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Top Holiday Rentals in Poughkeepsie

Downtown Loft. In Poughkeepsie. Walking distance to Civic Center. Pet friendly
Fridge, microwave, oven, stovetop
Downtown Loft. In Poughkeepsie. Walking distance to Civic Center. Pet friendly
The price is £162
per night
5 May - 6 May
Downtown Loft. In Poughkeepsie. Walking distance to Civic Center. Pet friendly
Spacious restored Victorian w/ wraparound porch
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
The Farm at Hyde Park
Exterior
The Farm at Hyde Park
9.6 out of 10, Exceptional, (45)
"We booked the Chapel for a quick weekend to check out the FDR Home and other sights around Hyde Park and Dutchess County. The place was perfect for our needs! Glen was very helpful and communication was excellent. We loved that the property has chickens and a wild turkey."
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
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 £119
per night
5 May - 6 May
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Streamside Cottage Walking Distance to Town of Woodstock
Property grounds
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 £266
per night
13 May - 14 May
Streamside Cottage Walking Distance to Town of Woodstock
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, (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
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)
"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 £219
per night
6 May - 7 May
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
1 bedroom, desk, iron/ironing board, travel cot
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."
The price is £212
per night
6 May - 7 May
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
The Studio at the Inn at High Falls
Exterior
The Studio at the Inn at High Falls
8.8 out of 10, Excellent, (16)
"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 £209
per night
5 May - 6 May
The Studio at the Inn at High Falls
Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool
Pool
Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool
8.8 out of 10, Excellent, (5)
"Stay, house, check in were all great. It was pretty far to Hunter mountain but the house was perfect for our little getaway!"
Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool
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)
"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.
Cozy Relaxing Retreat in Saugerties, NY
Property grounds
Cozy Relaxing Retreat in Saugerties, NY
10.0 out of 10, Exceptional, (29)
"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
Cabin in the heart of the Hudson Valley, Cabin 4
Exterior
Cabin in the heart of the Hudson Valley, Cabin 4
8.4 out of 10, Very good, (10)
"Pleasant overbite getaway. Cabin fit the bill!"
The price is £134
per night
5 May - 6 May
Cabin in the heart of the Hudson Valley, Cabin 4
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, (34)
"Comfy place and great communication. Would stay again!"
The price is £280
per night
6 May - 7 May
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
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, (151)
"Beautiful private property. House is huge, plenty of space for our gang to spread out and get some privacy if needed. Comfortable living room with window views of nature. Great communication home owner. We will definitely be back!"
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
Cozy family-friendly home!
Fridge, microwave, oven, stovetop
Cozy family-friendly home!
10.0 out of 10, Exceptional, (2)
"The property was beautiful and just as pictured. The host was more than attentive and helpful. He went above and beyond to make sure my stay was fantastic. I highly recommend this property!"
Cozy family-friendly home!
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Private kitchen
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
10.0 out of 10, Exceptional, (10)
"We had a lovely weekend at this updated farm house. The house is a great combination of old comfortable farm house and updated and clean kitchens and bathrooms. We loved having Artie, the kitty, as our welcoming party."
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
High Point Mtn House~April Adventure~2 hrs from NYC ULTIMATE PRIVACY!
Property grounds
High Point Mtn House~April Adventure~2 hrs from 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~April Adventure~2 hrs from NYC ULTIMATE PRIVACY!
Romantic Luxury Chalet With Private Pool
1 bedroom, free WiFi, bed sheets
Romantic Luxury Chalet With Private Pool
10.0 out of 10, Exceptional, (259)
"Richard was very kind and thoughtful. The stay was very comfortable and Richard provided many ideas for things to in the vicinity. We will definitely consider staying here again if we're back in the area."
Romantic Luxury Chalet With Private Pool
Mid-Century DJ’s Dream
Property grounds
Mid-Century DJ’s Dream
10.0 out of 10, Exceptional, (13)
"Exactly as described. Clean & comfortable with all the amenities of home . Great for a long weekend getaway. Just a short drive from plenty of restaurants, store and attractions."
The price is £174
per night
13 May - 14 May
Mid-Century DJ’s Dream
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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 Holiday Rental Travel Info

Number of holiday rentals
2
Popular accommodation
Poughkeepsie private holiday homes
Known landmarks
Chance Theatre, 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, (957)
"Great stay. Hotel staff was friendly. Rooms were clean and hotel is just steps away from the concert hall venue. Easy free parking. "
The price is £110
per night
28 May - 29 May
DoubleTree by Hilton Poughkeepsie
Hyatt Place Poughkeepsie / Hudson Valley
Exterior
Hyatt Place Poughkeepsie / Hudson Valley
3.0 star property
8.8 out of 10, Excellent, (1000)
"Great Property! The room was fantastic and shower had abundant water pressure. Breakfast was 10/10, bacon, hash, real eggs and hashbrowns. One of the better properties we have stayed at in three years of over the road work."
The price is £92
per night
20 May - 21 May
Hyatt Place Poughkeepsie / Hudson Valley
Courtyard by Marriott Poughkeepsie
Exterior
Courtyard by Marriott Poughkeepsie
3.0 star property
8.8 out of 10, Excellent, (1002)
"Mackenzie at the front desk was incredibly helpful. Kyrie from housekeeping was friendly, helpful, with great energy. "
The price is £117
per night
28 May - 29 May
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Poughkeepsie holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Poughkeepsie holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Poughkeepsie holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Poughkeepsie holiday rentals we have selected for you start as low as £119 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Poughkeepsie rentals

At Expedia, we put the best Poughkeepsie holiday 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 holiday.

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 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.

Recent reviews of Poughkeepsie properties
Expedia verified reviews

Holiday Inn Express Poughkeepsie, an IHG Hotel

Holiday Inn Express Poughkeepsie, an IHG Hotel

5/5 Excellent
"It’s good "
A verified traveller stayed at Holiday Inn Express Poughkeepsie, an IHG Hotel
Posted 2 days ago
Holiday Inn Express Poughkeepsie, an IHG Hotel