Seasonal and Monthly Winter Rentals near Stratton, VT

For a whole ski season or a month at a time, Stay Stratton lists three options: the Ledge Loft in South Londonderry for the full winter (Dec 1 – Apr 1, $15,000 plus utilities), furnished monthly rooms at the Three Mountain Inn in Jamaica village (28-night minimum, including seasonal workforce housing), and the Jamaica Tiny Cabin, which welcomes long stays.

RentalWhereStaySleepsPrice
Ledge LoftSouth Londonderry, ~15 min to StrattonFull winter, Dec 1 – Apr 16$15,000 plus utilities
Three Mountain InnJamaica village28 nights minimumRoomsAsk the owner
Jamaica Tiny CabinJamaica, ~10 mi to StrattonNightly; long stays welcome2Ask the owner

What to know about a Stratton seasonal rental

  • Most seasonal rentals run December 1 to April 1 and are paid up front or in a few installments.
  • Utilities are often extra. Ask what heat and electricity typically cost per month in January.
  • Expect to need references, renters insurance and snow tires.
  • Check who plows the driveway and how trash is handled; many Winhall and Jamaica homes use the town transfer station.
  • Pets are case by case. The Ledge Loft considers well-mannered pets with approval.

FAQ

How much is a seasonal ski rental near Stratton?

It varies with size and distance to the mountain. On this site, the Ledge Loft, a newly built 3-bedroom about 15 minutes from Stratton, rents for $15,000 for December 1 to April 1 plus utilities.

Is there housing near Stratton for seasonal workers?

Yes. The Three Mountain Inn in Jamaica offers furnished rooms by the month, including coliving and workforce housing, with a 28-night minimum.

Do you list my seasonal rental?

Yes, for free. See List your home.