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
Dec 12 – 19
Guesthouse in Pine Plains
4.97 out of 5 average rating, 76 reviewsCozy Cottage by the Pond
Oct 11 – 18
Guesthouse in Tivoli
4.94 out of 5 average rating, 211 reviewsLight-filled guest cottage
Jul 18 – 25
Guesthouse in Stormville
4.99 out of 5 average rating, 159 reviewsHudson Valley Cottage with Pond Access
Dec 14 – 21
Guesthouse in Millbrook
4.86 out of 5 average rating, 224 reviewsQuaint Cottage near Millbrook Village
Jul 7 – 14
Guesthouse in Beacon
4.94 out of 5 average rating, 367 reviewsCozy Mountainside Suite - Minutes from Beacon
Mar 2 – 9
Guest house rentals with a patio
Guesthouse in Rhinebeck
4.79 out of 5 average rating, 14 reviewsCharming Rhinebeck Cottage with Wood Burning Stove
Mar 29 – Apr 5
Guesthouse in Saugerties
5.0 out of 5 average rating, 28 reviewsLittle Bliss Pond House
Sep 17 – 24
Guesthouse in Brewster
4.94 out of 5 average rating, 100 reviewsSherwood Barn - close to ski mountain
Sep 12 – 19
Guesthouse in Poughkeepsie
New place to stayCharming and Relaxing Home
Nov 5 – 12
Guesthouse in Millerton
5.0 out of 5 average rating, 4 reviewsThree Corner Farm
Apr 13 – 20
Guesthouse in Saugerties
The Residence @ Roming Lane
Dec 8 – 15
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
May 12 – 19
Guesthouse in Red Hook
4.93 out of 5 average rating, 75 reviewsPrivate Cottage, Walk to Restaurants and Shops
Jan 27 – Feb 3
Guesthouse in Pine Plains
4.96 out of 5 average rating, 47 reviewsSerene Lakefront Retreat on private peninsula
Sep 13 – 20
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
Jun 20 – 25
Guesthouse in Millerton
4.98 out of 5 average rating, 80 reviewsLoft in the Pines
Nov 17 – 24
Guesthouse in Millbrook
5.0 out of 5 average rating, 28 reviewsCottage on Coddington Lane
Jun 19 – 26
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