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Poughkeepsie, NY vacation rentals
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Best Vacation rentals and Airbnb offers in Poughkeepsie, NY

Discover Family-Friendly Vacation Rentals in Poughkeepsie, NY

Booking a family-oriented vacation rental in Poughkeepsie, NY keeps you close to top city attractions for a stress-free getaway.

Cozy Escape With Stunning Hudson River Views - Poughkeepsie, NY
10 2 reviews
Poughkeepsie, NY
08/22 – 08/28
$643/nighttotal: $3858 (6 )

Cozy Escape With Stunning Hudson River Views

1 5
apartment , Milton
This family-friendly apartment in Milton offers sweeping Hudson River views from its location in the scenic Hudson Valley, placing you near wineries, farms, and dining options. This spacious, three-story home accommodates up to 8 guests with 4 bedrooms, 2 bathrooms, air conditioning, internet, a full kitchen, fitness center, garden, and parking, providing exclusive access to the entire residence and an outdoor deck.
Timeless Three-story Treasure W/ Pool, Rolling Hills And Fireplace - Poughkeepsie, NY
10 2 reviews
Poughkeepsie, NY
06/20 – 06/22
$1030/nighttotal: $2060 (2 )

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

4 10
apartment , Freedom Plains
The Todd Hill Farmhouse, a four-bedroom, four-bathroom house rental in Lagrangeville, offers easy access to Freedom Plains attractions like the Mid-Hudson Civic Center and Stormville Airport Antique Show & Flea Market.
This spacious three-story colonial-style home sleeps ten guests and boasts a fireplace, library, multiple seating areas, a full kitchen with dishwasher, and a terrace; nearby activities include the Mid-Hudson Children's Museum and Fun Central.
Maple Branch Manor: Large Groups | Events, Parties - Poughkeepsie, NY
Poughkeepsie, NY
08/22 – 08/28
$2692/nighttotal: $16152 (6 )

Maple Branch Manor: Large Groups | Events, Parties

7 5
apartment , Milton
Maple Branch Manor, a large estate, is situated less than 2 hours from New York City and 5 minutes from Milton, offering proximity to the Hudson River and towns like Highland and New Paltz.
This family-friendly estate accommodates 14 guests with 7 bedrooms and 7 bathrooms, featuring a party barn with a pool table, a beauty room, a library with a fireplace, a formal dining area with a bar, and outdoor living spaces with a BBQ and firepit.
Hudson Escape W/ Hot Tub + Bridge View - Poughkeepsie, NY
9.7 38 reviews
Poughkeepsie, NY
06/20 – 06/27
$522/nighttotal: $3654 (7 )

Hudson Escape W/ Hot Tub + Bridge View

3 2
apartment , Highland
This Highland, New York apartment boasts stunning Hudson River and bridge views from its private deck and hot tub.
The three-bedroom, one-bathroom rental sleeps six, features a full kitchen with dishwasher, in-unit laundry, Wi-Fi, on-site parking for up to three cars, and provides noise-canceling headphones.

Best Poughkeepsie, NY vacation rentals with parking

Hudson Escape W Hot Tub Bridge View - Poughkeepsie, NY
Poughkeepsie, NY
06/20 – 06/27
$580/nighttotal: $4060 (7 )

Hudson Escape W Hot Tub Bridge View

3 2
house , Highland
This Hudson Valley home near Highland, New York, is 4.4 miles from the Bardavon Opera House and 10 miles from both New Paltz and Historic Huguenot Street.
This 10,760-square-foot house features three bedrooms, one bathroom, a fully equipped kitchen with a dishwasher and microwave, a private hot tub, free Wi-Fi, parking, and can accommodate up to 10 guests.
Beautiful Home With Hudson River Views & Adjacent Rushing Waterfall In Hyde Park - Poughkeepsie, NY
10 6 reviews
Poughkeepsie, NY
08/22 – 08/28
$373/nighttotal: $2238 (6 )

Beautiful Home With Hudson River Views & Adjacent Rushing Waterfall In Hyde Park

3 5
apartment , Hyde Park
This Hyde Park cottage offers direct Hudson River views across from the Vanderbilt Mansion's Lower Gate and is within walking distance to FDR's Home & Library, providing a scenic and historically rich setting.
This 3-bedroom vacation rental accommodates up to 7 guests with a fully equipped kitchen, a wood-burning fireplace, a 55" TV, and direct access to hiking trails, all within a short drive to Norrie Point for kayaking.
Charming Townhouse In Historic District - Poughkeepsie, NY
9.8 50 reviews
Poughkeepsie, NY
06/20 – 06/27
$613/nighttotal: $4291 (7 )

Charming Townhouse In Historic District

1 2
apartment , Poughkeepsie
This charming five-bedroom townhouse is located in the Poughkeepsie Historic District, just a short walk from the city's attractions, restaurants, and shops. The apartment consistently receives excellent ratings for cleanliness, location, and overall user experience.
The spacious home offers ample room for families or groups of friends, accommodating up to eight guests. Enjoy modern conveniences like air conditioning, a dishwasher, and a garden, perfect for relaxing or dining outdoors.
Newly Renovated 1 Bd Apartment - Poughkeepsie, NY
9.3 35 reviews
Poughkeepsie, NY
08/22 – 08/28
$309/nighttotal: $1854 (6 )

Newly Renovated 1 Bd Apartment

1 5
apartment , Poughkeepsie
This Poughkeepsie apartment is located in a central district, within walking distance of the Walkway Over the Hudson and four nearby colleges. This makes it an excellent choice for travelers who want to explore the city and enjoy the scenic beauty of the Hudson River. The apartment has received excellent ratings for cleanliness and location, and guests have consistently praised its peaceful atmosphere.
The apartment has one bedroom and one bathroom, comfortably accommodating up to four guests. It features modern amenities like air conditioning, internet access, and a fully equipped kitchen with a fridge, freezer, and microwave. Enjoy the convenience of a central location, explore the city's attractions, and relax in the peaceful environment of this well-maintained apartment.

Frequently Asked Questions about vacation rentals in Poughkeepsie, NY

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

    For a first-timer, you absolutely can't miss the Walkway Over the Hudson State Historic Park. It's a 1.28-mile-long pedestrian bridge offering stunning views of the Hudson River and the surrounding area. Another must-see is the Vassar College campus, known for its beautiful architecture and historical significance.
  • What are the best Airbnb and vacation rentals in Poughkeepsie, NY?

    3 Bdrm - Near Hudson Valley Colleges & Attractions, Spacious And Stylish Entire One Bedroom Apartment and Lovely Hudson Valley Guest Cottage are the most popular Airbnb and vacation rentals in Poughkeepsie, NY among travelers.

  • Which neighborhood in Poughkeepsie, NY should you consider for a vacation rental?

    The area around the Walkway Over the Hudson is great for vacation rentals. It's close to the park, restaurants, and shops. You can also consider the historic district, which has charming old homes and is within walking distance of the city center.
  • 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 great place for kids, with interactive exhibits and educational activities. The Poughkeepsie Farm Project also offers family-friendly events, like farm tours and workshops. Don't forget the Dutchess County Fairgrounds, which hosts the annual Dutchess County Fair, a popular event for families.
  • What are the best vacation 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 get better rates compared to the peak summer months.
  • What are the best rentals for families and kids in Poughkeepsie, NY?

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

    The Walkway Over the Hudson is free to walk, and offers stunning views. The Poughkeepsie Farmers' Market, held on Saturdays, is a great place to find local produce and crafts at affordable prices. And you can't beat the free concerts at the Walkway Over the Hudson Amphitheater.
  • What are the best rentals or Airbnbs with a jacuzzi in Poughkeepsie, NY?

    The best vacation 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 restaurants with local dishes in Poughkeepsie, NY?

    For local dishes, head to The Dutch, which serves up classic American comfort food with a modern twist. The Red Jug Pub is another great option, known for its traditional Irish fare and lively atmosphere. If you're looking for something more upscale, try The Grandview, which offers a fine dining experience with breathtaking views of the Hudson River.
  • What are the best walking or cycling routes in Poughkeepsie, NY?

    The Walkway Over the Hudson itself is a great walking or cycling route, offering stunning views of the river. The Dutchess Rail Trail is another popular option, a 13-mile paved trail that runs through scenic farmland and forests. For a more challenging ride, try the 30-mile loop around the city, which takes you through the historic district and along the riverfront.
  • Are there pet-friendly attractions in Poughkeepsie, NY?

    The Walkway Over the Hudson is pet-friendly, allowing dogs on leash. The Poughkeepsie Farm Project also welcomes dogs, and they have a dedicated dog park. Many restaurants in the city offer outdoor seating that is dog-friendly.

Destinations nearby

Top Vacation Rentals with Balconies in Poughkeepsie, NY

Start your morning right with a vacation rental in Poughkeepsie, NY featuring a private balcony and stunning views.

Summit Sanctuary With Ev Ready Mountain Views - Poughkeepsie, NY
9.0 6 reviews
Poughkeepsie, NY
08/22 – 08/28
$522/nighttotal: $3132 (6 )

Summit Sanctuary With Ev Ready Mountain Views

4 5
house , Haviland
This Poughkeepsie residence offers mountain top views, located 6.7 miles from Vassar College and 10 miles from Marist College.
This 3,400 square foot house accommodates up to 15 guests with 4 bedrooms and 4 bathrooms, featuring a well-equipped kitchen, air conditioning, a terrace, garden, and convenient EV charging.
Lucious Lagrangeville - Poughkeepsie, NY
Poughkeepsie, NY
06/20 – 06/22
$701/nighttotal: $1402 (2 )

Lucious Lagrangeville

1 10
house , Freedom Plains
This spacious vacation home is located in Lucious Lagrangeville, Lagrangeville, offering convenient access to Vassar College (9 miles) and Bardavon Opera House (10 miles).
This 10,760 square foot house accommodates up to 19 guests and features air conditioning, a kitchen, swimming pool, jacuzzi, terrace, balcony, parking, and complimentary WiFi.

Find the Best Dog-Friendly Vacation Rentals in Poughkeepsie, NY

Discover pet-friendly vacation rentals in Poughkeepsie, NY that prioritize comfort for both you and your dog.

Elixir Apartment - Poughkeepsie, NY
Poughkeepsie, NY
06/20 – 06/22
$470/nighttotal: $940 (2 )

Elixir Apartment

3 10
apartment , Clintondale
Elixir Apartment in Highland offers proximity to SUNY New Paltz and Historic Huguenot Street, both 6 miles away, with convenient access to Loren Campbell Baseball Field (6.1 miles) and Bardavon Opera House (8.2 miles).
This pet-friendly apartment features air conditioning, complimentary WiFi, free private parking, a fully equipped kitchen, and garden access, located 10 miles from Vassar College and 16 miles from Stewart International Airport.
Your Own Pied-a-terre "Walkway Over The Hudson" #1 - Poughkeepsie, NY
9.8 192 reviews
Poughkeepsie, NY
06/20 – 06/27
$120/nighttotal: $840 (7 )

Your Own Pied-a-terre "Walkway Over The Hudson" #1

1 2
apartment , Poughkeepsie
This studio apartment is conveniently located in central Poughkeepsie, just a short distance from the Dutchess County Civic Center, Marist and Vassar Colleges, Vassar Brothers Medical Center, the Walkway Over the Hudson, the train station, and Hudson River Park. The apartment has received excellent ratings for its cleanliness, location, and overall user experience.
The studio has a private entrance and parking, and can accommodate up to two guests. You'll enjoy amenities such as a fully equipped kitchen, air conditioning, a private garden, and complimentary bicycles for exploring the nearby Walkway Over the Hudson and Rail Trails.
Wonderful Washington - Poughkeepsie, NY
10 5 reviews
Poughkeepsie, NY
08/22 – 08/28
$424/nighttotal: $2544 (6 )

Wonderful Washington

1 5
apartment , Poughkeepsie
This 4-bedroom, 2-bathroom apartment in Poughkeepsie offers a prime central location in the Mid-Hudson Valley, within walking distance to Marist University, Walkway Over the Hudson, Mid Hudson Regional Hospital, and Palace Diner. The spacious residence accommodates up to 9 guests and features a full kitchen, air conditioning, and internet, with 30+ day bookings available starting mid-March, making it ideal for those visiting Marist University or working at nearby medical facilities.
Stylish, Mid-century Designer Home - Poughkeepsie, NY
9.6 137 reviews
Poughkeepsie, NY
08/22 – 08/28
$360/nighttotal: $2160 (6 )

Stylish, Mid-century Designer Home

1 5
apartment , Poughkeepsie
This studio in Poughkeepsie is a tranquil retreat in the Historic Hudson Valley, surrounded by mature trees and within easy reach of Hyde Park and Walkway Over the Hudson. It has excellent user, location, and cleanliness ratings.
The studio has an open floor plan, two private bedrooms, two bathrooms, and a guest capacity of five. It features a well-equipped kitchen, a private patio with a grill, a media room with a daybed, and convenient in-house amenities like laundry and outdoor space.
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