Holiday Rentals in Poughkeepsie, NY

109 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Poughkeepsie, NY holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

109 Holiday rentals and Airbnb in Poughkeepsie, NY

Best family friendly Poughkeepsie, NY holiday rentals

Among the 109 accommodations in Poughkeepsie, NY, here are the 4 best family friendly rentals

Zen Peaks Retreat - Poughkeepsie, NY
9.9 19 reviews

Zen Peaks Retreat

apartment, Highland
This Highland, New York colonial farmhouse, situated approximately 48 kilometres from the Mohonk Mountains and Lake Minnewaska, offers easy access to a rail trail just 8 kilometres away.
Sleeping up to 12 guests in four bedrooms and two bathrooms, this self-catering property boasts a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, a garden, fitness centre, parking, and Wi-Fi.
Splendid Isolation: Private Luxury. Breathtaking Modern Villa On Hudson Bluffs. - Poughkeepsie, NY
9.9 154 reviews

Splendid Isolation: Private Luxury. Breathtaking Modern Villa On Hudson Bluffs.

apartment, Highland
This stunning private residence is located on a peninsula overlooking the Hudson River in Highland, just 1.5 hours from New York City and a short drive from FDR's Birthplace & Summer White House. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The villa spans 381 square metres and can accommodate up to eight guests in its four bedrooms. The property offers a wide range of amenities and activities, including a heated saltwater pool, a tennis court, a hot tub, a gourmet kitchen, a 10' screen media room, a huge deck, a screened porch, Jacuzzis, steam showers, a sauna, and a private sculpture garden.
Beautiful Home - 4br/2.5ba - Hot Tub And Patio - Minutes From New Paltz - Poughkeepsie, NY
9.6 93 reviews

Beautiful Home - 4br/2.5ba - Hot Tub And Patio - Minutes From New Paltz

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.
Spacious 4bd Country Gem - Fire Pit & Chill Vibes - Poughkeepsie, NY
10 25 reviews

Spacious 4bd Country Gem - Fire Pit & Chill Vibes

apartment, Hyde Park
This Highland holiday home, situated in a rural setting within 9.6km of the Walkway Over the Hudson State Historic Park, Berean Park Beach, and the Franklin D. Roosevelt Presidential Library and Museum, offers a tranquil escape near popular attractions.
This 278 square metre property boasts four bedrooms, four bathrooms, and sleeps eight, featuring a fully equipped kitchen, private balcony, garden, parking, and free Wi-Fi.

Best Poughkeepsie, NY holiday rentals with parking

Hudson Valley Estate 90 Min From Nyc Pool&gameroom - Poughkeepsie, NY
10 52 reviews

Hudson Valley Estate 90 Min From Nyc Pool&gameroom

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.
Riverbirch Buttermilkfallsinn - Poughkeepsie, NY
No reviews

Riverbirch Buttermilkfallsinn

apartment, Milton
This four-bedroom, four-bathroom flat is situated on a secluded 75-acre estate on the Hudson River, part of the Buttermilk Falls grounds, offering a tranquil retreat near Henrys at the Farm restaurant and Millstone Farm.
Accommodating up to eight guests, this property boasts four king bedrooms, each with a private bathroom, an accessible bedroom, a main floor half-bath, a fully equipped kitchen, and open living and dining areas, with the added benefit of on-site fitness facilities and parking.
Spacious 4bd Country Gem - Fire Pit & Chill Vibes - Poughkeepsie, NY
9.5 4 reviews

Spacious 4bd Country Gem - Fire Pit & Chill Vibes

house, Hyde Park
This Hyde Park holiday home is conveniently located near the Bardavon 1869 Opera House (10.3 km) and SUNY New Paltz (13.5 km), offering easy access to both cultural attractions and the scenic Highland hiking trails.
This recently renovated four-bedroom property boasts a fully equipped kitchen in each unit, private parking, air conditioning, a terrace, garden, and barbecue facilities, ideal for families seeking a comfortable stay.
Nature's Serenity Retreat - Poughkeepsie, NY
No reviews

Nature's Serenity Retreat

apartment, Milton
This four-bedroom flat is located in a peaceful, nature-filled district of Milton, offering direct access to scenic views and wildlife, perfect for a tranquil escape.
This spacious residence accommodates up to 12 guests and features a large kitchen, two bathrooms, air conditioning, and parking, with nearby natural attractions providing opportunities for rejuvenation.

Frequently asked questions about holiday rentals in Poughkeepsie, NY

  • What should a first-time visitor not miss in Poughkeepsie, NY?

    You definitely want to check out the Vassar College campus, it's a beautiful place to wander around. The Walkway Over the Hudson is a must-see as well, offering stunning views of the Hudson River. And for a dose of history, head to the Franklin D. Roosevelt Presidential Library and Museum.
  • What are the best Airbnb and holiday rentals in Poughkeepsie, NY?

  • 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's close to the river and offers easy access to the city centre. The historic district is also a good option, with charming Victorian architecture and plenty of restaurants and shops.
  • What are the most popular Airbnbs in Poughkeepsie, NY?

  • 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, with interactive exhibits and plenty of space to run around. The Poughkeepsie Farm Project is a working farm that offers educational tours and activities for families. And of course, you can't go wrong with a trip to the Dutchess County Fairgrounds, which hosts a variety of events throughout the year.
  • What are the best holiday rentals with a pool in Poughkeepsie, NY?

  • When is the best time to book a vacation rental in Poughkeepsie, NY?

    You'll want to book your vacation rental in advance, especially if you're planning to visit during peak season, which runs from June to August. You can also get good deals if you book outside of peak season, but you might have to compromise on availability.
  • What are the best rentals for families and kids in Poughkeepsie, NY?

  • What are the best budget-friendly activities in Poughkeepsie, NY?

    The Walkway Over the Hudson is free to walk, and offers stunning views of the Hudson River. You can also enjoy a picnic in the park at the Vassar College campus, or take a stroll through the historic district and admire the Victorian architecture.
  • What are the best rentals or Airbnbs with a jacuzzi in Poughkeepsie, NY?

    The best vacation rentals or Airbnb with a jacuzzi in Poughkeepsie, NY are House In Highland: Secluded Retreat, Beautiful Home - 4br\/2 -5ba - Hot Tub And Patio - Minutes From New Paltz and Pentimento.

  • What are the best restaurants with local dishes in Poughkeepsie, NY?

    For a taste of local cuisine, head to The Grandview, a popular spot known for its Hudson Valley-inspired menu. Another option is The Dutch, which offers a modern take on classic American dishes with a focus on fresh, seasonal ingredients.
  • What are the best walking or cycling routes in Poughkeepsie, NY?

    The Walkway Over the Hudson is a great option for both walking and cycling, offering stunning views of the Hudson River. The Dutchess Rail Trail is another popular choice, offering a scenic route through the countryside.
  • Are there pet-friendly attractions in Poughkeepsie, NY?

    The Walkway Over the Hudson welcomes dogs on leashes, and there are plenty of dog-friendly parks and restaurants in the area. The Vassar College campus is also dog-friendly, with plenty of open spaces for your furry friend to run around.
  • What are the benefits of choosing a vacation rental in Poughkeepsie, NY?

    Vacation rentals offer more space and privacy than a hotel room, and are often located in more convenient locations. They can also be more affordable, especially for families or groups.
  • What are the top sports attractions and facilities in Poughkeepsie, NY?

    The city is home to the Marist College Athletics program, which offers a variety of sporting events throughout the year. The Mid-Hudson Athletic Club is a popular spot for fitness enthusiasts, offering a range of facilities and classes.

Popular destinations

Best Poughkeepsie, NY holiday rentals with a balcony

Summit Sanctuary With Ev Ready Mountain Views - Poughkeepsie, NY
8.2 9 reviews

Summit Sanctuary With Ev Ready Mountain Views

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.
Summit Sanctuary: Ev Ready Mountain Views - Poughkeepsie, NY
9.2 16 reviews

Summit Sanctuary: Ev Ready Mountain Views

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.
The House In Highland- Secluded Retreat - Poughkeepsie, NY
9.8 28 reviews

The House In Highland- Secluded Retreat

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.
Secluded Country Getaway - Poughkeepsie, NY
9.6 27 reviews

Secluded Country Getaway

cottage, Highland
This secluded lodge in Highland, Ulster County, is located moments from the Hudson River and offers easy access to historic sites such as Walkway Over the Hudson, 13 kilometres away, and Franny Reese State Park, 10 kilometres away.
This detached cottage accommodates up to six guests with two bedrooms, a kitchen, a living room, and a bathroom, and features a garden, terrace, spa, and parking, with complimentary continental breakfast items provided.

Best pet friendly Poughkeepsie, NY holiday rentals

Among the 109 accommodations in Poughkeepsie, NY, here are the 4 best pet friendly rentals

Historic 4br Family Home Near Buttermilk Falls - Poughkeepsie, NY
9.5 236 reviews

Historic 4br Family Home Near Buttermilk Falls

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.
Private Retreat On 12 Acres W Hot Tub And Bbq - Poughkeepsie, NY
10 11 reviews

Private Retreat On 12 Acres W Hot Tub And Bbq

apartment, Freedom Plains
This six-bedroom Lagrangeville house, ideal for large groups, is situated 4.2km from James Baird State Park, with Tymor Park and Beekman Golf Course under 10km away.
The 465 square metre property boasts a private pool, jacuzzi, fitness centre, tennis court, and ample amenities including a fully equipped kitchen, accommodating up to 10 guests.
Classy Canvas Furnished Yurt - Poughkeepsie, NY
9.9 22 reviews

Classy Canvas Furnished Yurt

yurt, Fairview
This Fairview guest house, near woodland, offers a glamping experience with queen and double beds, shared kitchen facilities, and two bathrooms, sleeping up to four guests.
The self-catering accommodation includes a fridge, freezer, microwave, and dishwasher, plus Wi-Fi, parking, and a garden; on-site hosts and volunteers provide assistance.
2 Full Beds | Non-smoking, Kitchen - Poughkeepsie, NY
9.0 20 reviews

2 Full Beds | Non-smoking, Kitchen

apartment, Fishkill
This Fishkill flat is located on Route 9, 19 kilometres from Stewart International Airport and within driving distance of the Mid Hudson Children's Museum (11 kilometres) and Marist College (14 kilometres).
This 28 square metre apartment offers one bedroom, one bathroom, sleeps up to four guests, and includes a fully equipped kitchen, air conditioning, free on-site parking, and complimentary WiFi.
©2026 cozycozy.com