Dutchess County Vacation Rentals

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Top cities in Dutchess County

Poughkeepsie which includes fall colors and a river or creek
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Poughkeepsie

Poughkeepsie
Exploring an old abandoned brick factory!!!
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Beacon

Beacon
Really pretty Winery to visit! You can sit on the porch outside or at the picnic tables by the pond with the view of the vineyards. Especially vibrant in the fall!
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Millbrook

Millbrook

Dutchess County Vacation Rentals

The Farm at Hyde Park

The Farm at Hyde Park

Staatsburg NY
Guests staying at this vacation home have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

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

Fishkill NY
$280 nightly
The price is $316 total per night
$316 total
Dec 21 - Dec 22
Total with taxes and fees
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has a garden.
Kitchen
Washer
Mid-Century DJ’s Dream

Mid-Century DJ’s Dream

Staatsburg NY
$174 nightly
The price is $197 total per night
$197 total
Dec 21 - Dec 22
Total with taxes and fees
Guests staying at this apartment have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!

Fishkill NY
$398 nightly
The price is $452 total per night
$452 total
Dec 22 - Dec 23
Total with taxes and fees
Guests staying at this cabin have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

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

Poughkeepsie NY
$550 nightly
The price is $644 total per night
$644 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has barbecue grills.
Washer
Dryer
Hamptons on the Hudson in South Saugerties

Hamptons on the Hudson in South Saugerties

Glasco NY
Guests of this vacation home enjoy features like an outdoor pool, a hot tub, and laundry facilities. Other amenities at this family-friendly vacation home include local meal delivery service, barbecue grills, and a garden.
Pool
Hot Tub
Large,Cozy,Bright Apartment, Business Themed.

Large,Cozy,Bright Apartment, Business Themed.

Newburgh NY
$399 nightly
The price is $471 total per night
$471 total
Dec 21 - Dec 22
Total with taxes and fees
This vacation home features a water park and barbecue grills.
Kitchen
Air conditioning
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Kingston NY
$230 nightly
The price is $258 total per night
$258 total
Jan 20 - Jan 21, 2026
Total with taxes and fees
Guests staying at this apartment enjoy a hot tub, laundry facilities, and a garden. This smoke-free apartment building also has barbecue grills.
Hot Tub
Kitchen
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

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

Saugerties NY
$145 nightly
The price is $162 total per night
$162 total
Dec 21 - Dec 22
Total with taxes and fees
At this cabin, guests have access to features like laundry facilities. This cabin also has barbecue grills.
Pet friendly
Laundry
Esopus Creek modern Tiny house Retreat!

Esopus Creek modern Tiny house Retreat!

Kingston NY
$232 nightly
The price is $260 total per night
$260 total
Dec 21 - Dec 22
Total with taxes and fees
At this vacation home, guests have access to barbecue grills.
Kitchen
Pet friendly
A Spectacular 50 Mile View of the Hudson Valley in all seasons

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

Saugerties NY
At this apartment, guests have access to a garden.
Kitchen
Free WiFi
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery NY
$269 nightly
The price is $304 total per night
$304 total
Dec 21 - Dec 22
Total with taxes and fees
Guests staying at this cottage have access to local meal delivery service, a garden, and barbecue grills.
Kitchen
Pet friendly
Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock

Woodstock NY
Guests staying at this cottage have access to barbecue grills and a garden.
Kitchen
Free WiFi
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

woodstock NY
$277 nightly
The price is $310 total per night
$310 total
Dec 28 - Dec 29
Total with taxes and fees
At this cottage, guests have access to barbecue grills.
Kitchen
Pet friendly
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2 out of 5
282 Cairo Junction Rd Catskill NY
$169 nightly
The price is $183 total per night
$183 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
There's free parking if you drive.
Kitchen
Pet friendly
Relaxing Catskill Mountain Cottage.

Relaxing Catskill Mountain Cottage.

West Shokan NY
Guests staying at this cottage have access to barbecue grills and a garden.
Kitchen
Pet friendly
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Bearsville NY
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has barbecue grills.
Kitchen
Washer
Micosta Leisure Inn

Micosta Leisure Inn

3 out of 5
3007 County Rd 20 Hudson NY
Free Cancellation
Reserve now, pay when you stay
$133 nightly
The price is $150 total per night
$150 total
Jan 10 - Jan 11, 2026
Total with taxes and fees
Guests of Micosta Leisure Inn enjoy free WiFi in public areas, a terrace, and laundry facilities. If you drive, put free parking to good use. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include a picnic area, barbecue grills, and a garden.
Kitchen
Pet friendly
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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.

Hotel Options in Dutchess County

    Hampton Inn & Suites Poughkeepsie

    Hampton Inn & Suites Poughkeepsie

    2361 South Rd Poughkeepsie NY
    $101 nightly
    The price is $117 total per night from Dec 28 to Dec 29
    $117 total
    Dec 28 - Dec 29
    Total with taxes and fees
    8.8/10 Excellent! (1,005 reviews)
    Hyatt Place Poughkeepsie / Hudson Valley

    Hyatt Place Poughkeepsie / Hudson Valley

    2165 South Road Poughkeepsie NY
    $101 nightly
    The price is $117 total per night from Dec 30 to Dec 31
    $117 total
    Dec 30 - Dec 31
    Total with taxes and fees
    8.8/10 Excellent! (1,008 reviews)
    Quality Inn Poughkeepsie

    Quality Inn Poughkeepsie

    536 Haight Ave, Building A Poughkeepsie NY
    $93 nightly
    The price is $108 total per night from Dec 28 to Dec 29
    $108 total
    Dec 28 - Dec 29
    Total with taxes and fees
    7.6/10 Good! (498 reviews)

Orbitz makes it easy to find vacation rentals in Dutchess County 

🏠 What is the best price for a Dutchess County vacation rental?


Dutchess County rentals range between $108 and $644 per night. At Orbitz, we have a vacation rental for every budget.


🏠 What types of vacation rentals in Dutchess County can I rent?


Choose from apartments to beautifully decorated vacation homes, condo resorts or even B&Bs or motels for your next Dutchess County getaway. Orbitz filters your search results so you can find the best Dutchess County vacation rental for you. We have tons of options.


🏠 Are cancellations free on Dutchess County vacation rentals with Orbitz?


You may be able to cancel or amend your Dutchess County vacation rental booking free of charge before a pre-agreed deadline. Make sure to check the terms of cancellation before you book—so you know exactly where you stand. 


🏠 How do I find the best vacation rental deals in Dutchess County?


Enter your travel dates, and we’ll do the rest. You can then browse our exciting deals and all the tempting vacation rentals we have on offer in Dutchess County by filtering your search by amenities, prices, and property types and look at customers ratings to help you pick.


🏠 How do I cancel my vacation rental booking through Orbitz


Vacation rentals have slightly different rules to other bookings on Orbitz. Usually, you need to contact your property manager, you may be able to get a full refund before the cancellation date. Click My TripsOpens in a new window on your Orbitz account page to find the right information contact. If you need more help, visit our Customer ServiceOpens in a new window page. 


🏠 What are the advantages of booking a vacation rental in Dutchess County?


When you book a Dutchess County vacation rental, you have the privacy of home and can add on those luxury amenities of a hotel. Filter your vacation rental results to find a place with a hot tub or pool, games rooms or large patio with a barbecue. With so much choice on offer, it’s easy to plan the perfect trip with Orbitz. 


🏠 Where can I find vacation rentals in Dutchess County?


Escape back to nature and check out some of the smaller towns. You’ll find great vacation rentals right across Dutchess County—with plenty of hidden gems. We also have plenty of inventory in Dutchess County main cities and near popular attraction spots.


🏠 Why should I book my Dutchess County vacation rental with Orbitz?


At Orbitz, we search the market for the best accommodation, flights, and car rental deals, so you don’t have to. We’ll help you build your dream Dutchess County vacation. With plenty of vacation rentals on offer, you can be sure to find the one that’s right for you in just a few clicks. 


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