Tiny house vacation rentals in Windsor County
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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
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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
Jun 20 – 27
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
Oct 3 – 10
Cabin in Bridgewater Corners
4.82 out of 5 average rating, 186 reviewsCozy Mountain Cabin Close to Killington &Woodstock
Aug 2 – 9
Cabin in Sharon
4.92 out of 5 average rating, 246 reviewsCozy Cabin ‘birds nest’ off-grid seclusion
Dec 23 – 30
Cabin in Londonderry
4.75 out of 5 average rating, 354 reviewsArt Studio Barn - hot tub & sauna access #1 Airbb
Jun 19 – 26
Cabin in Hartford
4.81 out of 5 average rating, 171 reviewsRustic Cabin Retreat
Nov 10 – 17
Cabin in Londonderry
4.95 out of 5 average rating, 75 reviewsQuaint cottage near 4 ski resorts
Mar 27 – Apr 3
Tiny house rentals with a patio
Home in West Windsor
4.96 out of 5 average rating, 56 reviewsBirdie's Nest Guesthouse
Nov 22 – 29
Tiny home in Rutland
4.95 out of 5 average rating, 19 reviewsCurious Little Cottage
Apr 3 – 10
Cabin in Rochester
5.0 out of 5 average rating, 17 reviewsThe Creek Cabin at Sky Hollow
Sep 28 – Oct 5
Tiny home in Chester
5.0 out of 5 average rating, 82 reviewsBearfoot Cottage: Tiny House w/ Hot Tub near Okemo
Sep 11 – 18
Tiny home in Chester
5.0 out of 5 average rating, 19 reviewsZen of the Woods Tiny Cabin in Okemo Valley
Jul 17 – 24
Cabin in Bethel
4.96 out of 5 average rating, 48 reviewsThe Gourmet Cabin at Stitchdown Farm
Sep 5 – 12
Cottage in Ludlow
5.0 out of 5 average rating, 4 reviewsNEW Guest Cottage on 23 Acres
May 22 – 29
Tiny home in Ludlow
4.6 out of 5 average rating, 20 reviewsCozy Tiny Home on Black River - Walk to Town
Oct 30 – Nov 6
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
Dec 11 – 18
Cabin in Royalton
4.94 out of 5 average rating, 232 reviewsScandinavian design Cabin w/ private hiking trail
Dec 16 – 23
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
Dec 18 – 25
Cabin in Fairlee
4.94 out of 5 average rating, 114 reviewsFairlee Log Cabin
Apr 15 – 22
Treehouse in Hartland
4.93 out of 5 average rating, 107 reviewsLovely Treehouse Stay at Wise Pines- SoBo
Aug 7 – 14
Tiny home in Chester
4.9 out of 5 average rating, 156 reviewsSage House at Camp Greenwood Vermont - w/ sauna!
Aug 8 – 15
Guesthouse in Hartland
4.86 out of 5 average rating, 42 reviewsCozy Guest Cabin w/private hot tub and bath
Oct 20 – 27
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