Holiday Rentals in Poughkeepsie, NY

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Poughkeepsie, NY holiday rentals
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93 Holiday Rentals and Airbnb in Poughkeepsie, NY

Best family friendly Poughkeepsie, NY holiday rentals

Among the 93 accommodations in Poughkeepsie, NY, here are the 4 best family friendly rentals

The House In Highland-\nsecluded Retreat - Poughkeepsie, NY
10 21 reviews
Poughkeepsie, NY
22/08 – 28/08
NZ$1373/nighttotal: NZ$8238 (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.
Charming Vacation House W/ Pool & Hottub - Poughkeepsie, NY
10 36 reviews
Poughkeepsie, NY
22/08 – 28/08
NZ$1806/nighttotal: NZ$10836 (6 )

Charming Vacation House W/ Pool & Hottub

1 5
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 Secret Cottage

Luxury Stay In Prime Location - Poughkeepsie, NY
10 34 reviews
Poughkeepsie, NY
24/08 – 29/08
NZ$632/nighttotal: NZ$3160 (5 )

The Secret Cottage Luxury Stay In Prime Location

1 2
house , Crown Heights
This modern cottage, ideal for a Crown Heights stay, is situated in a safe Poughkeepsie suburb, conveniently close to Rhinebeck, Beacon, and New Paltz, with Metro-North trains approximately 16km away.
The single-bedroom, single-bathroom property sleeps three guests and offers a fully equipped kitchen, private patio, two large TVs with Netflix, free Wi-Fi, and a wheelchair-accessible interior (except for the laundry room), plus a children's playground within a one-minute walk.
Modern Scandinavian Villa - Poughkeepsie, NY
10 3 reviews
Poughkeepsie, NY
27/06 – 04/07
NZ$2137/nighttotal: NZ$14959 (7 )

Modern Scandinavian Villa

1 8
house , Gardnertown
This luxurious, renovated 1920s stone barn, situated in Wallkill, Hudson Valley, offers a secluded 6-acre property with a private gravel driveway, approximately 145km from New York City and within easy driving distance of Beacon, Kingston, Rhinebeck, and West Point.
The three-storey villa boasts four bedrooms, two bathrooms, sleeping up to nine guests, and features a chef's kitchen, high-speed internet (1 Gigabit Verizon Fios), a ping pong table, an outdoor deck overlooking a pond, and ample space for relaxation and entertainment.

Best Poughkeepsie, NY holiday rentals with parking

Newly Renovated 1 Bd Apartment - Poughkeepsie, NY
9.3 35 reviews
Poughkeepsie, NY
22/08 – 28/08
NZ$532/nighttotal: NZ$3192 (6 )

Newly Renovated 1 Bd Apartment

1 5
apartment , Poughkeepsie
This one-bedroom flat is conveniently located in the heart of Poughkeepsie, within a kilometre of the Walkway Over the Hudson and four local colleges, offering a lively and engaging atmosphere. The property has received excellent ratings for cleanliness, location, and overall user experience.
The flat is perfect for a group of up to four people, featuring a well-equipped kitchen with a fridge, freezer, and microwave. Guests can enjoy modern amenities, such as air conditioning, internet access, and the convenience of being pet-friendly.
Welcome To New Paltz. Charming 3-bedroom House With Ac, Wifi, - Poughkeepsie, NY
8.6 7 reviews
Poughkeepsie, NY
27/06 – 28/06
NZ$1586/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.
Historic 4br Family Home Near Buttermilk Falls - Poughkeepsie, NY
9.5 234 reviews
Poughkeepsie, NY
22/08 – 28/08
NZ$743/nighttotal: NZ$4458 (6 )

Historic 4br Family Home Near Buttermilk Falls

1 5
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.
Scenic Hudson Valley Getaway  Farms & Vineyards - Poughkeepsie, NY
9.4 3 reviews
Poughkeepsie, NY
24/08 – 29/08
NZ$635/nighttotal: NZ$3175 (5 )

Scenic Hudson Valley Getaway Farms & Vineyards

2 2
cottage , Marlboro
This two-bedroom Marlboro cottage is situated on over 4 hectares of land, close to top-rated vineyards and within easy reach of Franny Reese State Park and the Walkway Over the Hudson State Historic Park.
The self-catering property sleeps four, boasts air conditioning, internet access, and permits pets; nearby attractions include the Gomez Mill House and McCann Ice Arena.

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.

Destinations nearby

Best Poughkeepsie, NY holiday rentals with a balcony

Luxury 4br Home With Mountain Views - Poughkeepsie, NY
Poughkeepsie, NY
27/06 – 28/06
NZ$1772/nightfor 1 night

Luxury 4br Home With Mountain Views

1 5
house , Clintondale
This property in Highland offers stunning mountain views and is located 14 kilometres from Loren Campbell Baseball Field and 14 kilometres from Bardavon Opera House, with SUNY New Paltz 14 kilometres away.
This 1-bedroom dwelling accommodates up to 15 guests and features a fully equipped kitchen, air conditioning, complimentary WiFi, and a terrace with garden views, providing a non-smoking retreat with convenient access to Stewart International Airport, 19 kilometres distant.
Summit Sanctuary With Ev Ready Mountain Views - Poughkeepsie, NY
8.8 7 reviews
Poughkeepsie, NY
22/08 – 28/08
NZ$898/nighttotal: NZ$5388 (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.
Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat - Poughkeepsie, NY
10 5 reviews
Poughkeepsie, NY
26/06 – 28/06
NZ$1016/nighttotal: NZ$2032 (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.
Beautiful Home With Hudson River Views & Adjacent Rushing Waterfall In Hyde Park - Poughkeepsie, NY
10 6 reviews
Poughkeepsie, NY
22/08 – 28/08
NZ$641/nighttotal: NZ$3846 (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.

Best pet friendly Poughkeepsie, NY holiday rentals

Among the 93 accommodations in Poughkeepsie, NY, here are the 4 best pet friendly rentals

2bed 1bath House ~ Lagrange, Ny - Poughkeepsie, NY
Poughkeepsie, NY
27/06 – 28/06
NZ$353/nightfor 1 night

2bed 1bath House ~ Lagrange, Ny

1 5
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.
Gindelle Suite Buttermilkfalls - Poughkeepsie, NY
Poughkeepsie, NY
26/06 – 27/06
NZ$1882/nightfor 1 night

Gindelle Suite Buttermilkfalls

1 4
cabin , Milton
The Gindelle getaway suite, a self-catering lodge situated on a 75-acre estate at Buttermilk Falls in Milton, on the Hudson River, offers easy access to the Henrys at the Farm restaurant and Millstone Farm animal rescue.
This two-bedroom, one-bathroom retreat sleeps four, boasting a king and queen-size bed, a fully equipped kitchen, a whirlpool tub, two gas fireplaces, and stunning garden and pond views; on-site amenities include a fitness centre, parking, and access to walking trails.
Stunning 5-bedroom House With Ac / Heat In Charming Poughkeepsie Ny - Poughkeepsie, NY
9.6 4 reviews
Poughkeepsie, NY
27/06 – 04/07
NZ$1850/nighttotal: NZ$12950 (7 )

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

5 8
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.
Zen Peaks Retreat - Poughkeepsie, NY
9.9 15 reviews
Poughkeepsie, NY
27/06 – 04/07
NZ$796/nighttotal: NZ$5572 (7 )

Zen Peaks Retreat

1 8
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.
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