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
Cabin in Woodstock
4.96 out of 5 average rating, 191 reviewsCabin by the Stream on 27 Acres
Sep 1 – 8
Cabin in Cavendish
4.96 out of 5 average rating, 138 reviewsThe Cozy Little Red Cabin
Jul 17 – 24
Cabin in Royalton
4.92 out of 5 average rating, 168 reviewsApple Hill Cabin at Four Springs Farm
Jun 26 – Jul 3
Cabin in Bridgewater Corners
4.82 out of 5 average rating, 186 reviewsCozy Mountain Cabin Close to Killington &Woodstock
Aug 23 – 30
Cabin in Sharon
4.92 out of 5 average rating, 246 reviewsCozy Cabin ‘birds nest’ off-grid seclusion
Oct 13 – 20
Cabin in Londonderry
4.75 out of 5 average rating, 354 reviewsArt Studio Barn - hot tub & sauna access #1 Airbb
Jun 29 – Jul 6
Cabin in Hartford
4.81 out of 5 average rating, 171 reviewsRustic Cabin Retreat
May 7 – 14
Cabin in Londonderry
4.95 out of 5 average rating, 75 reviewsQuaint cottage near 4 ski resorts
Mar 22 – 29
Tiny house rentals with a patio
Tiny home in Rutland
4.95 out of 5 average rating, 19 reviewsCurious Little Cottage
Nov 11 – 18
Tiny home in Chester
5.0 out of 5 average rating, 19 reviewsZen of the Woods Tiny Cabin in Okemo Valley
May 22 – 29
Cabin in Rochester
5.0 out of 5 average rating, 17 reviewsThe Creek Cabin at Sky Hollow
Sep 28 – Oct 5
Home in West Windsor
4.96 out of 5 average rating, 56 reviewsBirdie's Nest Guesthouse
Feb 26 – Mar 5
Cabin in Bethel
4.96 out of 5 average rating, 48 reviewsThe Gourmet Cabin at Stitchdown Farm
Oct 1 – 8
Tiny home in Chester
5.0 out of 5 average rating, 82 reviewsBearfoot Cottage: Tiny House w/ Hot Tub near Okemo
Apr 19 – 26
Cottage in Ludlow
5.0 out of 5 average rating, 4 reviewsNEW Guest Cottage on 23 Acres
Jun 19 – 26
Tiny home in Ludlow
4.6 out of 5 average rating, 20 reviewsCozy Tiny Home on Black River - Walk to Town
Oct 25 – Nov 1
Tiny house rentals with outdoor seating
Cottage in Quechee
4.98 out of 5 average rating, 193 reviews“The Maple Moose”, modern cabin near Woodstock
Sep 9 – 16
Treehouse in Hancock
4.94 out of 5 average rating, 641 reviewsThe Beaver Pond Treehouse @ Vermont ReTREEt
Sep 11 – 18
Campsite in Vershire
4.87 out of 5 average rating, 153 reviewsCamping on a private pond
Sep 17 – 24
Cabin in Mount Holly
4.98 out of 5 average rating, 206 reviewsPrivate Cabin/Pets OK/Minutes to Okemo/ Fast Wifi
Sep 22 – 29
Cabin in Royalton
4.94 out of 5 average rating, 232 reviewsScandinavian design Cabin w/ private hiking trail
Dec 13 – 20
Cabin in Fairlee
4.94 out of 5 average rating, 114 reviewsFairlee Log Cabin
Dec 2 – 9
Treehouse in Hartland
4.93 out of 5 average rating, 106 reviewsLovely Treehouse Stay at Wise Pines- SoBo
Nov 18 – 25
Guesthouse in Hartland
4.86 out of 5 average rating, 42 reviewsCozy Guest Cabin w/private hot tub and bath
Jul 8 – 15
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