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Select Board weighs software, enforcement changes after $166K in short‑term rental fees

Town of Winhall Select Board · July 1, 2026
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Summary

Christie Boswell told the board the town collected $166,000 in STR fees through Nov. 30 and proposed a $19,000 contract for new STR software; board discussed incorporating transfer‑station enforcement and Good Neighbor Guidelines into the STR ordinance and distributing guidance before Christmas.

The Town of Winhall has collected $166,000 in short‑term rental (STR) fees through Nov. 30, Select Board member Christie Boswell reported Dec. 3, and asked the board to approve a switch to new management software that would improve enforcement and reporting.

Boswell briefed the board on a proposed contract with David Deckert costing $19,000. "The new software contract (with David Deckert) would be $19K," she said, noting the town would pay half upon signing and the balance when the system goes live, with a target transition away from GovOS by March. The board discussed adding rules to the STR ordinance requiring homeowners to provide proof of guest waste removal and allowing the town to assess transfer‑station fees against hosts when renters improperly use town services. Isaacs asked that the Good Neighbor Guidelines packet be prepared and distributed before Christmas; Beth Grant requested the board be sent supporting information to include in that packet.

Board members also discussed operational details such as notices to hosts, the timing of contract payments, and a March deadline to give notice to the current vendor. Staff were directed to proceed with contracting steps after confirming terms and timing.