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
Jan 6 – 13
Guesthouse in Pine Plains
4.97 out of 5 average rating, 76 reviewsCozy Cottage by the Pond
Aug 17 – 24
Guesthouse in Tivoli
4.94 out of 5 average rating, 211 reviewsLight-filled guest cottage
Jun 24 – Jul 1
Guesthouse in Stormville
4.99 out of 5 average rating, 159 reviewsHudson Valley Cottage with Pond Access
Feb 2 – 9
Guesthouse in Millbrook
4.86 out of 5 average rating, 223 reviewsQuaint Cottage near Millbrook Village
Jun 5 – 12
Guesthouse in Beacon
4.94 out of 5 average rating, 367 reviewsCozy Mountainside Suite - Minutes from Beacon
Apr 28 – May 5
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 26 – May 3
Guesthouse in Saugerties
5.0 out of 5 average rating, 28 reviewsLittle Bliss Pond House
Jul 10 – 17
Guesthouse in Brewster
4.94 out of 5 average rating, 99 reviewsSherwood Barn - close to ski mountain
Oct 6 – 13
Guesthouse in Poughkeepsie
New place to stayCharming and Relaxing Home
Sep 17 – 24
Guesthouse in Millerton
5.0 out of 5 average rating, 4 reviewsThree Corner Farm
Apr 12 – 19
Guesthouse in Saugerties
The Residence @ Roming Lane
Dec 6 – 13
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
Nov 9 – 16
Guesthouse in Red Hook
4.93 out of 5 average rating, 75 reviewsPrivate Cottage, Walk to Restaurants and Shops
Jan 26 – Feb 2
Guesthouse in Pine Plains
4.96 out of 5 average rating, 47 reviewsSerene Lakefront Retreat on private peninsula
Sep 7 – 14
Guesthouse in Beacon
5.0 out of 5 average rating, 23 reviewsNewly renovated guest house in the heart of Beacon
Sep 1 – 8
Guesthouse in Ulster Park
4.99 out of 5 average rating, 374 reviewsEscape to a Sleek, Serene Studio on the Riverbank
Dec 27 – Jan 1
Guesthouse in Millerton
4.98 out of 5 average rating, 80 reviewsLoft in the Pines
Apr 14 – 21
Guesthouse in Millbrook
5.0 out of 5 average rating, 28 reviewsCottage on Coddington Lane
Jul 24 – 31
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