Question 1

Which is better for STR bonus depreciation in 2026: Winter Park, CO or Killington, VT?

Accepted Answer

Different price tiers, different investors. Winter Park has the highest Diamond density in the Study (81%) but at a $2.8M median entry price — ski-in/ski-out condos with resort-grade FF&E and heavy HOA common-area allocation. Killington is a viable entry-level ski market at $929K but with meaningfully weaker depreciation math.

Question 2

What is the typical Year-1 bonus depreciation write-off on a Winter Park short-term rental vs a Killington short-term rental?

Accepted Answer

On the median Winter Park STR ($2.8M), Year-1 bonus depreciation is approximately ~$728K (26% bonus-eligible of purchase price). On the median Killington STR ($929K), Year-1 is approximately ~$214K (23% bonus-eligible). Higher bonus-eligible % combined with lower purchase price typically yields the best return-on-tax-dollars.

Question 3

When should an STR investor choose Winter Park over Killington?

Accepted Answer

Choose Winter Park if: High-earner STR investors targeting the $2M+ tier who want the strongest ski-market depreciation profile in the U.S. and the credential of a top Colorado resort. Choose Killington if: Sub-$1M ski-market investors. Accept lower Diamond density (52%) for a Vermont ski market at a workable entry price.

Winter Park, CO vs Killington, VT — short-term rental bonus depreciation head-to-head

Winter Park wins on depreciation math

Winter Park vs Killington — data head-to-head

When to choose Winter Park

When to choose Killington

Not sure which is right? Run the numbers on a specific property.

Metric	Winter Park, CO	Killington, VT
Median bonus-eligible % (of purchase price)	26%Better tax math	23%
Median STR purchase price	$2.8M	$929K
Typical Year-1 write-off	~$728K	~$214K
Median land ratio	15%	22%
Diamond density (≥24% bonus-eligible listings)	81%	52%