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

Beautiful, Fun, Spacious 5 Acre Family Retreat - Poughkeepsie, NY
9.8 105 reviews
Poughkeepsie, NY
27/06 – 04/07
NZ$642/nighttotal: NZ$4494 (7 )

Beautiful, Fun, Spacious 5 Acre Family Retreat

3 2
apartment , Fairview
This Fairview apartment is situated just a mile from Plan Bee Brewery and Peach Hill Park, offering a peaceful escape close to attractions like Vassar College, Marist College, and the Walkway Over the Hudson. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The property provides three bedrooms and two bathrooms, comfortably accommodating up to eleven guests. It boasts a spacious garden room ideal for family gatherings, a separate living room for relaxation, and a fully equipped kitchen with modern appliances. Enjoy the private balcony, explore the surrounding nature, or take advantage of the proximity to the Dutchess Rail Trail for cycling and hiking.
2bed 1bath House ~ Lagrange, Ny - Poughkeepsie, NY
Poughkeepsie, NY
29/06 – 31/08
NZ$394/nighttotal: NZ$24822 (63 )

2bed 1bath House ~ Lagrange, Ny

1 2
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.
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.
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.

Best Poughkeepsie, NY holiday rentals with parking

Hudson Escape W Hot Tub Bridge View - Poughkeepsie, NY
Poughkeepsie, NY
24/08 – 29/08
NZ$1107/nighttotal: NZ$5535 (5 )

Hudson Escape W Hot Tub Bridge View

3 2
house , Highland
This Highland holiday home, situated 7km from the Bardavon Opera House and 16km from both SUNY New Paltz and Historic Huguenot Street, offers stunning bridge views.
This 930 square metre property boasts three bedrooms sleeping ten guests, a fully equipped kitchen including dishwasher and microwave, a private hot tub, free Wi-Fi, parking, and a washing machine.
Cabin In The Heart Of The Hudson Valley, Cabin 1 - Poughkeepsie, NY
10 34 reviews
Poughkeepsie, NY
27/07 – 31/12
NZ$367/nighttotal: NZ$57619 (157 )

Cabin In The Heart Of The Hudson Valley, Cabin 1

1 2
cabin , Marlboro
This charming cabin is situated just a short distance from Marlboro, conveniently located near the Shawangunk Wine Trail, Minnewaska State Park Preserve, and the Walkway Over the Hudson. It has received excellent reviews from previous guests, highlighting its peaceful and quiet atmosphere.
The cosy cabin, spanning 14 square metres, comfortably accommodates two guests in a single bedroom and bathroom. It offers a fully equipped kitchen, a comfortable living space with a fireplace, and access to shared amenities like a grill and picnic table for enjoying the outdoors.
Cabin In The Heart Of The Hudson Valley, Cabin 3 - Poughkeepsie, NY
9.8 14 reviews
Poughkeepsie, NY
27/07 – 31/12
NZ$367/nighttotal: NZ$57619 (157 )

Cabin In The Heart Of The Hudson Valley, Cabin 3

1 2
cabin , Marlboro
This cosy cabin is located just a short distance from Marlboro, near the Shawangunk Wine Trail, Minnewaska State Park Preserve, and the Walkway Over the Hudson, offering easy access to popular attractions. It has received very good user ratings.
The one-bedroom cabin is 13 square metres in size and can accommodate two guests. It features a fully equipped kitchen, a comfortable king-size bed, a cosy sitting area, a fireplace, central air conditioning and heating, a private garden, and parking.

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

The New Paltz Moondance Ridge - Poughkeepsie, NY
10 1 review
Poughkeepsie, NY
27/06 – 04/07
NZ$4185/nighttotal: NZ$29295 (7 )

The New Paltz Moondance Ridge

1 8
house , New Paltz
This detached house is located in a peaceful area of New Paltz, offering easy access to the region's natural beauty and attractions.
This spacious 437 square metre property accommodates up to 35 guests with 1 bedroom and 5 bathrooms, featuring air conditioning, a kitchen, a swimming pool, a jacuzzi, a terrace, a sauna, and private parking.

Best pet friendly Poughkeepsie, NY holiday rentals

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

Your Own Pied-a-terre "Walkway Over The Hudson" #4 - Poughkeepsie, NY
9.9 33 reviews
Poughkeepsie, NY
27/06 – 04/07
NZ$229/nighttotal: NZ$1603 (7 )

Your Own Pied-a-terre "Walkway Over The Hudson" #4

1 2
apartment , Poughkeepsie
This studio apartment is conveniently located in central Poughkeepsie, just a 10-minute walk from Marist and Vassar Colleges, Vassar Bros. Medical Center, and the Walkway Over the Hudson. The studio has received excellent ratings for cleanliness, location, and user experience.
The self-contained apartment has one bedroom and one bathroom, suitable for up to two guests. This charming studio offers a private entrance, parking, a landscaped garden, and a fully equipped kitchen including a fridge, microwave, and dishwasher.
Lake Side Tiny House - Poughkeepsie, NY
9.7 179 reviews
Poughkeepsie, NY
24/08 – 29/08
NZ$347/nighttotal: NZ$1735 (5 )

Lake Side Tiny House

1 2
house , Fairview
This charming cottage is situated in a secluded wooded area, just a short distance from Fairview, offering a peaceful escape from the hustle and bustle. It has received excellent ratings for its location, cleanliness, and overall experience.
The property features a full bathroom and a well-equipped kitchen, perfect for preparing meals. Guests can enjoy the lakefront location, with opportunities for swimming, fishing, and kayaking, or simply relax and reconnect with nature in the tranquil surroundings.
Wooded Rhinebeck-beacon Area Escape W/outdoor Spa - Poughkeepsie, NY
10 74 reviews
Poughkeepsie, NY
24/08 – 29/08
NZ$1131/nighttotal: NZ$5655 (5 )

Wooded Rhinebeck-beacon Area Escape W/outdoor Spa

1 2
apartment , Fairview
This Fairview apartment is situated in Hyde Park, New York, just a short drive from Poughkeepsie and Rhinebeck, making it a great base for exploring the Hudson Valley. It has received excellent ratings for its location, cleanliness, and overall experience.
The apartment is a comfortable and spacious property with two bedrooms, sleeping up to four guests. It offers a range of amenities, including a hot tub, a fully equipped kitchen, and a screened-in porch, perfect for relaxing after a day of exploring the local attractions.
Gindelle Suite Buttermilkfalls - Poughkeepsie, NY
Poughkeepsie, NY
28/08 – 29/08
NZ$1713/nightfor 1 night

Gindelle Suite Buttermilkfalls

1 2
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.
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