Search Vacation Homes in Poughkeepsie

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Vacation Homes in Poughkeepsie

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (55)
"The property was beautiful. Quiet area but close enough to all the places we wanted to go. Our hosts were very gracious, attentive and friendly. Enjoyed our weekend retreat. "
The price is AED 545
AED 878 total
includes taxes & fees
1 Oct - 2 Oct
Esopus Creek modern Tiny house Retreat!

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

9.4 out of 10, Exceptional, (30)
"Stayed here to visit family and it was perfect for what we needed. Would recommend staying here. "
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Tiny Cat Tiny House

10.0 out of 10, Exceptional, (4)
"An ideal place to forget about the city, perfect for a long weekend"
The price is AED 430
AED 863 total
includes taxes & fees
1 Oct - 2 Oct
Tiny Cat Tiny House

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

9.8 out of 10, Exceptional, (16)
"The house was beautiful inside and out. Owners were so nice and made sure we had everything we needed for our weekend getaway."
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (90)
"My family and I loved this property! We enjoyed walking around the woods and exploring. The house was well equipped and was really charming. We also loved sightseeing around the near by towns. Definitely a place to come back to stay again. "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

The House In Highland- Secluded Retreat

10.0 out of 10, Exceptional, (11)
"Very nice location and private."
The House In Highland- Secluded Retreat

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (30)
"Lovely property, well-maintained, clean and comfortable, and the host was especially responsive to all communications. Highly recommend."
Hamptons on the Hudson in South Saugerties

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

9.6 out of 10, Exceptional, (36)
"Great place for a quiet stay"
The price is AED 1,010
AED 1,288 total
includes taxes & fees
1 Oct - 2 Oct
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill

10.0 out of 10, Exceptional, (21)
"Really enjoyed this place . Very clean , beautiful views, close to Woodstock town !"
New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill

The Chicken Coop

9.4 out of 10, Exceptional, (10)
"Very cool place everything u need is just a short drive away "
The Chicken Coop

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

8.8 out of 10, Excellent, (23)
"We were very happy with the accommodations. The cottage was neat, clean and well kept, as was the property. All the amenities were as described. We had a great weekend and would highly recommend this lake house."
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Peaceful River Retreat with Fireplace & Panoramic Views

10.0 out of 10, Exceptional, (15)
"House was great and very clean. The only issue was the smell of sewer when turning on the hot water on the showers."
Peaceful River Retreat with Fireplace & Panoramic Views

New Paltz Modern Zen Cabin

10.0 out of 10, Exceptional, (8)
"Great property with everything you need!"
New Paltz Modern Zen Cabin

Bohemian style open LOFT

8.8 out of 10, Excellent, (15)
"A beautiful space in a great jumping off point for exploring the area!"
Bohemian style open LOFT

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (308)
"We had the most relaxing 3 night stay at Don's vacation home. It is spacious and comfortable. Orange Lake right out the back door was a beautiful backdrop all throughout the day. Don gave us great recommendations for local restaurants too.It was the perfect weekend."
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

Large,Cozy,Bright Apartment, Business Themed.

8.8 out of 10, Excellent, (15)
"Very cozy stay with responsive host"
The price is AED 1,488
AED 2,503 total
includes taxes & fees
1 Oct - 2 Oct
Large,Cozy,Bright Apartment, Business Themed.

Mountain Peak Retreat - Pool - Hot Tub

10.0 out of 10, Exceptional, (5)
The price is AED 1,837
AED 3,645 total
includes taxes & fees
1 Oct - 2 Oct
Mountain Peak Retreat - Pool - Hot Tub

Our home is perfect for relaxing and having lots of fun, with near by activity’s

9.8 out of 10, Exceptional, (6)
"My family and I had a great time at this property. Located on a beautiful property. Very relaxing and coordinating with the property owner was very easy. "
Our home is perfect for relaxing and having lots of fun, with near by activity’s

Hickory on Willow Lake

9.6 out of 10, Exceptional, (4)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
The price is AED 1,561
AED 2,242 total
includes taxes & fees
1 Oct - 2 Oct
Hickory on Willow Lake

The Studio at the Inn at High Falls

8.2 out of 10, Very Good, (30)
"I had a great stay here, it’s just as listed; simple but has everything that I needed, check in was easy, communication was good, and bed was comfortable!"
The price is AED 413
AED 985 total
includes taxes & fees
5 Oct - 6 Oct
The Studio at the Inn at High Falls
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