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Guesthouse vacation rentals in Dutchess County
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in Dutchess County
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Dutchess County guesthouse rentals
Family-friendly guest house rentals
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Guesthouse in Red Hook
4.88 out of 5 average rating, 105 reviewsCharming country cottage near Rhinebeck
![](https://a0.muscache.com/im/pictures/71bb41e4-26e6-409c-91e7-d1e68a850cd2.jpg?im_w=720)
Guesthouse in Pine Plains
4.97 out of 5 average rating, 76 reviewsCozy Cottage by the Pond
![](https://a0.muscache.com/im/pictures/25452bb4-e540-462b-8889-2b8ab655b735.jpg?im_w=720)
Guesthouse in Millbrook
4.86 out of 5 average rating, 224 reviewsQuaint Cottage near Millbrook Village
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Guesthouse in Tivoli
4.94 out of 5 average rating, 217 reviewsLight-filled guest cottage
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Guesthouse in Stormville
4.99 out of 5 average rating, 161 reviewsHudson Valley Cottage with Pond Access
![](https://a0.muscache.com/im/pictures/miso/Hosting-1751443/original/57f19f69-459d-4aae-9dce-e1c9a37e03ba.jpeg?im_w=720)
Guesthouse in Beacon
4.94 out of 5 average rating, 369 reviewsCozy Mountainside Suite - Minutes from Beacon
Guest house rentals with a patio
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Guesthouse in Rhinebeck
4.8 out of 5 average rating, 15 reviewsCharming Rhinebeck Cottage with Wood Burning Stove
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Guesthouse in Saugerties
5 out of 5 average rating, 34 reviewsLittle Bliss Pond House
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Guesthouse in Saugerties
5 out of 5 average rating, 3 reviewsThe Residence @ Roming Lane
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Guesthouse in Millerton
5 out of 5 average rating, 7 reviewsThree Corner Farm
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Guesthouse in Rhinebeck
New place to stayLimon Cottage
Guest house rentals with a washer and dryer
![](https://a0.muscache.com/im/pictures/13368839-e32d-4485-993f-9207efc8834b.jpg?im_w=720)
Guesthouse in Red Hook
4.94 out of 5 average rating, 79 reviewsPrivate Cottage, Walk to Restaurants and Shops
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Guesthouse in Clinton Corners
5 out of 5 average rating, 22 reviewsStunning lake side modern barn in Hudson Valley
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Guesthouse in Marlboro
4.9 out of 5 average rating, 29 reviewsCharming 1850's Guest House in Nature
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Guesthouse in Pine Plains
4.96 out of 5 average rating, 48 reviewsSerene Lakefront Retreat on private peninsula
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Guesthouse in Beacon
5 out of 5 average rating, 24 reviewsNewly renovated guest house in the heart of Beacon
![](https://a0.muscache.com/im/pictures/6ff36ae2-322a-4267-a730-c0d6dec289f1.jpg?im_w=720)
Guesthouse in Ulster Park
4.99 out of 5 average rating, 378 reviewsEscape to a Sleek, Serene Studio on the Riverbank
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Guesthouse in Millerton
4.98 out of 5 average rating, 85 reviewsLoft in the Pines
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Guesthouse in Millbrook
5 out of 5 average rating, 29 reviewsCottage on Coddington Lane
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- Family travel hub Tips and inspiration
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