Poughkeepsie holiday lettings
We found 638 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Poughkeepsie, NY (POU-All Airports)
Showing deals for:7 Nov - 14 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
7% off
Price is £5,879
£5,879
£840 per night
includes taxes & fees
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
11% off
Price is £3,124
£3,124
£446 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 £2,924
£2,924
£418 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 £9,904
£9,904
£1,415 per night
includes taxes & fees
Image gallery for Charming Cottage in the Heart of the Shawangunks
1010 out of 10 rating
Exceptional
(15 reviews)
Charming Cottage in the Heart of the Shawangunks
Wallkill, NY
7% off
Price is £1,823
£1,823
£260 per night
includes taxes & fees
Image gallery for NEW! FOLEY'S LOG CABIN with Hot Tub
1010 out of 10 rating
Exceptional
(6 reviews)
NEW! FOLEY'S LOG CABIN with Hot Tub
Pine Bush, NY
8% off
Price is £3,979
£3,979
£568 per night
includes taxes & fees
Image gallery for Brookview Farm Country Living
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Brookview Farm Country Living
New Paltz, NY
8% off
Price is £3,235
£3,235
£462 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 £3,902
£3,902
£557 per night
includes taxes & fees
Image gallery for West Park/Esopus Victorian - 2 King and 1 Queen Bed
1010 out of 10 rating
Exceptional
(11 reviews)
West Park/Esopus Victorian - 2 King and 1 Queen Bed
Esopus, NY
8% off
Price is £1,571
£1,571
£224 per night
includes taxes & fees
Image gallery for The Chicken Coop
9.09.0 out of 10 rating
Wonderful
(6 reviews)
The Chicken Coop
Staatsburg, NY
6% off
Price is £1,266
£1,266
£181 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 £4,015
£4,015
£574 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 £1,345
£1,345
£192 per night
includes taxes & fees
Image gallery for Green Haven House
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Green Haven House
Campbell Hall, NY
8% off
Price is £5,741
£5,741
£820 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
11% off
Price is £5,745
£5,745
£821 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 £5,693
£5,693
£813 per night
includes taxes & fees
Image gallery for Higashi: New Paltz family home with King bed minutes to downtown
9.69.6 out of 10 rating
Exceptional
(15 reviews)
Higashi: New Paltz family home with King bed minutes to downtown
New Paltz, NY
8% off
Price is £2,056
£2,056
£294 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
15% off
Price is £5,843
£5,843
£835 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
(24 reviews)
1890's Log Cabin ~ 230 Acre Private Reserve ~ 150’ Waterfall ~ Hiking Trails
Wallkill, NY
8% off
Price is £7,004
£7,004
£1,001 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 £4,806
£4,806
£687 per night
includes taxes & fees
Image gallery for CHARMING Mid Century Vintage 1BR Guest Suite - 2 Min to Downtown
8.48.4 out of 10 rating
Very good
(6 reviews)
CHARMING Mid Century Vintage 1BR Guest Suite - 2 Min to Downtown
New Paltz, NY
8% off
Price is £902
£902
£129 per night
includes taxes & fees
Image gallery for The Scenic Mansion With Breathtaking View
8.88.8 out of 10 rating
Excellent
(16 reviews)
The Scenic Mansion With Breathtaking View
Highland, NY
8% off
Price is £6,085
£6,085
£869 per night
includes taxes & fees
Image gallery for The House In Highland- Secluded Retreat
1010 out of 10 rating
Exceptional
(9 reviews)
The House In Highland- Secluded Retreat
Highland, NY
8% off
Price is £3,474
£3,474
£496 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 £7,402
£7,402
£1,057 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 £1,173
£1,173
£168 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Poughkeepsie
6 Acre Private Hudson Valley Estate
Sleeps 8 · 4 bedrooms · 2+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
Spacious A-Frame w/ Game Room, Fire Pit & Modern Comforts in Hudson Valley
Sleeps 8 · 4 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
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)
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)
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 Scenic Mansion With Breathtaking View
Sleeps 10 · 4 bedrooms · 6 bathrooms
8.88.8 out of 10
Excellentexcellent
16 reviews(16 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, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value