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

Highland Mansion - Poughkeepsie, NY
8.2 12 reviews

Highland Mansion

house, Milton
This Milton manor house, perfect for families, offers a luxurious stay with stunning views, conveniently located near Milton's major attractions (distance unspecified).
Sleeping up to 10 guests across 4 bedrooms and 6 bathrooms, this spacious property boasts a swimming pool, garden, and parking, alongside modern amenities including air conditioning and internet access.
Hamptons On The Hudson: Pool, Spa, Bbq, Views! - Poughkeepsie, NY
9.8 48 reviews

Hamptons On The Hudson: Pool, Spa, Bbq, Views!

apartment, Milton
This waterfront property in Milton offers stunning views of the Hudson River, just 0.8km from the riverfront and within 5km of Live At The Falcon and Marlboro Free Library. The apartment has consistently received excellent ratings for user experience, location, and cleanliness.
This spacious 5-bedroom home, spanning 465 square metres, can comfortably accommodate up to 10 guests. The property provides a range of amenities including a private pool, a jacuzzi, a terrace, a garden, and a spa, ensuring a luxurious and relaxing stay.
Summit Sanctuary With Ev Ready Mountain Views - Poughkeepsie, NY
8.2 9 reviews

Summit Sanctuary With Ev Ready Mountain Views

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.
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

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.
Industry Style Open Concept Downtown - Poughkeepsie, NY
No reviews

Industry Style Open Concept Downtown

apartment, Poughkeepsie
This Poughkeepsie flat offers easy access to local attractions from its convenient district, a short drive from the Walkway Over the Hudson State Historic Park and close to Vassar College, with the Poughkeepsie Train Station facilitating travel to and from New York City. This two-bedroom, one-bathroom flat accommodates up to six guests and features air conditioning, internet, and a kitchen, making it suitable for group travel, families, and business trips with ample dining and entertainment options nearby.
Hudson Valley Highland Retreat W/ Fire Pit - Poughkeepsie, NY
9.8 44 reviews

Hudson Valley Highland Retreat W/ Fire Pit

apartment, Highland
The Highland Cottage is situated in the Town of Lloyd, just a short distance from New Paltz and a short walk to Berean Park, offering easy access to the Walkway over the Hudson, the Mid Hudson Bridge, and the Culinary Institute of America. This charming cottage provides a peaceful retreat for those seeking a blend of rural tranquility and convenient access to local attractions.
The Highland Cottage is a spacious 3-bedroom home that comfortably sleeps 8 guests. It offers a fully equipped kitchen, a comfortable living area, and a private patio with a swimming pool and a gas BBQ, perfect for relaxing evenings.
Private 37 Acre Lake Estate On 164 Acres - 11 Br - Poughkeepsie, NY
9.4 3 reviews

Private 37 Acre Lake Estate On 164 Acres - 11 Br

apartment, Rifton
This spacious Highland dwelling in Rifton boasts a waterfront location, 4.5km from the Franklin D. Roosevelt Presidential Library and Museum, and within 10km of Apple Greens Golf Course and Historic Huguenot Street.
The 1189 square metre property sleeps 29 guests across 14 bedrooms and 8 bathrooms, offering a Jacuzzi, terrace, garden, free Wi-Fi, and parking; water activities are readily accessible from its lakeside position.

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

Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat - Poughkeepsie, NY
10 6 reviews

Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat

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.
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.
The House In Highland- Secluded Retreat - Poughkeepsie, NY
9.8 28 reviews

The House In Highland- Secluded Retreat

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.
Spacious 4bd Country Gem - Fire Pit & Chill Vibes - Poughkeepsie, NY
9.5 4 reviews

Spacious 4bd Country Gem - Fire Pit & Chill Vibes

house, Hyde Park
This Hyde Park holiday home is conveniently located near the Bardavon 1869 Opera House (10.3 km) and SUNY New Paltz (13.5 km), offering easy access to both cultural attractions and the scenic Highland hiking trails.
This recently renovated four-bedroom property boasts a fully equipped kitchen in each unit, private parking, air conditioning, a terrace, garden, and barbecue facilities, ideal for families seeking a comfortable stay.

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
9.6 5 reviews

Scenic Hudson Valley Getaway Farms & Vineyards

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.
Timeless Three-story Treasure W/ Pool, Rolling Hills And Fireplace - Poughkeepsie, NY
10 2 reviews

Timeless Three-story Treasure W/ Pool, Rolling Hills And Fireplace

apartment, Freedom Plains
Todd Hill Farmhouse, situated in Lagrangeville, a short drive from Freedom Plains and conveniently close to attractions such as the Mid-Hudson Civic Center and the Stormville Airport Antique Show & Flea Market, offers a spacious family-friendly residence. This four-bedroom, four-bathroom property sleeps ten guests and boasts a fully equipped kitchen (fridge, microwave, dishwasher), air conditioning, a terrace, garden, parking, and multiple relaxing areas including a fireplace and library.
Private 37 Acre Lake Estate On 164 Acres - 11 Br - Poughkeepsie, NY
10 1 review

Private 37 Acre Lake Estate On 164 Acres - 11 Br

house, Rifton
This Highland, New York estate, approximately 11km from New Paltz and 21km from Poughkeepsie, boasts a private 37-acre lake within a 164-acre property, offering seclusion near Huguenot Street.
This 14-bedroom, 8-bathroom property, spanning 930 square metres, comfortably accommodates 33 guests and features a fully equipped kitchen, jacuzzi, spa, terrace, and ample parking, alongside free Wi-Fi.
Classy Canvas Furnished Yurt - Poughkeepsie, NY
9.9 22 reviews

Classy Canvas Furnished Yurt

yurt, Fairview
This Fairview guest house, near woodland, offers a glamping experience with queen and double beds, shared kitchen facilities, and two bathrooms, sleeping up to four guests.
The self-catering accommodation includes a fridge, freezer, microwave, and dishwasher, plus Wi-Fi, parking, and a garden; on-site hosts and volunteers provide assistance.
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