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Vacation rentals in Dutchess County

Vacation rentals in Dutchess County

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Dutchess County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Modern cottage with Hudson River view
SUPERHOSTEntire guesthouse · 2 guests · 0 beds · 1 bath
Modern cottage with Hudson River view

Relax and enjoy your stay in a bright, modern cottage with windows overlooking the river and a wraparound deck. Whether you are looking to relax along the river, explore Hyde Park historic properties or discover the incredible natural beauty of the Hudson Valley, this cottage is an ideal escape.

What guests are saying:

“This little home on the water is perfect for a weekend getaway from the city. The grill worked great, the kitchen essentials were all there, the place was spotless. The view is unbelievable. The train runs right behind the house so it's very loud, but only for a few seconds per hour or so. We're definitely planning on coming back. Thanks for giving us an amazing escape from NYC (our first in three months!).”

Lakefront Writer's Cottage in Rhinebeck
SUPERHOSTEntire cottage · 4 guests · 2 beds · 1 bath
Lakefront Writer's Cottage in Rhinebeck

Our serene lakefront cottage in pastoral Rhinebeck is located on Silverlake, one of the largest private lakes in the state. In summer months, you can swim, boat, fish. In winter, cozy up by the fireplace or skate. Bright and stylish space with minimal aesthetic, direct water access and expansive lake vistas. Less than 2 hour drive from NYC, 5 min drive to Omega, and 8 min drive to trendy Rhinebeck Village where you can find a multitude of dining options and shops. Instagram - @silverlakecottage

What guests are saying:

“Truly, the coziest, quaintest nook of perfection in the heart of the Hudson Valley. This home is simply sublime, with every inch well thought out and well-designed - from the gas fireplace to the modern kitchen. Only 10 minutes from the main Rhinebeck Village, it’s still very much secluded, planted directly on a quiet, beautiful lakeside. Check-in was easy, and Tim was super easy to communicate with. Will definitely return, without question.”

Hudson Valley Hideout – w/Pool & Gorgeous Grounds
SUPERHOSTEntire guesthouse · 3 guests · 2 beds · 1 bath
Hudson Valley Hideout – w/Pool & Gorgeous Grounds

Next level glamping! This gorgeous little hideout is surrounded by Japanese Maples, pines and a variety of other tall, lush trees. There's a pool steps from your door. Admire wildlife (birds, chipmunks, deer) all around you in this private oasis that makes you feel like you're away from it all, yet super close to the region's best restaurants, charming cafes and bars in Beacon, Newburgh, Fishkill, Wappinger's and Poughkeepsie. Full kitchen and bath, flatscreen TV, WiFi... it's a rustic paradise!

What guests are saying:

“The cottage is perfectly serviceable, and the pool area is absolutely idyllic. This was a perfect home base for a quiet weekend of hiking and reading in pool floats. We would happily come back.”

Vacation rentals for every style

Get the amount of space that is right for you

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Dutchess County vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Dutchess County

Orchard Views from a Light-Filled Tiny Home with a Fire Pit
PLUSTiny house
Orchard Views from a Light-Filled Tiny Home with a Fire Pit
Price:€ 220 / night
Modern Upstate cabin + hot pool near Rhinebeck NY.
SUPERHOSTEntire cabin
Modern Upstate cabin + hot pool near Rhinebeck NY.
Price:€ 290 / night
The Beech House - Light and Open, Stunning Views
SUPERHOSTEntire house
The Beech House - Light and Open, Stunning Views
Price:€ 174 / night
Gorgeous private apartment in Rhinebeck Village
SUPERHOSTEntire apartment
Gorgeous private apartment in Rhinebeck Village
Price:€ 97 / night
Creekside Cottage
SUPERHOSTEntire house
Creekside Cottage
Price:€ 157 / night
The Glass House: A Hudson Valley Tiny Home Escape
SUPERHOSTTiny house
The Glass House: A Hudson Valley Tiny Home Escape
Price:€ 212 / night
Casa del Arte welcomes you!
SUPERHOSTPrivate room
Casa del Arte welcomes you!
Price:€ 62 / night
Bluestone Burrow, a luxury Hudson Valley retreat
SUPERHOSTEntire guest suite
Bluestone Burrow, a luxury Hudson Valley retreat
Price:€ 351 / night
Waterfront Petfriendly cottage in Saugerties
SUPERHOSTEntire cottage
Waterfront Petfriendly cottage in Saugerties
Price:€ 241 / night
Pine Plains Cottage
SUPERHOSTEntire cottage
Pine Plains Cottage
Price:€ 89 / night
bright serene + spacious barn
SUPERHOSTEntire cottage
bright serene + spacious barn
Price:€ 281 / night
Red Barn at Turtle Rock Pond - Historic Hyde Park
SUPERHOSTEntire house
Red Barn at Turtle Rock Pond - Historic Hyde Park
Price:€ 161 / night
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