Chester, VT Airbnb Market Data, Statistics, and Occupancy Rates

Chester Short-Term Rental Market Overview

Chester, VT is a small but compelling short-term rental market that punches above its weight on revenue relative to property costs. With an average annual revenue of $34,502 against an average home value of $512,886, the revenue-to-price ratio rates above average for the region. The market's 80 active listings and strong winter seasonality — driven by Vermont's ski and holiday tourism — create a distinct investment profile that rewards operators who can capture peak-season demand. An ADR of $360 (below the $452 state average) keeps nightly rates accessible to a broad guest audience while still generating meaningful returns.

Key Market Statistics

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

Data sources: Rabbu proprietary analytics as of Apr, 27 2026 and Zillow Home Value Index (ZHVI) as of Mar, 17 2026.

Why Investors Consider Chester

Chester's favorable revenue-to-price ratio and seasonal tourism appeal make it an attractive entry point for investors seeking Vermont exposure without the premium price tags of larger resort towns.

Expert Market Assessment

"Chester represents an attractive opportunity for STR investors who can tolerate seasonal cash-flow variability. Revenue swings dramatically from a February high of $5,248 down to just $1,025 in April, so the market clearly rewards winter-focused operators and those who can capture autumn foliage traffic. The above-average revenue-to-price ratio and growing supply signal a healthy demand floor, though the below-average occupancy stability (46% vs. 51% statewide) means consistent year-round booking strategies are essential. Investors targeting 3- to 5-bedroom properties stand to capture the strongest returns, with annual revenues ranging from roughly $39,600 to $42,200 in those segments."

— Rabbu Market Analysis Team

Key Airbnb Metrics & Trends in Chester

Average revenue by month in Chester

Chester shows pronounced seasonality, with February leading at $5,248 and April bottoming out at just $1,025 — a roughly 5:1 peak-to-trough ratio. Winter months (December through February) collectively drive the bulk of annual income, while a secondary bump in July–August and October reflects summer and foliage tourism.

Active Airbnb listings by property size in Chester

One-bedroom units (23 listings) and 3-bedroom homes (21 listings) dominate Chester's supply, while 2-bedroom properties are surprisingly scarce at just 10 listings. The 5-bedroom segment has only 6 listings, which could signal a less competitive niche for investors willing to acquire larger properties.

Average daily rate (ADR) by property size in Chester

ADR scales steeply with size in Chester, jumping from $204 for 1-bedroom units to $528 for 4-bedroom homes — the highest rate of any segment. Interestingly, 5-bedroom properties command a lower ADR of $472 than 4-bedrooms, suggesting a pricing ceiling where the premium-to-cost trade-off may favor the 4-bedroom category.

Average RevPAN by property size in Chester

RevPAN climbs steadily with property size, from $94 for 1-bedroom units to $238 for 5-bedroom homes, indicating that larger properties generate substantially more revenue per available night even after accounting for occupancy differences. The jump from 3-bedroom ($181) to 5-bedroom ($238) represents a 31% increase, making larger homes the clear RevPAN leaders.

Average occupancy rates by property size in Chester

Occupancy rates are relatively flat across most sizes (46–49%), but 5-bedroom properties stand out at 51% — the highest in the market — while 4-bedroom homes lag notably at just 37%. Investors eyeing 4-bedroom properties should factor in this occupancy gap when projecting cash flow, despite those units commanding the highest ADR.

Average monthly revenue by property size in Chester

Five-bedroom properties top the monthly revenue chart at $3,518, closely followed by 4-bedrooms at $3,490 and 3-bedrooms at $3,299. One- and 2-bedroom units cluster near $1,600 per month, earning roughly half of what their larger counterparts generate — a significant gap that underscores the revenue advantage of investing in bigger homes.

Average annual revenue by property size in Chester

Annual revenue nearly doubles from 1-bedroom units ($19,760) to 3-bedroom homes ($39,593), and peaks at $42,218 for 5-bedroom properties. The relatively small gap between 3-, 4-, and 5-bedroom annual revenue ($39,593–$42,218) suggests that the incremental return on acquiring a larger property diminishes beyond three bedrooms.

Most common amenities for Airbnb listings in Chester

Parking (98%) and kitchen access (93%) are near-universal expectations in Chester, reflecting the market's rural, drive-to nature. Outdoor features like backyards (79%), patios (66%), and BBQ grills (66%) are also highly prevalent, signaling that guests expect a full retreat-style experience — while premium amenities like hot tubs (15%) and saunas (8%) remain differentiators that could help a listing stand out.

Understanding Chester's ROI Score: 62/100

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

Chester's ROI Score of 62 out of 100 places it in the 'Attractive Opportunity' band, driven primarily by an above-average revenue-to-price ratio that makes the market accessible relative to earning potential. The above-average market growth trend adds confidence, though below-average occupancy stability reflects the seasonal swings that investors need to plan for. Pairing this data with thorough local regulatory research and a conservative cash-flow model will give investors the clearest picture of what Chester can deliver.

Short-Term Rental Regulations in Chester

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

Permit Requirements

Chester, Vermont may require short-term rental operators to register or obtain permits at the municipal level, and Vermont has statewide lodging registration requirements that apply to STR hosts. Investors should verify current permit obligations directly with the Town of Chester and the Vermont Department of Taxes before listing a property.

Key Restrictions

Common restrictions in Vermont STR markets include occupancy limits, noise and nuisance ordinances, parking requirements, and fire safety standards. HOA covenants or deed restrictions may further limit short-term rental activity in certain neighborhoods, so it's important to review all applicable local rules and community guidelines before purchasing.

Tax Obligations

Vermont imposes a 9% rooms and meals tax on short-term accommodations, which platforms like Airbnb typically collect and remit on behalf of hosts. Operators should also confirm whether Chester levies any additional local option tax and ensure they remain compliant with state income tax reporting requirements.

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

Future Outlook & Long-Term Forecast

"Over the next 12–18 months, Chester's short-term rental market is expected to benefit from continued above-average growth trends, with listing counts having expanded 93% year over year. Peak-season months like February (averaging $5,248) and December ($3,962) should continue to anchor annual revenue, with estimates suggesting ADRs could edge up 2–5% as demand for Vermont getaways remains robust. Occupancy, currently at 46% versus the 51% state average, may tighten modestly as the market matures and operators refine pricing strategies, though the spring shoulder season will likely remain softer. Investors should plan cash-flow projections that account for the pronounced swing between peak winter months and the sub-$1,500 April–May lull."

— Rabbu Market Analysis Team

Frequently asked questions about Airbnb in Chester, VT

What is the average Airbnb occupancy rate in Chester?

The average Airbnb occupancy rate in Chester, VT is currently 46%, which sits slightly below the Vermont state average of 51%. Occupancy varies by property size, with 5-bedroom homes leading at 51% and 4-bedroom properties at 37%. The lower overall occupancy reflects Chester's pronounced seasonality, with strong winter demand offset by quieter spring and early summer months.

How much do Airbnb hosts make in Chester?

Airbnb hosts in Chester earn an average of $2,875 per month and approximately $34,502 per year, based on the trailing 12 months of booking performance. Earnings vary significantly by property size — 1- and 2-bedroom units average around $19,000–$20,000 annually, while 4- and 5-bedroom homes can generate over $41,000–$42,000 per year. Peak months like February can bring in over $5,200, while April may drop below $1,100.

Is Chester a good market for Airbnb investment?

Chester scores a 62 out of 100 on Rabbu's ROI Score, placing it in the 'Attractive Opportunity' category. The market's above-average revenue-to-price ratio is a standout strength, meaning earnings are healthy relative to what you'll pay for property. However, occupancy stability is below average, so investors should be prepared for seasonal income fluctuations and plan their finances around a strong winter peak with quieter shoulder months.

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

The average daily rate for Airbnb listings in Chester is $360, which is below the Vermont state average of $452. ADR scales considerably with property size: 1-bedroom units average $204 per night, while 4-bedroom homes command $528 per night. This range gives investors flexibility to target different guest segments and price points depending on their property type.

Are short-term rentals legal in Chester?

Short-term rentals are generally permitted in Chester, VT, though hosts should verify current local ordinances and any registration requirements with the Town of Chester. Vermont requires statewide lodging registration and collects a 9% rooms and meals tax on short-term accommodations. As regulations can evolve, it's always wise to confirm the latest rules with local authorities and the Vermont Department of Taxes before purchasing or listing a property.

When is peak season for Airbnb in Chester?

Peak season in Chester runs through the winter months, with February generating the highest average revenue at $5,248, followed by January at $4,194 and December at $3,962. A secondary peak occurs in late summer and early fall, with August averaging $3,406 and October reaching $3,010 — likely driven by fall foliage tourism. The quietest period falls in spring, with April averaging just $1,025 in monthly revenue.

How many Airbnbs are there in Chester?

Chester currently has 80 active Airbnb listings as of April 2026. The market has seen significant growth, with a 93% year-over-year increase in active listings. Supply is distributed across property sizes, with 1-bedroom units (23 listings) and 3-bedroom homes (21 listings) being the most common, while 5-bedroom properties (6 listings) represent a smaller, potentially less competitive segment.

How is Airbnb revenue calculated in Chester?

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

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 Chester, VT market
• Occupancy rates, average daily rates, and seasonal revenue trends based on trailing 12-month booking data
• Revenue and yield metrics broken down by property size and bedroom count
• Home value data sourced from the Zillow Home Value Index (ZHVI)
• Amenity prevalence data across active listings to benchmark guest expectations

Sources and disclaimers

Rabbu proprietary analytics as of Apr, 27 2026 and Zillow Home Value Index (ZHVI) as of Mar, 17 2026. Revenue projections are estimates based on comparable properties and do not guarantee future performance. Data reflects trailing 12-month averages and market conditions as of April 2026; actual results may differ as conditions evolve. Local regulations and tax obligations are subject to change — investors should verify current rules with Chester municipal authorities and the State of Vermont.