Guesthouse vacation rentals in Dutchess County
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Top-rated guesthouse rentals in Dutchess County
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
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Popular amenities for Dutchess County guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Red Hook
4.87 out of 5 average rating, 103 reviewsCharming country cottage near Rhinebeck
Oct 28 – Nov 4
Guesthouse in Pine Plains
4.97 out of 5 average rating, 76 reviewsCozy Cottage by the Pond
Oct 7 – 14
Guesthouse in Tivoli
4.94 out of 5 average rating, 211 reviewsLight-filled guest cottage
Jul 20 – 27
Guesthouse in Stormville
4.99 out of 5 average rating, 159 reviewsHudson Valley Cottage with Pond Access
Jul 16 – 23
Guesthouse in Millbrook
4.86 out of 5 average rating, 223 reviewsQuaint Cottage near Millbrook Village
Jun 6 – 13
Guesthouse in Beacon
4.94 out of 5 average rating, 367 reviewsCozy Mountainside Suite - Minutes from Beacon
Jun 29 – Jul 6
Guest house rentals with a patio
Guesthouse in Rhinebeck
4.79 out of 5 average rating, 14 reviewsCharming Rhinebeck Cottage with Wood Burning Stove
Apr 21 – 28
Guesthouse in Brewster
4.94 out of 5 average rating, 99 reviewsSherwood Barn - close to ski mountain
Sep 6 – 13
Guesthouse in Saugerties
5.0 out of 5 average rating, 28 reviewsLittle Bliss Pond House
Sep 20 – 27
Guesthouse in Poughkeepsie
New place to stayCharming and Relaxing Home
Sep 30 – Oct 7
Guesthouse in Millerton
5.0 out of 5 average rating, 4 reviewsThree Corner Farm
Mar 15 – 22
Guesthouse in Saugerties
The Residence @ Roming Lane
Dec 2 – 9
Guest house rentals with a washer and dryer
Guesthouse in Clinton Corners
5.0 out of 5 average rating, 22 reviewsStunning lake side modern barn in Hudson Valley
Aug 6 – 13
Guesthouse in Red Hook
4.93 out of 5 average rating, 75 reviewsPrivate Cottage, Walk to Restaurants and Shops
Jan 22 – 29
Guesthouse in Pine Plains
4.96 out of 5 average rating, 47 reviewsSerene Lakefront Retreat on private peninsula
May 29 – Jun 5
Guesthouse in Beacon
5.0 out of 5 average rating, 23 reviewsNewly renovated guest house in the heart of Beacon
Oct 10 – 17
Guesthouse in Ulster Park
4.99 out of 5 average rating, 373 reviewsEscape to a Sleek, Serene Studio on the Riverbank
Dec 25 – 30
Guesthouse in Millerton
4.98 out of 5 average rating, 80 reviewsLoft in the Pines
Nov 11 – 18
Guesthouse in Millbrook
5.0 out of 5 average rating, 28 reviewsCottage on Coddington Lane
Jul 19 – 26
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