Book Holiday Homes in Poughkeepsie

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Featured Holiday Homes in Poughkeepsie

Esopus Creek modern Tiny house Retreat!

Esopus Creek modern Tiny house Retreat!

Kingston
The price is NZ$404 per night from 29 Apr to 30 Apr
NZ$404
includes taxes & fees
29 Apr - 30 Apr
Stay at this vacation home in Kingston. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Thorn Preserve - Catskill Center and ...
Esopus Creek modern Tiny house Retreat!
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
The price is NZ$554 per night from 2 May to 3 May
NZ$554
includes taxes & fees
2 May - 3 May
Stay at this vacation home in Fishkill. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions SplashDown Beach and Van Wyck Homestead Museum ...
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
HOT TUB w/ POOL,  STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN

HOT TUB w/ POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN

Woodstock
Book a stay at this family-friendly vacation home in Woodstock. Enjoy free WiFi, private pools, and a water park. Popular attractions Woodstock Public Library ...
HOT TUB w/ POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN
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Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska

Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska

New Paltz
Book a stay at this family-friendly vacation home in New Paltz. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Mohonk Preserve Visitor ...
Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska
Spacious New Luxurious holiday house in lovely Hudson Valley

Spacious New Luxurious holiday house in lovely Hudson Valley

Poughkeepsie
The price is NZ$1,546 per night from 1 May to 2 May
NZ$1,546
includes taxes & fees
1 May - 2 May
Stay at this vacation home in Poughkeepsie. Enjoy a garden, patios, and in-room jetted tubs. Popular attractions Overlook Drive-In Theater and Richard L. Skimin ...
Spacious New Luxurious holiday house in lovely Hudson Valley
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

Stony Point
Book a stay at this family-friendly vacation home in Stony Point. Enjoy private pools, a fitness center, and furnished patios. Popular attractions Bear Mountain ...
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Hamptons on the Hudson in South Saugerties

Hamptons on the Hudson in South Saugerties

Glasco
Book a stay at this family-friendly vacation home in Glasco. Enjoy free WiFi, private pools, and a garden. Popular attractions Falling Waters Preserve and West ...
Hamptons on the Hudson in South Saugerties
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

Hopewell Junction
Stay at this vacation home in Hopewell Junction. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Chuang Yen Monastery and Canopus Beach ...
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

Danbury
Stay at this vacation home in Danbury. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Bear Mountain Reservation and Candlewood ...
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake
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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.

Poughkeepsie Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Poughkeepsie vacation homes are the perfect way for you to wing it.

Holiday houses in Poughkeepsie let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Poughkeepsie in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Poughkeepsie adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Poughkeepsie with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Poughkeepsie vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Poughkeepsie Holiday Homes essential information

Accommodation
1059 Holiday Homes
Lowest Price
NZ$200
Highest Price
NZ$1,546
Popular accommodation
Esopus Creek modern Tiny house Retreat!, Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo, HOT TUB w/ POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN, Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska, Spacious New Luxurious holiday house in lovely Hudson Valley, Updated Getaway w/ Pool & Hot Tub on < 3 Acres!, Hamptons on the Hudson in South Saugerties, 1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views, Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

Top trending hotels in Poughkeepsie

DoubleTree by Hilton Poughkeepsie

DoubleTree by Hilton Poughkeepsie

4 out of 5
40 Civic Center Plz, Poughkeepsie, NY
Fully refundableReserve now, pay when you stay
The price is NZ$232 per night from 11 May to 12 May
NZ$232
includes taxes & fees
11 May - 12 May
Stay at this 4-star business-friendly hotel in Poughkeepsie. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
DoubleTree by Hilton Poughkeepsie
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road, Poughkeepsie, NY
Fully refundableReserve now, pay when you stay
The price is NZ$251 per night from 11 May to 12 May
NZ$251
includes taxes & fees
11 May - 12 May
Stay at this 3-star business-friendly hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hyatt Place Poughkeepsie / Hudson Valley
Quality Inn Poughkeepsie

Quality Inn Poughkeepsie

2.5 out of 5
536 Haight Ave, Building A, Poughkeepsie, NY
Fully refundableReserve now, pay when you stay
The price is NZ$200 per night from 4 May to 5 May
NZ$200
includes taxes & fees
4 May - 5 May
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Quality Inn Poughkeepsie
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Courtyard by Marriott Poughkeepsie

Courtyard by Marriott Poughkeepsie

3 out of 5
2641 South Road/Route 9, Poughkeepsie, NY
Fully refundableReserve now, pay when you stay
The price is NZ$209 per night from 19 May to 20 May
NZ$209
includes taxes & fees
19 May - 20 May
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Courtyard by Marriott Poughkeepsie
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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.

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^Subject to availability and chosen travel dates.