
Tiny house vacation rentals in Windsor County
Find and book unique tiny house rentals on Airbnb
Top-rated tiny house rentals in Windsor County
Guests agree: these tiny house rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Windsor County tiny house rentals
Family-friendly tiny house 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 house 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 house 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
- Kid-friendly rentals Windsor County
- Rentals with a fire pit Windsor County
- Villa rentals Windsor County
- Rentals with an accessible height toilet Windsor County
- Rentals with a fireplace Windsor County
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- Rentals with pools Windsor County
- Farmstay rentals Windsor County
- Townhouse rentals Windsor County
- Rentals with lake access Windsor County
- Rentals with a kayak Windsor County
- Rentals with a patio Windsor County
- Bed and breakfasts Windsor County
- Rentals with breakfast Windsor County
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- Family-friendly rentals Windsor County
- Rentals with outdoor seating Windsor County
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- Rentals with an EV charger Windsor County
- Fitness-friendly rentals Windsor County
- Rentals with an accessible height bed Windsor County
- Rentals with a hot tub Windsor County
- Rentals with a sauna Windsor County
- Apartment rentals Windsor County
- Rentals with beach access 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
- Dorset Field Club
- Ekwanok Country Club
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Fort Ticonderoga
- Autumn Mountain Winery
- Cozy Cottages & Otter Valley Winery
- Crotched Mountain Ski and Ride
- Country Club of New Hampshire
- Brattleboro Ski Hill
- Bretwood Golf Course
- Veterans Memorial Recreation Area Ski Hill
- Fox Run Golf Club
- Hooper Golf Course
- Things to do Windsor County
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- Family travel hub Tips and inspiration
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- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes