Dutchess County vacation rentals
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Top-rated vacation rentals in Dutchess County
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
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Popular amenities for Dutchess County vacation rentals
Other great vacation rentals in Dutchess County
Guest favorite
Guest suite in Dover Plains
4.91 out of 5 average rating, 263 reviewsHoppy Hill Farm House
Guest favorite
Guest suite in Marlboro
4.97 out of 5 average rating, 406 reviewsSpacious & Private Hudson Valley Getaway
Guest favorite
Apartment in Rhinebeck
4.99 out of 5 average rating, 162 reviewsRhinebeck Ridge - A Woodland Studio Retreat
Guest favorite
Home in Hyde Park
4.85 out of 5 average rating, 187 reviewsVillage Cape Getaway
Guest favorite
Cottage in Ulster Park
4.94 out of 5 average rating, 188 reviewsHidden Gem Cottage β cozy escape to play or WFH
Guest favorite
Cabin in Red Hook
4.96 out of 5 average rating, 311 reviewsModern Upstate Cabin, near Rhinebeck NY
Guest favorite
Apartment in Kent
4.93 out of 5 average rating, 128 reviewsLoft 22
Guest favorite
Home in Kingston
4.98 out of 5 average rating, 222 reviewsDeMew House in Historic Kingston
Other great vacation rentals in Dutchess County
Guest favorite
Guest suite in Sherman
4.97 out of 5 average rating, 138 reviewsCozy Scenic New England country retreat w/ hiking
Guest favorite
Apartment in Dover Plains
4.95 out of 5 average rating, 140 reviews*The Ridge House*
Guest favorite
Cottage in Red Hook
4.98 out of 5 average rating, 602 reviewsbright serene + spacious barn
Guest favorite
Guesthouse in Tivoli
4.94 out of 5 average rating, 214 reviewsLight-filled guest cottage
Guest favorite
Loft in Pleasant Valley
5.0 out of 5 average rating, 18 reviewsBe our guest at The Nest!
Guest favorite
Apartment in Amenia
5.0 out of 5 average rating, 34 reviewsAmenia Main St Cozy Studio
Superhost
Guesthouse in Dover Plains
4.89 out of 5 average rating, 89 reviewsSpilt Milk Cottage - Hudson Valley, NY
Guest favorite
Apartment in Fishkill
5.0 out of 5 average rating, 23 reviews1 Bedroom Apartment on Main St.
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- Family travel hubΒ Tips and inspiration
- Family budget travelΒ Get there for less
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- Travel Europe on a budgetΒ How to take the kids to Europe for less
- Outdoor adventureΒ Explore nature with the family
- Bucket list national parksΒ Must-see parks for family travel
- Kid-friendly state parksΒ Check out these family-friendly hikes