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

Orchard Views From A Light-filled Tiny Home With A Fire Pit - Poughkeepsie, NY
9.9 365 reviews

Orchard Views From A Light-filled Tiny Home With A Fire Pit

cabin, Marlboro
This Marlboro cottage sits on a 30-acre farm in the Shawangunk Mountains, part of the Shawangunk Wine Trail, approximately 32km from Beacon and 145km from New York City.
The two-bedroom, one-bathroom self-catering property sleeps four, boasting a king-size bed, modern kitchen, Laveo toilet, outdoor fire pit, and access to farm-fresh eggs; guests can also opt for camping on-site.
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.
Modern Designer Cabin In Woods W/ 5-star Amenities - Poughkeepsie, NY
9.7 33 reviews

Modern Designer Cabin In Woods W/ 5-star Amenities

cabin, Highland
This Highland, New York log cabin retreat is situated on a secluded 0.8-hectare wooded plot, a short 16-kilometre drive from both New Paltz and Poughkeepsie.
The four-bedroom, four-bathroom property sleeps eight guests and boasts a 100-inch screen cinema room, games room, private gym, saltwater pool, cedar sauna, and hot tub, alongside a fully equipped kitchen and ample parking.
Modern Ranch: Heated Pool & Fire Pit, Pizza Oven, Grill, Screened-in Porch - Poughkeepsie, NY
No reviews

Modern Ranch: Heated Pool & Fire Pit, Pizza Oven, Grill, Screened-in Porch

apartment, New Paltz
This detached house in Highland is situated in a secluded cul-de-sac, a mere 3-minute drive from New Paltz village and 5 minutes from SUNY New Paltz, offering convenient access from the Trailways bus stop and proximity to the Huguenot Street Historic District.
Sleeping up to six guests, this family-friendly property boasts a heated in-ground swimming pool, a screened-in porch, a fully equipped kitchen with a large island, a ground-level family room with a 55-inch television, and multiple outdoor entertainment options including two fire pits, a pizza oven, and a gas grill.

Best Poughkeepsie, NY holiday rentals with parking

Hudson Riverfront Escape - Poughkeepsie, NY
No reviews

Hudson Riverfront Escape

apartment, Highland
This historic 1860 apartment in Highland offers unparalleled Hudson Riverfront views from every room and is situated across the street from the Marist Boathouse, with the Walkway Over the Hudson, Culinary Institute of America, Vassar College, and SUNY New Paltz all within a few kilometres.
This two-bedroom, two-bathroom residence accommodates four guests and features a fully equipped kitchen, air conditioning, a garden, private outdoor dining and relaxation spaces, and garage parking for vehicles up to 2.31 metres wide and 2.06 metres high.
Villa Sabrina: A Serene 700 Sq Ft Studio On A 5.6-acre Estate In Lagrangeville - Poughkeepsie, NY
No reviews

Villa Sabrina: A Serene 700 Sq Ft Studio On A 5.6-acre Estate In Lagrangeville

studio, Freedom Plains
This Lagrangeville apartment is located 8 minutes by car from Tymor Park and 37 minutes from SplashDown Beach, offering convenient access to local attractions.
This studio apartment, covering 65 square meters, accommodates two guests and features a swimming pool, garden, balcony, Wi-Fi, air conditioning, and on-site parking.
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.
Your Own Pied-a-terre "Walkway Over The Hudson" #3 - Poughkeepsie, NY
9.9 82 reviews

Your Own Pied-a-terre "Walkway Over The Hudson" #3

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.

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

Hudson Valley Duplex: Hike, Sip + Explore! - Poughkeepsie, NY
No reviews

Hudson Valley Duplex: Hike, Sip + Explore!

house, Highland
This Hudson Valley duplex in Highland is located 5.96 kilometres from Bardavon Opera House and 9.98 kilometres from Vassar College.
This spacious three-bedroom, three-bathroom holiday home offers 139 square metres of living space, accommodates up to 11 guests, and features a fully equipped kitchen, air conditioning, a garden, terrace, and is ideal for exploring the hiking and sipping opportunities of the region.
Villa Sabrina - Poughkeepsie, NY
No reviews

Villa Sabrina

apartment, Freedom Plains
This Lagrangeville flat, Villa Sabrina, is located approximately 14.5 to 17.7 kilometres from Vassar College, Bardavon Opera House, Mid Hudson Children's Museum, and Marist College.
This 65 square metre one-bedroom flat accommodates up to three guests and features a private balcony, free WiFi, a kitchenette, and complimentary private parking, with an American breakfast offered on-site.
Wake-up To Hudson River Sunrises- Historic Riverfront Retreat. - Poughkeepsie, NY
10 1 review

Wake-up To Hudson River Sunrises- Historic Riverfront Retreat.

apartment, Highland
This riverside flat in Highland offers spectacular Hudson River sunrises and direct riverfront access, located across from the Marist Boathouse and minutes from Marist University, Vassar College, and the Culinary Institute of America.
This 127 square meter residence accommodates four guests across two bedrooms and two bathrooms, boasting modern comforts, a fully equipped kitchen, Sonos sound system, solar power, and a unique river-view attic space, with parking for one vehicle in a garage.
For The Creative Spirit, Swimming Dock On Pond, Horses To Pet, Fire Pit - Poughkeepsie, NY
9.9 243 reviews

For The Creative Spirit, Swimming Dock On Pond, Horses To Pet, Fire Pit

apartment, Rifton
This artist's loft is located in Rifton, just 10km from New Paltz and Kingston, offering easy access to Woodstock and Rhinebeck. The studio has received excellent ratings for its location, cleanliness, and overall experience.
The studio spans 121 square metres and comfortably accommodates up to three guests. It features a fully equipped kitchen, a spacious living area, a bedroom, and a bathroom, plus a private terrace with stunning views of the surrounding 30-acre property. Guests can enjoy swimming in the pond, paddleboarding, hiking, or simply relaxing by the water.

Best pet friendly Poughkeepsie, NY holiday rentals

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

Scenic Hudson Valley Getaway  Farms & Vineyards - Poughkeepsie, NY
9.9 16 reviews

Scenic Hudson Valley Getaway Farms & Vineyards

cabin, Marlboro
This Marlboro, New York lodge is situated on over 4 hectares of land near farms, orchards, wineries, and a top-rated Hudson Valley vineyard, approximately 145 kilometres from New York City.
The two-bedroom property sleeps four guests and boasts a fully equipped kitchen, wood-burning fireplace, smart TVs, and access to the entire house, including parking; nearby attractions include Marlboro's bars, restaurants, markets, and breweries.
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.
Luxe Wooded Modern Getaway With Saltwater Pool - Poughkeepsie, NY
10 80 reviews

Luxe Wooded Modern Getaway With Saltwater Pool

apartment, Crown Heights
This modern house is located in Wappingers Falls, a 90-minute drive from New York City, and is situated along the Hudson River, between Beacon and Rhinebeck, just outside of Poughkeepsie. The property has excellent user, location, and cleanliness ratings.
The house has three bedrooms and two bathrooms, accommodating up to six guests. It offers a range of amenities, including a swimming pool, a hot tub, a fitness centre, and a private garden, alongside a well-equipped kitchen, a fireplace, and a Peloton bike.
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.
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