Poughkeepsie holiday rentals: compare the best deals
10 2 reviews
Poughkeepsie
06/27 – 07/04
HK$10156/nightTotal: HK$71092 (7 )
Serenity Now Come Jump In The Pool
4 8
apartment , Clintondale
This four-bedroom apartment is located just a short distance from the charming town of New Paltz, with its shops, restaurants and attractions, and is surrounded by the beautiful wineries of the region. The apartment has received excellent ratings for its cleanliness, location and overall experience. The apartment has four bedrooms and four bathrooms, accommodating up to eight guests, and offers a private pool, a garden, a fitness center, parking, and air conditioning. Guests can also enjoy stunning views of the surrounding countryside and the peaceful atmosphere of this tranquil retreat.
Poughkeepsie
06/26 – 06/28
HK$6164/nightTotal: HK$12328 (2 )
Views On Hudson River / Luxury Modern Home
4 2
apartment , Highland
This luxurious dwelling offers a waterfront bluff experience on the Hudson River, located approximately 320 kilometres north of New York City within the scenic Hudson Valley. This designer mid-century residence features 4 bedrooms and 3 bathrooms accommodating up to 8 guests, with a fully equipped kitchen, air conditioning, a garden, and an expansive deck providing spectacular views and exclusive access to the entire property and ample parking.
Poughkeepsie
06/29 – 08/31
HK$1065/nightTotal: HK$67095 (63 )
House ∙ 3 Bedrooms ∙ 4 Guests
3 2
house , Pleasant Valley
This three-bedroom house is situated on a 20-acre wooded plot in Pleasant Valley, New York, offering seclusion yet convenient proximity to the Culinary Institute of America, the Home of Franklin D. Roosevelt National Historic Site, and the Dutchess County Wine Trail (distances unstated). The property boasts a spacious three-bedroom layout sleeping four guests, features air conditioning, and offers on-site owner assistance; nearby activities include wildlife viewing on the extensive grounds.
9.9 147 reviews
Poughkeepsie
08/22 – 08/28
HK$3414/nightTotal: HK$20484 (6 )
Charming Brick House -Hudson Valley
1 5
apartment , Haviland
This charming house, situated just a short drive from the Culinary Institute of America in Poughkeepsie/Hyde Park, offers a peaceful retreat with its secluded location across from a wooded area. The property has consistently received excellent ratings for its cleanliness, location, and overall experience. The house, spanning 186 square metres, boasts three bedrooms and a bathroom, providing ample space for families or groups. Guests can enjoy a well-equipped kitchen, a private garden, a terrace, and a range of amenities including Netflix, Hulu, and an Apple TV, along with a washer and dryer.
9.9 81 reviews
Poughkeepsie
08/24 – 08/29
HK$1270/nightTotal: HK$6350 (5 )
Your Own Pied-a-terre "Walkway Over The Hudson" #3
1 2
apartment , Poughkeepsie
This studio apartment is conveniently located in Poughkeepsie, within easy walking distance of the Dutchess County Courthouse, Marist and Vassar Colleges, Vassar Brothers Medical Center, the Walkway Over the Hudson, the train station, and Hudson River Park. The property has received excellent ratings for cleanliness, location, and overall guest experience. The self-contained apartment has a private entrance and can comfortably accommodate two guests. Enjoy the convenience of a fully equipped kitchen, a private garden, complimentary bicycles, and access to a gas and charcoal grill, a fire pit, and a patio.
9.5 234 reviews
Poughkeepsie
06/26 – 06/28
HK$5815/nightTotal: HK$11630 (2 )
Historic 4br Family Home Near Buttermilk Falls
1 2
apartment , Milton
This charming house in Milton, New York, is situated directly across the street from Buttermilk Falls Resort & Spa and a short walk from the Hudson River, offering easy access to the area's attractions. The property has received excellent user ratings for location, cleanliness, and overall experience. This four-bedroom, two-bathroom house can accommodate up to 10 guests, making it ideal for families or groups of friends. The house offers modern amenities, including a fully equipped kitchen, air conditioning, and a garden with a fire pit, as well as unique features like a sunroom with dining for 10 and a dressing room with a makeup table.
9.5 191 reviews
Poughkeepsie
08/24 – 08/29
HK$2265/nightTotal: HK$11325 (5 )
Historic 1 Br Family Home Near Buttermilk Falls
1 2
apartment , Milton
This charming 1790 Stagecoach Stop is situated in Milton, New York, directly across the street from Buttermilk Falls Resort & Spa and just a short drive from Walkway Over The Hudson. The property has received excellent ratings for location, cleanliness, and overall user experience. This one-bedroom, one-bathroom cottage can comfortably accommodate up to four guests and features a spacious kitchen, living room, and a sunroom with stunning views. Guests can enjoy a private garden, a fire pit, and modern conveniences like air conditioning, a coded deadbolt, and Roku Guest Mode for streaming entertainment.
Poughkeepsie
06/29 – 08/31
HK$1111/nightTotal: HK$69993 (63 )
Night And Armor
3 2
apartment , Poughkeepsie
This Poughkeepsie flat is located in a neighbourhood providing convenient access to local attractions. This three-bedroom flat accommodates up to four guests and features air conditioning, internet, and a kitchen, with a fitness centre available for use.
8.6 7 reviews
Poughkeepsie
06/27 – 06/28
HK$7228/nightfor 1 night
Welcome To New Paltz. Charming 3-bedroom House With Ac, Wifi,
3 5
apartment , New Paltz
This New Paltz house offers comfortable accommodation near the Samuel Dorsky Museum of Art and G. Steve Jordan Gallery, conveniently located for exploring the town's cultural attractions. The three-bedroom property, sleeping up to eight guests, features air conditioning, Wi-Fi, and is within easy reach of Loren Campbell Memorial Field and McCann Arena.
10 47 reviews
Poughkeepsie
08/22 – 08/28
HK$12297/nightTotal: HK$73782 (6 )
Hudson Valley Estate 90 Min From Nyc Pet Friendly
1 5
apartment , Highland
This spacious waterfront estate is situated in the Hudson Valley, just 90 minutes from New York City, offering a peaceful retreat from the city's hustle and bustle. The property has received excellent ratings for its location, cleanliness, and overall experience. This large holiday home boasts four bedrooms and two bathrooms, comfortably accommodating up to 10 guests. The estate features a chef's kitchen, a private garden, a swimming pool, and a host of other amenities perfect for relaxation and entertainment.
10 1 review
Poughkeepsie
06/27 – 06/28
HK$22433/nightfor 1 night
The New Paltz Moondance Ridge
1 5
house , New Paltz
This detached house is located in a peaceful area of New Paltz, offering easy access to the region's natural beauty and attractions. This spacious 437 square metre property accommodates up to 35 guests with 1 bedroom and 5 bathrooms, featuring air conditioning, a kitchen, a swimming pool, a jacuzzi, a terrace, a sauna, and private parking.
8.9 11 reviews
Poughkeepsie
08/28 – 08/29
HK$4255/nightfor 1 night
Quiet Hudson Valley Escape
1 2
apartment , Highland
This Highland, New York apartment is situated near the Mid-Hudson Bridge, offering easy access to Marist College and Vassar College (distances not specified). The three-bedroom, three-bathroom property sleeps six guests and includes a fully equipped kitchen with dishwasher, air conditioning, parking, and internet access; nearby attractions include the Walkway Over the Hudson.
Best family friendly Poughkeepsie holiday rentals
Among the 93 accommodations in Poughkeepsie, here are the 4 best family friendly rentals
10 2 reviews
Poughkeepsie
08/22 – 08/28
HK$6612/nightTotal: HK$39672 (6 )
The House In Highland
1 5
apartment , Highland
This three-bedroom flat offers a secluded Highland location, just a few kilometres from the Walkway Over the Hudson State Park and convenient access to New Paltz and Poughkeepsie. This family-friendly property accommodates up to six guests, boasting high-speed internet, a kitchen, air conditioning, a jacuzzi, a garden, a fitness centre, and an entertainment zone with an 85-inch television, arcade machines, and a record player, along with outdoor amenities including a hot tub and wood-burning fireplace.
Poughkeepsie
06/29 – 08/31
HK$1793/nightTotal: HK$112959 (63 )
2bed 1bath House ~ Lagrange, Ny
1 2
apartment , Red Oaks Mill
This Red Oaks Mill property is situated in a peaceful, private setting just 5 kilometres from the TSP, 10 kilometres from Route 84, and 15 kilometres from Route 9. The accommodation is perfect for a family or group of friends, with 2 bedrooms and 1 bathroom, comfortably sleeping 5 guests. The self-catering cottage has a fully equipped kitchen, including a fridge, freezer, microwave oven, and dishwasher, as well as air conditioning, parking, and internet access.
8.8 7 reviews
Poughkeepsie
08/22 – 08/28
HK$4090/nightTotal: HK$24540 (6 )
Summit Sanctuary With Ev Ready Mountain Views
4 5
house , Haviland
This Poughkeepsie residence provides spectacular mountain-top views and is located 10.8 kilometres from Vassar College and 16.1 kilometres from Marist College. This spacious 316 square metre dwelling offers four bedrooms, four bathrooms, and accommodates up to fifteen guests, featuring air conditioning, a full kitchen with a dishwasher, Wi-Fi, private parking, and EV charging, with a balcony to enjoy the vistas.
9.6 86 reviews
Poughkeepsie
08/24 – 08/29
HK$5422/nightTotal: HK$27110 (5 )
Beautiful Home - 4br/2.5ba - Hot Tub And Patio - Minutes From New Paltz
4 2
apartment , Highland
This family-friendly holiday home is located in Highland, just a short distance from the Hudson River and within easy reach of Berean Park Beach and Walkway Over the Hudson State Historic Park. The property has received excellent ratings for location, cleanliness and overall user experience. The house offers spacious accommodation for up to eight guests and includes four bedrooms and three bathrooms. Guests can enjoy a range of amenities, including a swimming pool, jacuzzi, spa, and a fully equipped kitchen with modern appliances. There is also a fireplace, a jetted tub, and a laundry room for added convenience.
Best Poughkeepsie holiday rentals with parking
9.0 14 reviews
Poughkeepsie
08/22 – 08/28
HK$3679/nightTotal: HK$22074 (6 )
Summit Sanctuary: Ev Ready Mountain Views
4 5
apartment , Haviland
This Haviland holiday home boasts a superb mountainside location, approximately 5 kilometres from the Eleanor Roosevelt National Historic Site and Richard L. Skimin Memorial Baseball Field. This 316-square-metre property sleeps eight guests across four bedrooms and four bathrooms, and includes a swimming pool, spa, fitness centre, and fully equipped kitchen.
8.8 18 reviews
Poughkeepsie
08/24 – 08/29
HK$9345/nightTotal: HK$46725 (5 )
The Scenic Mansion With Breathtaking View
4 2
house , Milton
This luxurious Milton mountain villa boasts stunning views, situated 1.8km from Franny Reese State Park and under 5km from the Hudson River and Walkway Over the Hudson State Historic Park. Sleeping up to 10 guests, this four-bedroom, six-bathroom property offers a private pool, tennis court, and ample amenities including a fully equipped kitchen, fireplace, and jetted tub, perfect for a family holiday near Berean Park Beach (5km).
Poughkeepsie
06/27 – 06/28
HK$1938/nightfor 1 night
Elixir Apartment
2 5
apartment , Clintondale
This Highland flat, Elixir Apartment, is situated approximately 9.7 kilometres from SUNY New Paltz and Historic Huguenot Street, offering convenient access to educational institutions and historical sites. Guests can enjoy air-conditioned units with free WiFi and private parking, featuring fully equipped kitchens, private bathrooms, and access to an on-site garden, with Stewart International Airport 25.7 kilometres away.
Poughkeepsie
07/27 – 12/31
HK$1079/nightTotal: HK$169403 (157 )
Cozy Residentialhome 5mins From Stores And Hospital.
3 2
apartment , Arlington
This Poughkeepsie holiday home, near Overlook Drive-In Theatre (2.7 km) and Vassar College (4 km), offers easy access to King Street Dog Park and the Frances Lehman Loeb Art Centre within a 9.6 km radius. The four-bedroom, three-bathroom property sleeps four guests and boasts a fully equipped kitchen, Smart TV, parking, and internet access; nearby attractions include the Overlook Drive-In and Vassar College.
Frequently asked questions about holiday rentals in Poughkeepsie
What should a first-time visitor not miss in Poughkeepsie, NY?
You definitely want to visit the Vassar College campus, it's a beautiful place with a rich history. The Walkway Over the Hudson is also a must-see, it offers stunning views of the Hudson River. And if you're interested in history, the Franklin D. Roosevelt Presidential Library and Museum is a great place to learn about the life and presidency of FDR.
What are the best Airbnb and vacation rentals in Poughkeepsie?
Which neighborhood in Poughkeepsie, NY should you consider for a vacation rental?
The area around the Walkway Over the Hudson is a popular choice for vacation rentals, as it offers easy access to the riverfront and the city centre. The historic district near the Vassar College campus is another good option with lots of character and charm.
What are the most popular Airbnbs in Poughkeepsie?
What are the top family-friendly attractions in Poughkeepsie, NY?
The Mid-Hudson Children's Museum is a great place for kids of all ages, they have interactive exhibits and plenty of space to run around. The Poughkeepsie Farm Project is a great place to learn about agriculture and enjoy the outdoors.
What are the best vacation rentals with a pool in Poughkeepsie?
When is the best time to book a vacation rental in Poughkeepsie, NY?
The best time to book a vacation rental in Poughkeepsie is during the shoulder seasons, from April to May and from September to October. You'll avoid the crowds and the prices are usually lower.
What are the best rentals for families and kids in Poughkeepsie?
What are the best budget-friendly activities in Poughkeepsie, NY?
You can enjoy a scenic walk or bike ride along the Hudson River, explore the many parks and gardens in the area, or visit the free exhibits at the Poughkeepsie Public Library.
What are the best rentals or Airbnbs with a jacuzzi in Poughkeepsie?
What are the best restaurants with local dishes in Poughkeepsie, NY?
For a taste of local fare, try the Poughkeepsie Wine & Dine, they have a great selection of local wines and dishes. The Arlington Tavern is another local favourite, serving up classic American comfort food.
What are the best walking or cycling routes in Poughkeepsie, NY?
The Walkway Over the Hudson is a popular walking and cycling route, offering stunning views of the Hudson River. The Dutchess Rail Trail is another great option, a 13-kilometre paved trail that runs through scenic countryside.
Are there pet-friendly attractions in Poughkeepsie, NY?
The Walkway Over the Hudson is pet-friendly, and many of the parks and gardens in the area also welcome dogs on leash. The Poughkeepsie Farm Project also welcomes dogs.
What are the benefits of choosing a vacation rental in Poughkeepsie, NY?
Vacation rentals offer more space and privacy than a hotel, and they often come with amenities that are not available in hotels, such as kitchens and laundry facilities. They can also be a more affordable option.
Destinations nearby
Best Poughkeepsie holiday rentals with a balcony
10 6 reviews
Poughkeepsie
08/22 – 08/28
HK$2923/nightTotal: HK$17538 (6 )
Beautiful Home With Hudson River Views & Adjacent Rushing Waterfall In Hyde Park
3 5
apartment , Hyde Park
This Hyde Park cottage offers a unique location directly opposite the Vanderbilt Mansion's Lower Gate and Coach Houses, providing views of Crum Elbow Creek's waterfall and immediate access to hiking trails, with FDR's Home & Library a short walk south. This 3-bedroom, 1-bathroom holiday home accommodates up to 7 guests and features air conditioning, a fully equipped kitchen with a dishwasher, a wood-burning fireplace, a sun-filled porch, and year-round Hudson River views, perfect for exploring local attractions and outdoor activities.
Poughkeepsie
06/27 – 06/28
HK$5492/nightfor 1 night
Lucious Lagrangeville
1 5
house , Freedom Plains
This spacious holiday home in Lagrangeville, Freedom Plains, is situated 14 kilometres from Vassar College and 16 kilometres from the Bardavon Opera House, with the Mid Hudson Children's Museum also 16 kilometres away. This non-smoking detached house offers 1000 square meters of floor area, air conditioning, a swimming pool, jacuzzi, terrace, balcony, kitchen, and parking for up to 19 guests, with WiFi provided.
10 21 reviews
Poughkeepsie
08/22 – 08/28
HK$6257/nightTotal: HK$37542 (6 )
The House In Highland-\nsecluded Retreat
3 5
apartment , Highland
This Highland house, minutes from the Walkway Over the Hudson State Park and the Highland hamlet, offers complete privacy whilst being conveniently located. Sleeping six guests, this three-bedroom, three-bathroom property boasts a well-equipped kitchen with added extras like a pasta maker and ice cream maker, a game room with arcade machines, a hot tub, and fast 1 gigabit internet.
10 5 reviews
Poughkeepsie
06/26 – 06/28
HK$4628/nightTotal: HK$9256 (2 )
Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat
3 2
apartment , Fairview
This Fairview holiday home is situated within 5km of King Street Dog Park, Richard L. Skimin Memorial Baseball Field, Chance Theatre, Mid-Hudson Heritage Center, and Walkway Over the Hudson State Historic Park, offering easy access to local attractions. This 214 square metre property sleeps six guests, boasting three bedrooms, three bathrooms, a fully equipped kitchen with dishwasher, free Wi-Fi, a terrace, garden, parking, and a fireplace; ideal for families.
Best pet friendly Poughkeepsie holiday rentals
Among the 93 accommodations in Poughkeepsie, here are the 4 best pet friendly rentals
Poughkeepsie
06/27 – 07/04
HK$9055/nightTotal: HK$63385 (7 )
Serenity Wildflower-creekside Escape W Pool, Sauna
6 8
apartment , Marlboro
This secluded six-bedroom flat offers a peaceful retreat at the end of a long driveway, surrounded by orchards and wildflower farms, a short distance from Marlboro's agricultural landscape. This spacious accommodation accommodates up to 12 guests, featuring a private creek-side escape, a swimming pool, a sauna, and ample outdoor space for enjoying nature.
Poughkeepsie
08/24 – 08/29
HK$5045/nightTotal: HK$25225 (5 )
Hudson Escape W Hot Tub Bridge View
3 2
house , Highland
This Highland holiday home, situated 7km from the Bardavon Opera House and 16km from both SUNY New Paltz and Historic Huguenot Street, offers stunning bridge views. This 930 square metre property boasts three bedrooms sleeping ten guests, a fully equipped kitchen including dishwasher and microwave, a private hot tub, free Wi-Fi, parking, and a washing machine.
9.6 138 reviews
Poughkeepsie
08/24 – 08/29
HK$3314/nightTotal: HK$16570 (5 )
Stylish, Mid-century Designer Home
1 2
apartment , Poughkeepsie
This recently renovated studio apartment is situated on a peaceful, tree-lined street in Poughkeepsie, just a short distance from Vassar College and a 10-kilometre drive from the Walkway Over the Hudson. The property has consistently received excellent ratings from guests for its cleanliness, location, and overall experience. The apartment features a spacious open-plan layout, comfortably accommodating up to five guests. The studio is fully equipped with modern amenities, including a kitchen with a fridge, microwave, and dishwasher, as well as a private patio with a barbecue, perfect for enjoying the outdoors.
9.7 23 reviews
Poughkeepsie
06/27 – 07/04
HK$6803/nightTotal: HK$47621 (7 )
Historic Spacious Home 5 Bed/2 Bath
1 8
apartment , Poughkeepsie
This five-bedroom house, perfect for large groups, is situated in a quiet Poughkeepsie neighbourhood, conveniently close to local universities and restaurants. The property boasts a spacious layout across two floors, accommodating up to ten guests with amenities including a Peloton bike, a screened-in porch, and a deck (although the deck railings require caution), all set within over 0.4 kilometres of land.