Catskills ski + summer market with a strong cabin-and-condo inventory mix. New York decouples from federal §168(k), so investors capture the federal Year-1 deduction only — Windham's low mountain land ratios and family-STR amenity stack keep it competitive on the federal side despite the missing state benefit.
Town of Windham has no adopted STR ordinance; a 2021 draft (150-permit cap, 100 rental days/year) was withdrawn after community pushback and no new local law has been adopted since. Permit: No · Cap: No · Min stay: None · Owner-occ.: No. Verified 2026-08-16 against primary jurisdiction sources — read the full regulations profile →
New York decouples from federal §168(k). The federal Year-1 deduction applies at 100%, but New York requires a state add-back — the effective savings for high-earner investors are the federal figure only. That still lands at meaningful money on a median-priced STR, but the state layer that boosts full-conformity markets is not available here. Model with your CPA against New York's 10.9% top marginal rate without a §168(k) offset.
Windham ranks #38 because the Catskills ski + summer market supports year-round STR demand, the cabin-and-condo inventory mix carries family-friendly amenity stacks that classify heavily to 15-year property, and mountain land ratios stay reasonable (~22%). New York decouples from federal §168(k), so the play is purely federal — but the 23.4% market-median bonus-eligible % on typical prices makes the federal-only math still compelling.
Windham STRs lean on the amenity categories the IRS classifies as 15-year land improvements — hot tub or spa, fire pit / fire feature, outdoor deck or wraparound porch, and mud room / ski storage. All 100% bonus-eligible in Year 1 under §168(k). Combined with land ratios that stay in the 19–25% band (leaving 75–81% of purchase price as depreciable basis), that amenity density pushes the market-median bonus-eligible % to 23.4%.
Federal Year 1 benefit applies; state add-back required on the New York return — the federal figure IS the effective savings. On a median-priced $599k Windham STR, that's ~$52k in federal savings at a 37% bracket. Model with your CPA before committing.
Prevalence of 15-year land improvements we typically see across Windham short-term rentals — all 100% bonus-eligible in Year 1 under IRS §168(k):
Windham and the two DepreciMax Top 50 markets ranked immediately adjacent by median bonus-eligible %. The comparison is intentionally close-ranked so the deltas that matter — price point, Diamond density, state §168(k) conformity — are directly visible.
| Market | Rank | Diamond Density | Median Bonus % | Median Y1 Deduction | State Conformity |
|---|---|---|---|---|---|
| Windham, NY | 38 | 39% | 23.4% | ~$140k on $599k STR | Decoupled |
| Red Lodge, MT | 37 | 39% | 23.4% | ~$170k on $725k STR | Full |
| Williams / Grand Canyon, AZ | 39 | 39% | 23.4% | ~$121k on $515k STR | Full |
Deeper comparative reading: The best STR markets for bonus depreciation in 2026.
Windham spans multiple sub-markets across the Windham corridor with materially different STR economics. The calculator below has a zip dropdown — switch it to your area. The bonus-eligible percentage (Windham's market-typical 23.4%) stays constant across zips because it reflects the property type, not the location.
See IRS Publication 946 for §168(k) rules. Use the interactive calculator below to model your specific deal.
Looking for a deeper read on your specific property, not just the market median? Run the $99 Windham property report — our AI analyzes 7–9 listing photos against the IRS classification rules and returns a line-item §168(k) estimate closely calibrated to a formal $5K–$8K cost seg study.
Three representative Windham listings spanning entry, mid, and high price tiers. Year 1 deduction is estimated as a range around the Windham market bonus-eligible average (23.4% ± 3 percentage points). Click any card to run a full property report to tighten to one exact number.
The market-median numbers on this page are a screening tool, not a final answer. Here's how STR investors and their CPAs actually convert a market rank + median bonus-eligible % into an underwriting number for a specific offer.
For further reading on the pre-offer bonus-depreciation workflow, see how to use §168(k) before closing on a short-term rental. To catch missed prior-year bonus depreciation using Form 3115, see the Form 3115 catch-up guide.
Verified as of 2026-08-16 against primary jurisdiction sources. See the full Windham STR regulations page for jurisdiction breakdown, ordinance section numbers, and 5-question FAQ.
Read the full Windham STR regulations profile →Verified as of 2026-08-16 against primary jurisdiction sources. See the full Windham STR regulations page for jurisdiction breakdown, ordinance section numbers, and 5-question FAQ.
Read the full Windham STR regulations profile →Windham's #38 rank comes from the DepreciMax Top 50 methodology: we score every active STR-suitable listing across the nation's most-watched STR markets on land value, state §168(k) conformity, and amenity mix, then rank markets by the median bonus-eligible % of their active listings. Individual property estimates are closely calibrated to a formal cost segregation study.
More detail in the Top 50 Markets methodology section.
Run any active Windham listing through the DepreciMax property scorer. Free market search shows you every listing ranked by bonus depreciation potential. $99 per detailed AI report on a specific property — closely calibrated to a formal cost seg study.
Score Windham Properties →All 50 markets ranked by bonus depreciation score, with category filters and the full methodology.
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