An aerial view of a town with a river, a bridge, and autumn-colored trees.

Holiday Homes in Poughkeepsie

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Poughkeepsie holiday homes

A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

1. Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful property with ample space for parking. Host was super nice and met all of our needs!"
United States
Nicole Y.
The price is NZ$747
includes taxes & fees
19 Oct - 20 Oct
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A spacious living area with a staircase, a dining table, and a sofa.

2. 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
Highland
9.6 out of 10, Exceptional, (13 reviews)
"We had was great time and the host Mary was amazing and excellent at communicating. Everything was perfect in the home. Thank you"
United States
Pinal
The price is NZ$1,266
includes taxes & fees
17 Nov - 18 Nov
Our home is perfect for relaxing and having lots of fun, with near by activity’s
An outdoor patio area with a covered seating area, a pool, and potted plants.

3. 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
9.2 out of 10, Wonderful, (80 reviews)
"It’s was nice, clean and the outdoor out area was really nice."
United States
Roger S.
The price is NZ$592
includes taxes & fees
28 Oct - 29 Oct
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A lakeside seating area with Adirondack chairs arranged around a central fire pit.

4. Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
Fishkill
The price is NZ$748
includes taxes & fees
11 Nov - 12 Nov
Red Cottage - Lakeside Property!
A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

5. Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"Our family enjoyed a relaxing weekend before R-day at West Point and it was perfect! A beautiful property and we hope to be back another time!"
United States
Quintina R.
The price is NZ$967
includes taxes & fees
11 Nov - 12 Nov
Chestnut on Willow Lake
A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

6. Hickory on Willow Lake

Hickory on Willow Lake
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"Clean, quiet and great location. Beautiful property."
United States
Sheila B.
The price is NZ$989
includes taxes & fees
1 Nov - 2 Nov
Hickory on Willow Lake
A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

7. A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail

A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
Wallkill
9.2 out of 10, Wonderful, (18 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
The price is NZ$228
includes taxes & fees
20 Oct - 21 Oct
A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
A refrigerator with shelves containing bottles of beer and a carton of milk.

8. Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (33 reviews)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
The price is NZ$436
includes taxes & fees
3 Nov - 4 Nov
Campfire Cottage: Fireplace, fire pit & no chores!
A living room with a sofa, a coffee table, a wooden chair, a striped rug, and a wall-mounted wreath.

9. The DeVita House Est. 1900

The DeVita House Est. 1900
Gardiner
10.0 out of 10, Exceptional, (42 reviews)
"Great house, well equipped, very accommodating hosts!"
United States
Christopher T.
The price is NZ$767
includes taxes & fees
19 Oct - 20 Oct
The DeVita House Est. 1900
A forest campsite with a tent, a fire pit, and a bench.

10. Glamping Tent & Campsite by Minnewaska State Park

Glamping Tent & Campsite by Minnewaska State Park
Kerhonkson
9.0 out of 10, Wonderful, (4 reviews)
"This place was amazing and our hosts were as equally as awesome as their campsite. My family highly recommends this place! It's got everything you need and is close to so many beautiful hiking and swimming areas!"
United States
Andie C.
The price is NZ$269
includes taxes & fees
19 Oct - 20 Oct
Glamping Tent & Campsite by Minnewaska State Park
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

11. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.4 out of 10, Exceptional, (13 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
The price is NZ$490
includes taxes & fees
25 Oct - 26 Oct
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A bedroom with a bed, a TV mounted on the wall, a window with a view of greenery, and a small seating area with a table and chairs.

12. The Studio at the Inn at High Falls

The Studio at the Inn at High Falls
High Falls
8.0 out of 10, Very good, (46 reviews)
"Great property in a serene setting. We enjoyed it very much!"
United States
John M.
The price is NZ$477
includes taxes & fees
20 Oct - 21 Oct
The Studio at the Inn at High Falls
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

13. Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Kingston
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful house to stay in, convenient to numerous restaurants and hikes. Our host was very communicative and had great recommendations for the area!"
United States
Brendan B.
The price is NZ$424
includes taxes & fees
2 Nov - 3 Nov
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
A modern living room with a fireplace, a dining area with a wooden table, and a large window with curtains.

14. Zen House at the Mountain Ridge

Zen House at the Mountain Ridge
Gardiner
10.0 out of 10, Exceptional, (12 reviews)
"Great space! Very nicely decorated. Host was very responsive and answered questions quickly. Also close to a great bakery and coffee shop!"
United States
Julie
The price is NZ$531
includes taxes & fees
1 Nov - 2 Nov
Zen House at the Mountain Ridge
A hot tub on a wooden deck with a view of a river and trees.

15. Welcome to The Boathouse! Waterfront/Boats/Hot tub

Welcome to The Boathouse! Waterfront/Boats/Hot tub
New Paltz
9.6 out of 10, Exceptional, (12 reviews)
"We enjoyed our stay very much! Everything was as described, inside was very clean, host was excellent with communication. Scenic, serene spot!"
United States
Jessica B.
The price is NZ$735
includes taxes & fees
5 Nov - 6 Nov
Welcome to The Boathouse! Waterfront/Boats/Hot tub
A wooden deck with a wood-burning stove and a door leading to an outdoor area with chairs.

16. Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet

Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet
Stone Ridge
10.0 out of 10, Exceptional, (5 reviews)
"Great tastefully kept property. Our family including the 8 year felt we should have stayed here longer."
United States
Tarun
The price is NZ$532
includes taxes & fees
1 Nov - 2 Nov
Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet
A neatly made bed with white bedding and a few colorful pillows, a wooden headboard, and a wall-mounted light fixture.

17. Retro Retreat: renovated 2BR, desk, no chore list!

Retro Retreat: renovated 2BR, desk, no chore list!
Kingston
9.6 out of 10, Exceptional, (15 reviews)
"Great, easy, full of everything you’d need. Stayed with 2 others for a work trip and it was perfect! "
United States
Kelley Marie
The price is NZ$519
includes taxes & fees
2 Nov - 3 Nov
Retro Retreat: renovated 2BR, desk, no chore list!
A kitchen with wooden shelves, a window with a view of trees, and a vase with flowers on the windowsill.

18. Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Kerhonkson
10.0 out of 10, Exceptional, (46 reviews)
"Sweet place, very close to Minnewaska State Park which was great for us"
United States
Sueane
The price is NZ$346
includes taxes & fees
17 Nov - 18 Nov
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
A wooden gate leading to a driveway with a stone pathway, surrounded by greenery and a house in the background.

19. Maple Ridge Modern Rustic Retreat where Modern comfort meets Rustic Charm

Maple Ridge Modern Rustic Retreat where Modern comfort meets Rustic Charm
Ulster Park
9.8 out of 10, Exceptional, (20 reviews)
"Easy access and checkout, extremely clean, accurate pictures, comfy beds, well stocked kitchen. Great for groups. Would gladly stay again!"
United States
Emily F.
The price is NZ$1,424
includes taxes & fees
26 Oct - 27 Oct
Maple Ridge Modern Rustic Retreat where Modern comfort meets Rustic Charm
A kitchen with grey cabinets, a stone floor, and a view of a garden through an open door.

20. Historic Cottage * Steam Shower * Chef’s Kitchen

Historic Cottage * Steam Shower * Chef’s Kitchen
Kingston
10.0 out of 10, Exceptional, (1 review)
"We had a great time staying here! The house is a gorgeous historic house with modern amenities. It was a short drive to Kingston which was super convenient. We loved that we could bring our dog with us as well. It is on a main road, but we didn't find that to be a disturbance at all. I would definitely come back here again!!"
United States
Laura D.
The price is NZ$888
includes taxes & fees
18 Nov - 19 Nov
Historic Cottage * Steam Shower * Chef’s Kitchen
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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Top Poughkeepsie Hotel Reviews

DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

8/10 Good
"Walking distance to train station and to the walkway across the Hudson and to a very good bbq brisket place. But the neighborhood is run down and the staff was not always helpful."
judy 1-night trip
Posted 8 hours ago
DoubleTree by Hilton Poughkeepsie Convention Center

Find out more about Poughkeepsie

Poughkeepsie Holiday Homes information

Number of reviews
370
Accommodation
855 Holiday Homes
Lowest Price
NZ$228
Highest Price
NZ$1,424