A lake surrounded by hills with autumn foliage, a small island with a historic building, and a cloudy sky.

Vacation Rentals in Dutchess County

Where to?

Dates

November 2026

December 2026

Top cities in Dutchess County

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

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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

Catskill

Darryl

$192 nightly

Dec 10 - Dec 11

Total with taxes and fees

A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

2. Micosta Leisure Inn

Hudson

George

$79 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

Germantown

AYANO

$263 nightly

Nov 12 - Nov 13

Total with taxes and fees

A cabin with a triangular window, wooden walls, and a bed with pillows.

4. Gather Greene

Coxsackie

Jabari

$273 nightly

Dec 11 - Dec 12

Total with taxes and fees

A two-story house with a porch, a table, and chairs outside.

5. Historic Horse Barn Apartment in Goshen

Goshen

$153 nightly

Nov 12 - Nov 13

Total with taxes and fees

A hot tub in a backyard with a house, trees, and a clear sky.

6. Las Flores Villa

New Preston

$1,343 nightly

Nov 12 - Nov 13

Total with taxes and fees

A spacious living room with a fireplace, a ceiling fan, and a large window.

7. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Monroe

Scott

$457 nightly

Nov 30 - Dec 1

Total with taxes and fees

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Find vacation rentals that suit your style

Top Dutchess County Hotel Reviews

A breakfast table with a teapot, milk, and a bagel, set against a brick wall with a framed picture above.

Inn at Pine Plains

Pine Plains

10/10 Excellent

Kevin

A large, multi-story hotel with a symmetrical facade, multiple balconies with flower boxes, and a central entrance with a fountain.

Mirbeau Inn & Spa

Rhinebeck Village

10/10 Excellent

Paula

A multi-story hotel with a central entrance, stone pillars, and a brick facade.

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Hyde Park

10/10 Excellent

Sheri

An outdoor patio area with a stone fire pit, seating, and a Marriott sign in the background.

SpringHill Suites by Marriott Fishkill

Fishkill

10/10 Excellent

MICHELLE

A room with a view of a lake, a balcony with a table and chairs, and a sofa.

Rhinecliff Hotel

Rhinecliff

10/10 Excellent

Sandra

A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.

Little Cat Lodge

Copake Falls

10/10 Excellent

Elisabeth

An outdoor seating area with stone walls, a fire feature, and yellow chairs.

Home2 Suites By Hilton Poughkeepsie

Poughkeepsie

10/10 Excellent

Comfy. Homey. Clean. Brightly lit and cheery lobby area. Great breakfast setup. Nice bedding. Spacious suite style. Easy and quick drive to Marist. Very small downers: Parking lot a tad cramped and narrow. Muddy construction lot in front. Desk staff tends to stray away from the desk and there was no telling when they would be back. Could use a desk sign or something saying "Back in 15 minutes."

David

A buffet with various food items, including omelets and baked goods, served in metal containers.

Holiday Inn Express & Suites Kingston-Ulster by IHG

Lake Katrine

10/10 Excellent

Maria

A modern hotel room with a large bed, a sitting area with a sofa, a small table, a TV, and a bathtub.

The Factory

Beacon

10/10 Excellent

JAYANTI

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

10/10 Excellent

We were greeted by extremely friendly staff. Check in and check out was seamless. Room was very nice and immaculate. We especially liked the bathroom design - didn't have to trip over the toilet to get in the shower as in most hotels! Free breakfast was the usual fare, but in a very pleasant and uncrowded room. Appreciated the free US News and NY Times Beautiful indoor pool - wish we'd brought our bathing suits!

Anonymous traveler

Frequently Asked Questions

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 $80 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.