Chestertown Airbnb Market Analysis 2025: Short Term Rental Data & Vacation Rental Statistics in Maryland, United States
Is Airbnb profitable in Chestertown in 2025? Explore comprehensive Airbnb analytics for Chestertown, Maryland, United States to uncover income potential. This 2025 STR market report for Chestertown, based on AirROI data from April 2024 to March 2025, reveals key trends in the niche market of 52 active listings.
Whether you're considering an Airbnb investment in Chestertown, optimizing your existing vacation rental, or exploring rental arbitrage opportunities, understanding the Chestertown Airbnb data is crucial. Leveraging the low regulation environment is key to maximizing your short term rental income potential. Let's dive into the specifics.
Key Chestertown Airbnb Performance Metrics Overview
Monthly Airbnb Revenue Variations & Income Potential in Chestertown (2025)
Understanding the monthly revenue variations for Airbnb listings in Chestertown 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 Chestertown is typically July, while February often presents the lowest earnings, highlighting opportunities for strategic pricing adjustments during shoulder and low seasons. Explore the typical Airbnb income in Chestertown across different performance tiers:
- Best-in-class properties (Top 10%) achieve $8,215+ monthly, often utilizing dynamic pricing and superior guest experiences.
- Strong performing properties (Top 25%) earn $5,018 or more, indicating effective management and desirable locations/amenities.
- Typical properties (Median) generate around $2,951 per month, representing the average market performance.
- Entry-level properties (Bottom 25%) see earnings around $1,804, often with potential for optimization.
Average Monthly Airbnb Earnings Trend in Chestertown
Chestertown Airbnb Occupancy Rate Trends (2025)
Maximize your bookings by understanding the Chestertown STR occupancy trends. Seasonal demand shifts significantly influence how often properties are booked. Typically, Augustsees the highest demand (peak season occupancy), while January 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 Chestertown:
- Best-in-class properties (Top 10%) achieve 69%+ occupancy, indicating high desirability and potentially optimized availability.
- Strong performing properties (Top 25%) maintain 53% or higher occupancy, suggesting good market fit and guest satisfaction.
- Typical properties (Median) have an occupancy rate around 36%.
- Entry-level properties (Bottom 25%) average 21% occupancy, potentially facing higher vacancy.
Average Monthly Occupancy Rate Trend in Chestertown
Average Daily Rate (ADR) Airbnb Trends in Chestertown (2025)
Effective short term rental pricing strategy in Chestertown involves understanding monthly ADR fluctuations. The Average Daily Rate (ADR) for Airbnb in Chestertown typically peaks in November and dips lowest during October. 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 $554+ per night, often due to premium features or locations.
- Strong performing properties (Top 25%) achieve nightly rates of $390 or more.
- Typical properties (Median) charge around $242 per night.
- Entry-level properties (Bottom 25%) earn around $173 per night.
Average Daily Rate (ADR) Trend by Month in Chestertown
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Airbnb Seasonality Analysis & Trends in Chestertown (2025)
Peak Season (July, August, May)
- Revenue averages $5,456 per month
- Occupancy rates average 47.7%
- Daily rates average $304
Shoulder Season
- Revenue averages $3,886 per month
- Occupancy maintains around 37.5%
- Daily rates hold near $306
Low Season (January, February, March)
- Revenue drops to average $2,298 per month
- Occupancy decreases to average 30.2%
- Daily rates adjust to average $315
Seasonality Insights for Chestertown
- The Airbnb seasonality in Chestertown shows highly seasonal trends requiring careful strategy. 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 Chestertown's highest earning potential, with monthly revenues capable of climbing to $5,659, occupancy reaching a high of 53.8%, and ADRs peaking at $325.
- 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 $2,262, occupancy could drop to 28.6%, and ADRs may adjust down to $294.
- 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 Chestertown.
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 Chestertown seasonality benchmarks and adjust your pricing and availability strategy accordingly.
Best Areas for Airbnb Investment in Chestertown (2025)
Exploring the top neighborhoods for short-term rentals in Chestertown? 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 / Area | Why Host Here? (Target Guests & Appeal) | Key Attractions & Landmarks |
|---|---|---|
| Historic Chestertown | Charming waterfront town with rich colonial history and beautiful historic architecture. Attracts visitors interested in history and small-town charm, making it ideal for cultural experiences. | Chestertown Historic District, Washington College, Custom House, Chestertown Farmers Market |
| Kent County | Picturesque rural area surrounding Chestertown, known for its scenic landscapes and outdoor activities. Ideal for nature lovers and those seeking relaxation away from urban life. | Chester River, Blackwater National Wildlife Refuge, Sassafras Natural Resource Management Area |
| Downtown Chestertown | The heart of the town, featuring quaint shops, restaurants, and art galleries. A perfect location for guests wanting to experience local culture and cuisine. | The Garfield Center for the Arts, The Blue Heron Cafe, Local art galleries |
| Eastern Shore Wine Country | Renowned for its wineries and vineyards. Attracts wine enthusiasts and those looking for a peaceful countryside getaway. | Crow Vineyard and Winery, 2021 Wine Festival, Chesapeake Wine Trail |
| Cannon Street | A historic residential area with Victorian-style homes and a close-knit community feel. Popular for family visits and those interested in heritage. | Historic homes, Local eateries, Chestertown's annual events |
| Riverfront Park | A scenic area by the river, perfect for outdoor activities and events. It draws visitors looking for recreation and scenic views. | Riverfront Park, Kayaking on the Chester River, Community events and festivals |
| Kent Narrows | A vibrant area with restaurants and access to boating and fishing. Great for visitors looking for waterfront dining and water activities. | Kent Narrows water access, Dining at waterfront restaurants, Fishing and boating opportunities |
| Rock Hall | A nearby small town known for its maritime heritage and outdoor activities. Perfect for those looking for a cozy retreat with water access. | Rock Hall Harbor, Local seafood dining, Maritime Museum, Chesapeake Bay access |
Understanding Airbnb License Requirements & STR Laws in Chestertown (2025)
While Chestertown, Maryland, United States currently shows low STR regulations, specific Airbnb license requirements might still exist or change. Always verify the latest short term rental regulations and Airbnb license requirements directly with local government authorities for Chestertown to ensure full compliance before hosting.
(Source: AirROI data, 2025, finding no licensed listings among those analyzed)
Top Performing Airbnb Properties in Chestertown (2025)
Benchmark your potential! Explore examples of top-performing Airbnb properties in Chestertownbased on Trailing Twelve Month (TTM) revenue. Analyze their characteristics, revenue, occupancy rate, and ADR to understand what drives success in this market.
Chestertown Watson Family Farm
Entire Place • 5 bedrooms
Harbor View Haven | Waterfront w/ HOT TUB + Dock!
Entire Place • 3 bedrooms
Down by the River
Entire Place • 3 bedrooms
Piney Grove Farm
Entire Place • 5 bedrooms
Stepne Manor
Entire Place • 5 bedrooms
The Portside Manor - Queen Street Chestertown
Entire Place • 3 bedrooms
Note: Performance varies based on location, size, amenities, seasonality, and management quality. Data reflects the past 12 months.
Top Performing Airbnb Hosts in Chestertown (2025)
Learn from the best! This table showcases top-performing Airbnb hosts in Chestertown based on the number of properties managed and estimated total revenue over the past year. Analyze their scale and performance metrics.
| Host Name | Properties | Grossing Revenue | Stay Reviews | Avg Rating |
|---|---|---|---|---|
| Landon | 2 | $179,971 | 74 | 4.86/5.0 |
| Hannah | 3 | $121,848 | 79 | 4.98/5.0 |
| Molly | 1 | $117,704 | 22 | 5.00/5.0 |
| Beth | 1 | $112,323 | 33 | 5.00/5.0 |
| Bob And Beth | 2 | $108,752 | 399 | 4.99/5.0 |
| Jennifer | 2 | $100,190 | 139 | 4.97/5.0 |
| Matthew | 2 | $90,921 | 114 | 4.93/5.0 |
| Host #211012304 | 2 | $75,801 | 34 | 5.00/5.0 |
| Natalie | 1 | $75,712 | 16 | 5.00/5.0 |
| Gregory | 1 | $70,599 | 8 | 5.00/5.0 |
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 Chestertown.
Dive Deeper: Advanced Chestertown STR Market Data (2025)
Ready to unlock more insights? AirROI provides access to advanced metrics and comprehensive Airbnb data for Chestertown. Explore detailed analytics beyond this report to refine your investment strategy, optimize pricing, and maximize your vacation rental profits.
Explore Advanced MetricsChestertown Short-Term Rental Market Composition (2025): Property & Room Types
Room Type Distribution
Property Type Distribution
Market Composition Insights for Chestertown
- The Chestertown Airbnb market composition is heavily skewed towards Entire Home/Apt listings, which make up 94.2% of the 52 active rentals. This indicates strong guest preference for privacy and space.
- Looking at the property type distribution in Chestertown, House properties are the most common (65.4%), reflecting the local real estate landscape.
- Houses represent a significant 65.4% portion, catering likely to families or larger groups.
- The presence of 5.8% Hotel/Boutique listings indicates integration with traditional hospitality.
- Smaller segments like unique stays (combined 1.9%) offer potential for unique stay experiences.
Chestertown Airbnb Room Capacity Analysis (2025): Bedroom Distribution
Distribution of Listings by Number of Bedrooms
Room Capacity Insights for Chestertown
- The dominant room capacity in Chestertown is 3 bedrooms listings, making up 32.7% of the market. This suggests a strong demand for properties suitable for families or small groups.
- Together, 3 bedrooms and 2 bedrooms properties represent 50.0% of the active Airbnb listings in Chestertown, indicating a high concentration in these sizes.
- A significant 59.6% of listings offer 3+ bedrooms, catering to larger groups and families seeking more space in Chestertown.
Chestertown Vacation Rental Guest Capacity Trends (2025)
Distribution of Listings by Guest Capacity
Guest Capacity Insights for Chestertown
- The most common guest capacity trend in Chestertown vacation rentals is listings accommodating 8+ guests (40.4%). This suggests the primary traveler segment is likely larger groups.
- Properties designed for 8+ guests and 6 guests dominate the Chestertown STR market, accounting for 57.7% of listings.
- 59.6% of properties accommodate 6+ guests, serving the market segment for larger families or group travel in Chestertown.
- On average, properties in Chestertown are equipped to host 5.6 guests.
Chestertown Airbnb Booking Patterns (2025): Available vs. Booked Days
Available Days Distribution
Booked Days Distribution
Booking Pattern Insights for Chestertown
- The most common availability pattern in Chestertown falls within the 181-270 days range, representing 40.4% of listings. This suggests many properties have significant open periods on their calendars.
- Approximately 71.2% 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 Chestertown (40.4%), reflecting common guest stay durations or potential owner blocking patterns.
- A notable 30.8% of properties secure long booking periods (181+ days booked per year), highlighting successful long-term rental strategies or significant owner usage.
Chestertown Airbnb Minimum Stay Requirements Analysis
Distribution of Listings by Minimum Night Requirement
1 Night
10 listings
20.4% of total
2 Nights
24 listings
49% of total
3 Nights
8 listings
16.3% of total
4-6 Nights
1 listings
2% of total
30+ Nights
6 listings
12.2% of total
Key Insights
- The most prevalent minimum stay requirement in Chestertown is 2 Nights, adopted by 49% of listings. This highlights the market's preference for shorter, flexible bookings.
- A strong majority (69.4%) of the Chestertown Airbnb data shows acceptance of very short stays (1-2 nights), indicating a dynamic, high-turnover market.
- A significant segment (12.2%) caters to monthly stays (30+ nights) in Chestertown, pointing to opportunities in the extended-stay market.
Recommendations
- Align with the market by considering a 2 Nights minimum stay, as 49% of Chestertown hosts use this setting.
- If feasible, allowing 1-night stays, especially midweek or during low season, could capture last-minute bookings, as only 20.4% currently do.
- Explore offering discounts for stays of 30+ nights to attract the 12.2% of the market seeking extended stays.
- Adjust minimum nights based on seasonality – potentially shorter during low season and longer during peak demand periods in Chestertown.
Chestertown Airbnb Cancellation Policy Trends Analysis (2025)
Flexible
10 listings
20.8% of total
Moderate
15 listings
31.3% of total
Firm
13 listings
27.1% of total
Strict
10 listings
20.8% of total
Cancellation Policy Insights for Chestertown
- The prevailing Airbnb cancellation policy trend in Chestertown is Moderate, used by 31.3% of listings.
- There's a relatively balanced mix between guest-friendly (52.1%) and stricter (47.9%) policies, offering choices for different guest needs.
Recommendations for Hosts
- Consider adopting a Moderate policy to align with the 31.3% market standard in Chestertown.
- Regularly review your cancellation policy against competitors and market demand shifts in Chestertown.
Chestertown STR Booking Lead Time Analysis (2025)
Average Booking Lead Time by Month
Booking Lead Time Insights for Chestertown
- The overall average booking lead time for vacation rentals in Chestertown is 59 days.
- Guests book furthest in advance for stays during May (average 119 days), likely coinciding with peak travel demand or local events.
- The shortest booking windows occur for stays in February (average 35 days), indicating more last-minute travel plans during this time.
- Seasonally, Spring (79 days avg.) sees the longest lead times, while Winter (44 days avg.) has the shortest, reflecting typical travel planning cycles.
Recommendations for Hosts
- Use the overall average lead time (59 days) as a baseline for your pricing and availability strategy in Chestertown.
- For May stays, consider implementing length-of-stay discounts or slightly higher rates for bookings made less than 119 days out to capitalize on advance planning.
- Target marketing efforts for the Spring season well in advance (at least 79 days) to capture early planners.
- Monitor your own booking lead times against these Chestertown averages to identify opportunities for dynamic pricing adjustments.
Popular & Essential Airbnb Amenities in Chestertown (2025)
Amenity Prevalence
Amenity Insights for Chestertown
- Essential amenities in Chestertown that guests expect include: Smoke alarm, Heating, Wifi, Air conditioning, Dishes and silverware, Essentials, TV. Lacking these (any) could significantly impact bookings.
- Popular amenities like Hot water, Coffee maker, Kitchen are common but not universal. Offering these can provide a competitive edge.
Recommendations for Hosts
- Ensure your listing includes all essential amenities for Chestertown: Smoke alarm, Heating, Wifi, Air conditioning, Dishes and silverware, Essentials, TV.
- Prioritize adding missing essentials: Dishes and silverware, Essentials, TV.
- Consider adding popular differentiators like Hot water or Coffee maker 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 Chestertown to stay competitive.
Chestertown Airbnb Guest Demographics & Profile Analysis (2025)
Guest Profile Summary for Chestertown
- The typical guest profile for Airbnb in Chestertown consists of primarily domestic travelers (90%), often arriving from nearby Washington, typically belonging to the Post-2000s (Gen Z/Alpha) group (50%), primarily speaking English or Spanish.
- Domestic travelers account for 89.9% of guests.
- Key international markets include United States (89.9%) and DC (7.6%).
- Top languages spoken are English (68.8%) followed by Spanish (12.5%).
- 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 Washington and Baltimore.
- 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 Chestertown 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.
| Market | Active Properties | Monthly Revenue | Daily Rate | Avg. Occupancy |
|---|---|---|---|---|
| Lemont | 22 | $8,558 | $812.80 | 42% |
| State College | 158 | $7,525 | $751.34 | 44% |
| Centreville | 15 | $6,205 | $510.77 | 47% |
| Ferguson Township | 120 | $5,810 | $785.97 | 40% |
| Mayo | 13 | $5,786 | $439.15 | 52% |
| College Township | 65 | $5,752 | $809.46 | 40% |
| Stevensville | 70 | $5,476 | $499.46 | 43% |
| West Donegal Township | 13 | $5,399 | $450.85 | 39% |
| Chester | 17 | $5,299 | $437.72 | 43% |
| Shannondale | 47 | $5,288 | $292.94 | 56% |