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

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.
Green Sanctuary: Luxury Home Surrounded By Nature - Poughkeepsie, NY
10 6 reviews

Green Sanctuary: Luxury Home Surrounded By Nature

apartment, Rifton
This four-bedroom apartment is located in Ulster Park, just 10km from New Paltz and a short drive from the scenic Hudson Valley. It has an excellent user rating and is ideal for families or groups of up to eight people.
The property offers a spacious and airy layout with multiple living areas, including a dedicated home office and a media room. The apartment is fully equipped with modern appliances, a large deck with a fire pit and a BBQ grill, and a host of other amenities, making it perfect for both relaxing and entertaining.
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.
The Scenic Mansion With Breathtaking View - Poughkeepsie, NY
8.2 23 reviews

The Scenic Mansion With Breathtaking View

house, Highland
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).

Best Poughkeepsie, NY holiday rentals with parking

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

Hudson Valley Duplex: Hike, Sip + Explore!

house, Highland
This Highland detached house is situated near Wineries and State Parks, offering convenient access to the Walkway Over the Hudson and Poughkeepsie, with 3 bedrooms and 2 bathrooms accommodating up to 6 guests.
The property features a private patio, 3.2 kilometres of on-site trails, a garden, and parking, with a fully equipped kitchen including a fridge and microwave, plus air conditioning and on-site laundry facilities for a comfortable stay.
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.
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.
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.

Frequently asked questions about holiday rentals in Poughkeepsie, NY

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

    For a first-timer, you definitely want to check out the Vassar College campus, it's beautiful. The Walkway Over the Hudson is a must-do, a stunning pedestrian bridge with fantastic views of the Hudson River. And don't miss the chance to visit the Franklin D. Roosevelt Presidential Library and Museum, it's a fascinating look into American history.
  • 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 great choice. It's close to the riverfront, restaurants, and shops. You can find some lovely vacation rentals in the historic district, too, which is close to the Vassar College campus and the Poughkeepsie Galleria.
  • 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 big hit with families. It's interactive and educational, with plenty of exhibits to keep kids entertained. The Walkway Over the Hudson is also a great option, with plenty of space for kids to run around. You could also check out the Poughkeepsie Farm Park, which has a petting zoo, a playground, and lots of space to run around.
  • 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?

    The best time to book a vacation rental in Poughkeepsie is during the shoulder seasons, from April to May and September to October. You'll avoid the crowds and the prices are generally lower. If you want to experience the warmer weather, June to August is a good time to visit, but expect higher prices and more crowds.
  • What are the best rentals for families and kids in Poughkeepsie, NY?

  • What events or festivals should visitors check out in and around Poughkeepsie, NY?

    The Poughkeepsie Waterfront Festival is a big one, with music, food, and activities. The Dutchess County Fair is a popular local event. There's also the Hudson Valley Wine & Food Festival, which takes place in nearby Rhinebeck. You can find a full list of events on the Poughkeepsie Chamber of Commerce website.
  • What are the best rentals or Airbnbs with a jacuzzi in Poughkeepsie, NY?

    The best holiday 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 budget-friendly activities in Poughkeepsie, NY?

    The Walkway Over the Hudson is free to walk, and the views are incredible. You can also take a stroll through the Vassar College campus, which is beautiful and free to explore. The Poughkeepsie Farmers' Market is a great way to get a taste of local produce, and it's free to browse.
  • What are the best restaurants with local dishes in Poughkeepsie, NY?

    For a real taste of local food, check out the Poughkeepsie Farmers' Market. You can find fresh produce, baked goods, and local crafts. For a sit-down meal, try The Grandview, which serves classic American dishes with a modern twist, or the Arlington Tavern, which has a great selection of local beers.
  • What are the best walking or cycling routes in Poughkeepsie, NY?

    The Walkway Over the Hudson is a great place to walk or cycle, with stunning views of the Hudson River. For a shorter walk, try the Poughkeepsie Waterfront Walk, which runs along the riverfront. If you're looking for a longer ride, the Dutchess Rail Trail is a great option.
  • Are there pet-friendly attractions in Poughkeepsie, NY?

    The Walkway Over the Hudson is pet-friendly, and there are plenty of dog-friendly restaurants and cafes in the area. You can also take your dog for a walk in the Vassar College campus, which is open to the public.
  • What are the benefits of choosing a vacation rental in Poughkeepsie, NY?

    Vacation rentals in Poughkeepsie offer more space and privacy than a hotel, and they're often more affordable, especially for families or groups. They can also be more convenient, as you'll have a kitchen to prepare meals and a laundry to wash clothes.
  • What are the top sports attractions and facilities in Poughkeepsie, NY?

    The Mid-Hudson Civic Center is a major sports venue, hosting a variety of events, including concerts, ice hockey, and basketball games. The Walkway Over the Hudson is a popular spot for running, cycling, and walking. For outdoor sports, the Poughkeepsie Farm Park has a playground, a basketball court, and a baseball field.

Popular destinations

Best Poughkeepsie, NY holiday rentals with a balcony

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.
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.
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.
Lucious Lagrangeville - Poughkeepsie, NY
No reviews

Lucious Lagrangeville

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.

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 Pet-friendly  Nature Lover's Getaway Near Wineries & Hiking Trails - Poughkeepsie, NY
9.8 125 reviews

Owl's Nest: A Pet-friendly Nature Lover's Getaway Near Wineries & Hiking Trails

apartment, Plattekill
The Owls Nest apartment is located in the Marlboro Mountains, a peaceful area in the Hudson Valley, around 15 kilometres from the Walkway Over The Hudson. This apartment has received excellent ratings for location, cleanliness and overall experience.
The apartment has two bedrooms and one bathroom, suitable for up to four guests. It features a modern design with a spacious open plan layout, a sunroom with views of the wooded garden, a private patio with a fire pit, and access to a nearby trail.
Pony's Pad Buttermilkfallsinn - Poughkeepsie, NY
No reviews

Pony's Pad Buttermilkfallsinn

cabin, Milton
Pony's Pad Getaway Suite, a self-catering lodge situated on the 75-acre Buttermilk Falls estate in Milton-upon-Thames, offers easy access to Henrys at the Farm restaurant, a spa, and Millstone Farm animal rescue.
This two-storey suite features a spiral staircase, a California King bed and pull-out sofa sleeping four, a luxurious en-suite bathroom with a walk-in shower, a full kitchen, and a wrap-around deck with river and pond views; the estate also boasts nature trails for guests to explore.
1850s Barn Studio On 4.5 Hudson Valley Acres! - Poughkeepsie, NY
10 3 reviews

1850s Barn Studio On 4.5 Hudson Valley Acres!

studio, Rifton
This Rifton studio apartment is situated in Highland, providing convenient access to Minnewaska State Park and Mohonk Preserve, with Historic Huguenot Street and El Paso Winery also within easy reach.
This 46 square meter converted barn apartment accommodates two guests, offering a pet-friendly retreat with a kitchenette, air conditioning, and a private furnished patio, alongside shared amenities like a gazebo, treehouse, and fire pit.
Secluded House On 55 Ac W/pool 5 Mins To New Paltz - Poughkeepsie, NY
10 2 reviews

Secluded House On 55 Ac W/pool 5 Mins To New Paltz

apartment, Highland
This apartment is located on 55 acres of meadows and woodland, approximately 5 minutes by car from the centre of New Paltz, New York.
This property accommodates up to six guests in three bedrooms, offering a private outdoor swimming pool, a well-equipped kitchen, and laundry facilities.
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