Holiday Rentals in Poughkeepsie, NY

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Poughkeepsie, NY holiday rentals
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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

Black Walnut Tree Farm: 50-acres + Private Pond - Poughkeepsie, NY
9.6 5 reviews

Black Walnut Tree Farm: 50-acres + Private Pond

apartment, Clintondale
This Highland countryside farmhouse, a 33-minute (53km) drive from Mohonk Lake and 12-minute (19km) drive from the Walkway Over the Hudson State Historic Park, offers a convenient rural location near major attractions.
Sleeping up to eight guests, the property boasts three bathrooms, a fully equipped kitchen including dishwasher and microwave, Wi-Fi, laundry facilities, a private garden, and barbecue facilities, all within easy reach of Quartz Rock Vineyard and Franny Reese State Park.
The Bluff - Designer Home With Views, Pool & Hot T - Poughkeepsie, NY
9.8 9 reviews

The Bluff - Designer Home With Views, Pool & Hot T

apartment, Milton
This detached house is situated on a secluded 4-acre riverfront property in the Hudson Valley, offering panoramic views of the Hudson River and located approximately 3.2 kilometres from Marlboro and 320 kilometres from London.
The property boasts accommodation for six guests across three bedrooms and two bathrooms, featuring a private drive, floor-to-ceiling windows, a pool, hot tub, fire pit, and expansive decks for al fresco dining, alongside a chef's kitchen and a dedicated reading room/office.
Charming Vacation House W/ Pool & Hottub - Poughkeepsie, NY
10 39 reviews

Charming Vacation House W/ Pool & Hottub

apartment, Highland
This holiday home in the Hudson Valley is just minutes from hiking and biking trails, farms, wineries, breweries, and restaurants, and less than 45 minutes from Thunder Ridge Ski Area. It has excellent user, location and cleanliness ratings.
The property has three bedrooms and two bathrooms, comfortably accommodating up to eight guests. It includes a range of modern amenities, such as a heated pool, a spa tub, a gourmet kitchen, and multiple TVs with Netflix access.
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.

Best Poughkeepsie, NY holiday rentals with parking

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.
Totally Secluded Yurt Surrounded By Waterfalls, Brooks, Cliffs And Forest - Poughkeepsie, NY
10 333 reviews

Totally Secluded Yurt Surrounded By Waterfalls, Brooks, Cliffs And Forest

apartment, Rifton
This secluded yurt is located in Rifton, a short drive from New Paltz and Kingston, offering a peaceful escape into nature. It consistently receives excellent ratings for its location, cleanliness, and overall experience.
The spacious, circular dwelling covers 89 square metres and comfortably accommodates up to four guests. Enjoy a fully equipped kitchen, a private bathroom, and a cosy living area, as well as access to a fire pit, a porch for grilling, and the 120-acre property with waterfalls, brooks, cliffs, and forests.
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.
Stunning 5-bedroom House With Ac / Heat In Charming Poughkeepsie Ny - Poughkeepsie, NY
9.6 5 reviews

Stunning 5-bedroom House With Ac / Heat In Charming Poughkeepsie Ny

apartment, Poughkeepsie
This Poughkeepsie property is a five-bedroom dwelling situated near Franny Reese State Park and Vanderbilt Mansion National Historic Site, with attractions such as the Mid-Hudson Civic Centre and McCann Ice Arena also easily accessible.
This residence accommodates up to 18 guests across four queen beds and one king bed, offering air conditioning, heating, an iron, and a hairdryer, with a host available to assist during your stay.

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

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.
Rhinebrook Estate - 8 Bed/8bath + Pool (Sleeps 20) - Poughkeepsie, NY
9.6 19 reviews

Rhinebrook Estate - 8 Bed/8bath + Pool (Sleeps 20)

house, Haviland
This spacious estate, located 90 kilometres north of New York City and just 7 minutes from the Taconic Parkway, offers complete privacy and tranquillity on its 26 acres of land. The property has received excellent reviews from previous guests.
This impressive mansion has 8 bedrooms, 11 bathrooms and can accommodate up to 20 guests. The home provides a range of amenities, including a fully equipped kitchen, a large dining room, a lounge with a pool table, a yoga and fitness studio, a sauna, a massage room, a terrace and a garden.
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.
Private 37 Acre Lake Estate On 164 Acres - 11 Br - Poughkeepsie, NY
9.4 3 reviews

Private 37 Acre Lake Estate On 164 Acres - 11 Br

apartment, Rifton
This spacious Highland dwelling in Rifton boasts a waterfront location, 4.5km from the Franklin D. Roosevelt Presidential Library and Museum, and within 10km of Apple Greens Golf Course and Historic Huguenot Street.
The 1189 square metre property sleeps 29 guests across 14 bedrooms and 8 bathrooms, offering a Jacuzzi, terrace, garden, free Wi-Fi, and parking; water activities are readily accessible from its lakeside position.

Best pet friendly Poughkeepsie, NY holiday rentals

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

Owl's Nest A Nature Lover's Getaway - Poughkeepsie, NY
No reviews

Owl's Nest A Nature Lover's Getaway

house, Plattekill
This detached house in Marlboro, a district of Plattekill, offers stunning mountain views and is situated 3 kilometers from local walking trails, ideal for those seeking outdoor pursuits.
This property provides 184 square meters of living space for up to 7 guests, featuring a fully equipped kitchen, air conditioning, a garden with barbecue facilities, and complimentary WiFi and private parking.
Esopus Escape: Secluded Escape With Hot Tub & Fireplace - Poughkeepsie, NY
9.6 4 reviews

Esopus Escape: Secluded Escape With Hot Tub & Fireplace

apartment, Rifton
This three-bedroom, three-bathroom New Paltz apartment, a short 42km drive from Mohonk Lake and 16km from Huguenot Street, offers a convenient base for exploring the Hudson Valley.
The self-catering property boasts a private pool, hot tub, billiards table, fully equipped kitchen, in-unit laundry, Wi-Fi, and is close to El Paso Winery and New Paltz Golf Course.
Serenity Wildflower-creekside Escape W Pool, Sauna - Poughkeepsie, NY
10 2 reviews

Serenity Wildflower-creekside Escape W Pool, Sauna

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.
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.
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