Poughkeepsie Vacation Rentals

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Vacation Rentals in Poughkeepsie

Fridge, microwave, oven, stovetop
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
Exterior
Streamside Cottage Walking Distance to Town of Woodstock
10.0 out of 10, Exceptional, (198)
"Spent two nights and wanted a place where we could easily bike into town and got exactly that! The sound of the creek outside was so relaxing, accommodations were clean and comfy. Definitely would return!"
The price is CA $231
CA $454 total
includes taxes & fees
Jun 3 - Jun 4
Streamside Cottage Walking Distance to Town of Woodstock
Exterior
The Farm at Hyde Park
9.8 out of 10, Exceptional, (48)
"We thoroughly enjoyed our stay. It was a unique setting. Glen was very accommodating for our check in & out needs. Great location & central to everything we wanted to do & see. Definitely would come back."
The Farm at Hyde Park
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Property grounds
'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 CA $170
CA $198 total
includes taxes & fees
May 26 - May 27
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
On the beach, sun loungers
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
Property grounds
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 CA $251
CA $360 total
includes taxes & fees
May 27 - May 28
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
View from property
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
10.0 out of 10, Exceptional, (153)
"We had a great time, and the space was great. The house is so spacious, and that was perfect for us. We would have liked a few more towels, a bit more soap and shampoo, and the grill didn't get hot enough to cook the steak we had brought. Overall a wonderful time. Thank you very much."
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
1 bedroom, desk, iron/ironing board, travel crib
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
Property grounds
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 CA $245
CA $380 total
includes taxes & fees
Jun 2 - Jun 3
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Beach nearby, beach towels
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
Property grounds
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
9.6 out of 10, Exceptional, (35)
"Three nights here as we toured the area. Check in was easy. We were able to access the VRBO app 30 minutes prior to our arrival. By the time we reached the driveway, Ruben had sent the access code.The road to the house is gravel and only wide enough for one car. We were glad we had arrived during the day.The house has an antique store vibe. Lots of books for a rainy day activity. FYI, the photos on the listing are a bit different from what we saw in the rooms. The dining table is larger with...
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
Property grounds
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
10.0 out of 10, Exceptional, (82)
"Very clean home. Had everything we needed. Quiet location. All beds were extremely comfortable. Host was very helpful and quick to reply. Good location that was close to area attractions. Would definitely look to stay here again! Thank you Cristiana!"
The price is CA $169
CA $434 total
includes taxes & fees
Jun 20 - Jun 21
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
Fridge, microwave, oven, stovetop
Charming Artist's Retreat
10.0 out of 10, Exceptional, (113)
"The property is lovely and the entire experience of working with Maureen was amazing. Looking forward to a return trip!"
Charming Artist's Retreat
Exterior
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.
Exterior
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 CA $148
CA $222 total
includes taxes & fees
May 26 - May 27
Cabin in the heart of the Hudson Valley, Cabin 4
Exterior
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
9.0 out of 10, Wonderful, (28)
"For a woodsy getaway close to real highways, here’s your spot. A good home base for local activities. Cute not chic, clean and functional. Chickens and goats on the property added a great farm with no work charm."
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
Fridge, microwave, oven, stovetop
Campfire Cottage: Fireplace, fire pit & no chores!
10.0 out of 10, Exceptional, (16)
"An unassuming setting belies the well-appointed interior and thoughtful extras you’ll find within. Parking is tight but it is off-street and the location offers come-and-go convenience for exploring the area."
The price is CA $142
CA $318 total
includes taxes & fees
Jun 2 - Jun 3
Campfire Cottage: Fireplace, fire pit & no chores!
Property grounds
High Point Mtn House~Mother's Day on the Mountain~2 hrs to NYC ULTIMATE PRIVACY!
9.8 out of 10, Exceptional, (18)
"My recent weekend getaway to the Catskills was truly unforgettable, thanks to our wonderful host and their charming retreat nestled in the heart of this picturesque mountain region. From the moment we arrived, we were greeted with warm hospitality and a sense of tranquility that immediately set the tone for our stay. The accommodations were nothing short of perfect – cozy yet spacious, with rustic charm and modern amenities seamlessly blended together. Our host went above and beyond to ensure...
High Point Mtn House~Mother's Day on the Mountain~2 hrs to NYC ULTIMATE PRIVACY!
Property grounds
Hamptons on the Hudson in South Saugerties
9.8 out of 10, Exceptional, (6)
"Rainy but had a great time at the Wool and Sheep Festival.The fall colors were beautiful."
Hamptons on the Hudson in South Saugerties
1 bedroom, free WiFi
Cozy Cottage with a Pond 2
6.8 out of 10, (9)
"Safe quiet clean the only thing was the power went out (quick fix though) and the bed was so hard it hurt my back "
The price is CA $136
CA $177 total
includes taxes & fees
May 23 - May 24
Cozy Cottage with a Pond 2
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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.

Poughkeepsie Vacation Rental Travel Info

Other types of properties in Poughkeepsie you may be interested in

Exterior Standard Room, 2 Double Beds, Non Smoking, Annex Building
Quality Inn Poughkeepsie
2.5 star property
8.0 out of 10, Very good, (232)
"N/A"
The price is CA $146
CA $164 total
includes taxes & fees
May 27 - May 28
Quality Inn Poughkeepsie
Bar (on property)
DoubleTree by Hilton Poughkeepsie
4.0 star property
8.2 out of 10, Very good, (970)
"The signage for finding the hotel sucked. Basically no sign...they said they are awaiting approval from the city. We drove around the block 4 times before we found it. The food in the restaurant was terrible. The eggs benedict had hollandaise sauce that was like chicken gravy...inedible."
The price is CA $174
CA $202 total
includes taxes & fees
Jun 13 - Jun 14
DoubleTree by Hilton Poughkeepsie
Exterior
Courtyard by Marriott Poughkeepsie
3.0 star property
8.8 out of 10, Excellent, (1000)
"Very nice quite older property. "
The price is CA $173
CA $194 total
includes taxes & fees
Jun 2 - Jun 3
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Poughkeepsie?

Yes, we offer vacation rentals in Poughkeepsie near Mid-Hudson Civic Center, or you can choose a secluded option if you'd like a relaxing place to stay. Visitors like the college campus and scenic riverfront in Poughkeepsie. While you're in the area, you can also enjoy the top-notch restaurants and entertainment venues.

What's the top vacation rental in Poughkeepsie?

The Farm at Hyde Park: This vacation home rental near Poughkeepsie is located in a rural location and has a fireplace, a patio, and a barbecue grill 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 vacation rentals are there in Poughkeepsie?

Expedia has 24 vacation 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 vacation rentals like in Poughkeepsie?

Vacation rentals are private accommodations you can reserve for several days or more in Poughkeepsie. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll have everything you want. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a family trip.

Recent reviews of Poughkeepsie properties
Expedia verified reviews