Poughkeepsie holiday homes
We found 651 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Poughkeepsie, NY (POU-All Airports)
Showing deals for:17 Oct - 24 Oct
Image gallery for 4BR Home in Highland Near Wedding Venues with Mountain Views
1010 out of 10 rating
Exceptional
(20 reviews)
4BR Home in Highland Near Wedding Venues with Mountain Views
Highland, NY
8% off
Price is NZ$7,022
NZ$7,022
NZ$1,003 per night
includes taxes & fees
Image gallery for complete privacy vacation home [private pool]
9.89.8 out of 10 rating
Exceptional
(8 reviews)
complete privacy vacation home [private pool]
Newburgh, NY
11% off
Price is NZ$10,094
NZ$10,094
NZ$1,442 per night
includes taxes & fees
Image gallery for Lake House, ONE HOUR from NYC
9.89.8 out of 10 rating
Exceptional
(30 reviews)
Lake House, ONE HOUR from NYC
Newburgh, NY
8% off
Price is NZ$5,010
NZ$5,010
NZ$716 per night
includes taxes & fees
Image gallery for Mid-Hudson Estate on 11 acres with pool
1010 out of 10 rating
Exceptional
(7 reviews)
Mid-Hudson Estate on 11 acres with pool
Salisbury Mills, NY
19% off
Price is NZ$15,456
NZ$15,456
NZ$2,208 per night
includes taxes & fees
Image gallery for Charming Cottage in the Heart of the Shawangunks
1010 out of 10 rating
Exceptional
(13 reviews)
Charming Cottage in the Heart of the Shawangunks
Wallkill, NY
8% off
Price is NZ$3,985
NZ$3,985
NZ$569 per night
includes taxes & fees
Image gallery for Cozy Wallkill Inn family home.
9.69.6 out of 10 rating
Exceptional
(30 reviews)
Cozy Wallkill Inn family home.
Wallkill, NY
7% off
Price is NZ$6,308
NZ$6,308
NZ$901 per night
includes taxes & fees
Image gallery for Charming 3-bedroom house.
1010 out of 10 rating
Exceptional
(9 reviews)
Charming 3-bedroom house.
Cortlandt, NY
7% off
Price is NZ$4,132
NZ$4,132
NZ$590 per night
includes taxes & fees
Image gallery for The Perfect Essential Getaway!
9.69.6 out of 10 rating
Exceptional
(5 reviews)
The Perfect Essential Getaway!
Washingtonville, NY
8% off
Price is NZ$13,035
NZ$13,035
NZ$1,862 per night
includes taxes & fees
Image gallery for LOCATION LOCATION LOCATION IN THE HEART OF BEACON & RIGHT ON MAIN STREET.
1010 out of 10 rating
Exceptional
(16 reviews)
LOCATION LOCATION LOCATION IN THE HEART OF BEACON & RIGHT ON MAIN STREET.
Beacon, NY
16% off
Price is NZ$4,661
NZ$4,661
NZ$666 per night
includes taxes & fees
Image gallery for Fun, Friends, and Family Lakefront Home w/Dock and Beach
1010 out of 10 rating
Exceptional
(11 reviews)
Fun, Friends, and Family Lakefront Home w/Dock and Beach
Mahopac, NY
12% off
Price is NZ$8,654
NZ$8,654
NZ$1,236 per night
includes taxes & fees
Image gallery for Secluded House with hot tub at base of Shawangunk Ridge
1010 out of 10 rating
Exceptional
(8 reviews)
Secluded House with hot tub at base of Shawangunk Ridge
New Paltz, NY
8% off
Price is NZ$10,111
NZ$10,111
NZ$1,444 per night
includes taxes & fees
Image gallery for Contemporary Cozy Cottage
1010 out of 10 rating
Exceptional
(24 reviews)
Contemporary Cozy Cottage
Lake Peekskill, NY
8% off
Price is NZ$3,585
NZ$3,585
NZ$512 per night
includes taxes & fees
Image gallery for Wildflower Lotus Farm a Luxurious 5bd Home w/ Pool, Firepit and more
1010 out of 10 rating
Exceptional
(7 reviews)
Wildflower Lotus Farm a Luxurious 5bd Home w/ Pool, Firepit and more
Gardiner, NY
8% off
Price is NZ$17,644
NZ$17,644
NZ$2,521 per night
includes taxes & fees
Image gallery for 1890's Log Cabin ~ 230 Acre Private Reserve ~ 150’ Waterfall ~ Hiking Trails
9.89.8 out of 10 rating
Exceptional
(23 reviews)
1890's Log Cabin ~ 230 Acre Private Reserve ~ 150’ Waterfall ~ Hiking Trails
Wallkill, NY
8% off
Price is NZ$15,361
NZ$15,361
NZ$2,194 per night
includes taxes & fees
Image gallery for Spacious/Secluded Home w/Pool, Chefs Kitchen, Neighboring Farm Pastoral Views
1010 out of 10 rating
Exceptional
(40 reviews)
Spacious/Secluded Home w/Pool, Chefs Kitchen, Neighboring Farm Pastoral Views
High Falls, NY
8% off
Price is NZ$16,281
NZ$16,281
NZ$2,326 per night
includes taxes & fees
Image gallery for Bear Mountain House.
1010 out of 10 rating
Exceptional
(14 reviews)
Bear Mountain House.
Garrison, NY
8% off
Price is NZ$8,653
NZ$8,653
NZ$1,236 per night
includes taxes & fees
Image gallery for Glamping in the woods, beautiful property one hour from NYC.
1010 out of 10 rating
Exceptional
(5 reviews)
Glamping in the woods, beautiful property one hour from NYC.
Pleasant Valley, NY
11% off
Price is NZ$1,738
NZ$1,738
NZ$248 per night
includes taxes & fees
Image gallery for Sweet spot studio on village outskirts
1010 out of 10 rating
Exceptional
(28 reviews)
Sweet spot studio on village outskirts
New Paltz, NY
8% off
Price is NZ$3,181
NZ$3,181
NZ$454 per night
includes taxes & fees
Image gallery for Ultra Secluded mountaintop mansion amazing views-hot tub-arcade
8.48.4 out of 10 rating
Very good
(18 reviews)
Ultra Secluded mountaintop mansion amazing views-hot tub-arcade
Mahopac, NY
16% off
Price is NZ$10,424
NZ$10,424
NZ$1,489 per night
includes taxes & fees
Image gallery for Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
1010 out of 10 rating
Exceptional
(15 reviews)
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
Carmel, NY
19% off
Price is NZ$5,802
NZ$5,802
NZ$829 per night
includes taxes & fees
Image gallery for Private Home with Pool & Jacuzzi in the Hudson Valley
1010 out of 10 rating
Exceptional
(8 reviews)
Private Home with Pool & Jacuzzi in the Hudson Valley
Montgomery, NY
12% off
Price is NZ$8,640
NZ$8,640
NZ$1,234 per night
includes taxes & fees
Image gallery for 76 acres of peace and light in Hudson Valley
9.49.4 out of 10 rating
Exceptional
(14 reviews)
76 acres of peace and light in Hudson Valley
Campbell Hall, NY
8% off
Price is NZ$9,513
NZ$9,513
NZ$1,359 per night
includes taxes & fees
Image gallery for A Peaceful Bucolic Retreat by the Water at the Gateway of Hudson Valley
1010 out of 10 rating
Exceptional
(6 reviews)
A Peaceful Bucolic Retreat by the Water at the Gateway of Hudson Valley
Holmes, NY
8% off
Price is NZ$4,791
NZ$4,791
NZ$684 per night
includes taxes & fees
Image gallery for Modern Home in Gardiner NY - Hudson Valley
9.69.6 out of 10 rating
Exceptional
(8 reviews)
Modern Home in Gardiner NY - Hudson Valley
Gardiner, NY
6% off
Price is NZ$2,389
NZ$2,389
NZ$341 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Poughkeepsie
Showing deals for: 14 Oct - 17 Oct
Cozy Home with Hot Tub*, Game Room, and Fire Pit
Sleeps 7 · 3 bedrooms · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
The current price is NZ$1,651
NZ$1,651
for 3 nights, 1 home
NZ$550 per night
includes taxes & fees
Historic 1 BR Family Home Near Buttermilk Falls & Hudson River, on 5 Acres
Sleeps 4 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
19 reviews(19 reviews)
The current price is NZ$1,328
NZ$1,328
for 3 nights, 1 room
NZ$443 per night
includes taxes & fees
Cozy Getaway on a 50 Acre Historic Ranch
Sleeps 4 · 2 bedrooms · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
2 reviews(2 reviews)
The current price is NZ$1,870
NZ$1,870
for 3 nights, 1 home
NZ$623 per night
includes taxes & fees
The Scenic Mansion With Breathtaking View
Sleeps 10 · 4 bedrooms · 6 bathrooms
9.29.2 out of 10
Wonderfulwonderful
15 reviews(15 reviews)
The current price is NZ$6,768
NZ$6,768
for 3 nights, 1 villa
NZ$2,256 per night
includes taxes & fees
1890's Log Cabin ~ 230 Acre Private Reserve ~ 150’ Waterfall ~ Hiking Trails
Sleeps 12 · 5 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
23 reviews(23 reviews)
The current price is NZ$7,899
NZ$7,899
for 3 nights, 1 cabin
NZ$2,633 per night
includes taxes & fees
GORGEOUS COUNTRY ESTATE, VIEWS, YEAR-ROUND JACUZZI!
Sleeps 8 · 4 bedrooms · 4 bathrooms
9.89.8 out of 10
Exceptionalexceptional
54 reviews(54 reviews)
The current price is NZ$6,317
NZ$6,317
for 3 nights, 1 home
NZ$2,106 per night
includes taxes & fees
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value