Poughkeepsie Holiday Rentals

    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

This weekend
Next weekend

Holiday Rentals in Poughkeepsie

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (34)
"Had a fantastic stay for a quick overnight trip to ski."
The price is NZ$378
includes taxes & fees
1 July - 2 July
Esopus Creek modern Tiny house Retreat!

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 8

10.0 out of 10, Exceptional, (3)
"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 8

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (111)
"Great place and host!"
The price is NZ$516
includes taxes & fees
7 July - 8 July
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

The Farm at Hyde Park

9.8 out of 10, Exceptional, (71)
"Great location to the historic sites and the areas that I wanted to for me personally. Host was great, kind and informative."
The Farm at Hyde Park

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

9.8 out of 10, Exceptional, (18)
"Communication was easy, location and parking was great! Very clean and cozy!"
The price is NZ$556
includes taxes & fees
1 July - 2 July
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Romantic retreat with stunning views of Croton River Gorge, a birder haven

10.0 out of 10, Exceptional, (3)
"We loved our stay at the Carriage House. Patrick and Kathryn were wonderful hosts. They provided information in a timely manner, and were quick to respond to any questions. Our accommodations were clean, comfortable and well appointed, and Patrick and Kathryn included truly thoughtful touches. The location was perfect for exploring Croton-on-Hudson and the Hudson Valley. We'd love to come back!"
Romantic retreat with stunning views of Croton River Gorge, a birder haven

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

10.0 out of 10, Exceptional, (294)
"Beautiful, quiet property that was a great getaway from the city. A pair of bald eagles were circling the lake which was a really amazing surprise! "
The price is NZ$981
includes taxes & fees
6 July - 7 July
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.0 out of 10, Wonderful, (42)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is NZ$511
includes taxes & fees
13 July - 14 July
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

The Studio at the Inn at High Falls

8.0 out of 10, Very good, (25)
"This was a very nice place, great value and comfortable. I would definitely return."
The price is NZ$450
includes taxes & fees
26 June - 27 June
The Studio at the Inn at High Falls

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

8.2 out of 10, Very good, (42)
"Perfect place to reconnect with natural world and yourself"
The price is NZ$270
includes taxes & fees
29 June - 30 June
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (240)
"The house was just as advertised. It is cozy and clean, on a gorgeous stream, and close to town. We'll definitely be back!"
Streamside Cottage Half Mile to Town of Woodstock

Catskill Retreat: Cozy Cabin with Cedar Hot Tub & Pet-Friendly

9.2 out of 10, Wonderful, (25)
"The property is beautiful. The soft snow blanketing the area only made it more so. Everything was exactly where it was said to be and our hosts were ready and willing to help at a moments notice. Couldn't ask for a better place"
Catskill Retreat: Cozy Cabin with Cedar Hot Tub & Pet-Friendly

Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park

9.4 out of 10, Exceptional, (32)
"We had a great time! very thoughtful host! would definitely recommend :)"
The price is NZ$1,484
includes taxes & fees
9 July - 10 July
Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park

Cozy Cabin with Sauna & Firepit!

9.4 out of 10, Exceptional, (29)
"Excellent "
Cozy Cabin with Sauna & Firepit!

Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.

2.0 star property
The price is NZ$385
includes taxes & fees
26 June - 27 June
Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.

Quaint Cottage w/ Peloton & Sauna near Hiking

9.6 out of 10, Exceptional, (20)
"Nice area, cute cottage."
Quaint Cottage w/ Peloton & Sauna near Hiking

A-Frame of Mind

10.0 out of 10, Exceptional, (55)
"Fantastic location, excellent communication with Nick, cozy and well stocked with necessary supplies, very clean and quiet. Much needed vacation."
The price is NZ$626
includes taxes & fees
16 July - 17 July
A-Frame of Mind

A Spectacular 50 Mile View of the Hudson Valley in all seasons

9.8 out of 10, Exceptional, (87)
"This was exactly what we needed for a quick getaway after Christmas. Myra & Jerry were fantastic hosts, and the accommodations were cozy. We'd definitely come back. Thanks Myra & Jerry!"
A Spectacular 50 Mile View of the Hudson Valley in all seasons

Indoor Pool Paradise | 6BR + Huge Decks

Indoor Pool Paradise | 6BR + Huge Decks

The House In Highland- Secluded Retreat

10.0 out of 10, Exceptional, (5)
The House In Highland- Secluded Retreat
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

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?

Esopus Creek modern Tiny house Retreat!: This holiday home rental outside of Poughkeepsie is located on a river, and offers a BBQ, air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

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 Poughkeepsie Bridge.

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.