✨ As Featured by Dirt & GlassSimple Haven
Greater Jay Peak Region
Sleeps 2Pets
A beautifully designed retreat that blends modern comfort with natural Vermont surroundings. Perfect for those seeking a restorative escape.
Find Your Stay
Each stay is handpicked, locally managed, and ready to welcome you.
Reserve foliage now — October books by late July
Peak foliage weekends are our most-requested dates of the year.
✨ As featured by Dirt & Glass
Our tiny house was featured by Dirt and Glass — one of the most celebrated cabin photographers in the country. See what made it special.
View Simple Haven →
Where you'll find us
Loading map…
Coming soon
Direct booking on simplestayvt.com
Soon you'll be able to book any of our Vermont stays directly with us — no platform fees, the same boutique hospitality. In the meantime, message us anytime.
✨ As Featured by Dirt & Glass
Peak and Pine
Jay Peak Region
Sleeps 8PetsFamily
Ideally located just 4 miles from Jay Peak's Stateside slopes — the perfect base for a ski getaway or mountain retreat.
Blue Haven
Northeast Kingdom
Sleeps 8Family
Luxury custom timber framed home situated on 117 acres. Relax and recharge in this thoughtfully appointed space.
Craftsbury Carriage House
Northeast Kingdom
Sleeps 4PetsFamily
A charming carriage house near the Craftsbury Outdoor Center — ideal for outdoor enthusiasts and those craving a cozy, characterful stay.
MMH
Lake Willoughby
Sleeps 8Family
A modern and welcoming property with stunning views of Lake Willoughby. The perfect Vermont summer getaway.
Daniel's Pond
Northeast Kingdom
Sleeps 6Family
Wake up to tranquil pond views and birdsong. A peaceful Vermont escape for nature lovers and those looking to truly unplug.
Cottage on the Common
Jay Peak Region — Montgomery Center
Sleeps 6PetsFamily
A historic Vermont cottage full of charm and character, situated on the common in a picturesque local village.
Blue Haven Estate
Northeast Kingdom
Sleeps 13Family
The full Blue Haven experience — book the entire 117 acre estate for a private, spacious retreat perfect for groups and family gatherings spread out between two houses.
Maple Mountain
Northeast Kingdom
Sleeps 5PetsFamily
A true Vermont cabin escape tucked away in the woods making it close to nature and the ideal four-season destination.
Journey's End
Jay Peak Resort
Sleeps 2Family
A thoughtfully designed one-bedroom condo at Jay Peak — ski-in/ski-out in winter, golf and waterpark steps away in summer. Sleeps 2 with a cozy gas fireplace and private balcony.
Dutch Hollow Hideaway
Northeast Kingdom
Sleeps 4PetsFamily
A charming 2-bedroom cabin on 100+ private acres overlooking apple orchards, with a private swimming pond, hiking trails, and a stream bordering the property.
Coming SoonNew Stay Coming Soon
Jay Peak Region
Another thoughtfully managed Vermont home is being prepared for guests. Full listing details coming soon.