Vacation rentals in Dutchess County

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Top cities to explore in Dutchess County

Poughkeepsie which includes fall colors and a river or creek

Poughkeepsie

Vacation Rentals
Poughkeepsie

Top vacation rentals in Dutchess County

The Farm at Hyde Park

The Farm at Hyde Park

8.84 mi from city center
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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Magnificent Lake View

Magnificent Lake View

2 out of 5
16.5 mi from city center
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Book a stay at this family-friendly cottage in Holmes. Enjoy free WiFi, a pool table, and patios. Popular attractions Whaley Lake and Lake Dutchess are located nearby.
Kitchen
Free WiFi
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

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

18.06 mi from city center
$293 nightly
The price is $331 total per night
$331 total
Aug 31 - Sep 1
Total includes taxes and fees
This vacation home includes a garden and laundry facilities.
Kitchen
Washer
Postcard Cabins Eastern Catskills

Postcard Cabins Eastern Catskills

2 out of 5
282 Cairo Junction Rd, Catskill, NY
34.21 mi from city center
$204 nightly
The price is $220 total per night
$220 total
Aug 17 - Aug 18
Total includes taxes and fees
This cabin features a virtual front desk. Take advantage of the free self parking.
Kitchen
Pet friendly
Micosta Leisure Inn

Micosta Leisure Inn

3 out of 5
3007 County Rd 20, Hudson, NY
Free Cancellation
Reserve now, pay when you stay
35.12 mi from city center
$133 nightly
The price is $150 total per night
$150 total
Aug 18 - Aug 19
Total includes taxes and fees
This aparthotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the 50 onsite conference rooms. A restaurant, laundry facilities, and barbecue grills are also provided.
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

32.82 mi from city center
$284 nightly
The price is $321 total per night
$321 total
Sep 1 - Sep 2
Total includes taxes and fees
This cottage includes a garden and barbecue grills.
Kitchen
Pet friendly
'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

26.01 mi from city center
$145 nightly
The price is $162 total per night
$162 total
Sep 3 - Sep 4
Total includes taxes and fees
This cabin featured laundry facilities and barbecue grills.
Pet friendly
Laundry
The Studio at the Inn at High Falls

The Studio at the Inn at High Falls

22.21 mi from city center
$243 nightly
The price is $272 total per night
$272 total
Aug 19 - Aug 20
Total includes taxes and fees
A garden is available at this vacation home.
Kitchen
Pet friendly
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

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

22.81 mi from city center
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This vacation home featured laundry facilities and barbecue grills.
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

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

24.17 mi from city center
$510 nightly
The price is $602 total per night
$602 total
Aug 24 - Aug 25
Total includes taxes and fees
A gym is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Kitchen
Washer
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

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

27.63 mi from city center
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A hot tub is featured at this vacation home, along with a garden and laundry facilities. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site.
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

36.27 mi from city center
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This villa features an outdoor pool and a hot tub. Laundry facilities and barbecue grills are also provided.
LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!

LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!

37.51 mi from city center
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Ski-in/ski-out access and a hot tub are featured at this smoke-free vacation home. Families will appreciate the arcade/game room and onsite laundry facilities. A garden and barbecue grills are also provided.
Hot Tub
Kitchen
Hamptons on the Hudson in South Saugerties

Hamptons on the Hudson in South Saugerties

20.88 mi from city center
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This vacation home features an outdoor pool and a hot tub. Families will appreciate the playground and onsite laundry facilities. A garden and barbecue grills are also provided.
Sioux Tipi on Chloe's Lake

Sioux Tipi on Chloe's Lake

26.09 mi from city center
$130 nightly
The price is $146 total per night
$146 total
Aug 24 - Aug 25
Total includes taxes and fees
Stay at this vacation home in Saugerties. Enjoy in-room fireplaces. Popular attractions Vinnie's Farm Market and Kiwanis Ice Arena are located nearby.
Esopus Creek modern Tiny house Retreat!

Esopus Creek modern Tiny house Retreat!

21.49 mi from city center
$211 nightly
The price is $236 total per night
$236 total
Aug 24 - Aug 25
Total includes taxes and fees
This vacation home features barbecue grills.
Kitchen
Pet friendly
Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock

25.49 mi from city center
$301 nightly
The price is $337 total per night
$337 total
Sep 2 - Sep 3
Total includes taxes and fees
This cottage includes a garden and barbecue grills.
Kitchen
Free WiFi
Charming cottage with lake access, wood burning fire place, and WiFi

Charming cottage with lake access, wood burning fire place, and WiFi

2 out of 5
19.87 mi from city center
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This vacation home features a garden, laundry facilities, and barbecue grills.
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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.

The Best Way to Find Vacation Rentals in Dutchess County 

How cheap is a vacation rental in Dutchess County?


You can find Dutchess County vacation rentals from just $146 per night. 


How do you look for the best vacation rental deals in Dutchess County with Travelocity?


Simply enter your travel dates and filter by price, property type, bedrooms, amenities, and more. We put all the best deals in one place, so it’s easy to find your perfect stay. You’ll always find incredible deals on Dutchess County vacation rentals with Travelocity. 


Are cancellations free on vacation rentals with Travelocity?


You may be able to cancel your Dutchess County vacation rental for free. Cancellation policies differ between properties so check the terms of your stay before you book. Travelocity offers many flexible cancellation options as well as book now, pay later deals for peace of mind.


What types of vacation rentals are available in Dutchess County?


Whether you’re in search of adventure, planning a romantic getaway, or booking a trip for the whole family, you’re sure to find the perfect Dutchess County vacation rental. Check out our tempting selection of resorts, apartments, vacation homes, condos and more and start building a trip to really look forward to, whatever your budget and your wish list.


What are the benefits of booking a short-term rental in Dutchess County?


Whether you’re a winter wanderer or planning a summer sojourn, Dutchess County vacation rentals make for a great trip—find one at Travelocity for a fantastic price. With a range of amenities on offer, like swimming-pools, free WiFi, breakfast included, pet-friendly options and many more, it’s easy to book a vacation rental that checks all the boxes. And with Travelocity’s easy filtering system, you’ll find yours in no time. 


Where can I find vacation rentals in Dutchess County?


Take your pick from the excitement of the big Dutchess County cities. Or escape to nature in the miles of greenery that are waiting for you. Browse a selection of the best deals with Travelocity, enter your travel dates, or check out the map view to find a hidden gem. 


How do I find a family-friendly vacation rental in Dutchess County?


Simply enter your travel dates and hit search. From here, you can filter to find your family-friendly stay, as well as a range of other amenities, such as hot tubs, pools, and even waterparks. 


Why is Travelocity the best site to find your Dutchess County rentals?


Travelocity takes care of everything, bringing incredible deals on an impressive selection of accommodation into one simple-to-use portal. And because we always source incredible deals, you can make a saving on many bookings. Travelocity makes it easy.


How do I cancel my vacation rental with Travelocity?


It’s simple. Just contact the property manager. You’ll find their contact information in the itinerary section of your Travelocity account. In many cases, you may be able to get a full refund if you cancel before the cancellation deadline. Deadlines differ between properties, so it’s always best to check before you book. To find out more, visit the Customer Service PortalOpens in a new window.