Companies · Founder
Pendleton Places
Pendleton Places was a short-term rental management company in the Raleigh–Durham Triangle, founded by Justin Winter in 2020. It grew to 40+ properties and $2M+ in annual revenue by running them on a shared-operations hotel model rather than as isolated listings. The company is no longer operating.
- Properties
- 40+
- Annual revenue
- $2M+
- Market
- Raleigh–Durham
How it started
Pendleton Places began in 2020 with one property: Justin and his wife converted their former Durham home into a short-term rental shortly before the pandemic hit. It was not a business plan — the kind of decision that looks strategic only in hindsight. What followed was a stretch in which the Triangle absorbed an unusual amount of inbound relocation, and the gap between the housing people needed and the housing available widened fast.
Coming out of a career in ecommerce and software rather than real estate, the interesting problem was operational: short-term rentals are a logistics and systems business wearing a hospitality costume. Pendleton Places was built to run that system for other owners.
What the company did
Pendleton Places provided full-service management for short-term rental owners across Raleigh and Durham: listing and pricing, guest communication, turnover and cleaning coordination, maintenance, and the compliance overhead individual owners consistently underestimate. The operating model was the differentiator — the portfolio was run as a single distributed hotel with shared operations, rather than as isolated listings, and Justin did the interior design across it himself.
A meaningful share of stays were not the weekend-tourist use case the category is usually associated with. Guests stayed for weeks and months — people relocating for work, families between homes, medical stays — often at rates below what an extended hotel stay would have cost them.
The affordable housing question
In September 2022 the ABC11 I-Team investigated what the growth in short-term rentals was doing to the Triangle’s affordable housing supply, and interviewed Justin as an operator inside that market.
It is a fair question and it deserves a real answer rather than a defensive one. The honest version is that the category does both things at once: it removes units from the long-term rental pool, and it also houses people who would otherwise struggle to find anywhere to stay at all — frequently at a lower cost than the alternatives available to them. Both of those were true of this portfolio. Which effect dominates is a function of local supply, regulation, and concentration, and it is worth measuring rather than assuming.
Where it landed
Pendleton Places is no longer operating and its original website has been retired. This page is the canonical record of the company and the work.
FAQ
Is Pendleton Places still operating?
No. Pendleton Places was a short-term rental management company Justin Winter founded in 2020 in the Raleigh-Durham Triangle, growing it to 40+ properties and $2M+ in annual revenue before it ceased operating in 2025.
What did Pendleton Places do?
Pendleton Places managed short-term rental properties using a shared-operations hotel model across the Raleigh-Durham market, scaling to 40+ properties and $2M+ in annual revenue under founder and CEO Justin Winter.