Holiday Rentals in Poughkeepsie

93 available vacation rental offers

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Poughkeepsie holiday rentals
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Poughkeepsie holiday rentals: compare the best deals

Best family friendly Poughkeepsie holiday rentals

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

The Scenic Mansion With Breathtaking View - Poughkeepsie
8.8 19 reviews
Poughkeepsie
08/24 – 08/29
HK$9345/nighttotal: HK$46725 (5 )

The Scenic Mansion With Breathtaking View

4 2
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).
Old Farmhouse In The Hudson Valley - Poughkeepsie
10 3 reviews
Poughkeepsie
06/27 – 07/04
HK$5428/nighttotal: HK$37996 (7 )

Old Farmhouse In The Hudson Valley

4 8
apartment , Myers Corner
This 1734 farmhouse in Dutchess County, New York, is situated 0.4 kilometres from the Dutchess County Rail Trail and a short drive from local restaurants and historical sites.
The 173-square-metre property sleeps eleven guests across four bedrooms and two bathrooms, offering amenities such as a fully equipped kitchen, garden, ample parking, and a back porch with a swing; a pack 'n' play is also available.
Zen Peaks Retreat - Poughkeepsie
9.9 15 reviews
Poughkeepsie
06/27 – 07/04
HK$3627/nighttotal: HK$25389 (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.
Beautiful, Fun, Spacious 5 Acre Family Retreat - Poughkeepsie
9.8 105 reviews
Poughkeepsie
06/27 – 07/04
HK$2924/nighttotal: HK$20468 (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.

Best Poughkeepsie holiday rentals with parking

Bella Woods ~ A Hidden Gem In The Heart Of It All~ - Poughkeepsie
10 9 reviews
Poughkeepsie
08/28 – 08/29
HK$2743/nightfor 1 night

Bella Woods ~ A Hidden Gem In The Heart Of It All~

1 2
apartment , Highland
This Highland duplex apartment is situated less than 1.6km from the Walkway Over the Hudson, the Hudson Valley Rail Trail, and Highland Landing Park, offering easy access to these attractions and the Hamlet's amenities.
The self-catering property sleeps four guests in one bedroom and one bathroom, boasting a fully equipped kitchen, air conditioning, parking, a swimming pool, and excellent user reviews; ideal for exploring the Hudson Valley.
Charming Mid Century Vintage 1br Guest Suite - 2 Min To Downtown - Poughkeepsie
8.2 10 reviews
Poughkeepsie
07/27 – 12/31
HK$1222/nighttotal: HK$191854 (157 )

Charming Mid Century Vintage 1br Guest Suite - 2 Min To Downtown

1 2
apartment , New Paltz
This New Paltz apartment, situated within 5km of SUNY New Paltz and the Jenkinstown Day Spa, offers a tranquil mountainside setting with scenic views.
The one-bedroom, one-bathroom flat sleeps four guests and includes a fully equipped kitchen, private patio, free Wi-Fi, and access to a garden and spa facilities.
Cabin In The Heart Of The Hudson Valley, Cabin 3 - Poughkeepsie
9.8 14 reviews
Poughkeepsie
07/27 – 12/31
HK$1673/nighttotal: HK$262661 (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.
The New Paltz Moondance Ridge - Poughkeepsie
10 1 review
Poughkeepsie
06/27 – 07/04
HK$19068/nighttotal: HK$133476 (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.

Frequently asked questions about holiday rentals in Poughkeepsie

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

    You definitely want to visit the Vassar College campus, it's a beautiful place with a rich history. The Walkway Over the Hudson is also a must-see, it offers stunning views of the Hudson River. And if you're interested in history, the Franklin D. Roosevelt Presidential Library and Museum is a great place to learn about the life and presidency of FDR.
  • What are the best Airbnb and vacation rentals in Poughkeepsie?

  • 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 offers easy access to the riverfront and the city centre. The historic district near the Vassar College campus is another good option with lots of character and charm.
  • What are the most popular Airbnbs in Poughkeepsie?

  • 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, they have interactive exhibits and plenty of space to run around. The Poughkeepsie Farm Project is a great place to learn about agriculture and enjoy the outdoors.
  • What are the best vacation rentals with a pool in Poughkeepsie?

  • 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 from September to October. You'll avoid the crowds and the prices are usually lower.
  • What are the best rentals for families and kids in Poughkeepsie?

  • What are the best budget-friendly activities in Poughkeepsie, NY?

    You can enjoy a scenic walk or bike ride along the Hudson River, explore the many parks and gardens in the area, or visit the free exhibits at the Poughkeepsie Public Library.
  • What are the best rentals or Airbnbs with a jacuzzi in Poughkeepsie?

    The best vacation rentals or Airbnb with a jacuzzi in Poughkeepsie 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 fare, try the Poughkeepsie Wine & Dine, they have a great selection of local wines and dishes. The Arlington Tavern is another local favourite, serving up classic American comfort food.
  • What are the best walking or cycling routes in Poughkeepsie, NY?

    The Walkway Over the Hudson is a popular walking and cycling route, offering stunning views of the Hudson River. The Dutchess Rail Trail is another great option, a 13-kilometre paved trail that runs through scenic countryside.
  • Are there pet-friendly attractions in Poughkeepsie, NY?

    The Walkway Over the Hudson is pet-friendly, and many of the parks and gardens in the area also welcome dogs on leash. The Poughkeepsie Farm Project also welcomes dogs.
  • What are the benefits of choosing a vacation rental in Poughkeepsie, NY?

    Vacation rentals offer more space and privacy than a hotel, and they often come with amenities that are not available in hotels, such as kitchens and laundry facilities. They can also be a more affordable option.

Destinations nearby

Best Poughkeepsie holiday rentals with a balcony

Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat - Poughkeepsie
10 5 reviews
Poughkeepsie
06/26 – 06/28
HK$4628/nighttotal: HK$9256 (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.

Best pet friendly Poughkeepsie holiday rentals

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

Gindelle Suite Buttermilkfalls - Poughkeepsie
Poughkeepsie
08/28 – 08/29
HK$7805/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.
Hudson Escape W/ Hot Tub + Bridge View - Poughkeepsie
Poughkeepsie
08/24 – 08/29
HK$5604/nighttotal: HK$28020 (5 )

Hudson Escape W/ Hot Tub + Bridge View

3 2
apartment , Highland
This family-friendly holiday home in Highland offers a rural, waterfront setting, a 4-minute drive from the Walkway Over the Hudson State Historic Park and a 15-minute walk from the Hudson River.
The spacious 170-square-meter accommodation features 3 bedrooms, 1.5 bathrooms, and accommodates up to 6 guests with amenities including a hot tub, garden, Wi-Fi, air conditioning, and a full kitchen with a washer and dryer.
Your Own Pied-a-terre "Walkway Over The Hudson"#2 - Poughkeepsie
9.7 111 reviews
Poughkeepsie
06/29 – 08/31
HK$859/nighttotal: HK$54117 (63 )

Your Own Pied-a-terre "Walkway Over The Hudson"#2

1 2
apartment , Poughkeepsie
This charming flat is situated in the heart of Poughkeepsie, just under 10 kilometres from Vassar College, Marist College, and the Walkway Over the Hudson, making it a convenient base for exploring the city. The property has consistently received excellent ratings for location, cleanliness, and overall experience, making it a popular choice for travellers.
The apartment is a one-bedroom, one-bathroom flat with a private entrance and can accommodate up to two guests. Features include a well-equipped kitchen, air conditioning, complimentary bicycles, a garden, and parking, ensuring a comfortable and enjoyable stay.
Hudson Escape W Hot Tub Bridge View - Poughkeepsie
Poughkeepsie
08/24 – 08/29
HK$5045/nighttotal: HK$25225 (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.
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