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

Tonight
31 Dec - 1 Jan
Tomorrow
1 Jan - 2 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Poughkeepsie holiday rentals

Outdoor dining
Mid-Century DJ’s Dream

Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (44)
"Location is well furnished and near many attractionHost versatile and well versed"
United States
Alberto M.
The price is HK$870
HK$1,529 total
includes taxes & fees
4 Jan - 5 Jan 2026
Mid-Century DJ’s Dream
Exterior detail
Cozy private suite in the heart of beautiful Gardiner.

Cozy private suite in the heart of beautiful Gardiner.

Cozy private suite in the heart of beautiful Gardiner.
New Paltz
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$994
HK$2,010 total
includes taxes & fees
7 Jan - 8 Jan 2026
Cozy private suite in the heart of beautiful Gardiner.
Property grounds
Private Studio Close to Downtown Rhinebeck

Private Studio Close to Downtown Rhinebeck

Private Studio Close to Downtown Rhinebeck
Rhinebeck Village
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$714
HK$1,908 total
includes taxes & fees
12 Jan - 13 Jan 2026
Private Studio Close to Downtown Rhinebeck
Private kitchen
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
new paltz
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$1,399
HK$5,520 total
includes taxes & fees
3 Jan - 4 Jan 2026
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
Smart TV, fireplace
Private, Cozy, Clean apartment in lovely Hyde Park

Private, Cozy, Clean apartment in lovely Hyde Park

Private, Cozy, Clean apartment in lovely Hyde Park
2.0 star property
Hyde Park
The price is HK$980
HK$1,505 total
includes taxes & fees
4 Jan - 5 Jan 2026
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!

Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!

Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
Highland
9.8 out of 10, Exceptional, (26)
"Perfect location and stay"
United States
kareem e.
The price is HK$1,671
HK$2,542 total
includes taxes & fees
8 Jan - 9 Jan 2026
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
King Bed Private Parking Fast Internet

King Bed Private Parking Fast Internet

King Bed Private Parking Fast Internet
Poughkeepsie
The price is HK$591
HK$2,223 total
includes taxes & fees
21 Jan - 22 Jan 2026
King Bed Private Parking Fast Internet
Fridge, microwave, oven, stovetop
Cozy Escape -Strong Wi-Fi -Prime Location

Cozy Escape -Strong Wi-Fi -Prime Location

Cozy Escape -Strong Wi-Fi -Prime Location
Poughkeepsie
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$701
HK$2,442 total
includes taxes & fees
21 Jan - 22 Jan 2026
Cozy Escape -Strong Wi-Fi -Prime Location
Terrace/patio
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley

Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley

Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
Highland
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$1,283
HK$2,986 total
includes taxes & fees
5 Jan - 6 Jan 2026
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
Interior
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

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

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
10.0 out of 10, Exceptional, (2)
"Great host"
United States
Lindsey F.
The price is HK$1,462
HK$4,719 total
includes taxes & fees
4 Jan - 5 Jan 2026
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Property grounds
Wood Stove Nights, Quiet Yard, an Easy Escape Near New Paltz

Wood Stove Nights, Quiet Yard, an Easy Escape Near New Paltz

Wood Stove Nights, Quiet Yard, an Easy Escape Near New Paltz
New Paltz
10.0 out of 10, Exceptional, (4)
"The property was very homey and welcoming. Great for families. The backyard has lots of space for kids to run around. Great location, very close to attractions. Look forward to staying again in the future!"
United States
Bill T.
The price is HK$1,332
HK$4,498 total
includes taxes & fees
4 Jan - 5 Jan 2026
Wood Stove Nights, Quiet Yard, an Easy Escape Near New Paltz
Exterior
Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
10.0 out of 10, Exceptional, (3)
"Ideal cabin getaway. "
United States
Nadja E.
The price is HK$2,352
HK$3,453 total
includes taxes & fees
6 Jan - 7 Jan 2026
Rustic Cabin in Fishkill!
Fridge, microwave, oven, stovetop
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

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
2.0 star property
New Paltz
9.4 out of 10, Exceptional, (24)
"Beautiful comfortable, clean "
United States
Michal G.
The price is HK$1,826
HK$3,251 total
includes taxes & fees
5 Jan - 6 Jan 2026
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Smart TV
King Bed | Private Parking | Strong WiFi

King Bed | Private Parking | Strong WiFi

King Bed | Private Parking | Strong WiFi
Poughkeepsie
King Bed | Private Parking | Strong WiFi
Outdoor dining
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

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
9.6 out of 10, Exceptional, (50)
"Quiet, clean and comfortable! Great stay!"
United States
Joseph G.
The price is HK$1,924
HK$2,476 total
includes taxes & fees
8 Jan - 9 Jan 2026
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Exterior
Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
Fishkill
The price is HK$4,066
HK$5,715 total
includes taxes & fees
1 Jan - 2 Jan 2026
Red Cottage - Lakeside Property!
Dining tables
Chestnut on Willow Lake

Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
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$3,852
HK$5,452 total
includes taxes & fees
1 Jan - 2 Jan 2026
Chestnut on Willow Lake
Exterior
Charming Cabin in Fishkill!

Charming Cabin in Fishkill!

Charming Cabin in Fishkill!
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$2,352
HK$3,300 total
includes taxes & fees
1 Jan - 2 Jan 2026
Charming Cabin in Fishkill!
Children’s area
Hickory on Willow Lake

Hickory on Willow Lake

Hickory on Willow Lake
Fishkill
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$4,062
HK$5,472 total
includes taxes & fees
1 Jan - 2 Jan 2026
Hickory on Willow Lake
Terrace/patio
perfect studio, few minutes away to the heart of new Paltz & Mohonk Mountain

perfect studio, few minutes away to the heart of new Paltz & Mohonk Mountain

perfect studio, few minutes away to the heart of new Paltz & Mohonk Mountain
2.0 star property
New Paltz
2.0 out of 10, (1)
"When we arrived at the house, we unpacked and within a few minutes, we smelled something that smelled like sewer gas in the bathroom. The owners came over and accused us of pouring something down the drain to get out of paying them. We could not stay in the house it smelled so bad and they would not refund our money. VRBO took their side! This was a horrific experience. I hope they get the sewer smell figured out. I just wanted to visit my daughter and this turned into a nightmare. I understand...
United States
Susannah R.
The price is HK$875
HK$3,482 total
includes taxes & fees
1 Jan - 2 Jan 2026
perfect studio, few minutes away to the heart of new Paltz & Mohonk Mountain
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

Courtyard by Marriott Poughkeepsie

Courtyard by Marriott Poughkeepsie

10/10 Excellent
"Changed room without any hassle "
Arthur 1-night trip
Posted 2 days ago
Courtyard by Marriott Poughkeepsie

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?

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY: This highly rated holiday home rental in Poughkeepsie offers a fireplace, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

How many holiday rentals are there in Poughkeepsie?

Expedia has 21 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.