Poughkeepsie Vacation Rentals

Vacation Rentals in Poughkeepsie

Property grounds
Streamside Cottage Walking Distance to Town of Woodstock
10.0 out of 10, Exceptional, (196)
"The hostess reached out well before our stay with check in details and other local information. We stayed in early May. The main house and cottage are located down a long drive. The cottage sits a little off to the side with the bedroom/office facing the river. The layout of the cottage is very efficient. We especially enjoyed the front mudroom and staging area perfect for storing muddy hiking boots and backpacks. Our week long state was magical. Coffee in the Adirondack chairs next to the river...
The price is $159
$322 total
includes taxes & fees
20 May - 21 May
Streamside Cottage Walking Distance to Town of Woodstock
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!
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!"
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
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Fridge, microwave, oven, stovetop
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
Fridge, microwave, oven, stovetop
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!
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."
Campfire Cottage: Fireplace, fire pit & no chores!
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
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
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 $184
$265 total
includes taxes & fees
20 May - 21 May
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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
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
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
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
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
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 $180
$279 total
includes taxes & fees
2 Jun - 3 Jun
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Exterior
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
9.2 out of 10, Wonderful, (27)
"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!
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"
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
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."
Cabin in the heart of the Hudson Valley, Cabin 4
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 $100
$130 total
includes taxes & fees
23 May - 24 May
Cozy Cottage with a Pond 2
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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.

Poughkeepsie Vacation Rental Travel Info

Number of vacation rentals
2
Popular accommodation
Poughkeepsie private vacation homes
Known landmarks
Chance Theater, Hyde Park Historical Society Museum and Fun Central
International airports
Newburgh, NY (SWF-Stewart Intl.) and White Plains, NY (HPN-Westchester County)

Other types of properties in Poughkeepsie you may be interested in

Exterior
Courtyard by Marriott Poughkeepsie
3.0 star property
8.8 out of 10, Excellent, (1001)
"I was hit with allergy attack from NY pollen and mold. The front desk ladies could bot have been any nicer in helping me with correct OTC meds and advice. I was better by morning!"
The price is $127
$142 total
includes taxes & fees
23 May - 24 May
Courtyard by Marriott Poughkeepsie
Exterior
Hyatt Place Poughkeepsie / Hudson Valley
3.0 star property
8.6 out of 10, Excellent, (1007)
"The room was modern and very clean. The front desk staff were exceptionally friendly and helpful! I would stay here again next time."
The price is $97
$109 total
includes taxes & fees
27 May - 28 May
Hyatt Place Poughkeepsie / Hudson Valley
Bar (on property)
DoubleTree by Hilton Poughkeepsie
4.0 star property
8.2 out of 10, Very Good, (964)
"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 $123
$143 total
includes taxes & fees
27 May - 28 May
DoubleTree by Hilton 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.

Everything you need to know about Poughkeepsie vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Poughkeepsie vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Poughkeepsie vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Poughkeepsie vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Poughkeepsie. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Poughkeepsie in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as CNY585 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Poughkeepsie rentals

At Expedia, we put the best Poughkeepsie vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Poughkeepsie rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Poughkeepsie vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Poughkeepsie. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.

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 亿客行 verified reviews

Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

5/5 Excellent
"Amazing customer service. Great pool. Great stay with a family with kids of all ages. "
A verified traveler stayed at Hampton Inn & Suites Poughkeepsie
Posted 2 days ago
Hampton Inn & Suites Poughkeepsie