Short-Term Rental Management in the Shires of Vermont

What the Shires Are

Vermont's other 13 counties each have one shire town; Bennington County has two, which is where the name comes from. The Shires of Southwestern Vermont, a nonprofit destination marketing organization based in Bennington, uses the name for the county's towns, among them Arlington, Bennington, Dorset, Manchester, Peru, Pownal, Readsboro, Rupert, Sandgate, Searsburg, Shaftsbury, Sunderland, Winhall and Woodford. Historic Route 7A, now the Shires of Vermont Byway, ties them together between the Taconic and Green mountains.

The two ends of the county play different roles for guests:

• The North Shire around Manchester and Dorset is the resort end: Hildene, the Robert Lincoln estate in Manchester; Bromley Mountain in Peru; the Dorset Theatre Festival from June through September; and Emerald Lake State Park in East Dorset. Manchester is also a designated Appalachian Trail Community, about four miles from the Appalachian and Long Trails.
• The South Shire around Bennington is the working end: the 306-foot Bennington Battle Monument, Vermont's tallest structure; the Bennington Museum and its Grandma Moses collection; Bennington College; and Southwestern Vermont Medical Center, a member of Dartmouth Health.

The Seasons

Summer is the busiest season across the county: theater in Dorset, Hildene and hiking in Manchester, the monument (open from May) in Bennington, and swimming at the Dorset Quarry and Emerald Lake.

Fall is foliage along Route 7A and the back roads, the region's best-known draw, plus college visits in Bennington. See fall foliage towns for vacation rentals.

Winter centers on Bromley in Peru and the other southern Vermont ski areas, which favors the North Shire. Bennington winters lean toward hospital staff and other longer stays.

Spring is mud season and registration renewal time.

The Rules Landscape

The Shires show how far Vermont town rules can differ. As of 6 October 2026:

• Manchester Village requires annual registration ($300), a caretaker within 30 minutes, bear-proof trash and an occupancy cap of two per bedroom plus two, under its Short-Term Rental Ordinance. The rest of the Town of Manchester had no short-term rental chapter in its ordinance list.
• Dorset adopted a town-wide ordinance in April 2024 (amended January 2025) with the same $300 fee, caretaker and occupancy terms, plus a parking standard of 1.2 spaces per guest room.
• Bennington has no short-term rental ordinance; the town says rentals must meet the Vermont Rental Housing Codes and offers code enforcement inspections. The Village of North Bennington adopted its own ordinance with a $100 annual fee, and Shaftsbury was drafting a bylaw in September 2026, according to local reporting.

On taxes, the Department of Taxes lists Manchester (since 2008 for rooms) and Winhall with a 1% local option rooms tax, and Peru added one in July 2026. Bennington and Dorset are not on the list. A rental charges 12% or, in those towns, 13%. Statewide rules on platform collection, fire safety and the 8-person occupant load are on our Vermont rules and taxes page.

How New England Host Co Works in the Shires

New England Host Co works across Vermont, and every home must be within 45 minutes of its crew's base, so tell us your address in the Shires and we will confirm. We do not manage a home in Bennington County today; our Vermont home is in Ludlow, near Okemo. In towns with a caretaker rule, plan who fills that role before you register. Housekeeping and an inspection happen after every stay, pricing is reviewed daily with PriceLabs, and registration fees stay with the owner. See all Vermont areas on our Vermont page or ask on the contact page.

FAQ

Why Is It Called the Shires of Vermont?

Bennington County has two shire towns, or county seats: Bennington in the South Shire and Manchester in the North Shire. Every other Vermont county has one.

Which Shires Towns Require Short-Term Rental Registration?

As of October 2026, Manchester Village and Dorset require annual registration at $300, and North Bennington village has adopted a $100 annual fee. The Town of Bennington has no ordinance, and other towns may be drafting rules.

What Tax Does a Shires Rental Charge?

12% in most towns (9% rooms tax plus the 3% surcharge), and 13% in Manchester, Winhall and Peru, which have a 1% local option rooms tax.

This page is general information as of October 2026, not legal or tax advice.