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

Poughkeepsie Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Poughkeepsie vacation homes

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

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
9.8 out of 10, Exceptional, (6 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 CA $310
CA $691 total
includes taxes & fees
Nov 9 - Nov 10
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

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, (14 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 CA $318
CA $941 total
includes taxes & fees
Nov 9 - Nov 10
Our home is perfect for relaxing and having lots of fun, with near by activity’s

3. Chilly Days Hiking, Quiet Yard, an Easy Escape Near New Paltz

Chilly Days Hiking, Quiet Yard, an Easy Escape Near New Paltz
New Paltz
10.0 out of 10, Exceptional, (8 reviews)
"Superb property - comfortable, spotless, all the amenities you could need, and lots of space. "
United States
Thomas B.
The price is CA $246
CA $819 total
includes taxes & fees
Nov 9 - Nov 10
Chilly Days Hiking, Quiet Yard, an Easy Escape Near New Paltz

4. 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, (81 reviews)
"The property was as advertised and met our needs for our trip."
United States
Sara
The price is CA $369
CA $443 total
includes taxes & fees
Nov 15 - Nov 16
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

5. Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
New Paltz
9.6 out of 10, Exceptional, (42 reviews)
"Really nice, house. Location was great. There were 8 of us there for a girls weekend. Plenty of room for all.Clean, attentive host, kitchen was well stocked for our needs. Hot tub was great."
United States
Shirley A.
The price is CA $364
CA $563 total
includes taxes & fees
Nov 15 - Nov 16
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

6. 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 CA $544
CA $762 total
includes taxes & fees
Nov 11 - Nov 12
Chestnut on Willow Lake

7. Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
Fishkill
The price is CA $389
CA $568 total
includes taxes & fees
Nov 11 - Nov 12
Red Cottage - Lakeside Property!

8. 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 CA $544
CA $762 total
includes taxes & fees
Nov 9 - Nov 10
Hickory on Willow Lake

9. A Cozy Private Suite in a Country Home near New Paltz

A Cozy Private Suite in a Country Home near New Paltz
Wallkill
9.2 out of 10, Wonderful, (20 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
The price is CA $102
CA $188 total
includes taxes & fees
Nov 9 - Nov 10
A Cozy Private Suite in a Country Home near New Paltz

10. 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 CA $106
CA $328 total
includes taxes & fees
Nov 18 - Nov 19
Campfire Cottage: Fireplace, fire pit & no chores!

11. The DeVita House Est. 1900

The DeVita House Est. 1900
Gardiner
10.0 out of 10, Exceptional, (46 reviews)
"The house was in a perfect location! Host was very easy to communicate with!"
United States
Matthew
The price is CA $247
CA $642 total
includes taxes & fees
Nov 9 - Nov 10
The DeVita House Est. 1900

12. 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 CA $239
CA $380 total
includes taxes & fees
Nov 9 - Nov 10
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

13. The Studio at the Inn at High Falls

The Studio at the Inn at High Falls
High Falls
8.2 out of 10, Very good, (47 reviews)
"Great property in a serene setting. We enjoyed it very much!"
United States
John M.
The price is CA $159
CA $365 total
includes taxes & fees
Nov 9 - Nov 10
The Studio at the Inn at High Falls

14. 3BR Hudson Valley home perfect for families!

3BR Hudson Valley home perfect for families!
Wallkill
10.0 out of 10, Exceptional, (6 reviews)
"This property was lovely and peaceful! We enjoyed the stay in the area! Very clean and neat. Easy to use technology and check-in/out."
United States
Cheryl N.
The price is CA $289
CA $736 total
includes taxes & fees
Nov 9 - Nov 10
3BR Hudson Valley home perfect for families!

15. 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, (7 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 CA $106
CA $343 total
includes taxes & fees
Nov 10 - Nov 11
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

16. Zen House at the Mountain Ridge

Zen House at the Mountain Ridge
Gardiner
10.0 out of 10, Exceptional, (13 reviews)
"The house was perfect and really well decorated. The area it was in, proximity to everything. Couldn't have asked for a better spot."
United States
Theresa
The price is CA $151
CA $269 total
includes taxes & fees
Nov 9 - Nov 10
Zen House at the Mountain Ridge

17. 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, (6 reviews)
"Great tastefully kept property. Our family including the 8 year felt we should have stayed here longer."
United States
Tarun
The price is CA $159
CA $320 total
includes taxes & fees
Dec 3 - Dec 4
Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet

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

Welcome to The Boathouse! Waterfront/Boats/Hot tub
New Paltz
9.6 out of 10, Exceptional, (14 reviews)
"Seth was great and the property was really nice. Never did see any fitness center, not sure where that was, but it was a really nice place and I would definetly stay there again."
United States
Thomas S.
The price is CA $350
CA $553 total
includes taxes & fees
Nov 9 - Nov 10
Welcome to The Boathouse! Waterfront/Boats/Hot tub

19. 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 CA $122
CA $388 total
includes taxes & fees
Nov 18 - Nov 19
Retro Retreat: renovated 2BR, desk, no chore list!

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 CA $170
CA $675 total
includes taxes & fees
Nov 9 - Nov 10
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Poughkeepsie Hotel Reviews

Find out more about Poughkeepsie

Poughkeepsie Vacation Homes information

Number of reviews
291
Accommodation
849 Vacation Homes
Lowest Price
CA $188
Highest Price
CA $941

Explore a world of travel with Expedia