
Tiny house holiday rentals in Windsor County
Find and book unique tiny home rentals on Airbnb
Top-rated tiny home rentals in Windsor County
Guests agree: these tiny home rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for tiny home rentals in Windsor County
Family-friendly tiny home rentals

5BR Chalet in Historic Town bet Killington & Okemo

Beautiful Art Studio with hot tub/sauna #1 Airbnb

Rustic Cabin Retreat

Hideaway Cabin by the Stream on 27 Acres

Fernando’s hideaway - XCountry Skiing Cabin

Vermont Chalet

Springhouse Cabin

The Pond Cabin at Sky Hollow
Tiny home rentals with a patio

Cozy Cabin in the Woods

Cliffside Cabin # 2 South Royalton, VT

The Creek Cabin at Sky Hollow

The Gourmet Cabin at Stitchdown Farm

Curious Little Cottage

Red Barn Cabin Near Okemo

Andas Hus: Little Luxury

Cozy Tiny Home on Black River - Walk to Town
Tiny home rentals with outdoor seating

Twin Tiny Homes, A Truly Unique Vermont Escape!

Cozy tiny house w/private hot tub

Stunning Artist Retreat Cabin

Private Cabin/PetsOK/Minutes to Okemo/AC/Fast Wifi

Tiny Home: VT Mountain Cabin

Corncrib Tiny House Glamping Cabin

Camping on a Private Pond

Private Modern Cabin w/View of Fields, Hills
Destinations to explore
- Waterfront rentals Windsor County
- Rentals with a kayak Windsor County
- Rentals with outdoor seating Windsor County
- Rentals with a firepit Windsor County
- Rentals with an accessible-height toilet Windsor County
- Rentals with a fireplace Windsor County
- Apartment rentals Windsor County
- Family-friendly rentals Windsor County
- Beachfront rentals Windsor County
- Rentals with breakfast Windsor County
- Rentals with an accessible-height bed Windsor County
- Ski-in/ski-out rentals Windsor County
- Rentals with an EV charger Windsor County
- Villa rentals Windsor County
- Rentals with pools Windsor County
- Pet-friendly rentals Windsor County
- Farm stay rentals Windsor County
- Rentals with a hot tub Windsor County
- Rentals with a patio Windsor County
- Bed and breakfasts Windsor County
- Townhouse rentals Windsor County
- Cottage rentals Windsor County
- Flat rentals Windsor County
- Rentals with beach access Windsor County
- Family-friendly rentals Windsor County
- Rentals with a sauna Windsor County
- Rentals with a washing machine and dryer Windsor County
- Rentals with lake access Windsor County
- Cabin rentals Windsor County
- Chalet rentals Windsor County
- Guest house rentals Windsor County
- House rentals Windsor County
- Private suite rentals Windsor County
- Fitness-friendly rentals Windsor County
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- Okemo Mountain Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Pats Peak Ski Area
- Ragged Mountain Resort
- Monadnock State Park
- Tenney Mountain Resort
- Mount Snow Ski Resort
- Mount Sunapee Resort
- Ekwanok Country Club
- Dorset Field Club
- Hildene, The Lincoln Family Home
- Fort Ticonderoga
- Cozy Cottages & Otter Valley Winery
- Autumn Mountain Winery
- Brattleboro Ski Hill
- Bretwood Golf Course
- Santa's Land USA
- Crotched Mountain Ski and Ride
- Hooper Golf Course
- Bromley Mountain Ski Resort
- Baker Hill Golf Club
- Country Club of New Hampshire
- Things to do Windsor County
- Food and drink Windsor County
- Things to do Vermont
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