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Poughkeepsie vacation rentals

We found 1,457 vacation rentals — enter your dates for availability

Discover a selection of 18 homes, 13 apartments, and other vacation rentals in Poughkeepsie that are perfect for your trip. Whether you’re staying in a vacation home with family or friends, you'll find the amenities you need and want, which might include parking and a garden. Whatever you're looking for, you'll be sure to find a rental that has what everyone needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Poughkeepsie

Showing deals for:Jul 3 - Jul 10

Image gallery for the suite @ barn & bike - private, bucolic, serene setting

Mid-century furniture, books galore, and a quaint farmhouse kitchenette.
9.8 out of 10, Exceptional, (15 reviews)
Exceptional
(15 reviews)

the suite @ barn & bike - private, bucolic, serene setting

Red Hook

9% off
Price is $215
$1,503 for 7 nights
All fees included
the suite @ barn & bike - private, bucolic, serene setting

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Find out more about Poughkeepsie

Why visit Poughkeepsie

  • Rich history: Discover Poughkeepsie's historic sites and learn about its fascinating past.
  • Scenic views: Enjoy breathtaking views of the Hudson River and surrounding landscapes.
  • Outdoor activities: Engage in a variety of outdoor pursuits, perfect for nature lovers and families.
  • Cultural experiences: Explore local colleges, art scenes, and community events that showcase Poughkeepsie's vibrant culture.
  • Diverse accommodations: Choose from charming cottages, rustic cabins, or modern apartments for a comfortable stay.

Popular types of accommodation in Poughkeepsie

Poughkeepsie offers a variety of vacation rentals to suit every traveler's needs. Whether you're looking for houses, charming cottages, or rustic cabins, you'll find the perfect fit. For those seeking a vibrant urban experience, check out our downtown Poughkeepsie apartments for rent. With options for home rentals in Poughkeepsie, you'll enjoy transparency, savings, and reassurance while making unforgettable memories in this scenic destination.

  • Houses: The most sought-after option in Poughkeepsie, ideal for families or groups seeking spacious and homey accommodations.
  • Cottages: Charming and cozy, these rentals provide a quaint getaway experience, perfect for a peaceful retreat.
  • Cabins: Rustic and often nestled in nature, cabins offer a unique escape for those looking to unwind in a tranquil environment.
  • Apartments: Convenient and modern, apartments are perfect for solo travelers or couples wanting easy access to local attractions.
  • Chalets: These stylish mountain-style homes provide a cozy atmosphere, ideal for those seeking a comfortable stay.**

Top attractions in and around Poughkeepsie

Poughkeepsie offers a delightful mix of outdoor activities, family-friendly attractions, and rich cultural experiences. Visitors can explore modern colleges and universities, historic sites, and iconic bridges, making it an ideal destination for those seeking both adventure and history. Whether you're traveling with family or looking for a city-themed getaway, Poughkeepsie's diverse points of interest promise a memorable vacation.

  • Vassar College: A prestigious liberal arts college, Vassar College offers a blend of modern architecture and beautiful campus grounds. Visitors can enjoy its vibrant atmosphere, art galleries, and stunning gardens, making it a great spot for a leisurely stroll.
  • Culinary Institute of America: Renowned for its culinary programs, this historic institution is a must-visit for food enthusiasts. Experience world-class dining at its restaurants and explore the rich history of culinary arts through its engaging exhibits.
  • Walkway Over the Hudson State Historic Park: This former railroad bridge turned pedestrian walkway provides breathtaking views of the Hudson River. It's a perfect place for a scenic walk, offering cultural exhibits and a unique perspective of the surrounding landscape.

Things to do recommended for couples

Planning a romantic getaway in Poughkeepsie? Visit Benmarl Vineyards and Winery for a lovely wine tasting, catch a live show at The Falcon for some music, and unwind together at Jenkinstown Day Spa for a rejuvenating experience. Enjoy your couple's retreat.

Things to do recommended for families

Families visiting Poughkeepsie can cool off at SplashDown Beach waterpark, enjoy the relaxing atmosphere at Richard L. Skimin Memorial Baseball Field, and explore the beautiful trails at Bowdoin Park, perfect for wellness and family bonding time.

Things to do recommended for groups

Enjoy a movie night under the stars at the Overlook Drive-In Theater, hit the greens at Casperkill Golf Club for a fun day outdoors, or shop and dine at the Poughkeepsie Galleria, just 6 miles away, for a blend of entertainment and local culture.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Poughkeepsie

When planning your trip, whether you're traveling with a group, family, pets, or seeking extended stays, be sure to prioritize your preferences when filtering your options. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Poughkeepsie with a group: Think about how many bedrooms you require, as well as any additional features like a full kitchen or outdoor area for group gatherings. The good news is that you can easily filter for these options and more on Vrbo.
  • Traveling to Poughkeepsie with young kids: Traveling with young kids can be tough. It’s important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, it’s wise to think about how close you are to attractions that are enjoyable for families.
  • Taking your pets with you to Poughkeepsie: For many families, a vacation wouldn’t be the same without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Poughkeepsie: If you’re searching for vacation rentals that offer discounts for month-long stays, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Poughkeepsie

Poughkeepsie is a charming city perfect for outdoor enthusiasts and families alike. While exploring, you can soak in the area's rich history and stunning scenery. Nearby neighborhoods offer a friendly atmosphere, making it easy to relax and enjoy local attractions. Whether you're visiting the historic sites or taking in the beautiful Hudson River views, Poughkeepsie promises a delightful vacation experience filled with family-friendly activities and lovely surroundings.

  • Fishkill: Located 12 miles from Poughkeepsie, Fishkill is a vibrant city that offers a delightful mix of family-friendly activities and outdoor adventures. Travelers are drawn to its bustling shopping centers and malls, perfect for a day of retail therapy. The city is also home to several educational facilities and family-oriented attractions, including a theme park that promises fun for all ages. Notable landmarks such as symbolic monuments and a visitor center provide a glimpse into the local culture, making Fishkill an excellent spot for those seeking both urban excitement and community charm.
  • New Paltz: Situated 9 miles away from Poughkeepsie, New Paltz is a haven for outdoor enthusiasts and adventure seekers. Known for its stunning scenery, the city is surrounded by natural beauty, including a picturesque lake and nearby mountains. The area is popular for skiing and offers recreational spaces for hiking and other outdoor activities. Nature reserves provide opportunities for wildlife viewing and leisurely strolls, making New Paltz an ideal destination for those who appreciate the great outdoors and wish to immerse themselves in breathtaking landscapes.
  • Hyde Park: Just 5 miles from Poughkeepsie, Hyde Park is a charming city that combines outdoor recreation with cultural experiences. The area is perfect for families, featuring educational attractions and shopping areas. Visitors can enjoy skiing in the winter months or explore the beautiful lakes that dot the landscape. Hyde Park is also home to historic and modern colleges, adding to its cultural richness. Whether you're enjoying a day outdoors or diving into the local history, Hyde Park offers a well-rounded experience for all travelers.

Best time to go to Poughkeepsie

If you're planning a trip to Poughkeepsie, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in July to August and October, while off-peak times, like January to March tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January27.5°F (-2.5°C)Light RainMostly SunnyLowAverage
February29.3°F (-1.5°C)Light RainMostly SunnyLowSlightly Low
March36.9°F (2.7°C)Light RainMostly SunnyLowSlightly Low
April48.4°F (9.1°C)Light RainMostly SunnyAverageSlightly Low
May59.4°F (15.2°C)Light RainMostly SunnyAverageAverage
June67.5°F (19.7°C)Light RainMostly SunnyAverageAverage
July73.8°F (23.2°C)Light RainMostly SunnyHighSlightly High
August71.8°F (22.1°C)Light RainMostly SunnyHighSlightly High
September64.6°F (18.1°C)Light RainMostly SunnyAverageAverage
October53.6°F (12.0°C)Light RainMostly SunnyHighAverage
November41.5°F (5.3°C)Light RainMostly SunnyAverageAverage
December33.4°F (0.8°C)Light RainMostly SunnyAverageSlightly High

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental. We’re here to help you find the best options for your getaway.

Vrbo Trips: Planning as easy as it gets

Vrbo's user-friendly Trip Board offers you a convenient way to plan new trips, pick up right where you paused, or manage your travel arrangements. You can easily find the properties you’ve saved or booked in the sections for Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Explore the riverside setting in Poughkeepsie

Enjoy the area's entertainment, theater scene and history and make a vacation rental your home during your stay in Poughkeepsie. Travelers to this scenic city praise the riverfront, university setting and sporting events. If you're looking for accommodations with space to entertain friends and family, Vrbo has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in and around Poughkeepsie

Do you want to find attractions to visit in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Poughkeepsie a fun place to get away. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Benmarl Vineyards and Winery (8.2 mi / 13.1 km)
  • SplashDown Beach (10.8 mi / 17.4 km)
  • Mohonk Golf Course (11.9 mi / 19.2 km)
  • Robibero Winery (12.2 mi / 19.6 km)
  • Ice Time Sports Complex (15.6 mi / 25.1 km)
  • Millbrook Vineyards and Winery (15.6 mi / 25.1 km)

Exploring the natural landscape of Poughkeepsie

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Poughkeepsie is a great place to get out in nature. These are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city center:

  • Walkway Over the Hudson State Historic Park (1.3 mi / 2.1 km)
  • Mohonk Lake (12.6 mi / 20.3 km)
  • Mohonk Preserve Visitor Center (13.6 mi / 21.9 km)
  • Algonquin Park (14.2 mi / 22.8 km)
  • Shawangunk Mountains (15.2 mi / 24.5 km)
  • Kingston Point Beach (15.8 mi / 25.4 km)

How to get to and around Poughkeepsie

The nearest airport is in Stewart Intl. Airport (SWF), located 16.3 mi (26.2 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to Danbury, CT (DXR-Danbury Municipal), which is 32.3 mi (52 km) away.

If you'd rather travel by train, you can make your way to Poughkeepsie Station.

Frequently asked questions

What is the best area to stay in Poughkeepsie, New York, United States of America when booking a vacation rental?
When looking for a great area to stay in Poughkeepsie, New York, the waterfront neighborhood is an excellent choice. This area offers a vibrant setting with stunning views of the Hudson River. You'll find a variety of vacation rentals that cater to different preferences, from cozy apartments to spacious homes. Close by, you can visit the Walkway Over the Hudson, a spectacular pedestrian bridge that provides breathtaking panoramas of the river and surrounding landscapes. Additionally, the nearby Franklin D. Roosevelt Presidential Library and Museum is a fascinating site that offers insight into the life and legacy of one of America's most top presidents.

Another appealing neighborhood is the historic district, which is known for its charming architecture and rich history. Staying here places you in proximity to local cafes and restaurants, giving you a taste of the area's culinary scene. The Bardavon 1869 Opera House is a standout attraction, showcasing a variety of performances and events throughout the year.
How much does it cost to rent a vacation home in Poughkeepsie?
Prices for vacation rentals in Poughkeepsie vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Poughkeepsie to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Poughkeepsie vacation house rentals?
You can find great discounts on house rentals in Poughkeepsie on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Poughkeepsie?
In Poughkeepsie, vacation houses are the most popular type of rental, with about 15 available throughout the area. These homes typically offer multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups looking for a comfortable stay. Additionally, several apartments, cottages, and condos are scattered around the city, providing travelers with a variety of options to suit different preferences. Many of these rentals come equipped with amenities such as Wi-Fi, outdoor spaces, and sometimes even access to swimming pools or fitness centers.
Are there any family house rentals in Poughkeepsie?
In Poughkeepsie, there are about 16 family-friendly house rentals available, making it a great choice for those traveling with children. Neighborhoods like Arlington and the area near the Walkway Over the Hudson offer spacious homes that cater well to families. Many of these properties include features such as fully equipped kitchens, where you can prepare meals together, and cozy living spaces for relaxation after a day of exploring.

Additionally, outdoor areas are often present, providing spots for kids to play or for family gatherings. Visitors can enjoy easy access to local parks, such as the scenic Waryas Park, which has playgrounds and walking paths, as well as cultural attractions like the Franklin D. Roosevelt Presidential Library and Museum. See all family-friendly rentals in Poughkeepsie.
Can I rent a vacation home with a pool or hot tub in Poughkeepsie?
In Poughkeepsie, there are several vacation homes available for rent that feature pools and hot tubs, providing a refreshing escape in this charming Hudson Valley city. Travelers can find accommodations in picturesque neighborhoods, such as those near the Walkway Over the Hudson or along the banks of the Hudson River.

These properties often include amenities such as private pools, hot tubs, spacious outdoor areas for gatherings, and fully equipped kitchens, superb for both relaxation and family activities. Many rentals also come with additional features like fire pits and outdoor dining spaces, allowing guests to fully enjoy the beautiful surroundings and warm evenings.
Can I find long-stay vacation rentals in Poughkeepsie?
A long-stay vacation rental in Poughkeepsie is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Poughkeepsie?
In Poughkeepsie, there are several pet-friendly house rentals available, making it a welcoming destination for travelers with furry companions. Many of these rentals feature comfortable amenities such as fully equipped kitchens, spacious living areas, and often outdoor spaces like patios or yards where pets can play.

The neighborhoods around Poughkeepsie provide access to various parks and recreational areas, which are great for pet owners. For instance, the Walkway Over the Hudson State Historic Park offers scenic views and walking paths suitable for leisurely strolls with pets. Additionally, the nearby Franny Reese State Park features hiking trails and picnic areas that are pet-friendly, allowing for enjoyable outdoor excursions.
Are there any Poughkeepsie vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Poughkeepsie with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Poughkeepsie?
In Poughkeepsie, popular rental amenities include fully equipped kitchens, which allow guests to prepare their own meals, and coffee or tea makers for a convenient morning brew. Many rentals also offer onsite parking, making it easier for travelers to explore the area. Cozy fireplaces are a common feature, providing a warm atmosphere during colder months, while sofa beds are available in several units to accommodate extra guests.
When is the best time to visit Poughkeepsie for a vacation rental?
The best time to visit Poughkeepsie for a vacation rental is during September, when the summer crowds begin to thin, yet the weather remains pleasantly warm. This month marks the tail end of the peak season, which spans from July to September, making it an ideal time for travelers who appreciate both vibrant outdoor activities and a more relaxed atmosphere.

With temperatures typically ranging from the low 50s to mid-70s Fahrenheit, September offers comfortable conditions for exploring the area's scenic beauty. Visitors can enjoy leisurely strolls along the Hudson River, take in the stunning views from the Walkway Over the Hudson, or visit local vineyards and orchards as they start to transition into fall.

For those looking for a more budget-friendly option, December can be a great choice to experience Poughkeepsie's cozy charm during the holiday season. While this is considered the low season, it provides a unique opportunity to enjoy holiday festivities, local markets, and beautiful winter landscapes without the bustling crowds.

Ultimately, your choice of when to visit Poughkeepsie depends on whether you desire the vibrant energy of summer or the peaceful ambiance of early winter.
How early should I book a Poughkeepsie vacation rental?
Book your Poughkeepsie vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Poughkeepsie, New York, United States of America?
In Poughkeepsie, visitors can explore several popular attractions that showcase the area's rich history and natural beauty. The Walkway Over the Hudson, a converted railroad bridge, provides breathtaking views and is great for walking or biking across the Hudson River. Nearby, the Franklin D. Roosevelt Presidential Library and Museum offers a deep dive into the life and legacy of the 32nd President, surrounded by beautifully landscaped grounds.

The historic Locust Grove Estate, a former home of artist Samuel Morse, features stunning gardens and walking trails along the river, making it a lovely spot for leisurely strolls. For those interested in culture, the Bardavon 1869 Opera House hosts a variety of performances and events throughout the year, highlighting local and national talent.

Just a short drive away, the scenic beauty of the Hudson Valley is exemplified at the Mid-Hudson Children's Museum, which focuses on engaging young minds with hands-on exhibits.
Can I change or cancel my Poughkeepsie home rental booking on Vrbo?
To find Poughkeepsie vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Poughkeepsie vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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