Poughkeepsie Holiday Rentals

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Holiday Rentals in Poughkeepsie

Spacious New Luxurious holiday house in lovely Hudson Valley

9.8 out of 10, Exceptional, (8)
"The house had room for all of us, spacious and comfortable with modern amenities. We enjoyed the large open kitchen, well equipped for making big meals, and especially loved the walk in pantry with sink, oven and coffee bar. The beds were comfy, the bathrooms deluxe. Large couch and huge TV in living room with cozy gas fireplace for us to gather and relax. Located on a quiet cul de sac, easy to get to local attractions. We enjoyed every minute of our stay."
The price is AU$1,300
includes taxes & fees
1 Mar - 2 Mar
Spacious New Luxurious holiday house in lovely Hudson Valley

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (14)
"We had an absolutely wonderful stay at this Vrbo! From the moment we arrived, everything was spotless, beautifully decorated, and thoughtfully equipped with everything we needed. The hosts went above and beyond to ensure a comfortable and seamless experience, providing clear instructions and even thoughtful touches that made us feel right at home.The location was perfect—close enough to attractions and restaurants but still peaceful and private. The beds were incredibly comfortable, the kitchen...
Hamptons on the Hudson in South Saugerties

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (228)
"We totally enjoyed our stay at the cottage! Exactly as advertised, except the views of the river from the home are are even better than pictured. We would definitely recommend!"
Streamside Cottage Half Mile to Town of Woodstock

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (107)
"Spectacular view and very convenient to USMA. "
The price is AU$395
includes taxes & fees
23 Feb - 24 Feb
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!

10.0 out of 10, Exceptional, (172)
"This was an incredible place to stay for a snowy weekend with the family. The house is huge and and just beautiful. The hosts even had the long driveway plowed and stairs/walkway shoveled for us, would definitely recommend staying here. "
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (23)
"Great little house for the holidays. We were looking for a place nearby or family where we could have our own space but still be close by. "
The price is AU$360
includes taxes & fees
24 Feb - 25 Feb
Esopus Creek modern Tiny house Retreat!

Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!

9.6 out of 10, Exceptional, (83)
"No complaints. Stayed during the winter so ne er got the full experience with the lake but it was a great home."
Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!

Luxurious 7 Bedroom Estate with Heated Pool and Hot Tub

2.0 out of 10, (1)
"There was rats inside the house and there was no amenities like toilet paper. And host was very unresponsive."
Luxurious 7 Bedroom Estate with Heated Pool and Hot Tub

Remodeled Lakefront retreat!! Come join us for Ski Season!!

9.6 out of 10, Exceptional, (5)
"We skied, we played in the snow and overall just relaxed at this perfect home!"
Remodeled Lakefront retreat!! Come join us for Ski Season!!

Cedar Cottage with hot tub as seen in New York Times escape section.

9.4 out of 10, Exceptional, (80)
"This was our fifth time staying at the cabin and as always it was perfect. We stayed the week of Thanksgiving and cooked a full feast easily with the appliances and cookware found in the kitchen. We even woke up to snow a few times that week. We enjoyed the hot tub at night and the fireplace each day. Beds are comfy, rooms are cozy and location is ideal. With close proximity to Woodstock, Tannersville and West Kill we were able visit some of our favorite places in the mountains. We’ll be back....
Cedar Cottage with hot tub as seen in New York Times escape section.

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

9.4 out of 10, Exceptional, (9)
"We stayed here for work event and the location was perfect. Not too close, not too far away. Its snowed one evening but the driveway was not slippery at all. The house was very clean and kept in order. Plenty of room in the bedrooms and bathroom. The operational fireplace was also an added bonus. "
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Beautiful Private Stone Home in the Hudson Valley

10.0 out of 10, Exceptional, (139)
"We had a wonderful time together. Room for everyone. We were 11. Clean and spacious. We would stay there again."
Beautiful Private Stone Home in the Hudson Valley

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

10.0 out of 10, Exceptional, (2)
"Communication was easy, location and parking was great! Very clean and cozy!"
The price is AU$461
includes taxes & fees
23 Feb - 24 Feb
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

10.0 out of 10, Exceptional, (281)
"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 AU$426
includes taxes & fees
11 Mar - 12 Mar
Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

Mid-Century DJ’s Dream

10.0 out of 10, Exceptional, (27)
"When I found the place online, it was just the right place for us, peace and quiet. The place was just like the pictures and if I have to described it in one word (COZY) Kevin, the owner met us and helped us and walked us through the place and has a Washer/Dryer. The weekend was perfect, we got snowed in which was perfect in which we order in and Netflix and chilled, PERFECT Timing.Thank you Kevin, we will see you again!"
The price is AU$280
includes taxes & fees
26 Feb - 27 Feb
Mid-Century DJ’s Dream

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

9.4 out of 10, Exceptional, (18)
"We had a friend group boardgaming weekend and this was perfect for our purposes. The table was large enough for our biggest games and the pool table doubled as a backup playing space. The race cars are a nice touch of whimsy too :-) Our only suggestion would be to replace the oversized, too-low chandelier over the table but really only a minor thing."
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Lakeview Estate - Chef's Kitchen - NYC Getaway

9.8 out of 10, Exceptional, (25)
"Great place, great service!!"
Lakeview Estate - Chef's Kitchen - NYC Getaway

A-Frame of Mind

10.0 out of 10, Exceptional, (48)
"What has become a regular winter Woodstock retreat turned into something magical with the beauty, warmth and smart comfort of Nick’s home. His friendly affect and many small touches made this one of the best home-bases for me in my decades of solo retreats. Secluded, woodsy with beautiful A-Frame design but 10 minutes to either Woodstock or Saugerties. Great cooking kitchen, treadmill, great sound and entertainment or quiet nooks for writing and reading. Good heat and warm floors. Bathtub....
A-Frame of Mind

Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

10.0 out of 10, Exceptional, (110)
"super easy - we'll be back"
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool

9.4 out of 10, Exceptional, (13)
"We had a lovely stay for our family of 5 during the week before xmas. The home was well appointed, with all the normal needs we have to cook, etc... The house was very quiet despite 5 of us being there. Everyone had their own space. Very cozy. Loved that there were games to play, we had a great family round of monopoly!The property manager was so responsive. We felt very supported and attended to. Despite the cold weather the house stayed plenty warm as well!We highly recommend this home and...
Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool
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.
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Other types of properties in Poughkeepsie you may be interested in

Hyatt Place Poughkeepsie / Hudson Valley

3.0 star property
8.8 out of 10, Excellent, (1004)
"Snowed heavily, snow and ice everywhere upon arrival and departure "
The price is AU$158
includes taxes & fees
20 Mar - 21 Mar
Hyatt Place Poughkeepsie / Hudson Valley

DoubleTree by Hilton Poughkeepsie

4.0 star property
8.2 out of 10, Very good, (1000)
"Staff was very friendly and room clean and cozy"
The price is AU$194
includes taxes & fees
3 Mar - 4 Mar
DoubleTree by Hilton Poughkeepsie

Courtyard by Marriott Poughkeepsie

3.0 star property
8.8 out of 10, Excellent, (1000)
"Great little property, fantastic and love the smart tvs "
The price is AU$185
includes taxes & fees
23 Feb - 24 Feb
Courtyard by Marriott Poughkeepsie
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.

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?

Hamptons on the Hudson in South Saugerties: This holiday home rental outside of Poughkeepsie is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Poughkeepsie?

Expedia has 23 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.