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