Vacation Rentals in Dutchess County

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    bed illustration

    Be picky

    Search almost a million properties worldwide

Top Cities in Dutchess County

Top Vacation Rentals in Dutchess County

The Farm at Hyde Park

9.8 out of 10, Exceptional, (76)
"We were visiting the Culinary Institute highly recommend it."
The Farm at Hyde Park

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

9.8 out of 10, Exceptional, (29)
"Great place for a quiet stay"
$296 nightly
The price is $335
Aug 31 - Sep 1
Total with taxes and fees
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Rustic Cabin in Fishkill!

10.0 out of 10, Exceptional, (1)
"Beautiful property with many different areas to explore. We originally intended to spend more time in beacon but decided it was more fun hanging out here. "
$371 nightly
The price is $422
Aug 27 - Aug 28
Total with taxes and fees
Rustic Cabin in Fishkill!

1 Br Private Victorian Apt in Convenient City Location on Half Acre Sleeps 4

2.0 star property
9.6 out of 10, Exceptional, (7)
"Gary is a great host and provides a wonderful experience. He is the best and it was a very nice stay. Best host I have had before."
$174 nightly
The price is $204
Aug 27 - Aug 28
Total with taxes and fees
1 Br Private Victorian Apt in Convenient City Location on Half Acre Sleeps 4

Postcard Cabins Eastern Catskills

2.0 star property
9.6 out of 10, Exceptional, (63)
"Really beautiful place to enjoy nature with family!!"
$174 nightly
The price is $188
Sep 1 - Sep 2
Total with taxes and fees
Postcard Cabins Eastern Catskills

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (117)
"Great stay!"
$133 nightly
The price is $150
Aug 27 - Aug 28
Total with taxes and fees
Micosta Leisure Inn

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

8.2 out of 10, Very Good, (46)
"Perfect place to reconnect with natural world and yourself"
$145 nightly
The price is $162
Sep 3 - Sep 4
Total with taxes and fees
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (26)
"Beautiful home and great location . "
Hamptons on the Hudson in South Saugerties

A Spectacular 50 Mile View of the Hudson Valley in all seasons

9.8 out of 10, Exceptional, (91)
"Had an absolutely fantastic time. Beautiful property and the owners are incredibly kind and welcoming "
A Spectacular 50 Mile View of the Hudson Valley in all seasons

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

9.8 out of 10, Exceptional, (27)
"Great location "
$305 nightly
The price is $330
Aug 28 - Aug 29
Total with taxes and fees
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (120)
"Nice view on the top of the mountain….I admired the river with the bridge and the surroundings until late in the night. The accommodation was excellent, we had everything we needed.… we are thinking of coming back sometime…."
$268 nightly
The price is $303
Sep 7 - Sep 8
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

9.4 out of 10, Exceptional, (28)
"Stayed here to visit family and it was perfect for what we needed. Would recommend staying here. "
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

10.0 out of 10, Exceptional, (1)
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.2 out of 10, Wonderful, (43)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
$275 nightly
The price is $308
Sep 7 - Sep 8
Total with taxes and fees
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Jessie's Harvest House

10.0 out of 10, Exceptional, (1)
"For the location it is located it is a great place to stay. The rooms were clean and the beds and sheets were great. There is a restaurant on property so need to go far for something to eat. If I am ever in the area again I would definitely stay again. "
$180 nightly
The price is $190
Aug 27 - Aug 28
Total with taxes and fees
Jessie's Harvest House

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (304)
"The lake views at this house are absolutely worth the trip and the money. It's a beautiful spot. And the host, Don, is super responsive, thoughtful and accommodating. Highly recommend!"
$512 nightly
The price is $605
Aug 28 - Aug 29
Total with taxes and fees
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

Our home is perfect for relaxing and having lots of fun, with near by activity’s

9.8 out of 10, Exceptional, (6)
"Really liked that each room had it's own temperature control"
Our home is perfect for relaxing and having lots of fun, with near by activity’s

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

9.0 out of 10, Wonderful, (21)
"We really enjoyed our stay. The house is walking distance from the lake and a good break for anyone trying to escape the bustle of NYC. The house was very clean and we felt safe and comfortable here’s the outdoor fire pit was a very nice touch."
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

The Studio at the Inn at High Falls

8.0 out of 10, Very Good, (27)
"I had a great stay here, it’s just as listed; simple but has everything that I needed, check in was easy, communication was good, and bed was comfortable!"
$243 nightly
The price is $272
Aug 27 - Aug 28
Total with taxes and fees
The Studio at the Inn at High Falls

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (48)
"We stayed one night, and it was great! We met one of the owners too. He was very nice and helpful. The property was neat and clean. It has one bedroom, one loft bedroom area, and one pull out couch. We really enjoyed our stay!"
$215 nightly
The price is $240
Sep 1 - Sep 2
Total with taxes and fees
Esopus Creek modern Tiny house Retreat!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Dutchess County Hotel Reviews

Find out more about Dutchess County

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.