Investing in an STR in Upstate NY or Poconos

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Investing in an STR in Upstate NY or Poconos

Gokce Sahin
Member since 2025 · 1 post · 2 votes

We are considering buying an investment property in Upstate NY. Are there any STR owners here from the Catskills & Hudson Valley area? I'm aware that Woodstock and Shandaken capped the non-resident STR permits, so I'm avoiding those areas. I occasionally see some properties on sale that are currently operating as Airbnb. We were told by one real estate agent that an STR in this area won't cash flow much. Another option for us would be buying in the Poconos. Appreciate any advice.

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Bailey Rankin
Member since 2025 · 5 posts · 7 votes
11mo
Quote from @Gokce Sahin:

We are considering buying an investment property in Upstate NY. Are there any STR owners here from the Catskills & Hudson Valley area? I'm aware that Woodstock and Shandaken capped the non-resident STR permits, so I'm avoiding those areas. I occasionally see some properties on sale that are currently operating as Airbnb. We were told by one real estate agent that an STR in this area won't cash flow much. Another option for us would be buying in the Poconos. Appreciate any advice.


Hey there! I've designed a few homes in the Poconos for STR Investors and one thing I'll point out is that the competition is quite saturated. This is a huge market for Techvestor who have deep pockets. They focus in on a market and buy a lot of properties - quantity game. If you do buy in the Poconos, know you're going up against highly designed homes with a ton of amenities. Obviously I'm biased as an STR designer, but I really do recommend working with a designer that has a data-driven approach. Buying the right house is just step one. You have to design it in a way that crushes your competition.

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  • Joseph Chiofalo
    Banker · Henderson, NV · Member since 2023 · 316 posts · 74 votes
    1y

    Hi Gokce, 

    There are programs available to help investors with financing if the property is not cash flowing enough to meet debt service requirements. 

    How is your credit history and what price range are you targeting?

    0Reply
  • Andrew SteffensBusiness Member
    Tampa, FL · Member since 2022 · 3k+ posts · 3k+ votes
    1y

    I would recommend connecting with a STR specialist agent in both locations to get the best advice. I do have one for the Poconos, if you need it please DM me. Good luck!

    [email protected]813-563-0877
    Vacation Rentals of Florida53 Reviews
    WebsiteView Page
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  • Michael Lipari
    Member since 2022 · 29 posts · 23 votes
    1y

    I own and operate one in the area I could help you out finding a location / getting started. Please send me a PM.

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  • Phillip CostaPro Member
    Rental Property Investor · Poconos, PA · Member since 2018 · 32 posts · 17 votes
    11mo

    I’ve owned/managed STRs in nearby markets and both the Catskills and Hudson Valley can work — they just perform differently. The Catskills tend to have strong weekend and seasonal demand but watch local permit caps and short-term rental rules (Woodstock/Shandaken are examples), which can actually be more profitable since they are squeezing the supply of STRs in the area but can also be a risk if they end up restricting them in the future.

    The Poconos can offer lower entry prices and better initial cash flow, though expect more seasonality and competition. Run 12-month pro formas using comparable listings (realistic occupancy, management/cleaning fees, and capex), check permit/regulation status for any town you’re considering, and talk to local hosts. Shoot me a DM if you would need contacts in the Poconos.

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  • Bailey Rankin
    Member since 2025 · 5 posts · 7 votes
    11mo
    Quote from @Gokce Sahin:

    We are considering buying an investment property in Upstate NY. Are there any STR owners here from the Catskills & Hudson Valley area? I'm aware that Woodstock and Shandaken capped the non-resident STR permits, so I'm avoiding those areas. I occasionally see some properties on sale that are currently operating as Airbnb. We were told by one real estate agent that an STR in this area won't cash flow much. Another option for us would be buying in the Poconos. Appreciate any advice.


    Hey there! I've designed a few homes in the Poconos for STR Investors and one thing I'll point out is that the competition is quite saturated. This is a huge market for Techvestor who have deep pockets. They focus in on a market and buy a lot of properties - quantity game. If you do buy in the Poconos, know you're going up against highly designed homes with a ton of amenities. Obviously I'm biased as an STR designer, but I really do recommend working with a designer that has a data-driven approach. Buying the right house is just step one. You have to design it in a way that crushes your competition.

    1Reply
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