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 Royalton
4.92 out of 5 average rating, 168 reviewsApple Hill Cabin at Four Springs Farm
Jul 21 – 28
Cabin in Cavendish
4.96 out of 5 average rating, 138 reviewsThe Cozy Little Red Cabin
Dec 20 – 27
Cabin in Bridgewater Corners
4.82 out of 5 average rating, 187 reviewsCozy Mountain Cabin Close to Killington &Woodstock
Oct 11 – 18
Cabin in Sharon
4.92 out of 5 average rating, 246 reviewsCozy Cabin ‘birds nest’ off-grid seclusion
Dec 20 – 27
Cabin in Londonderry
4.75 out of 5 average rating, 354 reviewsArt Studio Barn - hot tub & sauna access #1 Airbb
Jul 3 – 10
Cabin in Hartford
4.81 out of 5 average rating, 171 reviewsRustic Cabin Retreat
Mar 28 – Apr 4
Home in Landgrove
5.0 out of 5 average rating, 21 reviewsLandgrove Charm - Post and Beam Barn House
Sep 3 – 10
Home in Tunbridge
4.9 out of 5 average rating, 83 reviewsPrivate house on a hill
Jan 3 – 8
Tiny house rentals with a patio
Home in West Windsor
4.96 out of 5 average rating, 56 reviewsBirdie's Nest Guesthouse
Jan 12 – 19
Cabin in Rochester
5.0 out of 5 average rating, 17 reviewsThe Creek Cabin at Sky Hollow
Aug 30 – Sep 6
Tiny home in Bethel
4.84 out of 5 average rating, 19 reviewsThe Cabin on the Pond
Sep 20 – 27
Tiny home in Rutland
4.95 out of 5 average rating, 20 reviewsCurious Little Cottage
Feb 24 – Mar 3
Tiny home in Chester
5.0 out of 5 average rating, 84 reviewsBearfoot Cottage: Tiny House w/ Hot Tub near Okemo
Aug 28 – Sep 4
Cabin in Bethel
4.96 out of 5 average rating, 48 reviewsThe Gourmet Cabin at Stitchdown Farm
Jul 8 – 15
Cottage in Ludlow
5.0 out of 5 average rating, 4 reviewsNEW Guest Cottage on 23 Acres
May 16 – 23
Cabin in Mount Holly
4.89 out of 5 average rating, 79 reviewsOkemo A-Frame - Floor Hammock, Sauna & Hot Tub
Dec 13 – 20
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
Jan 5 – 12
Campsite in Vershire
4.87 out of 5 average rating, 154 reviewsCamping on a Private Pond
Feb 11 – 18
Treehouse in Hancock
4.94 out of 5 average rating, 641 reviewsThe Beaver Pond Treehouse @ Vermont ReTREEt
Sep 11 – 18
Cabin in Fairlee
4.94 out of 5 average rating, 114 reviewsFairlee Log Cabin
Dec 6 – 13
Cabin in Royalton
4.94 out of 5 average rating, 231 reviewsScandinavian design Cabin w/ private hiking trail
Jan 31 – Feb 7
Tiny home in Chester
4.9 out of 5 average rating, 156 reviewsSage House at Camp Greenwood Vermont - w/ sauna!
Mar 15 – 22
Treehouse in Hartland
4.93 out of 5 average rating, 107 reviewsLovely Treehouse Stay at Wise Pines- SoBo
Mar 28 – Apr 4
Guesthouse in Hartland
4.86 out of 5 average rating, 43 reviewsCozy Guest Cabin w/private hot tub and bath
Jan 24 – 31
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