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  4. Chestertown

Chestertown, New York

Short-Term Rental Market Data & Investment Analysis

Data updated February 2026

Chestertown, New York Short-Term Rental Market Overview

Population: 2,700
Annual Visitors: 60,000
Total STRs: 154
ADR: $289.85

Visitor Profile

Chestertown, New York, is a quaint destination that attracts a diverse range of visitors, contributing significantly to the local economy. While specific annual visitor numbers are not readily available, the town’s charm and natural beauty draw many tourists, particularly during peak seasons in summer and fall. The demographic profile of visitors includes families, retirees, and outdoor enthusiasts, with a notable interest from younger generations seeking adventure and relaxation. The economic impact of tourism is substantial, with local businesses benefiting from the influx of visitors who come to enjoy outdoor activities, local festivals, and cultural events.

In-depth visitor analysis reveals that Chestertown sees a mix of demographics, primarily consisting of families and couples aged 30-65. Many visitors are drawn to the area for its outdoor recreational opportunities, including hiking, fishing, and boating, with the nearby Schroon Lake being a significant attraction. The average length of stay is typically two to three nights, allowing visitors to explore the local attractions fully. Peak seasons are characterized by a vibrant atmosphere, with summer and fall witnessing the highest visitor numbers, as tourists flock to enjoy the scenic landscapes and community events. According to the tourism bureau, Chestertown offers a variety of activities, as highlighted by AARP’s guide on things to do in the area (https://local.aarp.org/chestertown-ny/things-to-do/). This blend of natural beauty and community engagement makes Chestertown a compelling destination for a wide range of travelers. For more insights into the town’s history and visitor demographics, you can refer to the Chestertown Wikipedia page (https://en.wikipedia.org/wiki/Chestertown,_New_York).

Total word count: 299 words.

Chestertown, New York, is a quaint destination that attracts a diverse range of visitors, contributing significantly to the local economy. While specific annual visitor numbers are not readily available, the town’s charm and natural beauty draw many tourists, particularly during peak seasons in summer and fall. The demographic profile of visitors includes families, retirees, and outdoor enthusiasts, with a notable interest from younger generations seeking adventure and relaxation. The economic impact of tourism is substantial, with local businesses benefiting from the influx of visitors who come to enjoy outdoor activities, local festivals, and cultural events.

In-depth visitor analysis reveals that Chestertown sees a mix of demographics, primarily consisting of families and couples aged 30-65. Many visitors are drawn to the area for its outdoor recreational opportunities, including hiking, fishing, and boating, with the nearby Schroon Lake being a significant attraction. The average length of stay is typically two to three nights, allowing visitors to explore the local attractions fully. Peak seasons are characterized by a vibrant atmosphere, with summer and fall witnessing the highest visitor numbers, as tourists flock to enjoy the scenic landscapes and community events. According to the tourism bureau, Chestertown offers a variety of activities, as highlighted by AARP’s guide on things to do in the area (https://local.aarp.org/chestertown-ny/things-to-do/). This blend of natural beauty and community engagement makes Chestertown a compelling destination for a wide range of travelers. For more insights into the town’s history and visitor demographics, you can refer to the Chestertown Wikipedia page (https://en.wikipedia.org/wiki/Chestertown,_New_York).

Total word count: 299 words.

Top Attractions

Nestled in the heart of the Adirondack Mountains, Chestertown, New York, is a charming town that offers a delightful mix of outdoor adventures and cultural experiences. Known for its stunning natural beauty, Chestertown is a haven for nature lovers and families alike. Visitors can explore the serene waters of the Schroon River, perfect for kayaking and fishing, or take a leisurely hike through the picturesque trails of the surrounding forests. The town also boasts a rich history, with attractions that reflect its heritage. Whether you’re seeking a peaceful retreat or an exciting day of exploration, Chestertown attractions promise a variety of experiences that cater to all interests.

One of the top attractions in Chestertown is the Chester Historical Society, where visitors can delve into the local history through engaging exhibits and artifacts. This museum provides insight into the town’s past and is a must-visit for history buffs. For those who enjoy the great outdoors, the nearby Schroon Lake offers a plethora of activities, including swimming, boating, and hiking along its scenic shores. The lake is a perfect spot for family picnics and relaxation. Additionally, the Chestertown Farmer’s Market showcases local produce and crafts, providing a taste of the community’s vibrant culture. For more information on things to do in Chestertown, visit the official visitor guide at AARP (https://local.aarp.org/chestertown-ny/things-to-do/). With its blend of nature, history, and community spirit, Chestertown is a hidden gem waiting to be explored.

Nestled in the heart of the Adirondack Mountains, Chestertown, New York, is a charming town that offers a delightful mix of outdoor adventures and cultural experiences. Known for its stunning natural beauty, Chestertown is a haven for nature lovers and families alike. Visitors can explore the serene waters of the Schroon River, perfect for kayaking and fishing, or take a leisurely hike through the picturesque trails of the surrounding forests. The town also boasts a rich history, with attractions that reflect its heritage. Whether you’re seeking a peaceful retreat or an exciting day of exploration, Chestertown attractions promise a variety of experiences that cater to all interests.

One of the top attractions in Chestertown is the Chester Historical Society, where visitors can delve into the local history through engaging exhibits and artifacts. This museum provides insight into the town’s past and is a must-visit for history buffs. For those who enjoy the great outdoors, the nearby Schroon Lake offers a plethora of activities, including swimming, boating, and hiking along its scenic shores. The lake is a perfect spot for family picnics and relaxation. Additionally, the Chestertown Farmer’s Market showcases local produce and crafts, providing a taste of the community’s vibrant culture. For more information on things to do in Chestertown, visit the official visitor guide at AARP (https://local.aarp.org/chestertown-ny/things-to-do/). With its blend of nature, history, and community spirit, Chestertown is a hidden gem waiting to be explored.

Regulations

Chestertown, New York, has established specific regulations governing short-term rentals to ensure community standards and safety. Property owners interested in renting their homes on a short-term basis must comply with local laws, which include obtaining a special use permit, adhering to zoning restrictions, and fulfilling tax obligations. The town emphasizes the importance of maintaining neighborhood integrity while allowing property owners to benefit from short-term rental income. Additionally, safety requirements must be met to protect both guests and residents. Understanding these regulations is crucial for compliance and avoiding penalties.

To operate a short-term rental in Chestertown, property owners must first secure a special use permit from the town. This process involves submitting an application that outlines the intended use of the property and demonstrates compliance with local zoning laws. Owners are also required to collect and remit a local occupancy tax, which is typically a percentage of the rental income. It is essential to stay updated on the current tax rates and deadlines to avoid fines. Furthermore, safety requirements, such as smoke detectors and fire extinguishers, must be installed to ensure guest safety. Violations of these regulations can result in penalties, including fines or revocation of the rental permit. For detailed information on Chestertown’s short-term rental regulations, property owners can refer to the official town website at https://www.chestertownny.gov and the municipal code at https://library.municode.com/ny/chestertown/codes/code_of_ordinances. Understanding these regulations is vital for successful and compliant short-term rental operations in Chestertown.

(Word count: 299)

Chestertown, New York, has established specific regulations governing short-term rentals to ensure community standards and safety. Property owners interested in renting their homes on a short-term basis must comply with local laws, which include obtaining a special use permit, adhering to zoning restrictions, and fulfilling tax obligations. The town emphasizes the importance of maintaining neighborhood integrity while allowing property owners to benefit from short-term rental income. Additionally, safety requirements must be met to protect both guests and residents. Understanding these regulations is crucial for compliance and avoiding penalties.

To operate a short-term rental in Chestertown, property owners must first secure a special use permit from the town. This process involves submitting an application that outlines the intended use of the property and demonstrates compliance with local zoning laws. Owners are also required to collect and remit a local occupancy tax, which is typically a percentage of the rental income. It is essential to stay updated on the current tax rates and deadlines to avoid fines. Furthermore, safety requirements, such as smoke detectors and fire extinguishers, must be installed to ensure guest safety. Violations of these regulations can result in penalties, including fines or revocation of the rental permit. For detailed information on Chestertown’s short-term rental regulations, property owners can refer to the official town website at https://www.chestertownny.gov and the municipal code at https://library.municode.com/ny/chestertown/codes/code_of_ordinances. Understanding these regulations is vital for successful and compliant short-term rental operations in Chestertown.

(Word count: 299)

Frequently Asked Questions

What are the short-term rental regulations in Chestertown, New York?
Chestertown, New York, has established specific regulations governing short-term rentals to ensure community standards and safety. Property owners interested in renting their homes on a short-term basis must comply with local laws, which include obtaining a special use permit, adhering to zoning restrictions, and fulfilling tax obligations. The town emphasizes the importance of maintaining neighborhood integrity while allowing property owners to benefit from short-term rental income. Additionally, safety requirements must be met to protect both guests and residents. Understanding these regulations is crucial for compliance and avoiding penalties.To operate a short-term rental in Chestertown, property owners must first secure a special use permit from the town. This process involves submitting an application that outlines the intended use of the property and demonstrates compliance with local zoning laws. Owners are also required to collect and remit a local occupancy tax, which is typically a percentage of the rental income. It is essential to stay updated on the current tax rates and deadlines to avoid fines. Furthermore, safety requirements, such as smoke detectors and fire extinguishers, must be installed to ensure guest safety. Violations of these regulations can result in penalties, including fines or revocation of the rental permit. For detailed information on Chestertown's short-term rental regulations, property owners can refer to the official town website at https://www.chestertownny.gov and the municipal code at https://library.municode.com/ny/chestertown/codes/code_of_ordinances. Understanding these regulations is vital for successful and compliant short-term rental operations in Chestertown.(Word count: 299)
Do I need a permit to operate a short-term rental in Chestertown, New York?
Short-term rental regulations vary by location. In Chestertown, New York, operators should check local ordinances for permit requirements, zoning restrictions, and licensing obligations. Contact local authorities for the most current requirements.
Are there occupancy taxes for vacation rentals in Chestertown, New York?
Most jurisdictions require short-term rental operators to collect and remit occupancy taxes (also called hotel taxes or transient occupancy taxes). In Chestertown, New York, check with the local tax authority for current rates and collection requirements.

Vacation Rental Market Overview for Chestertown

Chestertown attracts visitors with its beaches and waterfront activities and outdoor recreation and natural beauty. 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, New York Market Performance Trends

LTM Avg. Daily Rate$299.00
LTM Occupancy Rate41.2%
LTM Avg. Revenue$2,830
Monthly Short-Term Rental Market Performance Data for Chestertown
MonthAverage Daily Rate (USD)Occupancy Rate (%)Average Monthly Revenue (USD)
Jul 24$288.5679.3%$5,006
Aug 24$280.1078.6%$5,139
Sep 24$292.7140%$2,826
Oct 24$284.5735.5%$2,550
Nov 24$295.8623.3%$2,000
Dec 24$320.0030%$2,459
Jan 25$339.0027.6%$2,629
Feb 25$330.9244%$3,242
Mar 25$314.0022.6%$1,980
Apr 25$258.8627.6%$1,979
May 25$313.0327.7%$1,575
Jun 25$289.8540%$2,320

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, New York Housing Market Data

Home Value Trends

Quarterly Home Value Trends in Chestertown
QuarterTypical Home Value (USD)
Q2 17$221,542
Q3 17$216,819
Q4 17$215,636
Q1 18$215,813
Q2 18$218,975
Q3 18$220,103
Q4 18$218,874
Q1 19$217,585
Q2 19$215,742
Q3 19$218,351
Q4 19$220,482
Q1 20$223,561
Q2 20$223,762
Q3 20$228,062
Q4 20$241,253
Q1 21$250,039
Q2 21$262,123
Q3 21$268,975
Q4 21$273,350
Q1 22$287,149
Q2 22$303,251
Q3 22$307,904
Q4 22$304,081
Q1 23$301,771
Q2 23$315,951
Q3 23$328,701
Q4 23$335,453
Q1 24$334,213
Q2 24$341,486
Q3 24$350,080
Q4 24$351,732
Q1 25$347,764
Q2 25$351,798
Q3 25$356,507
Q4 25$363,142

Market Overview

  • Typical Home Value:$360,597

Current Inventory

  • Homes For Sale:6

Detailed Market Analysis

The average home value in Chestertown, NY is $360,597, up 5.9% over the past year. Learn more about the Chestertown housing market and real estate trends.

Real Estate Market Analysis for Chestertown, New York

The residential real estate market in Chestertown, New York 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, New York benefit from diverse property options and stable neighborhood development. Prospective buyers and investors should consider both current market conditions and long-term growth indicators when evaluating opportunities in this market.

Chestertown, New York Rental Market Insights

10-Year Market Growth

Quarterly Short-Term Rental Listing Growth for Chestertown
QuarterNumber of Listings
Q3 1635
Q4 1639
Q1 1734
Q2 1783
Q3 1792
Q4 1788
Q1 1878
Q2 18101
Q3 18115
Q4 1899
Q1 19105
Q2 19134
Q3 19139
Q4 19126
Q1 2097
Q2 20123
Q3 20117
Q4 20104
Q1 2196
Q2 21117
Q3 21122
Q4 21123
Q1 22106
Q2 22140
Q3 22151
Q4 22158
Q1 23134
Q2 23167
Q3 23189
Q4 23165
Q1 24136
Q2 24158
Q3 24158
Q4 24138
Q1 25121
Q2 25154

Booking Activity

  • 1-3 Months:66.5% Booked
  • 4-6 Months:51.2% Booked
  • 7-9 Months:28.9% 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, New York Rental Market Composition

Entire Place by Beds

Short-Term Rental Property Distribution by Bedroom Count in Chestertown
Bedroom ConfigurationNumber of Properties
1 Bed10
2 Beds36
3 Beds51
4 Beds32
5+ Beds14

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.

    More Locations In New York

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    Related Short-Term Rental Markets

    Explore 179 vacation rental markets within New York. Each location offers unique investment opportunities with distinct seasonal patterns, pricing dynamics, and traveler demographics.

    StaySTRA’s comprehensive market coverage enables side-by-side comparison of rental performance, helping investors and property managers make data-driven location decisions.

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    Table of Contents

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    Quick Facts: Chestertown

    Active STRs
    154
    Avg Daily Rate
    $290
    Occupancy Rate
    40%
    Population
    2,700
    Annual Visitors
    60,000

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    • Bemus Point
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    • Brant Lake
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