A large, historic building with a symmetrical facade, green shutters, and a central entrance with steps leading up to it.

Vacation Rentals in Dutchess County

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Top Cities in Dutchess County

Our top choices for Dutchess County vacation rentals

Luxe Mountain Getaway on Private Rd Near Rhinebeck

Luxe Mountain Getaway on Private Rd Near Rhinebeck
3.0 star property
Hyde Park
$872 nightly
The price is $986
Jul 1 - Jul 2
Total with taxes and fees
Luxe Mountain Getaway on Private Rd Near Rhinebeck

Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (154 reviews)
"The room was cozy. In a very quiet part of town. The check in process was easy. I would definitely stay again while in town."
United States
Kathleen
$133 nightly
The price is $150
Jun 28 - Jun 29
Total with taxes and fees
Micosta Leisure Inn

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.5 star property
Catskill
9.6 out of 10, Exceptional, (251 reviews)
"Really great location and near great area."
United States
Sherwin
$209 nightly
The price is $226
Jul 27 - Jul 28
Total with taxes and fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Historic Horse Barn Apartment in Goshen

Historic Horse Barn Apartment in Goshen
4.0 star property
Goshen
$310 nightly
The price is $382
Jun 30 - Jul 1
Total with taxes and fees
Historic Horse Barn Apartment in Goshen

Jellystone Park Gardiner

Jellystone Park Gardiner
3.0 star property
Gardiner
$348 nightly
The price is $390
Jul 7 - Jul 8
Total with taxes and fees
Jellystone Park Gardiner

Carriage House Apartment Goshen NY

Carriage House Apartment Goshen NY
4.0 star property
Goshen
$431 nightly
The price is $531
Jul 13 - Jul 14
Total with taxes and fees
Carriage House Apartment Goshen NY

The Rosendale Roost

The Rosendale Roost
2.0 star property
Kingston
$425 nightly
The price is $478
Jul 6 - Jul 7
Total with taxes and fees
The Rosendale Roost

2BR Pet-friendly Walk to Cafes Trails Wineries

2BR Pet-friendly Walk to Cafes Trails Wineries
2.0 star property
Rosendale
$420 nightly
The price is $471
Jul 7 - Jul 8
Total with taxes and fees
2BR Pet-friendly Walk to Cafes Trails Wineries

Hay Loft Apartment in Barn - Goshen

Hay Loft Apartment in Barn - Goshen
2.0 star property
Goshen
$485 nightly
The price is $597
Jul 1 - Jul 2
Total with taxes and fees
Hay Loft Apartment in Barn - Goshen

Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (3 reviews)
"fantastic accommodations"
United States
David
$457 nightly
The price is $517
Jun 28 - Jun 29
Total with taxes and fees
Hudson Valley Retreat w/ Pool Near Greenwood Lake

West Point Summer Pool Jacuzzi Events Pets OK

West Point Summer Pool Jacuzzi Events Pets OK
2.0 star property
Cornwall
$1,398 nightly
The price is $1,651
Jun 29 - Jun 30
Total with taxes and fees
West Point Summer Pool Jacuzzi Events Pets OK
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Dutchess County Hotel Reviews

Find out more about Dutchess County

Discover your perfect Dutchess County vacation rental with Expedia

How many vacation rentals are available in Dutchess County?


Expedia has plenty of vacation rentals to choose from in and around  Dutchess County, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Dutchess County?


The selection of Dutchess County vacation rentals we have selected for you start as low as $150 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Dutchess County?


Vacation rentals in Dutchess County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Dutchess County vacation rentals to suit everyone. 


Why should I choose a vacation rental in Dutchess County?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Dutchess County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. 


How do I find the best deal on a vacation rental in Dutchess County?


Find vacation rentals in Dutchess County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Dutchess County.  


What amenities are available in a vacation rental in Dutchess County?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Dutchess County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Dutchess County?   


Everytime is a great time to head to Dutchess County! Staying in a Dutchess County vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Dutchess County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Dutchess County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Dutchess County, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Dutchess County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.