Vacation Rentals in Dutchess County

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Top Cities in Dutchess County

Top Vacation Rentals in Dutchess County

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

Fishkill
9.6 out of 10, Exceptional, (45)
"Great place for a quiet stay"
United States
Shawn M.
$295 nightly
The price is $334
Nov 30 - Dec 1
Total with taxes and fees
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

The Farm at Hyde Park

Staatsburg
9.8 out of 10, Exceptional, (85)
"Nice stay in an interesting building in an amazing setting. "
United States
Kristen S.
The Farm at Hyde Park

Mid-Century DJ’s Dream

Staatsburg
10.0 out of 10, Exceptional, (43)
"Location is well furnished and near many attractionHost versatile and well versed"
United States
Alberto M.
$174 nightly
The price is $197
Nov 22 - Nov 23
Total with taxes and fees
Mid-Century DJ’s Dream

Rustic Cabin in Fishkill!

Fishkill
10.0 out of 10, Exceptional, (3)
"Ideal cabin getaway. "
United States
Nadja E.
$387 nightly
The price is $440
Nov 24 - Nov 25
Total with taxes and fees
Rustic Cabin in Fishkill!

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Poughkeepsie
10.0 out of 10, Exceptional, (2)
"Great host"
United States
Lindsey F.
$497 nightly
The price is $582
Nov 24 - Nov 25
Total with taxes and fees
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Micosta Leisure Inn

3.0 star property
Hudson
9.2 out of 10, Wonderful, (131)
"Clean, pet friendly , just an overall super nice place to stay "
United States
Gail
$133 nightly
The price is $150
Nov 26 - Nov 27
Total with taxes and fees
Micosta Leisure Inn

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

Saugerties
8.2 out of 10, Very Good, (46)
"We had an amazing peaceful time at this property. Check in was seamless and we got lots of great recommendations from our hosts that we really enjoyed! It was very private and cozy and really helped us relax and renew! We will definitely be returning. "
United States
Josh M.
$145 nightly
The price is $162
Nov 23 - Nov 24
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

Glasco
10.0 out of 10, Exceptional, (34)
"Beautiful home and fantastic pool. Responsive and friendly host. Our whole family had a great time! "
United States
Courtney W.
Hamptons on the Hudson in South Saugerties

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

Brookfield
9.6 out of 10, Exceptional, (4)
"The host was very kind and welcoming. The home was spacious and the perfect setting for our celebration weekend. Everyone had their own space and we had multiple spaces for group activities. We enjoyed our time and appreciate the hospitality. "
United States
Valerie V.
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Streamside Cottage Half Mile to Town of Woodstock

Woodstock
10.0 out of 10, Exceptional, (259)
"Jane was very nice and accommodating, the cottage was very clean and comfortable, a very relaxing and calming place "
United States
Scott
$346 nightly
The price is $388
Dec 13 - Dec 14
Total with taxes and fees
Streamside Cottage Half Mile to Town of Woodstock

Esopus Creek modern Tiny house Retreat!

Kingston
9.8 out of 10, Exceptional, (60)
"The property was beautiful. Quiet area but close enough to all the places we wanted to go. Our hosts were very gracious, attentive and friendly. Enjoyed our weekend retreat. "
United States
Rebecca
$216 nightly
The price is $241
Nov 24 - Nov 25
Total with taxes and fees
Esopus Creek modern Tiny house Retreat!

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

Saugerties
9.8 out of 10, Exceptional, (95)
"Enjoyed our stay!"
United States
Mike T.
A Spectacular 50 Mile View of the Hudson Valley in all seasons

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

woodstock
9.0 out of 10, Wonderful, (45)
"I was in town for a few days to get some writing done and see friends. The cabin is beautiful and perfect for one or two people and a dog. The location is also perfect; it's in walking distance (or a very short drive) to town, but the main draw is that it's located on a beautiful stream. The rooster crowing in the background and the deer who visited the property were welcome. "
United States
Shannon F.
$276 nightly
The price is $309
Nov 23 - Nov 24
Total with taxes and fees
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery
9.8 out of 10, Exceptional, (128)
"It has an incredible mountain and water view. "
United States
MIHYUN
$271 nightly
The price is $307
Nov 23 - Nov 24
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Bearsville
10.0 out of 10, Exceptional, (123)
"A beautiful house on a stunning property. Looking forward to coming back!"
United States
A. M.
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Large,Cozy,Bright Apartment, Business Themed.

Newburgh
9.0 out of 10, Wonderful, (15)
"Very cozy stay with responsive host"
United States
Adhith P.
$585 nightly
The price is $691
Nov 22 - Nov 23
Total with taxes and fees
Large,Cozy,Bright Apartment, Business Themed.

Pet Friendly Riverfront Home in Great Barrington

Great Barrington
9.2 out of 10, Wonderful, (5)
$252 nightly
The price is $282
Nov 23 - Nov 24
Total with taxes and fees
Pet Friendly Riverfront Home in Great Barrington

Sexiest Lil Cabin in Saugerties, NY

Saugerties
9.0 out of 10, Wonderful, (13)
"A little piece of paradise!"
United States
Christi L.
Sexiest Lil Cabin in Saugerties, NY

The Studio at the Inn at High Falls

High Falls
8.0 out of 10, Very Good, (32)
"We loved our studio — it was cozy, charming, and fit our needs perfectly. Frank went above and beyond to make us feel comfortable, and his hospitality really stood out. Everything was spotless and well-kept, and we had everything we needed for a relaxing stay. The location was convenient, the space felt welcoming, and little touches made it even more enjoyable. We would definitely stay here again and highly recommend it to anyone looking for a comfortable and stress-free getaway!"
United States
Ya-elle G.
$240 nightly
The price is $268
Nov 23 - Nov 24
Total with taxes and fees
The Studio at the Inn at High Falls

Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

Croton-on-Hudson
9.6 out of 10, Exceptional, (15)
"We enjoyed our overnight stay at this quaint nicely appointed carriage house."
United States
Cathleen C.
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven
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.