Short-Term Rental Management in the Okemo Valley, VT

What the Okemo Valley Is

The Okemo Valley Regional Chamber of Commerce uses the name for 12 towns: Andover, Baltimore, Cavendish, Chester, Grafton, Londonderry, Ludlow, Mount Holly, Plymouth, Shrewsbury, Weathersfield and Weston. Route 100 and Route 103 tie them together, and most sit in Windsor County, with Mount Holly and Shrewsbury in Rutland County and Londonderry and Grafton in Windham County.

The towns play different roles for guests:

• Ludlow is the ski town. Okemo Mountain Resort lists 123 trails, 20 lifts and a 2,200-foot vertical drop, and it is on the Epic Pass. Jackson Gore keeps the resort busy in summer with a mountain coaster, golf and family activities.
• Weston is the village-green town, home to the original Vermont Country Store and the Weston Theater Company.
• Londonderry has Magic Mountain, a smaller ski area with lifts opening in early December.
• Plymouth draws history visitors to the President Calvin Coolidge State Historic Site at Plymouth Notch, and swimmers and anglers to the chain of lakes running south toward Ludlow.
• Chester, Grafton and Cavendish are village and foliage stops to the east rather than ski towns.

Okemo State Forest spans 7,983 acres across Andover, Ludlow, Mount Holly and Weston, with the Healdville Trail climbing to a summit fire tower.

The Seasons

Winter, from the first lift openings to early April, is the main season for most homes near Okemo and Magic. Fall foliage brings a second peak along Route 100, especially in Weston and the villages. Summer is steadier than many owners expect thanks to Jackson Gore, golf, the lakes and theater. Spring mud season is the slow stretch, and the right time for maintenance.

The Rules Landscape, as of October 2026

This is a region where the town line matters. Under 24 V.S.A. section 2291(29), each Vermont town can regulate short-term rentals by ordinance, and the Okemo Valley towns have gone different ways:

• Ludlow: no short-term rental ordinance or registry in the town or village ordinance lists, though a registry was debated through a public hearing in August 2025. See our Ludlow rules page.
• Weston: zoning amended July 14, 2026; no short-term rental ordinance on the town's list.
• Londonderry: an annual STR license is required, with a one-new-license-per-owner rule, a 50-night cap for first-time unhosted licenses, and licenses that expire each June 30.
• Chester: an ordinance amended June 19, 2024 caps the town at 65 registrations a year, limits each owner to two, sets a $600 annual fee for unhosted rentals, and imposes a one-year wait after a sale.

Taxes vary too. Every short-term rental pays the 9% Vermont rooms tax and the 3% short-term rental surcharge. Ludlow (since July 2025) and Londonderry (rooms since July 2023) add a 1% local option rooms tax, for 13%. The state picture, including fire safety's 8-occupant rule, is on our Vermont rules and taxes page.

How New England Host Co Works Here

Southern Vermont, centered on Ludlow at Okemo Mountain, is one of our service areas, and we manage a modern 3BR/2BA three minutes from Okemo. Every home must be within 45 minutes of its crew's base, so we confirm by address.

Full-service management covers listing, photography, pricing reviewed daily with PriceLabs, guest messaging, and housekeeping with an inspection after every stay, done by local crews we engage and manage. Co-hosting is offered instead for owners who want to keep part of the work. Read more on our Okemo management page or ask for a free property analysis on the contact page.

FAQ

Which Okemo Valley Towns Require Short-Term Rental Registration?

As of October 2026, Londonderry and Chester have short-term rental ordinances with annual registration or licensing. We found none published in Ludlow or Weston. Check with each town before you list.

What Is the Total Tax on an Okemo Valley Rental?

12% in most towns (9% rooms tax plus the 3% surcharge), and 13% in Ludlow and Londonderry, which add a 1% local option rooms tax.

Do You Manage Homes in the Okemo Valley?

Yes. We manage a 3-bedroom, 2-bath home three minutes from Okemo Mountain in Ludlow, and we confirm other homes by address against our 45-minute crew rule.