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

Magnificent Lake View

Magnificent Lake View

2 out of 5
At this cottage, guests have access to features like an arcade/game room.
Kitchen
Free WiFi
The Farm at Hyde Park

The Farm at Hyde Park

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

$292 nightly
The price is $330 total per night
$330 total
Aug 31 - Sep 1
Total includes 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
1 Br Private Victorian Apt in Convenient City Location on Half Acre Sleeps 4

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

2 out of 5
83 South Hamilton Street, Poughkeepsie, NY
$174 nightly
The price is $204 total per night
$204 total
Aug 21 - Aug 22
Total includes taxes and fees
This apartment features free WiFi in public areas and barbecue grills. Limited parking is available. This smoke-free apartment building also has a garden.
Free WiFi
Outdoor Space
Hamptons on the Hudson in South Saugerties

Hamptons on the Hudson in South Saugerties

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
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!

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

$145 nightly
The price is $162 total per night
$162 total
Sep 3 - Sep 4
Total includes taxes and fees
At this cabin, guests have access to features like laundry facilities. This cabin also has barbecue grills.
Pet friendly
Laundry
Sioux Tipi on Chloe's Lake

Sioux Tipi on Chloe's Lake

$130 nightly
The price is $146 total per night
$146 total
Aug 24 - Aug 25
Total includes taxes and fees
Guests of this vacation home have access to designated smoking areas.
Kitchen
Pet friendly
Our home is perfect for relaxing and having lots of fun, with near by activity’s

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

Guests staying at this vacation home enjoy a hot tub, laundry facilities, and barbecue grills. This family-friendly vacation home also has a garden.
Hot Tub
Kitchen
Esopus Creek modern Tiny house Retreat!

Esopus Creek modern Tiny house Retreat!

$216 nightly
The price is $241 total per night
$241 total
Aug 24 - Aug 25
Total includes taxes and fees
At this vacation home, guests have access to barbecue grills.
Kitchen
Pet friendly
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

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

$459 nightly
The price is $542 total per night
$542 total
Aug 24 - Aug 25
Total includes taxes and fees
At this vacation home, guests have access to a gym, laundry facilities, and barbecue grills. This smoke-free vacation home also has a garden.
Kitchen
Washer
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

$271 nightly
The price is $307 total per night
$307 total
Sep 8 - Sep 9
Total includes taxes and fees
Guests staying at this cottage have access to local meal delivery service, barbecue grills, and a garden.
Kitchen
Pet friendly
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

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

Guests of this vacation home enjoy a hot tub, an arcade/game room, and laundry facilities. Other amenities at this family-friendly vacation home include a garden and barbecue grills.
Hot Tub
Kitchen
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

$275 nightly
The price is $308 total per night
$308 total
Sep 7 - Sep 8
Total includes taxes and fees
At this cottage, guests have access to barbecue grills.
Kitchen
Pet friendly
The Studio at the Inn at High Falls

The Studio at the Inn at High Falls

$243 nightly
The price is $272 total per night
$272 total
Aug 21 - Aug 22
Total includes taxes and fees
At this vacation home, guests have access to a garden.
Kitchen
Pet friendly
Postcard Cabins Eastern Catskills

Postcard Cabins Eastern Catskills

2 out of 5
282 Cairo Junction Rd, Catskill, NY
$204 nightly
The price is $220 total per night
$220 total
Aug 21 - Aug 22
Total includes taxes and fees
There's free parking if you drive.
Kitchen
Pet friendly
LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!

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

Guests staying at this vacation home enjoy ski-in/ski-out access, a hot tub, and an arcade/game room. Other amenities at this ski vacation home include laundry facilities, barbecue grills, and a garden.
Hot Tub
Kitchen
Micosta Leisure Inn

Micosta Leisure Inn

3 out of 5
3007 County Rd 20, Hudson, NY
$133 nightly
The price is $150 total per night
$150 total
Aug 21 - Aug 22
Total includes 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 garden, barbecue grills, and a picnic area.
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

    Quality Inn & Suites Fishkill South near I-84

    Quality Inn & Suites Fishkill South near I-84

    849 Route 52, Fishkill, NY
    $99 nightly
    The price is $112 total per night from Sep 7 to Sep 8
    $112 total
    Sep 7 - Sep 8
    Total includes taxes and fees
    8.8/10 Excellent! (1,008 reviews)
    Quality Inn Hyde Park Poughkeepsie North

    Quality Inn Hyde Park Poughkeepsie North

    4142 Albany Post Rd, Hyde Park, NY
    $80 nightly
    The price is $91 total per night from Sep 7 to Sep 8
    $91 total
    Sep 7 - Sep 8
    Total includes taxes and fees
    8/10 Very Good! (1,010 reviews)
    Quality Inn Poughkeepsie

    Quality Inn Poughkeepsie

    536 Haight Ave, Building A, Poughkeepsie, NY
    $103 nightly
    The price is $120 total per night from Sep 8 to Sep 9
    $120 total
    Sep 8 - Sep 9
    Total includes taxes and fees
    7.6/10 Good! (394 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 $91 and $542 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. 


More Places To Stay in Dutchess County

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