Holiday Rentals in Poughkeepsie

    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

Cozy Escape -Strong Wi-Fi -Prime Location

7.4 out of 10, Good, (3)
"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."
Cozy Escape -Strong Wi-Fi -Prime Location

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (31)
"Had a fantastic stay for a quick overnight trip to ski."
The price is €200
includes taxes & fees
10 Jun - 11 Jun
Esopus Creek modern Tiny house Retreat!

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

9.8 out of 10, Exceptional, (15)
"Communication was easy, location and parking was great! Very clean and cozy!"
The price is €300
includes taxes & fees
8 Jun - 9 Jun
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, (2)
"Patrick and Katherine are excellent hosts with an incredible property in an amazing location. We had such an incredible time. The carriage house is so comfortable and welcoming. I absolutely loved just sitting on the balcony enjoying the beautiful view, birds, and my coffee. This was my first time using Vrbo, (glad to have found an alternative to another site I no longer support). Wow, I have been missing out!! The stocked fridge was such a lovely surprise. Everything was just fantastic. Our...
Romantic retreat with stunning views of Croton River Gorge, a birder haven

Cozy Cabin with Sauna & Firepit!

9.6 out of 10, Exceptional, (27)
"Excellent "
Cozy Cabin with Sauna & Firepit!

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

10.0 out of 10, Exceptional, (292)
"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 €520
includes taxes & fees
8 Jun - 9 Jun
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (110)
"Great place and host!"
The price is €272
includes taxes & fees
8 Jun - 9 Jun
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (22)
"Beautiful property- not too far from Hunter Mt or Woodstock. House has a lot to offer for adults and/or families with kids. Would highly recommend!"
Hamptons on the Hudson in South Saugerties

The Studio at the Inn at High Falls

8.0 out of 10, Very good, (25)
"This was a nice change from a hotel room. "
The price is €244
includes taxes & fees
7 Jun - 8 Jun
The Studio at the Inn at High Falls

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 €277
includes taxes & fees
8 Jun - 9 Jun
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

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

9.2 out of 10, Wonderful, (22)
"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

Quaint Cottage w/ Peloton & Sauna near Hiking

9.6 out of 10, Exceptional, (19)
"Nice area, cute cottage."
Quaint Cottage w/ Peloton & Sauna near Hiking

The Farm at Hyde Park

9.8 out of 10, Exceptional, (70)
"The church is amazing! Thank you for a wonderful stay. "
The Farm at Hyde Park

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

10.0 out of 10, Exceptional, (16)
"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

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

10.0 out of 10, Exceptional, (3)
"Enjoyed the stay. Nice place to relax for a weekend."
Our home is perfect for relaxing and having lots of fun, with near by activity’s

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

10.0 out of 10, Exceptional, (79)
"The house was super clean and very easy to take care of while we were here. It was perfect for a remote getaway, hiking and just being quiet. "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

'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 €146
includes taxes & fees
8 Jun - 9 Jun
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

Cabin in the heart of the Hudson Valley, Cabin 4

9.0 out of 10, Wonderful, (23)
"Clean, warm and comfortable. "
The price is €147
includes taxes & fees
8 Jun - 9 Jun
Cabin in the heart of the Hudson Valley, Cabin 4

Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

10.0 out of 10, Exceptional, (62)
"We had a great stay. The property was perfectly located just outside the town center. "
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

Whimsical Woodland Cottage in Stone Ridge NY

9.4 out of 10, Exceptional, (9)
"Whimsical cottage was just as described. The owner was very responsive with any questions. The location was perfect for our needs. It is definitely meant for a couples weekend away, but was sufficient for the three of us."
The price is €357
includes taxes & fees
10 Jun - 11 Jun
Whimsical Woodland Cottage in Stone Ridge NY
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?

Cultural attractions include Bardavon 1869 Opera House and Mid-Hudson Civic Center, whereas Walkway Over the Hudson State Historic Park and Richard L. Skimin Memorial Baseball Field are a couple of picturesque spots to enjoy the outdoors. 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.