Vermont Stays, Thoughtfully Managed.
Simple Stay Property Management — the Northeast Kingdom's trusted partner for guests and homeowners alike.
One more property onboarding for the 2026 season. Accepting select new owner partners →
Inside our Vermont stays
Romantic tiny house for two
Designer retreat on 117 acres
Right on Lake Willoughby
Sleeps 8, 4 mi to Jay Peak
Private pond on 100+ acres
Cozy cabin near Craftsbury Outdoor Center
Two homes, one 117-acre estate
Quiet foliage escape by the pond
Mountain-view kitchen, family-sized
On the historic village common
Cabin life in the mountains
Minutes to Jay Peak Resort
Off-grid feel, Jay Peak nearby
Light-filled estate for groups
Ski-weekend basecamp for 8
Plan your trip
Tell us how you travel — we'll point you to the right stay.
Skiing & snow weekends
Romantic getaway
Family reunion or large group
Foliage & quiet escape
Outdoor adventure & cabin life
Lakeside & summer escapes
Why guests choose Simple Stay
Handpicked Vermont stays
Every home personally inspected and prepped by our local team.
Real humans, anytime
Message us directly during your stay; no call centers, no bots.
Local Northeast Kingdom expertise
Insider tips on trails, restaurants, and seasons from people who live here.
Discover handpicked Vermont getaways
Browse our curated collection of short-term rentals across the Northeast Kingdom — each one thoughtfully prepared for an unforgettable stay.
View Lodging →Let your property work for you
We handle everything — from listing and photography to guest communication and inspections — so you can earn more with less stress.
Learn About Partnering →Thinking about partnering with us?
Common questions from Vermont homeowners considering Simple Stay.
Ready when you are.
Book a stay, or talk to us about managing your property.