Chester Airbnb Market Analysis 2025: Short Term Rental Data & Vacation Rental Statistics in Vermont, United States

Source: AirROI
Last updated: 2025-03-31

Is Airbnb profitable in Chester in 2025? Explore comprehensive Airbnb analytics for Chester, Vermont, United States to uncover income potential. This 2025 STR market report for Chester, based on AirROI data from April 2024 to March 2025, reveals key trends in the niche market of 71 active listings.

Whether you're considering an Airbnb investment in Chester, optimizing your existing vacation rental, or exploring rental arbitrage opportunities, understanding the Chester Airbnb data is crucial. Understanding the local regulations is key to maximizing your short term rental income potential. Let's dive into the specifics.

Key Chester Airbnb Performance Metrics Overview

Avg. Daily Rate (ADR)(?)
$298
The average rental revenue earned for an occupied room per day in Chester.
Occupancy Rate(?)
40.0%
Moderate demand with booking opportunities.
Median Annual Revenue(?)
$34,560
Typical annual income for an Airbnb listing in Chester. Factors like property type, size, and location influence actual earnings.
Revenue Growth YoY(?)
36.2%
Strong growth (36.2%) vs. last year.
Peak Revenue Month(?)
February
The month with the highest average earnings, indicating peak season in Chester.
Lowest Revenue Month(?)
September
The month with the lowest average earnings, indicating the low season in Chester.
STR Regulation Level(?)
Moderate
Regulation details vary. Check local government sources.
Active Airbnb Listings(?)
71
Total number of active short-term rentals listed.

Monthly Airbnb Revenue Variations & Income Potential in Chester (2025)

Understanding the monthly revenue variations for Airbnb listings in Chester is key to maximizing your short term rental income potential. Seasonality significantly impacts earnings. Our analysis, based on data from the past 12 months, shows that the peak revenue month for STRs in Chester is typically February, while September often presents the lowest earnings, highlighting opportunities for strategic pricing adjustments during shoulder and low seasons. Explore the typical Airbnb income in Chester across different performance tiers:

  • Best-in-class properties (Top 10%) achieve $8,098+ monthly, often utilizing dynamic pricing and superior guest experiences.
  • Strong performing properties (Top 25%) earn $5,194 or more, indicating effective management and desirable locations/amenities.
  • Typical properties (Median) generate around $2,912 per month, representing the average market performance.
  • Entry-level properties (Bottom 25%) see earnings around $1,494, often with potential for optimization.

Average Monthly Airbnb Earnings Trend in Chester

Chester Airbnb Occupancy Rate Trends (2025)

Maximize your bookings by understanding the Chester STR occupancy trends. Seasonal demand shifts significantly influence how often properties are booked. Typically, Februarysees the highest demand (peak season occupancy), while May experiences the lowest (low season). Effective strategies, like adjusting minimum stays or offering promotions, can boost occupancy during slower periods. Here's how different property tiers perform in Chester:

  • Best-in-class properties (Top 10%) achieve 71%+ occupancy, indicating high desirability and potentially optimized availability.
  • Strong performing properties (Top 25%) maintain 52% or higher occupancy, suggesting good market fit and guest satisfaction.
  • Typical properties (Median) have an occupancy rate around 34%.
  • Entry-level properties (Bottom 25%) average 19% occupancy, potentially facing higher vacancy.

Average Monthly Occupancy Rate Trend in Chester

Average Daily Rate (ADR) Airbnb Trends in Chester (2025)

Effective short term rental pricing strategy in Chester involves understanding monthly ADR fluctuations. The Average Daily Rate (ADR) for Airbnb in Chester typically peaks in February and dips lowest during May. Leveraging Airbnb dynamic pricing tools or strategies based on this seasonality can significantly boost revenue. Here's a look at the typical nightly rates achieved:

  • Best-in-class properties (Top 10%) command rates of $491+ per night, often due to premium features or locations.
  • Strong performing properties (Top 25%) achieve nightly rates of $373 or more.
  • Typical properties (Median) charge around $238 per night.
  • Entry-level properties (Bottom 25%) earn around $163 per night.

Average Daily Rate (ADR) Trend by Month in Chester

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Airbnb Seasonality Analysis & Trends in Chester (2025)

Peak Season (February, December, June)
  • Revenue averages $4,601 per month
  • Occupancy rates average 42.3%
  • Daily rates average $310
Shoulder Season
  • Revenue averages $3,834 per month
  • Occupancy maintains around 35.8%
  • Daily rates hold near $279
Low Season (July, September, November)
  • Revenue drops to average $3,295 per month
  • Occupancy decreases to average 37.8%
  • Daily rates adjust to average $270

Seasonality Insights for Chester

  • The Airbnb seasonality in Chester shows moderate seasonality with distinct peak and low periods. While the sections above show seasonal averages, it's also insightful to look at the extremes:
  • During the high season, the absolute peak month showcases Chester's highest earning potential, with monthly revenues capable of climbing to $5,056, occupancy reaching a high of 52.2%, and ADRs peaking at $340.
  • Conversely, the slowest single month of the year, typically falling within the low season, marks the market's lowest point. In this month, revenue might dip to $3,063, occupancy could drop to 19.6%, and ADRs may adjust down to $256.
  • Understanding both the seasonal averages and these monthly peaks and troughs in revenue, occupancy, and ADR is crucial for maximizing your Airbnb profit potential in Chester.

Seasonal Strategies for Maximizing Profit

  • Peak Season: Maximize revenue through premium pricing and potentially longer minimum stays. Ensure high availability.
  • Low Season: Offer competitive pricing, special promotions (e.g., extended stay discounts), and flexible cancellation policies. Target off-season travelers like remote workers or budget-conscious guests.
  • Shoulder Seasons: Implement dynamic pricing that balances peak and low rates. Target weekend travelers or specific events. Offer slightly more flexible terms than peak season.
  • Regularly analyze your own performance against these Chester seasonality benchmarks and adjust your pricing and availability strategy accordingly.

Best Areas for Airbnb Investment in Chester (2025)

Exploring the top neighborhoods for short-term rentals in Chester? This section highlights key areas, outlining why they are attractive for hosts and guests, along with notable local attractions. Consider these locations based on your target guest profile and investment strategy.

Neighborhood / AreaWhy Host Here? (Target Guests & Appeal)Key Attractions & Landmarks
Downtown Chester
Downtown Chester offers a charming small-town atmosphere with local shops and restaurants, making it appealing for visitors looking for a cozy getaway.
Chester Depot, Stone House, Mosaic Museum, local breweries, seasonal farmers market
Buttermilk Falls
A picturesque area known for its beautiful waterfall and scenic views, attracting nature enthusiasts and photographers.
Buttermilk Falls, Chester's Historic Walking Tour, nature trails, hiking opportunities, photo spots
Grafton
Nearby Grafton is known for its quintessential Vermont charm and scenic landscapes, attracting tourists interested in outdoor activities and small-town culture.
Grafton Village, Hiking Trails, Grafton Nature Museum, local art studios, scenic drives
Mount Holly
This area is great for outdoor enthusiasts, especially for skiing in winter and hiking in the summer, appealing to adventure seekers.
Okemo Mountain Resort, lakes and rivers, hiking trails, ski slopes, scenic vistas
Chester Depot
Chester Depot is a historic site with unique architecture and cultural significance, making it attractive to history lovers.
Chester Depot Museum, historic buildings, local art galleries, quaint shops, events in the village
Green Mountain National Forest
This vast forested area is ideal for those seeking nature and adventure, perfect for a vacation rental focused on outdoor activities.
hiking, camping, wildlife viewing, scenic drives, winter sports
Ludlow
A nearby town that is a hub for skiing and outdoor sports, drawing in visitors year-round for different activities.
Okemo Mountain Ski Resort, local dining, winter sports, golf courses, year-round events
Springfield
Just a short drive from Chester, Springfield offers additional amenities and attractions, serving as a good base for travelers exploring the area.
Springfield Art and Historical Society, local parks, dining options, shopping, community events

Understanding Airbnb License Requirements & STR Laws in Chester (2025)

With 11% of listings showing registration in 2025, understanding potential Airbnb license requirements is crucial in Chester. Always verify the latest short term rental regulations and Airbnb license requirements directly with local government authorities for Chester to ensure full compliance before hosting.

(Source: AirROI data, 2025, based on 11% licensed listings)

Top Performing Airbnb Properties in Chester (2025)

Benchmark your potential! Explore examples of top-performing Airbnb properties in Chesterbased on Trailing Twelve Month (TTM) revenue. Analyze their characteristics, revenue, occupancy rate, and ADR to understand what drives success in this market.

Work, Ski, Relax - Big Restored 1860s Farmhouse

Work, Ski, Relax - Big Restored 1860s Farmhouse

Entire Place • 6 bedrooms

$120,625
Revenue
62.8%
Occupancy
$689.11
Daily Rate
Vermont 1828 Reunion House, sleeps 16, near Okemo

Vermont 1828 Reunion House, sleeps 16, near Okemo

Entire Place • 8 bedrooms

$106,747
Revenue
43.5%
Occupancy
$743.04
Daily Rate
Stunning farmhouse-Historic village-Mins to Skiing

Stunning farmhouse-Historic village-Mins to Skiing

Entire Place • 3 bedrooms

$99,230
Revenue
51.3%
Occupancy
$433.29
Daily Rate
Bearfoot Cottage: Tiny House w/ Hot Tub near Okemo

Bearfoot Cottage: Tiny House w/ Hot Tub near Okemo

Entire Place • 1 bedroom

$90,047
Revenue
0.0%
Occupancy
$246.63
Daily Rate
Farmhouse w/ views close to skiing  sauna EV CHRGR

Farmhouse w/ views close to skiing sauna EV CHRGR

Entire Place • 4 bedrooms

$87,091
Revenue
54.4%
Occupancy
$334.99
Daily Rate
WhiSki Cabin *12-acres with mountain views!*

WhiSki Cabin *12-acres with mountain views!*

Entire Place • 4 bedrooms

$79,414
Revenue
24.1%
Occupancy
$525.07
Daily Rate

Note: Performance varies based on location, size, amenities, seasonality, and management quality. Data reflects the past 12 months.

Top Performing Airbnb Hosts in Chester (2025)

Learn from the best! This table showcases top-performing Airbnb hosts in Chester based on the number of properties managed and estimated total revenue over the past year. Analyze their scale and performance metrics.

Host NamePropertiesGrossing RevenueStay ReviewsAvg Rating
Bianca1$120,625524.90/5.0
Peg And Matt1$106,747904.79/5.0
Evolve3$104,4891524.85/5.0
Pat1$99,230404.95/5.0
Alli5$92,6942374.82/5.0
Kaitlyn1$90,0471184.99/5.0
Miguel1$87,091434.98/5.0
Tim And Caitlin2$79,703405.00/5.0
Jamie1$79,414184.83/5.0
Michaeline1$75,894855.00/5.0

Analyzing the strategies of top hosts, such as their property selection, pricing, and guest communication, can offer valuable lessons for optimizing your own Airbnb operations in Chester.

Dive Deeper: Advanced Chester STR Market Data (2025)

Ready to unlock more insights? AirROI provides access to advanced metrics and comprehensive Airbnb data for Chester. Explore detailed analytics beyond this report to refine your investment strategy, optimize pricing, and maximize your vacation rental profits.

Explore Advanced Metrics

Chester Short-Term Rental Market Composition (2025): Property & Room Types

Room Type Distribution

Property Type Distribution

Market Composition Insights for Chester

  • The Chester Airbnb market composition is heavily skewed towards Entire Home/Apt listings, which make up 85.9% of the 71 active rentals. This indicates strong guest preference for privacy and space.
  • Looking at the property type distribution in Chester, House properties are the most common (71.8%), reflecting the local real estate landscape.
  • Houses represent a significant 71.8% portion, catering likely to families or larger groups.
  • The presence of 7% Hotel/Boutique listings indicates integration with traditional hospitality.
  • Smaller segments like others (combined 2.8%) offer potential for unique stay experiences.

Chester Airbnb Room Capacity Analysis (2025): Bedroom Distribution

Distribution of Listings by Number of Bedrooms

Room Capacity Insights for Chester

  • The dominant room capacity in Chester is 4 bedrooms listings, making up 23.9% of the market. This suggests a strong demand for properties suitable for families or small groups.
  • Together, 4 bedrooms and 1 bedroom properties represent 45.0% of the active Airbnb listings in Chester, indicating a high concentration in these sizes.
  • A significant 56.3% of listings offer 3+ bedrooms, catering to larger groups and families seeking more space in Chester.

Chester Vacation Rental Guest Capacity Trends (2025)

Distribution of Listings by Guest Capacity

Guest Capacity Insights for Chester

  • The most common guest capacity trend in Chester vacation rentals is listings accommodating 8+ guests (43.7%). This suggests the primary traveler segment is likely larger groups.
  • Properties designed for 8+ guests and 6 guests dominate the Chester STR market, accounting for 62.0% of listings.
  • 64.8% of properties accommodate 6+ guests, serving the market segment for larger families or group travel in Chester.
  • On average, properties in Chester are equipped to host 5.7 guests.

Chester Airbnb Booking Patterns (2025): Available vs. Booked Days

Available Days Distribution

Booked Days Distribution

Booking Pattern Insights for Chester

  • The most common availability pattern in Chester falls within the 271-366 days range, representing 40.8% of listings. This suggests many properties have significant open periods on their calendars.
  • Approximately 78.8% of listings show high availability (181+ days open annually), indicating potential for increased bookings or specific owner usage patterns.
  • For booked days, the 91-180 days range is most frequent in Chester (42.3%), reflecting common guest stay durations or potential owner blocking patterns.
  • A notable 21.1% of properties secure long booking periods (181+ days booked per year), highlighting successful long-term rental strategies or significant owner usage.

Chester Airbnb Minimum Stay Requirements Analysis

Distribution of Listings by Minimum Night Requirement

1 Night (19.4%)

1 Night

13 listings

19.4% of total

2 Nights (52.2%)

2 Nights

35 listings

52.2% of total

3 Nights (11.9%)

3 Nights

8 listings

11.9% of total

4-6 Nights (1.5%)

4-6 Nights

1 listings

1.5% of total

30+ Nights (14.9%)

30+ Nights

10 listings

14.9% of total

Key Insights

  • The most prevalent minimum stay requirement in Chester is 2 Nights, adopted by 52.2% of listings. This highlights the market's preference for shorter, flexible bookings.
  • A strong majority (71.6%) of the Chester Airbnb data shows acceptance of very short stays (1-2 nights), indicating a dynamic, high-turnover market.
  • A significant segment (14.9%) caters to monthly stays (30+ nights) in Chester, pointing to opportunities in the extended-stay market.

Recommendations

  • Align with the market by considering a 2 Nights minimum stay, as 52.2% of Chester hosts use this setting.
  • If feasible, allowing 1-night stays, especially midweek or during low season, could capture last-minute bookings, as only 19.4% currently do.
  • A 2-night minimum appears standard (52.2%). Consider this for weekends or peak periods.
  • Explore offering discounts for stays of 30+ nights to attract the 14.9% of the market seeking extended stays.
  • Adjust minimum nights based on seasonality – potentially shorter during low season and longer during peak demand periods in Chester.

Chester Airbnb Cancellation Policy Trends Analysis (2025)

Flexible (14.1%)

Flexible

9 listings

14.1% of total

Moderate (18.8%)

Moderate

12 listings

18.8% of total

Firm (32.8%)

Firm

21 listings

32.8% of total

Strict (34.4%)

Strict

22 listings

34.4% of total

Cancellation Policy Insights for Chester

  • The prevailing Airbnb cancellation policy trend in Chester is Strict, used by 34.4% of listings.
  • A majority (67.2%) of hosts in Chester utilize Firm or Strict policies, indicating a market where hosts prioritize booking security.

Recommendations for Hosts

  • Consider adopting a Strict policy to align with the 34.4% market standard in Chester.
  • With 34.4% using Strict terms, this is a viable option in Chester, particularly for high-value properties or during peak demand periods.
  • Regularly review your cancellation policy against competitors and market demand shifts in Chester.

Chester STR Booking Lead Time Analysis (2025)

Average Booking Lead Time by Month

Booking Lead Time Insights for Chester

  • The overall average booking lead time for vacation rentals in Chester is 43 days.
  • Guests book furthest in advance for stays during December (average 68 days), likely coinciding with peak travel demand or local events.
  • The shortest booking windows occur for stays in April (average 39 days), indicating more last-minute travel plans during this time.
  • Seasonally, Winter (60 days avg.) sees the longest lead times, while Fall (44 days avg.) has the shortest, reflecting typical travel planning cycles.

Recommendations for Hosts

  • Use the overall average lead time (43 days) as a baseline for your pricing and availability strategy in Chester.
  • For December stays, consider implementing length-of-stay discounts or slightly higher rates for bookings made less than 68 days out to capitalize on advance planning.
  • Target marketing efforts for the Winter season well in advance (at least 60 days) to capture early planners.
  • Monitor your own booking lead times against these Chester averages to identify opportunities for dynamic pricing adjustments.

Popular & Essential Airbnb Amenities in Chester (2025)

Amenity Prevalence

Amenity Insights for Chester

  • Essential amenities in Chester that guests expect include: Smoke alarm, Free parking on premises, Hot water, Wifi, Coffee maker, Carbon monoxide alarm, Heating. Lacking these (any) could significantly impact bookings.
  • Popular amenities like Bed linens, TV, Kitchen are common but not universal. Offering these can provide a competitive edge.

Recommendations for Hosts

  • Ensure your listing includes all essential amenities for Chester: Smoke alarm, Free parking on premises, Hot water, Wifi, Coffee maker, Carbon monoxide alarm, Heating.
  • Prioritize adding missing essentials: Free parking on premises, Hot water, Wifi, Coffee maker, Carbon monoxide alarm, Heating.
  • Consider adding popular differentiators like Bed linens or TV to increase appeal.
  • Highlight unique or less common amenities you offer (e.g., hot tub, dedicated workspace, EV charger) in your listing description and photos.
  • Regularly check competitor amenities in Chester to stay competitive.

Chester Airbnb Guest Demographics & Profile Analysis (2025)

Guest Origin: Domestic vs. International
Top 5 Cities of Origin
Top 5 Countries of Origin
Top 5 Languages Spoken
Guest Age Distribution (Birth Decade)

Guest Profile Summary for Chester

  • The typical guest profile for Airbnb in Chester consists of primarily domestic travelers (96%), often arriving from nearby New York, typically belonging to the Post-2000s (Gen Z/Alpha) group (50%), primarily speaking English or Spanish.
  • Domestic travelers account for 95.9% of guests.
  • Key international markets include United States (95.9%) and Canada (1.5%).
  • Top languages spoken are English (73%) followed by Spanish (8.7%).
  • A significant demographic segment is the Post-2000s (Gen Z/Alpha) group, representing 50% of guests.

Recommendations for Hosts

  • Target domestic marketing efforts towards travelers from New York and Boston.
  • Tailor amenities and listing descriptions to appeal to the dominant Post-2000s (Gen Z/Alpha) demographic (e.g., highlight fast WiFi, smart home features, local guides).
  • Highlight unique local experiences or amenities relevant to the primary guest profile.
  • Consider seasonal promotions aligned with peak travel times for key origin markets.

Nearby Short-Term Rental Market Comparison

How does the Chester Airbnb market stack up against its neighbors? Compare key performance metrics like average monthly revenue, ADR, and occupancy rates in surrounding areas to understand the broader regional STR landscape.

MarketActive PropertiesMonthly RevenueDaily RateAvg. Occupancy
Middletown Springs11$8,614$550.2436%
Town of Stuyvesant10$6,757$533.7441%
Milford11$6,343$500.1059%
Pomfret13$6,142$449.7949%
Jefferson28$5,920$432.8350%
Fort Ann27$5,803$761.4438%
Stony Creek11$5,749$484.5143%
Hanover28$5,449$863.4939%
Town of Stillwater54$5,325$536.4846%
Craryville21$5,255$522.5338%

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