Poughkeepsie holiday lettings

We found 1,478 holiday rentals — enter your dates for availability

Discover a selection of 21 homes, 15 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 Oct - 10 Oct
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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!

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.

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

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.

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)
  • Ice Time Sports Complex (15.6 mi / 25.1 km)
  • Millbrook Vineyards and Winery (15.6 mi / 25.1 km)
  • Thunder Ridge Ski Resort (22.4 mi / 36.1 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)
  • Vanderbilt Mansion National Historic Site (6.4 mi / 10.2 km)
  • Innisfree Garden (10 mi / 16.1 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)

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?
If you're planning a holiday in Poughkeepsie, Crown Heights is one of the most in-demand locations to stay. No matter your style of travel, Vrbo is sure to have a property here that matches your needs.
What is the most popular type of holiday rental accommodation in Poughkeepsie?
Houses are the most popular style of holiday rental in Poughkeepsie, according to our data. Even if you have a different idea about what you want, Vrbo has holiday homes in a variety of sizes and shapes. Compare our options to find your perfect fit.
How much does it cost to rent a holiday rental in Poughkeepsie?
A range of factors can influence how much you pay for a holiday rental in Poughkeepsie, like the season, length of stay and type of property. Still, all of our holiday homes have one thing in common --- unbeatable value. Simply add your travel dates to find your ideal escape.
How much does it cost to rent a beach house in Poughkeepsie?
When you travel and the size and style of the property will influence how much you'll pay for your beachside holiday rental. Type in your Poughkeepsie travel dates to view your available options on Vrbo. Did someone just say "private pool"? Use our filters to pick the features and amenities you want.
Are there pet-friendly holiday rentals in Poughkeepsie?
Yes. You'll have a choice of three holiday rentals that cater to pets in Poughkeepsie. Some of our pet-friendly holiday rentals even have a garden for your furry pal to play around in, dog beds, complimentary treats and proximity to parks. Apply the "Pets allowed" filter to find a pad that'll set tails wagging on Vrbo.
What are popular rental amenities in Poughkeepsie?
Some of the most popular rental amenities people prefer in Poughkeepsie are ski-in/ski-out facilities, nearby museums and a nearby river. Whether you're on the road with buddies, family or even pets, Vrbo holiday rentals feature the best amenities for fun and relaxation with the people closest to you.
Are there large group holiday rentals in Poughkeepsie?
You can pick from two holiday rentals in Poughkeepsie that can accommodate 10 or more guests. Whether you're organising time away with the family or a celebration like a birthday, there's enough space to get your group together under one roof.
Are there holiday rentals in Poughkeepsie that welcome kids?
With three family-friendly holiday homes to pick from in Poughkeepsie, there's never been a better time to introduce the kiddos to the magic of travel. Click on our "Properties good for families" filter to locate stays that come with conveniences ideal for holidaying families, such as extra bedrooms, swimming pools, bunk beds and entertainment units.
What are the top attractions for families in Poughkeepsie?
Keep the kids happy at these fantastic family-friendly attractions in Poughkeepsie:

  • Fun Central
  • Hyde Park Historical Society Museum
  • Hyde Park Railroad Station

Are there one-bedroom holiday rentals in Poughkeepsie?
Yes, Poughkeepsie has two one-bedroom rentals available. Typically situated in sought-after areas because of their smaller size, a one-bedroom rental is ideal if you're travelling with your partner or a pal. And with home comforts like kitchens and more privacy than a standard hotel, you'll be able to kick back and relax while sightseeing around this exciting destination.
Are there holiday rentals with WiFi in Poughkeepsie?
Poughkeepsie has two holiday rentals with WiFi, so you can stay connected when you're away. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming TV shows with the family to writing and sending emails, these Vrbo homes make it a cinch to get online.
How can I find holiday rentals with air conditioning in Poughkeepsie?
Poughkeepsie has three holiday rentals where you'll be able to chill out in air-conditioned comfort. To locate a property on Vrbo that features this amenity, choose your travel dates and use the filters to select the "air conditioning" box.
How old do you have to be to rent a holiday rental in Poughkeepsie?
Age restrictions can vary across properties on Vrbo, so look at the rules of the holiday home in Poughkeepsie you're interested in. But in general, it's 16, 18 or 21.
How long can I rent a holiday rental in Poughkeepsie for?
How long you can book a holiday rental in Poughkeepsie differs according to the property. Just enter your desired travel dates to see a list of options offering extended stays. With lots of creature comforts like full kitchens and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to find someplace just right to call your home away from home in Poughkeepsie.

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