Poughkeepsie Vacation Rentals

Vacation Rentals in Poughkeepsie

Spacious restored Victorian w/ wraparound porch
Fridge, microwave, oven, stovetop
Spacious restored Victorian w/ wraparound porch
9.6 out of 10, Exceptional, 9 reviews
"We enjoyed our stay very much!"
Spacious restored Victorian w/ wraparound porch
The Farm at Hyde Park
Exterior
The Farm at Hyde Park
9.8 out of 10, Exceptional, 48 reviews
"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
Streamside Cottage Walking Distance to Town of Woodstock
Property grounds
Streamside Cottage Walking Distance to Town of Woodstock
10.0 out of 10, Exceptional, 199 reviews
"Very clean, just as advertised. The stream behind the cottage is beautiful! Will stay there again if we get a chance to revisit the area. The host was extremely accommodating and available🙂"
The price is $189
$359 total
includes taxes & fees
Jun 18 - Jun 19
Streamside Cottage Walking Distance to Town of Woodstock
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Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, 96 reviews
"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 $204
$284 total
includes taxes & fees
Jun 10 - Jun 11
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
Property grounds
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
9.6 out of 10, Exceptional, 35 reviews
"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
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
Beach nearby, beach towels
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
9.4 out of 10, Exceptional, 75 reviews
"We had such an awesome stay! Check in process was easy! Amazing scenery amazing adventure we had with our two furr babies!"
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Fridge, microwave, oven, stovetop
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, 62 reviews
"Stayed for West Point graduation. Beautiful home, scenic views, and everything we needed."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
1 bedroom, desk, iron/ironing board, travel crib
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, 35 reviews
"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
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
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 reviews
"Our trip was amazing. We do it again again and again"
The price is $125
$145 total
includes taxes & fees
Jun 9 - Jun 10
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
Property grounds
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
10.0 out of 10, Exceptional, 85 reviews
"Everything was as described, instructions to the house were precise and the facility was exactly what we 2 couples) needed for a weekend of strolls in Woodstock and trails around. We cooked 2 dinners, kitchen and BBQ were great."
The price is $111
$303 total
includes taxes & fees
Jun 20 - Jun 21
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
Exterior
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
9.0 out of 10, Wonderful, 29 reviews
"Lovely stay! Comfortable accommodation and welcoming family."
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
On the beach, sun loungers
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
9.6 out of 10, Exceptional, 59 reviews
"We had a lovely weekend stay for a quick family get-away. The main kitchen and living area has spectacular views onto the lake as does the deck where we spent most of our time. The lake is just across the very quiet street. The kitchen is incredibly well stocked, the host super responsive and the rooms very comfortable. We did not use the well equipped basement work-out and additional TV space but it looked great. Easy to get to grocery store, hikes, local attractions but honestly we just loved...
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
Charming Artist's Retreat
Fridge, microwave, oven, stovetop
Charming Artist's Retreat
10.0 out of 10, Exceptional, 114 reviews
"This is our second time staying at the cottage. What beautiful weather in such a beautiful setting. Incredible motorcycle ride through the mountains. Thank you Maureen. Robin & Bruce"
Charming Artist's Retreat
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Property grounds
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
9.2 out of 10, Wonderful, 32 reviews
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is $200
$302 total
includes taxes & fees
Jun 10 - Jun 11
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Pet-Friendly Cozy Cabin in the Catskills with Cedar Hot Tub
Dining
Pet-Friendly Cozy Cabin in the Catskills with Cedar Hot Tub
10.0 out of 10, Exceptional, 12 reviews
"We loved all the thoughtful touches and design details of this cozy cabin! P"
Pet-Friendly Cozy Cabin in the Catskills with Cedar Hot Tub
Historic former hotel with amazing kitchen, near great hiking; great for groups!
Property grounds
Historic former hotel with amazing kitchen, near great hiking; great for groups!
10.0 out of 10, Exceptional, 36 reviews
"I was looking for somewhere that had many rooms for single and couple adults to stay at for a long weekend birthday celebration. It was super difficult to find somewhere with rooms relatively the same size and separate/private, until I came upon this listing. That was the impetus, and the reality was even better than we could have imagined. We spent most of our time in the large kitchen/dining room: cooking, eating, laughing, conversing, and playing games. At nights we would all go into large...
Historic former hotel with amazing kitchen, near great hiking; great for groups!
Cozy Cottage with a Pond 2
1 bedroom, free WiFi
Cozy Cottage with a Pond 2
6.8 out of 10, 9 reviews
"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
Jun 8 - Jun 9
Cozy Cottage with a Pond 2
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
View from property
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
10.0 out of 10, Exceptional, 153 reviews
"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!
Hamptons on the Hudson in South Saugerties
Property grounds
Hamptons on the Hudson in South Saugerties
9.8 out of 10, Exceptional, 6 reviews
"Rainy but had a great time at the Wool and Sheep Festival.The fall colors were beautiful."
Hamptons on the Hudson in South Saugerties
Riverfront property in the beautiful Hudson Valley with many outdoor activities.
Property grounds
Riverfront property in the beautiful Hudson Valley with many outdoor activities.
9.4 out of 10, Exceptional, 41 reviews
"The house is decorated beautifully, and the view of the river is great. The beds and linens were soo comfortable. Would love to return in warmer weather to enjoy the outdoors 😀"
Riverfront property in the beautiful Hudson Valley with many outdoor activities.
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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

DoubleTree by Hilton Poughkeepsie
Bar (on property)
DoubleTree by Hilton Poughkeepsie
4.0 star property
8.2 out of 10, Very Good, 978 reviews
"Clean and very quiet"
The price is $122
$142 total
includes taxes & fees
Jun 19 - Jun 20
DoubleTree by Hilton Poughkeepsie
Holiday Inn Poughkeepsie, an IHG Hotel
Exterior
Holiday Inn Poughkeepsie, an IHG Hotel
3.0 star property
7.8 out of 10, Good, 580 reviews
"M"
The price is $86
$96 total
includes taxes & fees
Jun 16 - Jun 17
Holiday Inn Poughkeepsie, an IHG Hotel
Courtyard by Marriott Poughkeepsie
Exterior
Courtyard by Marriott Poughkeepsie
3.0 star property
8.8 out of 10, Excellent, 1,005 reviews
"Decent up to date hotel. Clean rooms and a gym. "
The price is $118
$132 total
includes taxes & fees
Jun 16 - Jun 17
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.

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 $100 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.

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

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

5/5 Excellent
"What a beautiful stay room was bigger then expected so much to do in area loved our stay"
A verified traveler stayed at Overlook Lodge at Bear Mountain
Posted 2 days ago
Overlook Lodge at Bear Mountain