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

Orchard Views From A Light-filled Tiny Home With A Fire Pit - Poughkeepsie, NY
9.9 365 reviews

Orchard Views From A Light-filled Tiny Home With A Fire Pit

cabin, Marlboro
This Marlboro cottage sits on a 30-acre farm in the Shawangunk Mountains, part of the Shawangunk Wine Trail, approximately 32km from Beacon and 145km from New York City.
The two-bedroom, one-bathroom self-catering property sleeps four, boasting a king-size bed, modern kitchen, Laveo toilet, outdoor fire pit, and access to farm-fresh eggs; guests can also opt for camping on-site.
Stylish And Spacious Centrally Located One Bedroom Apartment - Poughkeepsie, NY
9.4 9 reviews

Stylish And Spacious Centrally Located One Bedroom Apartment

apartment, Poughkeepsie
This Poughkeepsie holiday home is conveniently located within 1.6km of the Mid-Hudson Civic Center, McCann Ice Arena, and Mid-Hudson Heritage Center, offering easy access to Poughkeepsie Station (a 15-minute walk).
The two-bedroom, one-bathroom property sleeps three guests and features a fully equipped kitchen, a sofa bed, Smart TV, and on-site parking; nearby attractions include the Chance Theater and Bardavon 1869 Opera House.
Black Walnut Tree Farm: 50-acres + Private Pond - Poughkeepsie, NY
9.6 5 reviews

Black Walnut Tree Farm: 50-acres + Private Pond

apartment, Clintondale
This Highland countryside farmhouse, a 33-minute (53km) drive from Mohonk Lake and 12-minute (19km) drive from the Walkway Over the Hudson State Historic Park, offers a convenient rural location near major attractions.
Sleeping up to eight guests, the property boasts three bathrooms, a fully equipped kitchen including dishwasher and microwave, Wi-Fi, laundry facilities, a private garden, and barbecue facilities, all within easy reach of Quartz Rock Vineyard and Franny Reese State Park.
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

Stunning 5-bedroom House With Ac / Heat In Charming Poughkeepsie Ny - Poughkeepsie, NY
9.6 5 reviews

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

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.
Hudson Riverfront Escape - Poughkeepsie, NY
No reviews

Hudson Riverfront Escape

apartment, Highland
This historic 1860 apartment in Highland offers unparalleled Hudson Riverfront views from every room and is situated across the street from the Marist Boathouse, with the Walkway Over the Hudson, Culinary Institute of America, Vassar College, and SUNY New Paltz all within a few kilometres.
This two-bedroom, two-bathroom residence accommodates four guests and features a fully equipped kitchen, air conditioning, a garden, private outdoor dining and relaxation spaces, and garage parking for vehicles up to 2.31 metres wide and 2.06 metres high.
Black Walnut Farm: 50-acres + Private Pond - Poughkeepsie, NY
No reviews

Black Walnut Farm: 50-acres + Private Pond

apartment, Clintondale
This 50-acre Highland, New York farmhouse, near New Paltz and approximately 50km from Poughkeepsie, offers a tranquil Hudson Valley escape.
The property boasts a chef's kitchen with soapstone counters, four bedrooms sleeping eight guests, three bathrooms, and outdoor amenities including a swimming pond, fire pit, and gas grill; small events and weddings are available upon request.
The Bluff - Designer Home With Views, Pool & Hot T - Poughkeepsie, NY
9.8 9 reviews

The Bluff - Designer Home With Views, Pool & Hot T

apartment, Milton
This detached house is situated on a secluded 4-acre riverfront property in the Hudson Valley, offering panoramic views of the Hudson River and located approximately 3.2 kilometres from Marlboro and 320 kilometres from London.
The property boasts accommodation for six guests across three bedrooms and two bathrooms, featuring a private drive, floor-to-ceiling windows, a pool, hot tub, fire pit, and expansive decks for al fresco dining, alongside a chef's kitchen and a dedicated reading room/office.

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

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

Hudson Valley Duplex: Hike, Sip + Explore!

house, Highland
This Hudson Valley duplex in Highland is located 5.96 kilometres from Bardavon Opera House and 9.98 kilometres from Vassar College.
This spacious three-bedroom, three-bathroom holiday home offers 139 square metres of living space, accommodates up to 11 guests, and features a fully equipped kitchen, air conditioning, a garden, terrace, and is ideal for exploring the hiking and sipping opportunities of the region.
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.
Spacious 4bd Country Gem - Fire Pit & Chill Vibes - Poughkeepsie, NY
10 25 reviews

Spacious 4bd Country Gem - Fire Pit & Chill Vibes

apartment, Hyde Park
This Highland holiday home, situated in a rural setting within 9.6km of the Walkway Over the Hudson State Historic Park, Berean Park Beach, and the Franklin D. Roosevelt Presidential Library and Museum, offers a tranquil escape near popular attractions.
This 278 square metre property boasts four bedrooms, four bathrooms, and sleeps eight, featuring a fully equipped kitchen, private balcony, garden, parking, and free Wi-Fi.
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

Classy Canvas Furnished Yurt - Poughkeepsie, NY
9.9 21 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.
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.
Esopus Escape: Secluded Escape With Hot Tub & Fireplace - Poughkeepsie, NY
9.6 4 reviews

Esopus Escape: Secluded Escape With Hot Tub & Fireplace

apartment, Rifton
This three-bedroom, three-bathroom New Paltz apartment, a short 42km drive from Mohonk Lake and 16km from Huguenot Street, offers a convenient base for exploring the Hudson Valley.
The self-catering property boasts a private pool, hot tub, billiards table, fully equipped kitchen, in-unit laundry, Wi-Fi, and is close to El Paso Winery and New Paltz Golf Course.
Owl's Nest A Nature Lover's Getaway - Poughkeepsie, NY
No reviews

Owl's Nest A Nature Lover's Getaway

house, Plattekill
This detached house in Marlboro, a district of Plattekill, offers stunning mountain views and is situated 3 kilometers from local walking trails, ideal for those seeking outdoor pursuits.
This property provides 184 square meters of living space for up to 7 guests, featuring a fully equipped kitchen, air conditioning, a garden with barbecue facilities, and complimentary WiFi and private parking.
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