2026, there are 31 active Airbnb listings in Winthrop. The majority are 1-bedroom properties (16 listings), followed by 2-bedrooms (6 listings) and 3-bedrooms (5 listings). The market has grown 59% year-over-year in listing count, indicating increasing investor interest in this small coastal market.

How is Airbnb revenue calculated in Winthrop?

The annual and monthly revenue figures shown for Winthrop are derived from the trailing 12 months of historical booking performance for active comparable Airbnb listings in the market — they are not forward-looking projections. We average each comparable listing's actual revenue per available night (RevPAN) by month over the past year, remove regional outliers, and aggregate the results into a market-level historical average. This approach anchors the numbers to what hosts have actually earned recently, while naturally reflecting seasonal peaks and slower months because each month draws on its own historical data. Individual results can vary based on property quality, pricing strategy, and how the listing is managed.

About Rabbu Market Data

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.

What this data includes

• Regularly updated active Airbnb and STR listing counts for the Winthrop, MA market
• Average daily rate, occupancy, and RevPAN trends across property sizes
• Monthly and annual revenue metrics based on trailing 12-month historical booking data
• Home value benchmarks sourced from the Zillow Home Value Index (ZHVI)
• Popular amenity prevalence data across active listings

Sources and disclaimers

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 recent market shifts. Local regulations and tax requirements are subject to change; investors should verify current rules with municipal and state authorities.