Poughkeepsie Holiday Rentals

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Holiday Rentals in Poughkeepsie

Spacious restored Victorian w/ wraparound porch
9.8 out of 10, Exceptional, (7)
"We had a very pleasant stay for a momentous occasion where my wife's family and my family met for the first time. The kitchen will always be the gathering spot as both our cultures enjoy food and this kitchen proved to be an excellent space. The billiards room was also a great hang out room and the porch areas were perfect for photo taking."
Spacious restored Victorian w/ wraparound porch
Streamside Cottage Walking Distance to Town of Woodstock
10.0 out of 10, Exceptional, (194)
"My sister and I needed a quick getaway from the world and found refuge in this sweet little cottage that is right on the creek. The cottage was pristine, fully eqipped, quiet and tastefully decorated. My communication with the owner, Jane, was "easy breezy". Our favorite part of our stay were the sights and sounds of the water! It was truly magnificent. We came to the cottage a little tired from the pressures of life but left rejuvenated and filled with peace. Our short stay was delightful. We...
The price is NZ$540
includes taxes & fees
13 May - 14 May
Streamside Cottage Walking Distance to Town of Woodstock
The Farm at Hyde Park
9.8 out of 10, Exceptional, (47)
"Very unusual, appealing proportions, well stocked, perfect location"
The Farm at Hyde Park
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'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
8.4 out of 10, Very good, (37)
"Our trip was amazing. We do it again again and again"
The price is NZ$241
includes taxes & fees
19 May - 20 May
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (35)
"This is a cozy property in a very rural setting. The host is extremely responsive and very thorough. It is quiet and private. The furniture and bed are very comfortable. The wood burning stove is a pellet stove which provides enough heat to take the edge off. The hot tub could comfortably fit 4 people. The Village of Cold Spring is less than 10 minutes away, as is the Interstate 84 bridge across the Hudson. If you want to make your own food, bring it. There is no grocery store nearby."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
9.6 out of 10, Exceptional, (58)
"Property manager was very kind and responsive. Greatly enjoyed the views of the pond and the basement pool and ping pong tables. Great time playing these games with mybson as the weather wasn't conducive for water activities."
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
10.0 out of 10, Exceptional, (152)
"this was one of the most comfortable, easy to navigate vacation homes we have ever had. we used the grill, kitchen had everything you need, the deep sinks made washing dishes easy, (there was a dishwasher. but we didn't use it), windows allowed a 180 degree view of the back yard and forest beyond, where we saw a family of deer. Everyone slept like babies on mattresses that were heavenly! Or was super available and responsive to questions. A hannaford super market is 2.3 miles away. Bread Alone...
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (96)
"Comfortable apartment with a phenomenal view! The space could use a deep clean and some decluttering, but that view!!! Did I mention that the view was A-mazing?!?"
The price is NZ$440
includes taxes & fees
13 May - 14 May
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
10.0 out of 10, Exceptional, (81)
"We enjoyed our stay at this property. The location is very private and comfortable. The kitchen is well stocked with amenities."
The price is NZ$451
includes taxes & fees
28 May - 29 May
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
9.2 out of 10, Wonderful, (32)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is NZ$465
includes taxes & fees
2 Jun - 3 Jun
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Mid-Century DJ’s Dream
10.0 out of 10, Exceptional, (13)
"Our stay was quite nice, the place looked as the pictures showed it to be which is just amazing. everything was music themed and our host had an amazing selection of vinyls. The only complaints I would say I had was the small flying bugs near the Tv and we weren’t provided paper towels. Overall it was a nice place for the night and the property itself was beautiful."
The price is NZ$358
includes taxes & fees
27 May - 28 May
Mid-Century DJ’s Dream
Cabin in the heart of the Hudson Valley, Cabin 4
8.4 out of 10, Very good, (11)
"Everything was as it says it was. Place was spotless. In the evening and morning you didn’t hear any traffic noise at all. Was quiet and peaceful. Communication with the property owner was outstanding."
The price is NZ$271
includes taxes & fees
13 May - 14 May
Cabin in the heart of the Hudson Valley, Cabin 4
The Studio at the Inn at High Falls
8.4 out of 10, Very good, (17)
"Love staying at The Studio at the Inn at High Falls. It truly is my new home away from home. Soo Clean, Comfortable and incredible friendly helpful people who own and work there. Again Thank you Frank and too a New Year. Patricia"
The price is NZ$426
includes taxes & fees
13 May - 14 May
The Studio at the Inn at High Falls
Charming Artist's Retreat
10.0 out of 10, Exceptional, (112)
"The property is lovely and the entire experience of working with Maureen was amazing. Looking forward to a return trip!"
Charming Artist's Retreat
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
10.0 out of 10, Exceptional, (11)
"Perfect spot to visit grandkids Lots to do"
The price is NZ$423
includes taxes & fees
20 May - 21 May
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Cozy family-friendly home!
10.0 out of 10, Exceptional, (3)
"Older manufactured home has been updated. We appreciated that each area had its own mini split unit for individual climate control. Area felt safe and quiet. Good hot water and water pressure. Kitchen was stocked for stovetop cooking but not much for baking, and no water glasses. (We just drank everything from the coffee cups.) Split bedroom layout was good for two couples. "
Cozy family-friendly home!
Campfire Cottage: Fireplace, fire pit & no chores!
10.0 out of 10, Exceptional, (15)
"Matt is a wonderful host! I was very impressed by the cleanliness of the 1 bedroom cabin and how much thought went into providing guests with everything they need. I stayed for four nights and was very comfortable. The bed was so comfortable I slept great. Kingston is a city so some noise is expected. The neighborhood is very quiet at night and you can hear a little noise occasionally in the distance. Matt provides an adjustable sound machine. I put it on low and slept like a baby. Matt is very...
The price is NZ$362
includes taxes & fees
23 May - 24 May
Campfire Cottage: Fireplace, fire pit & no chores!
Luxury home filled with books and art, with great access. Sleeps up to thirteen.
Luxury home filled with books and art, with great access. Sleeps up to thirteen.
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
9.4 out of 10, Exceptional, (74)
"Thoroughly enjoyed our stay at Squantz Cottage. Property was well maintained, clean, and convenient. Parking at the cottage can be a little tricky backing out and getting on to the road. An option to park at the main house could be helpful. I would definitely rent again!"
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
Cozy Relaxing Retreat in Saugerties, NY
10.0 out of 10, Exceptional, (30)
"The accommodations were excellent. We were a couple, but the house would be great for two couples. We loved the setting! The host has thought of everything, and the place is equipped to the max. Just bring yourself! Perfect location to explore the area."
Cozy Relaxing Retreat in Saugerties, NY
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See all available properties in 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.

Other types of properties in Poughkeepsie you may be interested in

Bar (on property)
DoubleTree by Hilton Poughkeepsie
4.0 star property
8.2 out of 10, Very good, (960)
"Good hotel with restaurant located in central Poughkeepsie "
The price is NZ$229
per night
27 May - 28 May
DoubleTree by Hilton Poughkeepsie
Exterior Standard Room, 2 Double Beds, Non Smoking, Annex Building
Quality Inn Poughkeepsie
2.5 star property
8.0 out of 10, Very good, (224)
"Very clean rooms and friendly staff, but I only have three complaints. First, the beds were not queen size beds. More like twin. Second, when I looked up the hotel and it stated it served breakfast it would have been better to put continental breakfast. And last, my aunt left her belongings on the bed due to her health issues. We came back from my cousin funeral and her belongings were touched. I’ve stayed at several hotels and motels. Usually when the occupants belongings are on the bed the...
The price is NZ$199
per night
14 May - 15 May
Quality Inn Poughkeepsie
Exterior
Hyatt Place Poughkeepsie / Hudson Valley
3.0 star property
8.6 out of 10, Excellent, (1004)
"Clean and safe. "
The price is NZ$177
per night
27 May - 28 May
Hyatt Place Poughkeepsie / Hudson Valley
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Poughkeepsie holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Poughkeepsie. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Poughkeepsie. Seeing all the best attractions is bound to make you fall in love with Poughkeepsie. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Poughkeepsie short-term rentals, that won’t be hard to do.

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?

The Farm at Hyde Park: This holiday home rental outside of Poughkeepsie is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. 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 24 holiday rentals for your stay in Poughkeepsie.

What can I see and do in Poughkeepsie?

Cultural attractions include Chance Theater 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 Poughkeepsie Bridge and Eleanor Roosevelt National Historic Site.

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.

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