Photo by © City of Chicago

Poughkeepsie Holiday Rentals

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

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

Our top choices for Poughkeepsie holiday rentals

Exterior
Rustic Cabin in Fishkill!

Cabin in Fishkill

Rustic Cabin in Fishkill!
10.0 out of 10, Exceptional, (3)
"Ideal cabin getaway. "
United States
Nadja E.
The price is HK$2,355
HK$3,458 total
includes taxes & fees
12 Jan - 13 Jan
Rustic Cabin in Fishkill!
Terrace/patio
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley

Apartment in Highland

Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
10.0 out of 10, Exceptional, (1)
"Everyone was just right! The home is perfect for a photo shoot. We weren't there for that, but we thought the setting was unique and beautiful! Everything we needed!!"
United States
Rebecca D.
The price is HK$1,285
HK$2,974 total
includes taxes & fees
10 Jan - 11 Jan
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
Property grounds
Mid-Century DJ’s Dream

Apartment in Staatsburg

Mid-Century DJ’s Dream
10.0 out of 10, Exceptional, (44)
"We had a great overnight stay at DJ’s Dream. Kevin was welcoming and we had the perfect quiet spot to refresh and regroup. Don’t miss the Roosevelt and Vanderbilt attractions in Hyde Park!"
United States
Jean B.
The price is HK$870
HK$1,530 total
includes taxes & fees
14 Jan - 15 Jan
Mid-Century DJ’s Dream
Outdoor spa tub
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

Holiday Home in New Paltz

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
2.0 star property
9.4 out of 10, Exceptional, (24)
"Beautiful comfortable, clean "
United States
Michal G.
The price is HK$1,737
HK$3,121 total
includes taxes & fees
12 Jan - 13 Jan
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Outdoor dining
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Holiday Home in Fishkill

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
9.4 out of 10, Exceptional, (54)
"Quiet, clean and comfortable! Great stay!"
United States
Joseph G.
The price is HK$1,929
HK$2,464 total
includes taxes & fees
11 Jan - 12 Jan
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Smart TV
Cozy Escape -Strong Wi-Fi -Prime Location

Holiday Home in Poughkeepsie

Cozy Escape -Strong Wi-Fi -Prime Location
6.8 out of 10, (5)
"The property was perfect for our little weekend getaway. It was very clean and cozy and the host Christina made it so easy for check in and was available for any questions. We would definitely stay again."
United States
Andrea C.
The price is HK$651
HK$2,386 total
includes taxes & fees
12 Jan - 13 Jan
Cozy Escape -Strong Wi-Fi -Prime Location
Interior
Lux APT Your home away from home.

Apartment in Beacon

Lux APT Your home away from home.
10.0 out of 10, Exceptional, (2)
"Very clean and great place to stay. "
United States
Charlene D.
The price is HK$1,106
HK$2,124 total
includes taxes & fees
1 Feb - 2 Feb
Lux APT Your home away from home.
Smart TV, fireplace
Private, Cozy, Clean apartment in lovely Hyde Park

Apartment in Hyde Park

Private, Cozy, Clean apartment in lovely Hyde Park
2.0 star property
The price is HK$981
HK$1,506 total
includes taxes & fees
11 Jan - 12 Jan
Private, Cozy, Clean apartment in lovely Hyde Park
Property grounds
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!

Apartment in Highland

Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
9.8 out of 10, Exceptional, (26)
"Perfect location and stay"
United States
kareem e.
The price is HK$1,674
HK$2,529 total
includes taxes & fees
10 Jan - 11 Jan
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
Exterior detail
Cozy private suite in the heart of beautiful Gardiner.

Holiday Home in New Paltz

Cozy private suite in the heart of beautiful Gardiner.
10.0 out of 10, Exceptional, (7)
"Check-in was easy. Hosts very responsive to any questions and helpful to local recommendations. "
United States
Chanah B.
The price is HK$995
HK$2,013 total
includes taxes & fees
13 Jan - 14 Jan
Cozy private suite in the heart of beautiful Gardiner.
Smart TV
King Bed | Private Parking | Strong WiFi

Holiday Home in Poughkeepsie

King Bed | Private Parking | Strong WiFi
The price is HK$1,320
HK$3,481 total
includes taxes & fees
9 Feb - 10 Feb
King Bed | Private Parking | Strong WiFi
Exterior
Chestnut on Willow Lake

Holiday Home in Fishkill

Chestnut on Willow Lake
9.6 out of 10, Exceptional, (4)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
United States
Doria W.
The price is HK$3,854
HK$5,456 total
includes taxes & fees
12 Jan - 13 Jan
Chestnut on Willow Lake
1 bedroom, WiFi
King Bed Private Parking Fast Internet

Apartment in Poughkeepsie

King Bed Private Parking Fast Internet
The price is HK$677
HK$2,334 total
includes taxes & fees
22 Jan - 23 Jan
King Bed Private Parking Fast Internet
Interior
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Holiday Home in Poughkeepsie

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
10.0 out of 10, Exceptional, (2)
"Great host"
United States
Lindsey F.
The price is HK$1,464
HK$4,726 total
includes taxes & fees
12 Jan - 13 Jan
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Private kitchen
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

Holiday Home in new paltz

Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
9.4 out of 10, Exceptional, (6)
"5 stars!!! 100% recommended and I will be coming back! Host is prompt, attentive, and is great with communication!! No complaints at all!!! "
United States
Fantasia
The price is HK$1,401
HK$5,529 total
includes taxes & fees
12 Jan - 13 Jan
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
Property grounds
Red Cottage - Lakeside Property!

Holiday Home in Fishkill

Red Cottage - Lakeside Property!
The price is HK$4,068
HK$5,727 total
includes taxes & fees
12 Jan - 13 Jan
Red Cottage - Lakeside Property!
Property grounds
Private Studio Close to Downtown Rhinebeck

Apartment in Rhinebeck Village

Private Studio Close to Downtown Rhinebeck
9.8 out of 10, Exceptional, (26)
"This a an adorable, well designed, spotless space which was perfect for our over night stay in Rhinebeck. Property a quick walk away from the fairgrounds and downtown was also walkable…the host was absolutely amazing with great communication and detailed instructions! "
United States
Kathy
The price is HK$638
HK$1,814 total
includes taxes & fees
13 Jan - 14 Jan
Private Studio Close to Downtown Rhinebeck
Exterior
Charming Cabin in Fishkill!

Cabin in Fishkill

Charming Cabin in Fishkill!
9.6 out of 10, Exceptional, (4)
"What a sweet little spot in a gorgeous area - clean, simple, and beautiful. Thanks for a great stay! "
United States
Julia T.
The price is HK$2,355
HK$3,129 total
includes taxes & fees
12 Jan - 13 Jan
Charming Cabin in Fishkill!
Exterior
Hickory on Willow Lake

Holiday Home in Fishkill

Hickory on Willow Lake
9.6 out of 10, Exceptional, (5)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
United States
Rachel C.
The price is HK$4,068
HK$5,481 total
includes taxes & fees
12 Jan - 13 Jan
Hickory on Willow Lake
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Poughkeepsie Hotel Reviews

Hotel Zero Degrees Danbury

Hotel Zero Degrees Danbury

10/10 Excellent
","
Charles 1-night trip
Posted 21 hours ago
Hotel Zero Degrees Danbury

Find out more about Poughkeepsie

Search for holiday rentals in Poughkeepsie on Expedia! You can easily find your home rentals, villas, holiday apartments in Poughkeepsie using one of the methods below:

  • View our selection of featured holiday rentals in Poughkeepsie
  • Use the map to find apartments and other holiday homes in the Poughkeepsie neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Poughkeepsie while they last

Look no further and take a look at our great range of rental properties in Poughkeepsie!

Frequently asked questions

Are there holiday rentals in Poughkeepsie?

Yes, there are holiday rentals in Poughkeepsie close to Mid-Hudson Civic Center, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the university campus and scenic riverfront in Poughkeepsie. While you're in the area, you can also enjoy the top-notch restaurants and entertainment venues.

What are some of the best holiday rentals that Poughkeepsie has to offer?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of Poughkeepsie offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with an oven, a microwave and an electric kettle, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Poughkeepsie?

Expedia has 22 holiday rentals for your stay in Poughkeepsie.

What can I see and do in Poughkeepsie?

Mid-Hudson Civic Center and McCann Ice Arena are a couple of the family-friendly sights, whereas cultural attractions include Bardavon 1869 Opera House and Locust Grove. Other places in town to visit include Mid-Hudson Bridge and Walkway Over the Hudson State Historic Park.

What are holiday rentals like in Poughkeepsie?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Poughkeepsie. Holiday rentals offer extras such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from public hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a family getaway.