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Poughkeepsie holiday lettings

We found 1,466 holiday rentals — enter your dates for availability

Discover a selection of 18 homes, 13 apartments and other holiday rentals in Poughkeepsie that are perfect for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll find the amenities that you need and want, which might include a fireplace and a washer and dryer. At the end of the day, you'll be sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Poughkeepsie

Showing deals for:3 Jul - 10 Jul

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

8% off
Price is £1,273
for 7 nights, 1 room
£182 per night
includes taxes & fees
the suite @ barn & bike - private, bucolic, serene setting

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Why visit Poughkeepsie

  • Historic Sites: Poughkeepsie is rich in history, featuring notable landmarks, including the iconic Walkway Over the Hudson.
  • Outdoor Activities: Enjoy a variety of outdoor pursuits, from hiking trails to scenic parks, perfect for nature enthusiasts.
  • Family-Friendly Attractions: The area offers numerous attractions suitable for families, ensuring fun for all ages.
  • Charming Neighbourhoods: Explore vibrant neighbourhoods filled with local shops, eateries, and a warm community atmosphere.
  • Diverse Accommodation Options: Choose from a range of delightful lodging, including cosy cottages and spacious holiday rentals.

Popular types of accommodation in Poughkeepsie

If you’re considering a getaway to Poughkeepsie, you’ll find a delightful range of accommodation options to suit your needs. Our most popular choices include houses, charming cottages, and rustic cabins. Whether you're searching for a spacious bedroom apartment in Poughkeepsie or a cosy flat in downtown, we have an array of rentals that offer both comfort and convenience for your stay.

  • Houses: The top choice for visitors seeking a home away from home, perfect for families or groups wanting space and comfort.
  • Cottages: Charming and quaint, these rentals offer a picturesque retreat ideal for couples or small families.
  • Cabins: Nestled in nature, cabins provide a rustic experience for those wanting to escape the hustle and bustle.
  • Apartments: Conveniently located, apartments are a great option for those who prefer a more urban setting.
  • Chalets: These delightful lodgings combine luxury with a cozy atmosphere, perfect for a relaxing getaway.**

Top attractions in and around Poughkeepsie

Poughkeepsie offers a delightful blend of outdoor activities, family-friendly attractions, and urban experiences. Visitors can explore points of interest such as modern colleges, historic sites, and the iconic historic bridge. Whether seeking culture or adventure, Poughkeepsie caters to all types of travellers. A trip to Poughkeepsie promises a rich experience steeped in history and natural beauty, perfect for those looking to immerse themselves in the local charm.

  • Vassar College: This modern university, located in the heart of Poughkeepsie, boasts beautiful architecture and lush campus grounds. Visitors can enjoy a vibrant atmosphere infused with creativity and intellectual engagement, making it a delightful stop for those interested in arts and education.
  • Culinary Institute of America: Situated three miles away, this renowned culinary school offers a taste of exceptional cuisine and culture. Guests can explore world-class dining options and witness the artistry of aspiring chefs in action.
  • Walkway Over the Hudson State Historic Park: Just one mile from Poughkeepsie, this historic bridge provides stunning panoramic views of the Hudson River. It’s a fantastic spot for walking, cycling, and appreciating the natural beauty and history of the area.

Things to do recommended for couples

For a romantic getaway in Poughkeepsie, consider visiting Benmarl Vineyards and Winery for a delightful wine experience, enjoying live music at The Falcon, or indulging in a couples' treatment at Jenkinstown Day Spa for ultimate relaxation. Each offers a unique atmosphere perfect for couples.

Things to do recommended for families

Your family will have a fantastic time at SplashDown Beach, a thrilling waterpark located 6.8km from Poughkeepsie. Enjoy the recreational vibes at Richard L. Skimin Memorial Baseball Field in town, or unwind at the scenic Bowdoin Park, just 4.3km away, perfect for relaxation.

Things to do recommended for groups

Enjoy a round at Casperkill Golf Club for a sporty outing, catch a film at the Overlook Drive-In Theater for a charming evening, and immerse yourselves in culture at the Chance Theater. These group-friendly activities promise a delightful experience in Poughkeepsie!

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

If you're planning a trip with friends, family, or pets, or if you're seeking extended stays, be sure to apply the appropriate filters to meet your needs. Here are some helpful booking tips for using Vrbo.

  • Traveling to Poughkeepsie with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Poughkeepsie with young kids: Journeying with young children can indeed present its challenges. It's important to prioritise their comfort and safety, alongside ensuring access to suitable amenities, such as a private swimming pool. Additionally, it’s wise to take into account your closeness to family-friendly attractions.
  • Taking your pets with you to Poughkeepsie: For many, a family holiday isn’t truly complete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that are pet-friendly. Most of these accommodations come equipped with feeding bowls and beds, ensuring that all members of the family feel comfortable and at home.
  • Planning for a long term stay visiting Poughkeepsie: If you’re seeking holiday rentals that offer discounts for stays of a month or more, you’ve come to the perfect spot. By using the appropriate filter, you can effortlessly discover and save on monthly accommodations. You might also want to consider including amenities such as a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Poughkeepsie

Poughkeepsie, New York, offers a delightful blend of outdoor adventures and family-friendly experiences. Visitors can soak in the rich history and stunning scenery while exploring the charming town and nearby areas like Wappingers Falls. With a warm atmosphere and friendly locals, you'll find plenty of opportunities for relaxation and exploration. Whether you're wandering through the vibrant neighbourhoods or enjoying the picturesque surroundings, Poughkeepsie promises a memorable holiday experience.

  • New Paltz: Located a mere 5.6km from Poughkeepsie, New Paltz is a haven for outdoor enthusiasts and adventure seekers. Nestled amid stunning scenery, this vibrant city offers a plethora of activities, from skiing on nearby slopes to exploring expansive recreational areas. Nature lovers will be drawn to local landmarks such as the serene lake and picturesque nature reserves, while the surrounding mountains provide a breathtaking backdrop for hiking and climbing. New Paltz’s charming downtown area also features quaint shops and eateries, making it a delightful stop for visitors.
  • Fishkill: Situated 7.5km from Poughkeepsie, Fishkill is perfect for families seeking a city-themed experience. The town boasts a variety of attractions, including educational centres and bustling shopping malls that cater to all ages. Children will particularly enjoy the local theme park, which offers rides and entertainment for a fun-filled day. With symbolic landmarks and a visitor centre that provides insight into the area's history, Fishkill combines urban conveniences with family-friendly activities, ensuring a memorable outing.
  • Hyde Park: Just 3.1km from Poughkeepsie, Hyde Park is rich in culture and natural beauty, making it an excellent destination for families. Visitors can explore historic universities, including notable colleges that highlight the area's educational significance. The city also features lovely shopping areas and recreational activities like skiing. With a stunning lake as a focal point, Hyde Park offers numerous opportunities for outdoor activities and leisurely strolls, ensuring a delightful blend of culture and nature for all who visit.

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

Are you hoping to save on your next getaway? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you could enjoy considerable savings by opting for a longer stay. To locate a Vrbo property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a convenient platform to plan new trips, pick up from where you last left off, or manage your travel arrangements with ease. You can now easily access the properties you've saved and booked, organised under Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Explore the riverfront setting in Poughkeepsie

Enjoy the area's entertainment, theatre scene and history with a rental holiday home in Poughkeepsie. Travellers to this scenic city praise the riverfront, university setting and sporting events. If you're looking for accommodation options with space to entertain friends and family, HomeAway 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

Are you hoping to discover top things to see and do in the area? Venture out of your cosy holiday rental and check out everything that makes Poughkeepsie a one-of-a-kind holiday spot. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • 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 adventurous traveller or just want to take in the scenery, Poughkeepsie is a great place to spend some time outside. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • 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 Newburgh, NY (SWF-Stewart Intl.), located 16.3 mi (26.2 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Danbury, CT (DXR-Danbury Municipal), which is 32.3 mi (52 km) away.

If you prefer train travel, the main station serving the city is Poughkeepsie Station.

Frequently asked questions

What is the best area to stay in Poughkeepsie when booking a holiday rental?
When considering the best area to stay in Poughkeepsie for a holiday rental, the waterfront area is particularly appealing. This vibrant neighbourhood offers stunning views of the Hudson River and easy access to beautiful parks, such as the expansive Walkway Over the Hudson State Historic Park, which provides a fantastic vantage point for both walking and cycling.

Another excellent option is the historic district, where visitors can experience firsthand the rich history of the area. This neighbourhood features charming architecture and is close to attractions like the Franklin D. Roosevelt Presidential Library and Museum, which offers fascinating insights into the life of the former president.

While the exact number of properties can vary, the waterfront area typically hosts a variety of rentals, from cosy apartments to larger family homes, suiting different preferences and budgets.
How much does it cost to rent a holiday home in Poughkeepsie?
Prices for holiday 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 holiday 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 holiday rental accomodation in Poughkeepsie?
In Poughkeepsie, holiday houses are the most popular type of holiday rental, with approximately 60 available throughout the area. These spacious homes often feature multiple bedrooms, fully equipped kitchens, and inviting outdoor spaces, making them ideal for families or groups seeking comfort and privacy. Additionally, around 36 apartments can be found, typically situated in convenient locations close to the Hudson River and local attractions. These apartments generally come with modern amenities, including kitchen facilities and living areas. There are also several cottages and condos, providing additional options for those looking for a different style of accommodation.
Are there any family house rentals in Poughkeepsie?
In Poughkeepsie, there are 16 family-friendly house rentals available, making it a great choice for those travelling with children. The area boasts neighbourhoods such as the historic waterfront and the picturesque suburban surroundings, offering a mix of amenities and attractions. Many of these homes feature spacious living areas, fully equipped kitchens for easy meal preparation, and outdoor spaces where kids can enjoy some playtime.

Visitors can also find properties with additional features like game rooms or private gardens, enhancing the family experience. Nearby, the Walkway Over the Hudson provides stunning views and a unique walking experience, while the Franklin D. Roosevelt Presidential Library and Museum offers educational opportunities for all ages.
Can I rent a holiday home with a pool or hot tub in Poughkeepsie?
In Poughkeepsie, there are several holiday homes available for rent that come equipped with pools or hot tubs, providing a refreshing escape during your stay. This picturesque town, located in the scenic Hudson Valley, offers a range of options across various neighbourhoods, from tranquil residential areas to those closer to the vibrant waterfront.

Travellers can expect amenities such as private swimming pools, relaxing hot tubs, and spacious outdoor areas great for gatherings or family activities. Many of these properties also feature modern kitchens, comfortable living spaces, and convenient access to local attractions, making them ideal for both relaxation and exploration.
Can I find long-stay holiday rentals in Poughkeepsie?
A long-stay holiday rental in Poughkeepsie is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Poughkeepsie?
In Poughkeepsie, there are several pet-friendly house rentals available, offering a comfortable stay for those travelling with pets. Many of these properties are equipped with amenities such as spacious backyards, ideal for pets to roam freely, and fully equipped kitchens for convenient self-catering.

The area boasts charming neighbourhoods, including the historic district, where visitors can find homes with distinctive architectural features and easy access to local parks. For pet owners, the nearby Walkway Over the Hudson State Historic Park provides a scenic trail great for walks with dogs, offering stunning views of the Hudson River.

Additionally, the proximity to Vassar College and its expansive campus grounds provides further green space for outdoor activities.
Are there any remote work holiday rentals in Poughkeepsie?
In Poughkeepsie, there are numerous remote work holiday rentals available, with around 104 options to choose from. Many properties in this area cater specifically to remote workers, offering amenities such as free Wi-Fi, dedicated workspaces with desks and chairs, and comfortable living environments conducive to productivity.

The city is well-known for its picturesque views along the Hudson River, and staying here provides easy access to local attractions such as the Walkway Over the Hudson, a scenic pedestrian bridge that showcases stunning river vistas. Additionally, nearby parks and gardens, such as the Vassar College campus, offer serene spots for breaks or outdoor meetings.

For those looking to unwind after work, Poughkeepsie has a vibrant dining scene and cultural experiences, including museums and historic sites. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Poughkeepsie holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Poughkeepsie with parking available—perfect for families or travellers 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 holiday rental amenities include kitchens, which allow guests to prepare their own meals, along with coffee and tea makers for those who enjoy a warm beverage at any time. Onsite parking is often available, making it convenient for travellers with their own vehicles. Many rentals also feature fireplaces, adding a cosy touch, especially during the colder months. Additionally, sofa beds are common, providing extra sleeping arrangements for larger groups or families.
When is the best time to visit Poughkeepsie for a holiday rental?
September is the most popular time to visit Poughkeepsie, drawing travellers who appreciate the stunning autumn foliage and mild weather. The peak season runs from July to September, allowing visitors to indulge in a variety of outdoor activities, including hiking in the nearby Hudson Valley, exploring local vineyards, and enjoying the vibrant arts scene that the region is known for.

During this period, you can expect pleasant temperatures ranging from 10 to 25 degrees Celsius, making it ideal for sightseeing and leisurely strolls along the Walkway Over the Hudson, where breathtaking views await. The lively option is enhanced by local festivals and events, great for those seeking a memorable experience.

For those looking for better value, consider booking a holiday rental in December. This month offers a unique charm as the area transforms into a winter wonderland, and while it's a quieter time for tourism, you can enjoy a peaceful retreat with fewer crowds.
How early should I book a Poughkeepsie holiday rental?
Book your Poughkeepsie holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Poughkeepsie?
In Poughkeepsie, visitors can explore a variety of attractions that showcase the area's rich history and natural beauty. The Walkway Over the Hudson State Historic Park offers stunning views of the Hudson River and is great for walking or cycling. This elevated walkway connects Poughkeepsie to Highland and is an iconic spot for both locals and tourists.

The Franklin D. Roosevelt Presidential Library and Museum, located nearby in Hyde Park, provides a fascinating insight into the life and legacy of the former president, with exhibits that delve into American history.

For those interested in the arts, the Bardavon 1869 Opera House in downtown Poughkeepsie hosts a range of performances, from concerts to theatre productions.

Additionally, the scenic landscapes of the Hudson Valley can be appreciated at the Locust Grove Estate, which features beautiful gardens and walking trails.
Can I change or cancel my Poughkeepsie home rental booking on Vrbo?
To find Poughkeepsie holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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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