Chestertown, Maryland Short-Term Rental Market Overview

Population: Still gathering data
Annual Visitors: Still gathering data
Total STRs: 92
ADR: $310.53

Visitor Profile

Chestertown, Maryland, is a charming destination that attracts a diverse array of visitors each year. While specific annual visitor numbers are not readily available, the town’s rich history and vibrant arts scene contribute significantly to its appeal. Key demographic highlights indicate that visitors primarily fall within the age range of 30 to 65, with a strong interest in cultural experiences, outdoor activities, and local cuisine. The economic impact of tourism in Chestertown is notable, as it supports local businesses and contributes to the overall vitality of the community. Events like the Chestertown Tea Party Festival and various art exhibitions draw significant crowds, enhancing the town’s profile as a cultural hub.

In terms of visitor analysis, Chestertown sees a mix of leisure and cultural tourism, with many visitors coming for weekend getaways or day trips. The primary demographics include families, couples, and solo travelers, with a growing number of millennials seeking unique experiences. The average length of stay is typically around two to three days, allowing visitors to explore the historic downtown area and the picturesque waterfront. Peak seasons are generally in the spring and fall, coinciding with local festivals and favorable weather conditions. According to the tourism bureau, the visitor statistics report highlights that Chestertown’s tourism sector plays a crucial role in sustaining the local economy, with millions generated annually. For more information on attractions and visitor services, check out the Main Street Chestertown website (https://www.mainstreetchestertown.org/visit/) and the Chestertown Travel Guide (https://bramptoninn.com/chestertown-travel-guide). These resources provide valuable insights into the town’s offerings and visitor demographics, making Chestertown a noteworthy destination on Maryland’s Eastern Shore.

Top Attractions

Nestled along the picturesque Chester River, Chestertown, Maryland, is a charming town that offers a delightful mix of history, culture, and outdoor activities. Known for its well-preserved colonial architecture and vibrant arts scene, Chestertown attracts visitors year-round. Signature attractions such as the historic waterfront, the Chestertown Tea Party Festival site, and the beautiful Washington College create a unique experience for all who visit. Whether you’re a history buff, an art enthusiast, or simply looking to enjoy the scenic beauty of Maryland’s Eastern Shore, Chestertown is brimming with things to do that cater to every interest.

One of the top attractions in Chestertown is the historic downtown area, where visitors can stroll along cobblestone streets lined with charming shops, galleries, and eateries. The area is rich in history, with many buildings dating back to the 18th century. For a deeper dive into the town’s past, the official visitor guide (https://www.mainstreetchestertown.org/) provides insights into local history and attractions. Another must-see is the waterfront, where you can enjoy stunning views of the Chester River, perfect for picnicking or simply relaxing by the water.

Art lovers will appreciate the Chestertown Arts & Entertainment District, which hosts various galleries and studios showcasing local talent. Additionally, Washington College (https://bramptoninn.com/chestertown-travel-guide) offers beautiful grounds and cultural events throughout the year, making it a great spot for a leisurely walk or a campus tour. With its blend of history, culture, and natural beauty, Chestertown is a destination that promises memorable experiences for all visitors.

Regulations

Chestertown, Maryland, has specific regulations governing short-term rentals that property owners must understand to operate legally. These regulations include licensing requirements, tax obligations, zoning restrictions, and safety standards. Property owners must obtain a short-term rental license from the town, ensuring compliance with local laws. Additionally, short-term rentals are subject to a 6% hotel tax, which must be collected and remitted to the state. Zoning laws dictate where short-term rentals can operate, typically allowing them only in designated residential areas. Safety requirements, including smoke detectors and carbon monoxide detectors, are mandatory to ensure guest safety. Violations of these regulations can lead to fines or revocation of the rental license, making it crucial for owners to stay informed.

To operate a short-term rental in Chestertown, property owners must first apply for a short-term rental license through the town’s planning office. This process includes submitting an application, paying the required fees, and adhering to zoning regulations that restrict rentals in certain areas. The 6% hotel tax applies to all short-term rental transactions, and owners are responsible for collecting this tax from guests and remitting it to the state by the designated deadlines. Furthermore, safety requirements must be met, including the installation of smoke detectors and fire extinguishers. Failure to comply with these regulations can result in penalties, including fines or the loss of the rental license. For more detailed information on Chestertown short-term rental regulations, visit the Maryland Municipal Codes at https://www.mdcourts.gov/lawlib/research/gateway-to-md-law/municipal-codes. Understanding these regulations is essential for successful short-term rental management in Chestertown.

Vacation Rental Market Overview for Chestertown

Chestertown attracts visitors with its cultural attractions and historic sites and adventure sports and activities. The short-term rental market here serves diverse traveler demographics, from business professionals to family vacationers.

This destination’s rental market offers unique opportunities for property investors, with comprehensive data revealing seasonal patterns and demand drivers.

Chestertown, Maryland Market Performance Trends

LTM Avg. Daily Rate$330.00
LTM Occupancy Rate43.3%
LTM Avg. Revenue$3,377

Short-Term Rental Market Performance Analysis for Chestertown

The short-term rental market in Chestertown demonstrates dynamic pricing patterns and occupancy trends that savvy property investors and managers monitor closely. This comprehensive 12-month analysis reveals seasonal variations and revenue optimization opportunities.

Market Trend Summary

Current market indicators show: strong seasonal variation with peak summer demand

Market data updated daily. Professional-grade analytics trusted by thousands of property managers and real estate investors.

Chestertown, Maryland Housing Market Data

Home Value Trends

Market Overview

  • Typical Home Value:$381,552
  • Median List Price:$406,000

Current Inventory

  • Homes For Sale:57
  • New Listings:20

Detailed Market Analysis

The average home value in Chestertown, MD is $381,553, up 1.9% over the past year. Learn more about the Chestertown housing market and real estate trends.

Real Estate Market Analysis for Chestertown, Maryland

The residential real estate market in Chestertown, Maryland presents unique opportunities for investors and homebuyers alike. Current market dynamics show balanced market conditions with accessible entry points with inventory levels and pricing trends that reflect broader economic conditions and local demand factors.

Key Market Factors

Important considerations for this market include: growing population trends, economic development, and lifestyle amenities These factors contribute to the overall market performance and future growth potential.

Real estate investments in Chestertown, Maryland benefit from growing rental market potential and investment opportunities. Prospective buyers and investors should consider both current market conditions and long-term growth indicators when evaluating opportunities in this market.

Chestertown, Maryland Rental Market Insights

10-Year Market Growth

Booking Activity

  • 1-3 Months:72.1% Booked
  • 4-6 Months:68.8% Booked
  • 7-9 Months:34.4% Booked
  • 10-12 Months:0% Booked

Cancellation Policies

  • Flexible:0%
  • Moderate:0%
  • Strict:0%
  • Super Strict:0%

Minimum Stay

  • 1 Day:0
  • 2 Days:0
  • 3 Days:0
  • 4-6 Days:0
  • 7-29 Days:0
  • 30+ Days:0

Short-Term Rental Regulations and Booking Patterns in Chestertown

Chestertown vacation rental operators navigate specific local regulations and booking patterns that shape market dynamics. Understanding minimum stay requirements, cancellation policies, and booking windows is essential for successful property management.

Market analysis reveals flexible booking policies attracting last-minute travelers. These insights help property managers optimize their listing strategies and maximize occupancy.

Local regulations and platform policies influence rental operations. StaySTRA provides comprehensive policy tracking and compliance insights.

Chestertown, Maryland Rental Market Composition

Entire Place by Beds

Common Rental Amenities

Amenity data is not available for this location.

Guest Rating Highlights

    Vacation Rental Property Types in Chestertown

    The vacation rental market in Chestertown features a diverse mix of property types, from cozy studios to spacious family homes. Understanding the property composition helps investors identify market gaps and opportunities.

    Market characteristics include a balanced mix of entire homes and private rooms. This distribution reflects local demand patterns and traveler preferences.

    Premium amenities and guest ratings play a crucial role in rental performance, with data showing clear correlations between specific features and booking rates.

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