Dutchess County Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Top cities in Dutchess County

A large steel bridge spanning a wide river, with a cityscape and hills in the background.
Vacation Rentals

Poughkeepsie

Poughkeepsie

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Dutchess County vacation rentals

A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

1. 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, (341 reviews)
"Nice little cabin, well situated to sightseeing"
United States
Darryl
The price is CA $215
CA $293 total
includes taxes & fees
Dec 9 - Dec 10
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

2. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (197 reviews)
"Great stay"
United States
George
The price is CA $152
CA $170 total
includes taxes & fees
Nov 24 - Nov 25
Micosta Leisure Inn
A tented area with two wooden folding chairs and a table, a patterned rug, and a view of greenery and a white tent in the background.

3. Gatherwild Ranch

Gatherwild Ranch
3.0 star property
Germantown
10.0 out of 10, Exceptional, (1 review)
"Amazing sauna session"
United States
AYANO
The price is CA $315
CA $384 total
includes taxes & fees
Nov 11 - Nov 12
Gatherwild Ranch
A cabin with a triangular window, wooden walls, and a bed with pillows.

4. Gather Greene

Gather Greene
3.0 star property
Coxsackie
10.0 out of 10, Exceptional, (5 reviews)
"The room was spotless and very cozy! Everything was perfect, the scenery the smell, the atmosphere…EVRYTHING! The staff on the property were extremely friendly and generously helpful! Would 100% recommend for a couple’s getaway! Parking wasn’t a problem at all as well! Short walking distance to the cabins and back."
United States
Jabari
The price is CA $387
CA $418 total
includes taxes & fees
Dec 11 - Dec 12
Gather Greene
A two-story house with a porch, a table, and chairs outside.

5. Historic Horse Barn Apartment in Goshen

Historic Horse Barn Apartment in Goshen
4.0 star property
Goshen
The price is CA $212
CA $261 total
includes taxes & fees
Nov 11 - Nov 12
Historic Horse Barn Apartment in Goshen
A hot tub in a backyard with a house, trees, and a clear sky.

6. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is CA $1,264
CA $2,019 total
includes taxes & fees
Nov 13 - Nov 14
Las Flores Villa
A spacious living room with a fireplace, a ceiling fan, and a large window.

7. 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, (4 reviews)
"The house was very quiet and exactly as advertised. Would stay again!"
United States
Scott
The price is CA $300
CA $762 total
includes taxes & fees
Nov 30 - Dec 1
Hudson Valley Retreat w/ Pool Near Greenwood Lake
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.
View all properties

Find vacation rentals that suit your style

Apartment image
Apartments
Apartments
cabin image
Cabins
Cabins

Top Dutchess County Hotel Reviews

A modern lobby with a blue sofa, marble coffee table, and a reception desk with a blackboard.
The Heartwood

The Heartwood

The Heartwood
Arlington

10/10 Excellent

We’re currently on a road trip and had one night booked at the Heartwood. If we didn’t have prior commitments elsewhere, we would have stayed here longer. The room was great, beds comfortable , the staff were helpful and friendly & the food at the restaurant was delicious. Would definitely stay here again.
Canada
Denise
Reviewed September 4, 2026
The Heartwood

Find out more about Dutchess County

Everything you need to know about Dutchess County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Dutchess County vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Dutchess County vacation 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 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.  The selection of Dutchess County vacation rentals we have selected for you start as low as CA $99 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 vacation 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 vacation.

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.