Dutchess County Holiday Rentals

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Top Cities in Dutchess County

Franklin D. Roosevelt Presidential Library and Museum featuring heritage elements and heritage architecture

Top Holiday Rentals Destinations in Dutchess County

"The house had room for all of us, spacious and comfortable with modern amenities. We enjoyed the large open kitchen, well equipped for making big meals, and especially loved the walk in pantry with sink, oven and coffee bar. The beds were comfy, the bathrooms deluxe. Large couch and huge TV in living room with cozy gas fireplace for us to gather and relax. Located on a quiet cul de sac, easy to get to local attractions. We enjoyed every minute of our stay."

includes taxes & fees

1 Mar - 2 Mar

"Communication was easy, location and parking was great! Very clean and cozy!"

includes taxes & fees

23 Feb - 24 Feb

"When I found the place online, it was just the right place for us, peace and quiet. The place was just like the pictures and if I have to described it in one word (COZY) Kevin, the owner met us and helped us and walked us through the place and has a Washer/Dryer. The weekend was perfect, we got snowed in which was perfect in which we order in and Netflix and chilled, PERFECT Timing.Thank you Kevin, we will see you again!"

includes taxes & fees

26 Feb - 27 Feb

"Quiet spot out of the city but not too far from Hudson Valley sites. Large vaulted space, fresh eggs from the hen house next door, sky full of stars at night. Great host!"

"We love our Bartow cabin, it was so cozy and relaxing for us. A perfect getaway from the city life. Will definitely stay again. "

includes taxes & fees

5 Mar - 6 Mar

"We had an absolutely wonderful stay at this Vrbo! From the moment we arrived, everything was spotless, beautifully decorated, and thoughtfully equipped with everything we needed. The hosts went above and beyond to ensure a comfortable and seamless experience, providing clear instructions and even thoughtful touches that made us feel right at home.The location was perfect—close enough to attractions and restaurants but still peaceful and private. The beds were incredibly comfortable, the kitchen...

"Micosta is a wonderful surprise."

includes taxes & fees

7 Mar - 8 Mar

"We totally enjoyed our stay at the cottage! Exactly as advertised, except the views of the river from the home are are even better than pictured. We would definitely recommend!"

"Spectacular view and very convenient to USMA. "

includes taxes & fees

23 Feb - 24 Feb

"Great little house for the holidays. We were looking for a place nearby or family where we could have our own space but still be close by. "

includes taxes & fees

24 Feb - 25 Feb

"No complaints. Stayed during the winter so ne er got the full experience with the lake but it was a great home."

"The home was beautiful and it was a gorgeous property too. It had all the right amenities in the kitchen. "

"Great place and location. We have been staying at different condo places for the past 3 Winter Ski season. This is by far the best. Matt is great. "

includes taxes & fees

18 Mar - 19 Mar

"Beautiful, quiet property that was a great getaway from the city. A pair of bald eagles were circling the lake which was a really amazing surprise! "

includes taxes & fees

11 Mar - 12 Mar

"Quiet peaceful weekend"

"Spent Thanksgiving here. Great house set in the mountains. Never felt cramped with 12 people in the house. Great fireplace! Just a wonderful retreat. Close to Woodstock. Host was super. Highly Recommend this house!!"

"2 nights in a delightful cottage. It is small but delightfully appointed. The highlight was this clean, warm little cottage is perched directly on swft stream. We left the backdoor open at night!"

includes taxes & fees

23 Feb - 24 Feb

"We had a lovely stay for our family of 5 during the week before xmas. The home was well appointed, with all the normal needs we have to cook, etc... The house was very quiet despite 5 of us being there. Everyone had their own space. Very cozy. Loved that there were games to play, we had a great family round of monopoly!The property manager was so responsive. We felt very supported and attended to. Despite the cold weather the house stayed plenty warm as well!We highly recommend this home and...

"Master bath needs a taller toilet for older people Master shower needs an upgrade.."

"We stayed at the Lakefront Retreat for our annual ski trip with two other families. It was absolutely perfect for us. There was plenty of space for the kids and adults to spread out, everyone loved the game room downstairs, and the lake views are beautiful. The Hunter parking lot is less than a 3 minute drive from the house so it's easy to either shuttle skiiers back and forth or to just make the quick drive to the lot and park for the day. We didn't make use of the sauna, but nothing compares...

includes taxes & fees

9 Mar - 10 Mar

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Find out more about Dutchess County

Everything you need to know about Dutchess County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Dutchess County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Dutchess County holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Dutchess County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Dutchess County. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Dutchess County holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Dutchess County holiday rentals we have selected for you start as low as NZ$234 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Dutchess County rentals

At Expedia, we put the best Dutchess County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Dutchess County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Dutchess County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Dutchess County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.