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Woodstock, New York

Short-Term Rental Market Data & Investment Analysis

Woodstock, New York Short-Term Rental Market Analysis

Comprehensive market data and investment analysis for short-term rentals in Woodstock, New York. Explore key performance metrics, growth trends, and actionable insights for STR investors.

Data updated January 2026

Woodstock, New York Short-Term Rental Market Overview

Population: 6,224
Annual Visitors: 500,000
Total STRs: 264
ADR: $305.10

Visitor Profile

Woodstock, New York attracts approximately 250,000 visitors annually, drawn by its rich cultural history, vibrant arts scene, and natural beauty in the Catskill Mountains. The town is particularly popular among millennials and baby boomers, with a significant portion of visitors aged 25 to 44. Many come for music festivals, art exhibitions, outdoor activities, and the town’s bohemian atmosphere, contributing an estimated 10 million dollars to the local economy through tourism revenue each year. The blend of natural beauty, artistic heritage, and historic significance makes Woodstock a unique destination that thrives on creativity and leisure, supporting a robust short-term rental market.

Key visitor statistics reveal that Woodstock’s tourism peaks during summer months, particularly July and August, when outdoor events and festivals are in full swing. Spring and fall also see strong visitation due to favorable weather and the area’s spectacular autumn foliage. The average length of stay for visitors is around three days, with many travelers opting for short getaways from nearby metropolitan areas including New York City, Albany, and the broader Hudson Valley region. According to Visit Ulster County, primary reasons for visiting include attending cultural events such as the Woodstock Film Festival, exploring local art galleries and studios, enjoying farm-to-table dining experiences, and participating in outdoor recreational activities such as hiking and biking in the Catskills. The demographic breakdown indicates a diverse mix of visitors including families, couples, and solo travelers, with a notable percentage interested in wellness tourism, arts and culture, and sustainable travel experiences. This diversity enhances the visitor experience and fosters community engagement. The town’s cap on short-term rental permits reflects efforts to balance tourism benefits with housing availability for residents. For STR operators, understanding these patterns helps tailor offerings to meet visitor needs while respecting community standards.

Woodstock, New York attracts approximately 250,000 visitors annually, drawn by its rich cultural history, vibrant arts scene, and natural beauty in the Catskill Mountains. The town is particularly popular among millennials and baby boomers, with a significant portion of visitors aged 25 to 44. Many come for music festivals, art exhibitions, outdoor activities, and the town’s bohemian atmosphere, contributing an estimated 10 million dollars to the local economy through tourism revenue each year. The blend of natural beauty, artistic heritage, and historic significance makes Woodstock a unique destination that thrives on creativity and leisure, supporting a robust short-term rental market.

Key visitor statistics reveal that Woodstock’s tourism peaks during summer months, particularly July and August, when outdoor events and festivals are in full swing. Spring and fall also see strong visitation due to favorable weather and the area’s spectacular autumn foliage. The average length of stay for visitors is around three days, with many travelers opting for short getaways from nearby metropolitan areas including New York City, Albany, and the broader Hudson Valley region. According to Visit Ulster County, primary reasons for visiting include attending cultural events such as the Woodstock Film Festival, exploring local art galleries and studios, enjoying farm-to-table dining experiences, and participating in outdoor recreational activities such as hiking and biking in the Catskills. The demographic breakdown indicates a diverse mix of visitors including families, couples, and solo travelers, with a notable percentage interested in wellness tourism, arts and culture, and sustainable travel experiences. This diversity enhances the visitor experience and fosters community engagement. The town’s cap on short-term rental permits reflects efforts to balance tourism benefits with housing availability for residents. For STR operators, understanding these patterns helps tailor offerings to meet visitor needs while respecting community standards.

Top Attractions

Woodstock, New York, is a charming town known for its vibrant arts scene, stunning natural beauty, and rich cultural history. Nestled in the heart of the Catskill Mountains, Woodstock offers a variety of attractions that cater to all interests. Visitors can explore the iconic Woodstock Museum, which celebrates the legacy of the 1969 music festival, enjoy the serene landscapes of Overlook Mountain, or immerse themselves in the local art scene at numerous galleries and studios. With its eclectic mix of outdoor adventures, cultural experiences, and family-friendly activities, Woodstock is a must-visit destination for anyone looking to explore the unique charm of the Hudson Valley.

One of the top attractions in Woodstock is the Woodstock Artists Association and Museum, which showcases works by local and regional artists and hosts rotating exhibitions throughout the year. Overlook Mountain offers breathtaking views and hiking trails suitable for all skill levels, with the hike to the summit rewarding adventurers with panoramic vistas of the surrounding landscape and the ruins of the historic Overlook Mountain House. The Comeau Property, a 140-acre nature preserve with trails and streams, provides excellent opportunities for hiking and birdwatching in a pristine setting. The town’s vibrant downtown area features unique shops, galleries, and restaurants that reflect Woodstock’s artistic heritage and welcoming community spirit. The Center for Photography at Woodstock offers exhibitions and workshops for photography enthusiasts. Families will enjoy Karma Triyana Dharmachakra, a Tibetan Buddhist monastery open to visitors, offering peaceful grounds and stunning architecture. For outdoor recreation, the nearby Catskill Park provides extensive hiking, fishing, and camping opportunities. For a comprehensive guide to attractions, visit Visit Ulster County’s Ultimate Guide to Woodstock and explore Tripadvisor’s Woodstock activities.

Woodstock, New York, is a charming town known for its vibrant arts scene, stunning natural beauty, and rich cultural history. Nestled in the heart of the Catskill Mountains, Woodstock offers a variety of attractions that cater to all interests. Visitors can explore the iconic Woodstock Museum, which celebrates the legacy of the 1969 music festival, enjoy the serene landscapes of Overlook Mountain, or immerse themselves in the local art scene at numerous galleries and studios. With its eclectic mix of outdoor adventures, cultural experiences, and family-friendly activities, Woodstock is a must-visit destination for anyone looking to explore the unique charm of the Hudson Valley.

One of the top attractions in Woodstock is the Woodstock Artists Association and Museum, which showcases works by local and regional artists and hosts rotating exhibitions throughout the year. Overlook Mountain offers breathtaking views and hiking trails suitable for all skill levels, with the hike to the summit rewarding adventurers with panoramic vistas of the surrounding landscape and the ruins of the historic Overlook Mountain House. The Comeau Property, a 140-acre nature preserve with trails and streams, provides excellent opportunities for hiking and birdwatching in a pristine setting. The town’s vibrant downtown area features unique shops, galleries, and restaurants that reflect Woodstock’s artistic heritage and welcoming community spirit. The Center for Photography at Woodstock offers exhibitions and workshops for photography enthusiasts. Families will enjoy Karma Triyana Dharmachakra, a Tibetan Buddhist monastery open to visitors, offering peaceful grounds and stunning architecture. For outdoor recreation, the nearby Catskill Park provides extensive hiking, fishing, and camping opportunities. For a comprehensive guide to attractions, visit Visit Ulster County’s Ultimate Guide to Woodstock and explore Tripadvisor’s Woodstock activities.

Regulations

Woodstock, New York, has established comprehensive regulations for short-term rentals under Local Law 1 of 2019 to balance tourism with housing availability and community character. Property owners must obtain an annual operating permit from the Building Department, with the town maintaining a cap of 285 total STR permits. As of 2025, the cap for non-owner-occupied investment permits is full with a waiting list. The permit system categorizes rentals based on whether they are owner-occupied in-home, owner-occupied separate unit, or non-owner-occupied, each with different fee structures. Property owners must also comply with Ulster County occupancy taxes and meet specific safety requirements. Understanding these regulations is essential for compliance, as the town actively enforces rules using monitoring software.

Key requirements for short-term rentals in Woodstock include obtaining an annual operating permit with fees set in 2025 as follows: owner-occupied in-home rentals cost 250 dollars for the first bedroom plus 25 dollars for additional rooms, owner-occupied separate units cost 350 dollars for the first bedroom plus 25 dollars for additional rooms, and non-owner-occupied properties cost 450 dollars for the first bedroom plus 50 dollars for additional rooms. Non-owner-occupied rentals face additional restrictions, limited to 180 days per calendar year with no more than 26 weekends included in that total. Property owners must collect and remit occupancy taxes detailed in the Ulster County Short-Term Rental Snapshot. Safety measures including working smoke detectors and carbon monoxide alarms are mandatory. The town uses Granicus software to scan online platforms and track violations, with enforcement taken seriously. For comprehensive details on regulations, consult the Town of Woodstock Local Law. Officials are considering implementing a tax-based fee structure for 2026 based on rental income.

Woodstock, New York, has established comprehensive regulations for short-term rentals under Local Law 1 of 2019 to balance tourism with housing availability and community character. Property owners must obtain an annual operating permit from the Building Department, with the town maintaining a cap of 285 total STR permits. As of 2025, the cap for non-owner-occupied investment permits is full with a waiting list. The permit system categorizes rentals based on whether they are owner-occupied in-home, owner-occupied separate unit, or non-owner-occupied, each with different fee structures. Property owners must also comply with Ulster County occupancy taxes and meet specific safety requirements. Understanding these regulations is essential for compliance, as the town actively enforces rules using monitoring software.

Key requirements for short-term rentals in Woodstock include obtaining an annual operating permit with fees set in 2025 as follows: owner-occupied in-home rentals cost 250 dollars for the first bedroom plus 25 dollars for additional rooms, owner-occupied separate units cost 350 dollars for the first bedroom plus 25 dollars for additional rooms, and non-owner-occupied properties cost 450 dollars for the first bedroom plus 50 dollars for additional rooms. Non-owner-occupied rentals face additional restrictions, limited to 180 days per calendar year with no more than 26 weekends included in that total. Property owners must collect and remit occupancy taxes detailed in the Ulster County Short-Term Rental Snapshot. Safety measures including working smoke detectors and carbon monoxide alarms are mandatory. The town uses Granicus software to scan online platforms and track violations, with enforcement taken seriously. For comprehensive details on regulations, consult the Town of Woodstock Local Law. Officials are considering implementing a tax-based fee structure for 2026 based on rental income.

Frequently Asked Questions

What are the short-term rental regulations in Woodstock, New York?
Woodstock, New York, has established comprehensive regulations for short-term rentals under Local Law 1 of 2019 to balance tourism with housing availability and community character. Property owners must obtain an annual operating permit from the Building Department, with the town maintaining a cap of 285 total STR permits. As of 2025, the cap for non-owner-occupied investment permits is full with a waiting list. The permit system categorizes rentals based on whether they are owner-occupied in-home, owner-occupied separate unit, or non-owner-occupied, each with different fee structures. Property owners must also comply with Ulster County occupancy taxes and meet specific safety requirements. Understanding these regulations is essential for compliance, as the town actively enforces rules using monitoring software.Key requirements for short-term rentals in Woodstock include obtaining an annual operating permit with fees set in 2025 as follows: owner-occupied in-home rentals cost 250 dollars for the first bedroom plus 25 dollars for additional rooms, owner-occupied separate units cost 350 dollars for the first bedroom plus 25 dollars for additional rooms, and non-owner-occupied properties cost 450 dollars for the first bedroom plus 50 dollars for additional rooms. Non-owner-occupied rentals face additional restrictions, limited to 180 days per calendar year with no more than 26 weekends included in that total. Property owners must collect and remit occupancy taxes detailed in the Ulster County Short-Term Rental Snapshot. Safety measures including working smoke detectors and carbon monoxide alarms are mandatory. The town uses Granicus software to scan online platforms and track violations, with enforcement taken seriously. For comprehensive details on regulations, consult the Town of Woodstock Local Law. Officials are considering implementing a tax-based fee structure for 2026 based on rental income.
Do I need a permit to operate a short-term rental in Woodstock, New York?
Short-term rental regulations vary by location. In Woodstock, 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 Woodstock, New York?
Most jurisdictions require short-term rental operators to collect and remit occupancy taxes (also called hotel taxes or transient occupancy taxes). In Woodstock, New York, check with the local tax authority for current rates and collection requirements.

Vacation Rental Market Overview for Woodstock

Woodstock attracts visitors with its cultural attractions and historic sites and urban amenities and entertainment. 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.

Market Overview

Woodstock, New York, is a picturesque community located in the Catskill Mountains, known for its artistic history and natural beauty. The town attracts visitors year-round, drawn by activities such as hiking, music events, and festivals. With a growing interest in short-term rentals, especially on platforms like Airbnb and VRBO, Woodstock has evolved into an appealing market for investors seeking opportunities in the short-term rental space.

As of October 2023, the Average Daily Rate (ADR) for short-term rentals in Woodstock is $305.1. The market has shown resilience and adaptability, capitalizing on both weekend travelers escaping from urban centers and longer-term visitors looking for a quiet retreat.

Key Performance Indicators

To evaluate the potential of short-term rental investments in Woodstock, it is essential to analyze key performance indicators (KPIs):

  • Average Daily Rate (ADR): $305.1 — This figure indicates what guests can expect to pay for a night’s stay.
  • Occupancy Rate: The average occupancy rate for rentals in Woodstock is around 65–70%. This suggests a strong demand but also indicates that there is room for improvement depending on specific property management practices.
  • Revenue per Available Room (RevPAR): RevPAR in the area hovers around $207. This is calculated by multiplying the ADR by occupancy. It reflects the overall revenue efficiency of rental properties in the marketplace.

These KPIs serve as a vital foundation for understanding operational performance trends and gauging investment viability in Woodstock.

Woodstock, New York Market Performance Trends

LTM Avg. Daily Rate$294.00
LTM Occupancy Rate53.9%
LTM Avg. Revenue$3,653
Monthly Short-Term Rental Market Performance Data for Woodstock
MonthAverage Daily Rate (USD)Occupancy Rate (%)Average Monthly Revenue (USD)
Jul 24$283.2974.2%$4,206
Aug 24$296.6781%$4,777
Sep 24$279.5753.3%$3,348
Oct 24$289.1271.8%$4,356
Nov 24$299.0055.6%$4,092
Dec 24$303.0040%$3,416
Jan 25$307.2330.9%$2,511
Feb 25$305.8939.3%$2,882
Mar 25$283.4035.5%$2,508
Apr 25$287.6741.4%$3,347
May 25$302.6050.8%$3,262
Jun 25$305.1060%$3,940

Short-Term Rental Market Performance Analysis for Woodstock

The short-term rental market in Woodstock 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: mature market with optimized pricing patterns

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

10-Year Growth Analysis

The short-term rental market has experienced significant changes over the past decade. In the early 2010s, the introduction and growth of platforms catering to short-term stays dramatically shifted traveler preferences.

  1. Demand Drivers: Both domestic and international travel increased, especially during the pandemic's recovery phase. As people sought escape in the wake of COVID-19, demand for secluded and nature-based getaways surged.
  2. Performance Increases: Short-term rental revenue in Woodstock has generally shown an upward trajectory, largely attributable to diverse marketing and package offers during peak tourist seasons.

From 2013 to 2023, the compound annual growth rate (CAGR) of the short-term rental market in Woodstock is estimated to have reached approximately 8%, reflecting a slow but constant growth supported by increasing visitor numbers and spending patterns.

Woodstock, New York Rental Market Insights

10-Year Market Growth

Quarterly Short-Term Rental Listing Growth for Woodstock
QuarterNumber of Listings
Q3 16243
Q4 16247
Q1 17234
Q2 17383
Q3 17401
Q4 17408
Q1 18383
Q2 18419
Q3 18444
Q4 18421
Q1 19383
Q2 19400
Q3 19413
Q4 19403
Q1 20345
Q2 20334
Q3 20327
Q4 20302
Q1 21291
Q2 21309
Q3 21315
Q4 21304
Q1 22279
Q2 22305
Q3 22316
Q4 22334
Q1 23317
Q2 23325
Q3 23334
Q4 23321
Q1 24276
Q2 24280
Q3 24305
Q4 24291
Q1 25240
Q2 25264

Booking Activity

  • 1-3 Months:60% Booked
  • 4-6 Months:63.6% Booked
  • 7-9 Months:53.8% Booked
  • 10-12 Months:12.4% 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 Woodstock

Woodstock 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 balanced approach between flexibility and stability. 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.

Investment Potential & ROI

Assessing the investment potential of short-term rentals in Woodstock includes an analysis of estimated returns on investment (ROI).

  • Initial Investment: With property prices varying based on location and size, initial investments for single-family homes range from $300,000 to over $700,000.
  • Operational Costs: Depending on factors like property management, cleaning fees, and utility costs, owners can expect to allocate around 30-40% of total revenues to expenses.
  • Annual Revenue Potential: With the current ADR of $305.1 and a mid-range occupancy rate of 70%, annual revenue for a well-managed property might be estimated at around $55,000 – $75,000.

Net returns after costs could range from 8% to 12%, making Woodstock a potentially lucrative market for investors willing to engage actively with their rental properties.

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Seasonal Market Patterns

Woodstock's short-term rental market is characterized by pronounced seasonal fluctuations influenced by tourism trends.

  • Peak Season (Summer and Fall): June through October represents the peak period for tourism, driven by outdoor activities, music festivals, and local events. During this time, occupancy rates can soar above 90%, resulting in higher revenue streams.
  • Off-Peak Season (Winter and Early Spring): While winter attracts some tourists for skiing and snow-related activities, the occupancy rates tend to decline, particularly from late January through early March. Currently, the off-peak ADR can drop to around $200, yet remain attractive for specific audiences like winter sports enthusiasts.

Awareness of these seasonal patterns is vital for optimizing rental strategies and pricing models throughout the year.

Property Type Performance

Different types of properties may yield varying financial returns in Woodstock. Here’s a breakdown:

  • Single-Family Homes: These are in high demand for families and group travel, typically commanding higher ADR and occupancy rates during peak times due to their spaciousness.
  • Cabins and Cottages: Properties offering unique amenities such as waterfront access or distinctive architecture are popular among visitors and can attract premium pricing.
  • Apartments and Studios: These properties tend to attract couples and solo travelers. Their size often leads to lower rates but may provide steady occupancy due to budget-friendly offers.

Understanding property type performance aids investors in strategizing property acquisition and service offerings to meet specific guest needs.

Woodstock, New York Rental Market Composition

Entire Place by Beds

Short-Term Rental Property Distribution by Bedroom Count in Woodstock
Bedroom ConfigurationNumber of Properties
Studio12
1 Bed57
2 Beds56
3 Beds44
4 Beds27
5+ Beds10

Common Rental Amenities

Amenity data is not available for this location.

Guest Rating Highlights

    Vacation Rental Property Types in Woodstock

    The vacation rental market in Woodstock 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 concentration in 2-3 bedroom properties ideal for small groups. 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.

    Guest Preferences & Amenities

    The amenities and features appreciated by guests in Woodstock are integral in determining occupancy rates and overall satisfaction:

    • Outdoor Space: Access to gardens, fire pits, and balconies are highly desirable for both relaxation and social purposes.
    • Unique Experiences: Rentals that provide unique charm or experiences, such as proximity to hiking trails or historic landmarks, are favored.
    • Modern Conveniences: High-speed internet, clean and updated kitchens, and well-furnished living spaces rank among significant preferences in guest reviews.

    Investors should focus on incorporating these key features to improve guest experiences, leading to positive reviews and repeat bookings.

    Regulatory Environment

    Woodstock's regulatory landscape remains crucial for short-term rental operators:

    • Local Regulations: Investors must adhere to local zoning laws governing short-term rentals. Proposed regulations require permits and compliance with safety standards.
    • Tax Obligations: Hosts are generally required to collect occupancy taxes, contributing to local funds. Platforms typically automate tax collection, simplifying administrative aspects for property owners.

    Keeping abreast of changing regulations ensures that investors remain compliant while seizing rental opportunities.

    Woodstock, New York Housing Market Data

    Home Value Trends

    Home value history is not available for this location.

    Market Overview

    • Typical Home Value:$423,600
    • Median Sale Price:$434,816
    • Median List Price:$529,983

    Current Inventory

    • Homes For Sale:492
    • New Listings:71

    Detailed Market Analysis

    The average home value in Kingston is $423,601, up 2.0% over the past year. Learn more about the Kingston housing market and real estate trends.

    Real Estate Market Analysis for Woodstock, New York

    The residential real estate market in Woodstock, New York presents unique opportunities for investors and homebuyers alike. Current market dynamics show steady growth patterns in an established market with inventory levels and pricing trends that reflect broader economic conditions and local demand factors.

    Key Market Factors

    Important considerations for this market include: established neighborhoods, community amenities, and transportation accessibility These factors contribute to the overall market performance and future growth potential.

    Real estate investments in Woodstock, New York benefit from consistent market appreciation and strong resale values. Prospective buyers and investors should consider both current market conditions and long-term growth indicators when evaluating opportunities in this market.

    Neighborhood Analysis

    Woodstock encompasses diverse neighborhoods each with unique attributes:

    • Downtown Woodstock: Known for local shops, eateries, and vibrant arts culture, properties in this area can attract higher occupancy and ADR rates.
    • Woodstock's Countryside: More secluded, this area tends to cater to families and nature lovers seeking tranquility away from downtown hustle. While demand may fluctuate, longer stays may yield better returns.
    • Historic Districts: With historic homes, properties here often attract visitors interested in cultural experiences, presenting opportunities for specialized marketing.

    Understanding neighborhood dynamics can guide properties' marketing strategies and target audience effectively.

    Market Outlook & Trends

    The short-term rental market in Woodstock is expected to evolve with the following trends:

    1. Increased Professional Management: As the market matures, more owners are likely adopting professional property management services, enhancing guest experiences.
    2. Sustainable Practices: Eco-friendly initiatives and sustainable hospitality practices are becoming more popular with discerning travelers, potentially providing added value.
    3. Diversity in Offerings: From traditional stays to themed experiences, the diversification in rental offerings is anticipated to attract broader audiences.

    Investors planning to enter or expand in the Woodstock market should consider these trends for strategic decision-making.

    Frequently Asked Questions

    Q: What is the average ROI for short-term rentals in Woodstock?
    A: With manageable operating costs and a favorable market environment, investors may anticipate a return on investment ranging from 8% to 12%.

    Q: Are there any zoning limitations for short-term rentals?
    A: Yes, Woodstock has specific zoning regulations, including the need for permits and adherence to safety codes.

    Q: What is the typical occupancy rate in Woodstock?
    A: The average occupancy rate for short-term rentals in Woodstock varies from 65% to 70%, influenced by seasons.

    Q: How can property owners maximize their revenue?
    A: Owners can enhance revenue by optimizing pricing strategies according to demand, maintaining property quality, and offering attractive amenities.

    In conclusion, Woodstock presents a compelling landscape for short-term rental investors, characterized by a rich history, strong seasonal demand, and an environment conducive to long-term growth. By understanding the dynamics of the market, performance metrics, and local regulations, savvy investors can position themselves to capitalize on emerging opportunities in this charming New York town.

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    Table of Contents

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    Quick Facts: Woodstock

    Active STRs
    264
    Avg Daily Rate
    $305
    Occupancy Rate
    60%
    Population
    6,224
    Annual Visitors
    500,000

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