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
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
Feb 3 – 10
Cabin in Cavendish
4.96 out of 5 average rating, 138 reviewsThe Cozy Little Red Cabin
Oct 27 – Nov 3
Cabin in Royalton
4.92 out of 5 average rating, 168 reviewsApple Hill Cabin at Four Springs Farm
Oct 6 – 13
Cabin in Bridgewater Corners
4.82 out of 5 average rating, 187 reviewsCozy Mountain Cabin Close to Killington &Woodstock
Jun 14 – 21
Cabin in Sharon
4.92 out of 5 average rating, 246 reviewsCozy Cabin ‘birds nest’ off-grid seclusion
Aug 31 – Sep 7
Cabin in Londonderry
4.75 out of 5 average rating, 354 reviewsArt Studio Barn - hot tub & sauna access #1 Airbb
Jun 21 – 28
Cabin in Hartford
4.81 out of 5 average rating, 171 reviewsRustic Cabin Retreat
Jan 14 – 21
Home in Tunbridge
4.9 out of 5 average rating, 83 reviewsPrivate house on a hill
Dec 10 – 15
Tiny house rentals with a patio
Home in West Windsor
4.96 out of 5 average rating, 56 reviewsBirdie's Nest Guesthouse
Jan 29 – Feb 5
Cabin in Rochester
5.0 out of 5 average rating, 17 reviewsThe Creek Cabin at Sky Hollow
Oct 8 – 15
Tiny home in Rutland
4.95 out of 5 average rating, 20 reviewsCurious Little Cottage
Feb 21 – 28
Tiny home in Bethel
4.84 out of 5 average rating, 19 reviewsThe Cabin on the Pond
Aug 10 – 17
Cabin in Bethel
4.96 out of 5 average rating, 48 reviewsThe Gourmet Cabin at Stitchdown Farm
Sep 7 – 14
Tiny home in Chester
5.0 out of 5 average rating, 82 reviewsBearfoot Cottage: Tiny House w/ Hot Tub near Okemo
Apr 1 – 8
Cottage in Ludlow
5.0 out of 5 average rating, 4 reviewsNEW Guest Cottage on 23 Acres
Sep 3 – 10
Tiny home in Chester
5.0 out of 5 average rating, 20 reviewsZen of the Woods Tiny Cabin in Okemo Valley
Jul 15 – 22
Tiny house rentals with outdoor seating
Treehouse in Hancock
4.94 out of 5 average rating, 641 reviewsThe Beaver Pond Treehouse @ Vermont ReTREEt
Sep 11 – 18
Cabin in Royalton
4.94 out of 5 average rating, 232 reviewsScandinavian design Cabin w/ private hiking trail
Sep 8 – 15
Cabin in Fairlee
4.94 out of 5 average rating, 114 reviewsFairlee Log Cabin
Nov 19 – 26
Campsite in Vershire
4.87 out of 5 average rating, 153 reviewsCamping on a Private Pond
Dec 5 – 12
Tiny home in Chester
4.9 out of 5 average rating, 156 reviewsSage House at Camp Greenwood Vermont - w/ sauna!
Mar 12 – 19
Treehouse in Hartland
4.93 out of 5 average rating, 107 reviewsLovely Treehouse Stay at Wise Pines- SoBo
Aug 7 – 14
Guesthouse in Hartland
4.86 out of 5 average rating, 42 reviewsCozy Guest Cabin w/private hot tub and bath
Aug 27 – Sep 3
Tiny home in Pittsfield
5.0 out of 5 average rating, 18 reviewsTiny Home: VT Mountain Cabin
Dec 17 – 24
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