Tiny house holiday rentals in Dutchess County
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Top-rated tiny home rentals in Dutchess County
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Popular amenities for tiny home rentals in Dutchess County
Family-friendly tiny home rentals
Cottage in Tivoli
4.96 out of 5 average rating, 194 reviewsClausterhaus
3–8 Sept
Guest house in Tivoli
4.94 out of 5 average rating, 210 reviewsLight-filled guest cottage
18–25 Jul
Guest house in Millbrook
4.86 out of 5 average rating, 223 reviewsQuaint Cottage near Millbrook Village
12–19 Jul
Tiny home in Hopewell Junction
4.96 out of 5 average rating, 461 reviewsThe GlassHouse: Hudson Valley Tiny Home w/Firepit
7–14 May
Cabin in Red Hook
4.96 out of 5 average rating, 305 reviewsModern Upstate Cabin, near Rhinebeck NY
3–10 May
Cottage in Poughkeepsie
4.91 out of 5 average rating, 301 reviewsBe in Nature at this Gorgeous Riverfront Cabin
14–21 Feb
Home in Rhinebeck
4.91 out of 5 average rating, 254 reviewsArchitectural wonder in the woods
2–9 Oct
Tiny home rentals with a patio
Guest house in Rhinebeck
4.79 out of 5 average rating, 14 reviewsCharming Rhinebeck Cottage with Wood Burning Stove
17–24 Nov
Place to stay in Hopewell Junction
4.86 out of 5 average rating, 14 reviewsUnique 1845 Artist Retreat near Appalachian Trail
6–13 Oct
Cabin in Wassaic
4.92 out of 5 average rating, 12 reviewsOffsite Camp - NEW Minimalist Modern Cabin
4–11 Oct
Cottage in Livingston
4.97 out of 5 average rating, 37 reviewsWaterlily Lakehouse - Modern+Waterfront+Retreat
10–17 Sept
Cottage in Pawling
5.0 out of 5 average rating, 62 reviewsTwin Lakes Designer A-frame Stone Cottage
23–30 Jan
Chalet in Wappingers Falls
5.0 out of 5 average rating, 11 reviewsMCM Hudson Valley A-Frame, Near Beacon
26 Jun – 3 Jul
Tiny home rentals with outdoor seating
Cottage in Rhinebeck
4.94 out of 5 average rating, 120 reviewsRefined, Intimate Cottage on Private Estate
26 Nov – 3 Dec
Cottage in Red Hook
4.98 out of 5 average rating, 211 reviewsCoZy Newly Renovated Cottage in Red Hook Village
10–17 Aug
Cottage in Red Hook
4.92 out of 5 average rating, 324 reviewsGoose Landing Cottage by the lake with NEW Hot Tub
12–19 Nov
Cabin in Fishkill
4.97 out of 5 average rating, 68 reviewsSecluded Hilltop Cabin near Beacon & Cold Spring
18–25 Jul
Home in Ancram
5.0 out of 5 average rating, 24 reviewsModern Scandinavian Farmhouse w/ Vintage Camper
19–26 Feb
Island in Pine Plains
4.98 out of 5 average rating, 62 reviewsMagical Private Island Retreat in Pine Plains
27 Aug – 3 Sept
Home in Rhinebeck
4.94 out of 5 average rating, 51 reviewsRhinebeck Blue Door Cottage
12–19 May
Tiny home in Saugerties
4.94 out of 5 average rating, 69 reviewsWarm & Cozy Tiny Cabin Experience - Saugerties, NY
7–14 Sept
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