Poughkeepsie holiday rentals
We found 641 holiday rentals — enter your dates for availability
If you are looking to stay near Poughkeepsie, NY (POU-Dutchess County), take a look at private holiday rentals to choose your home away from home. Whether you're staying in a holiday rental with a group or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include Wi-Fi and a washer and dryer. You'll be able to choose a property to rent that has what everyone needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Poughkeepsie, NY (POU-Dutchess County)
Showing deals for:14 Nov - 21 Nov
Image gallery for Hillcrest Glasshouse - a minimalist modern retreat
1010 out of 10 rating
Exceptional
(12 reviews)
Hillcrest Glasshouse - a minimalist modern retreat
Newburgh, NY
8% off
Price is AU$11,512
AU$11,512
AU$1,645 per night
includes taxes & fees
Image gallery for 4BR Home in Highland Near Mountain Views and Wedding Venues
1010 out of 10 rating
Exceptional
(20 reviews)
4BR Home in Highland Near Mountain Views and Wedding Venues
Highland, NY
11% off
Price is AU$6,084
AU$6,084
AU$869 per night
includes taxes & fees
Image gallery for 6 Acre Private Hudson Valley Estate
9.69.6 out of 10 rating
Exceptional
(5 reviews)
6 Acre Private Hudson Valley Estate
Highland, NY
7% off
Price is AU$19,687
AU$19,687
AU$2,812 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 AU$4,554
AU$4,554
AU$651 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 AU$5,768
AU$5,768
AU$824 per night
includes taxes & fees
Image gallery for Majestic Oasis in Rhinebeck w/ Hot Tub, Pool, Lake, & Fire Pit
9.49.4 out of 10 rating
Exceptional
(68 reviews)
Majestic Oasis in Rhinebeck w/ Hot Tub, Pool, Lake, & Fire Pit
Rhinebeck, NY
8% off
Price is AU$13,668
AU$13,668
AU$1,953 per night
includes taxes & fees
Image gallery for Millbrook - Beautifully Restored 1840 Colonial - Dutchess Co. NY
9.89.8 out of 10 rating
Exceptional
(13 reviews)
Millbrook - Beautifully Restored 1840 Colonial - Dutchess Co. NY
Millbrook, NY
8% off
Price is AU$6,444
AU$6,444
AU$921 per night
includes taxes & fees
Image gallery for Brookview Farm Country Living
9.49.4 out of 10 rating
Exceptional
(8 reviews)
Brookview Farm Country Living
New Paltz, NY
8% off
Price is AU$6,372
AU$6,372
AU$910 per night
includes taxes & fees
Image gallery for CREATIVES DREAM GETAWAY
1010 out of 10 rating
Exceptional
(5 reviews)
CREATIVES DREAM GETAWAY
Gardiner, NY
8% off
Price is AU$3,955
AU$3,955
AU$565 per night
includes taxes & fees
Image gallery for West Park/Esopus Victorian - 2 King and 1 Queen Bed
9.69.6 out of 10 rating
Exceptional
(12 reviews)
West Park/Esopus Victorian - 2 King and 1 Queen Bed
Esopus, NY
8% off
Price is AU$3,094
AU$3,094
AU$442 per night
includes taxes & fees
Image gallery for Hidden Charm in Hudson Valley In Dutchess County
1010 out of 10 rating
Exceptional
(20 reviews)
Hidden Charm in Hudson Valley In Dutchess County
Salt Point, NY
14% off
Price is AU$5,168
AU$5,168
AU$738 per night
includes taxes & fees
Image gallery for Spacious A-Frame w/ Game Room, Fire Pit & Modern Comforts in Hudson Valley
1010 out of 10 rating
Exceptional
(7 reviews)
Spacious A-Frame w/ Game Room, Fire Pit & Modern Comforts in Hudson Valley
New Paltz, NY
8% off
Price is AU$7,361
AU$7,361
AU$1,052 per night
includes taxes & fees
Image gallery for Waterfront retreat near Kingston, NY w/ stunning views, firepit & trails nearby!
1010 out of 10 rating
Exceptional
(6 reviews)
Waterfront retreat near Kingston, NY w/ stunning views, firepit & trails nearby!
Ulster Park, NY
8% off
Price is AU$2,939
AU$2,939
AU$420 per night
includes taxes & fees
Image gallery for Luxury retreat w/ private deck, garden, firepit on organic farm
1010 out of 10 rating
Exceptional
(22 reviews)
Luxury retreat w/ private deck, garden, firepit on organic farm
Gardiner, NY
8% off
Price is AU$2,655
AU$2,655
AU$379 per night
includes taxes & fees
Image gallery for Private Tudor style 5 bedroom home in country setting.
1010 out of 10 rating
Exceptional
(9 reviews)
Private Tudor style 5 bedroom home in country setting.
Millbrook, NY
12% off
Price is AU$11,224
AU$11,224
AU$1,603 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 AU$14,507
AU$14,507
AU$2,072 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
(8 reviews)
Wildflower Lotus Farm a Luxurious 5bd Home w/ Pool, Firepit and more
Gardiner, NY
8% off
Price is AU$15,682
AU$15,682
AU$2,240 per night
includes taxes & fees
Image gallery for The Chicken Coop
9.29.2 out of 10 rating
Wonderful
(7 reviews)
The Chicken Coop
Staatsburg, NY
6% off
Price is AU$2,488
AU$2,488
AU$355 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 AU$6,957
AU$6,957
AU$994 per night
includes taxes & fees
Image gallery for Cheerful Circa 1700 3 Bedroom Farmhouse
1010 out of 10 rating
Exceptional
(6 reviews)
Cheerful Circa 1700 3 Bedroom Farmhouse
Hyde Park, NY
30% off
Price is AU$4,687
AU$4,687
AU$670 per night
includes taxes & fees
Image gallery for Sweet spot studio on village outskirts
1010 out of 10 rating
Exceptional
(29 reviews)
Sweet spot studio on village outskirts
New Paltz, NY
8% off
Price is AU$2,307
AU$2,307
AU$330 per night
includes taxes & fees
Image gallery for Storm King Lodge is a country retreat ready for you.
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Storm King Lodge is a country retreat ready for you.
Mountainville, NY
16% off
Price is AU$11,436
AU$11,436
AU$1,634 per night
includes taxes & fees
Image gallery for Stunning Light-Filled Contemporary Home on 7 Acres
1010 out of 10 rating
Exceptional
(25 reviews)
Stunning Light-Filled Contemporary Home on 7 Acres
Salt Point, NY
22% off
Price is AU$5,447
AU$5,447
AU$778 per night
includes taxes & fees
Image gallery for GORGEOUS COUNTRY ESTATE, VIEWS, YEAR-ROUND JACUZZI!
9.89.8 out of 10 rating
Exceptional
(55 reviews)
GORGEOUS COUNTRY ESTATE, VIEWS, YEAR-ROUND JACUZZI!
New Paltz, NY
8% off
Price is AU$9,511
AU$9,511
AU$1,359 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Poughkeepsie
Fun, Friends, and Family Lakefront Home w/Dock and Beach
Sleeps 12 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
12 reviews(12 reviews)
Pet-Friendly Beacon Area Vacation Rental: 6 Acres
Sleeps 13 · 5 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
17 reviews(17 reviews)
La Casita - A Home Away from Home
Sleeps 5 · 3 bedrooms · 1+ bathroom
8.88.8 out of 10
Excellentexcellent
5 reviews(5 reviews)
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
27 reviews(27 reviews)
Ultra Secluded mountaintop mansion amazing views-hot tub-arcade
Sleeps 16 · 6 bedrooms · 3+ bathrooms
8.48.4 out of 10
Very goodvery good
18 reviews(18 reviews)
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Sleeps 12 · 4 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
12 reviews(12 reviews)
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