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
Aug 30 – Sep 6
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
Jul 20 – 27
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 18 – 25
Cabin in South Londonderry
4.65 out of 5 average rating, 388 reviewsFernando’s picturesque hideaway - Lovebirds Cabin
Dec 1 – 8
Cabin in Hartford
4.81 out of 5 average rating, 171 reviewsRustic Cabin Retreat
May 1 – 8
Cabin in Londonderry
4.95 out of 5 average rating, 75 reviewsQuaint cottage near 4 ski resorts
Mar 24 – 31
Tiny house rentals with a patio
Tiny home in Rutland
4.95 out of 5 average rating, 19 reviewsCurious Little Cottage
Nov 8 – 15
Tiny home in Chester
5.0 out of 5 average rating, 19 reviewsZen of the Woods Tiny Cabin in Okemo Valley
Jul 20 – 27
Home in West Windsor
4.96 out of 5 average rating, 56 reviewsBirdie's Nest Guesthouse
Dec 30 – Jan 6
Cabin in Rochester
5.0 out of 5 average rating, 17 reviewsThe Creek Cabin at Sky Hollow
Sep 28 – Oct 5
Cabin in Bethel
4.96 out of 5 average rating, 48 reviewsThe Gourmet Cabin at Stitchdown Farm
May 5 – 12
Tiny home in Chester
5.0 out of 5 average rating, 82 reviewsBearfoot Cottage: Tiny House w/ Hot Tub near Okemo
Feb 24 – Mar 3
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 28 – Nov 4
Tiny house rentals with outdoor seating
Cabin in Mount Holly
4.98 out of 5 average rating, 206 reviewsPrivate Cabin/Pets OK/Minutes to Okemo/ Fast Wifi
Sep 24 – Oct 1
Cabin in Royalton
4.94 out of 5 average rating, 232 reviewsScandinavian design Cabin w/ private hiking trail
Jan 2 – 9
Campsite in Vershire
4.87 out of 5 average rating, 153 reviewsCamping on a private pond
Mar 21 – 28
Cabin in Fairlee
4.94 out of 5 average rating, 114 reviewsFairlee Log Cabin
Nov 28 – Dec 5
Treehouse in Hartland
4.93 out of 5 average rating, 107 reviewsLovely Treehouse Stay at Wise Pines- SoBo
Jan 8 – 15
Farm stay in South Royalton
4.83 out of 5 average rating, 209 reviewsCorncrib Tiny House Glamping Cabin
Dec 29 – Jan 5
Tiny home in Chester
4.9 out of 5 average rating, 155 reviewsSage House at Camp Greenwood Vermont - w/ sauna!
Oct 5 – 12
Guesthouse in Hartland
4.86 out of 5 average rating, 42 reviewsCozy Guest Cabin w/private hot tub and bath
Jun 30 – Jul 7
Destinations to explore
- House rentals United States
- Tiny house rentals Vermont
- House rentals Vermont
- Tiny house rentals Vermont
- House rentals Vermont
- House rentals New York
- Tiny house rentals New York
- House rentals New Hampshire
- Tiny house rentals New Hampshire
- Rentals with an accessible height toilet Windsor County
- Villa rentals Windsor County
- Rentals with a sauna Windsor County
- Beachfront rentals Windsor County
- Pet-friendly rentals Windsor County
- Cabin rentals Windsor County
- Bed and breakfasts Windsor County
- Rentals with outdoor seating Windsor County
- Rentals with an EV charger Windsor County
- House rentals Windsor County
- Kid-friendly rentals Windsor County
- Condo rentals Windsor County
- Rentals with a fire pit Windsor County
- Waterfront rentals Windsor County
- Monthly Rentals Windsor County
- Rentals with a fireplace Windsor County
- Farmstay rentals Windsor County
- Rentals with pools Windsor County
- Rentals with a hot tub Windsor County
- Guesthouse rentals Windsor County
- Ski-in/ski-out rentals Windsor County
- Apartment rentals Windsor County
- Family-friendly rentals Windsor County
- Rentals with a washer and dryer Windsor County
- Cottage rentals Windsor County
- Rentals with an accessible height bed Windsor County
- Rentals with a kayak Windsor County
- Rentals with breakfast Windsor County
- Private suite rentals Windsor County
- Fitness-friendly rentals Windsor County
- Chalet rentals Windsor County
- Rentals with a patio Windsor County
- Rentals with beach access Windsor County
- Townhouse rentals Windsor County
- Rentals with lake access Windsor County
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- 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