Poughkeepsie holiday rentals

We found 1,485 holiday rentals — enter your dates for availability
Discover a selection of 16 homes, 12 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:18 Dec - 25 Dec

Interior
Interior
Property grounds
Property grounds
Exceptional
(11 reviews)

Farmette Roquette Hudson Valley

Germantown

8% off
AU$7,341
for 7 nights, 1 room
AU$1,049 per night
includes taxes & fees
Farmette Roquette Hudson Valley
Our Sunny Living Room with Wood Stove
Rear Deck, Hot Tub and Screened Porch
Open kitchen.
A beautiful spot for our comfortable cabin
Exceptional
(119 reviews)

Secluded Cabin with Hot Tub - 5 Miles to Woodstock

Bearsville

8% off
AU$4,322
for 7 nights, 1 cabin
AU$617 per night
includes taxes & fees
Secluded Cabin with Hot Tub - 5 Miles to Woodstock
Private kitchen
Living area
Property grounds
Outdoor dining
Exceptional
(9 reviews)

6 Acre Private Hudson Valley Estate

Highland

8% off
AU$14,031
for 7 nights, 1 home
AU$2,004 per night
includes taxes & fees
6 Acre Private Hudson Valley Estate
Interior
Private kitchen
Outdoor dining
Room
Exceptional
(17 reviews)

Modern Hudson Valley Creekside Retreat + Hot Tub!

Hyde Park

16% off
AU$5,248
for 7 nights, 1 cottage
AU$750 per night
includes taxes & fees
Modern Hudson Valley Creekside Retreat + Hot Tub!
Living area
Living area
Dining
Dining
Exceptional
(127 reviews)

Modern, Artsy, & Lofty Log Home

Wallkill

21% off
AU$13,255
for 7 nights, 1 home
AU$1,894 per night
includes taxes & fees
Modern, Artsy, & Lofty Log Home
Dining
Terrace/patio
Private kitchen
Living area
Exceptional
(31 reviews)

Cabin 85: 2 Bedrooms + 2 Lofts Perfect Retreat!

Hurley

12% off
AU$2,605
for 7 nights, 1 cabin
AU$372 per night
includes taxes & fees
Cabin 85: 2 Bedrooms + 2 Lofts Perfect Retreat!
Front Entry
Outdoor dining
Exterior detail
Interior
Exceptional
(10 reviews)

Church Des Artistes a Hudson Valley retreat

Kingston

8% off
AU$17,525
for 7 nights, 1 home
AU$2,504 per night
includes taxes & fees
Church Des Artistes a Hudson Valley retreat
Private kitchen
Exterior
Outdoor dining
Living area
Exceptional
(49 reviews)

Secluded family retreat within minutes of Woodstock village

Saugerties

8% off
AU$4,580
for 7 nights, 1 home
AU$654 per night
includes taxes & fees
Secluded family retreat within minutes of Woodstock village
For those moments when you prefer a more private escape, we've created a tranquil area in the front yard.
Dining
A cozy bedroom boasts a unique charm with its stone wall and wide plank flooring. Queen size bed with luxury linens you'll find it hard to leave. For your comfort we installed a MiniSplit system for heating and AC. Creating warm ambiance to enjoy.
French Doors leading to a veranda offer a wonderful connection to the outdoors, making it the perfect spot to start your day with a cup of morning coffee or tea.
Exceptional
(26 reviews)

Spacious 4BD Country Gem - Fire Pit & Chill Vibes

Highland

7% off
AU$6,082
for 7 nights, 1 home
AU$869 per night
includes taxes & fees
Spacious 4BD Country Gem - Fire Pit & Chill Vibes
Living area
Outdoor dining
Property grounds
Room
Exceptional
(21 reviews)

Beautiful lake view home on Whaley Lake in Holmes, NY.

Holmes

8% off
AU$6,781
for 7 nights, 1 home
AU$969 per night
includes taxes & fees
Beautiful lake view home on Whaley Lake in Holmes, NY.
Comfortably seats 8 and also doubles as a large board game table.
Whip up delicious meals in the spacious, bright kitchen with ample counter space
View of valley and lush evergreens. Queen bed. Spacious closet
Sit together outside, enjoy fresh Hudson Valley air, share stories and memories
Exceptional
(40 reviews)

Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz

Highland

8% off
AU$6,385
for 7 nights, 1 home
AU$912 per night
includes taxes & fees
Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz
5 star ensuite bathroom with tub, hand shower, and rain shower.
450sqft of living space: super comfy kingsize bed (+ 2 optional twin beds)
Private, luxurious retreat in the heart of an organic farm in the Hudson Valley
You are welcome to fish, swim, or paddleboard in our 2 acre pond
Exceptional
(26 reviews)

Luxury retreat w/ private deck, garden, firepit on organic farm

Gardiner

8% off
AU$2,419
for 7 nights, 1 cabin
AU$346 per night
includes taxes & fees
Luxury retreat w/ private deck, garden, firepit on organic farm
Living area
Property grounds
Living area
Private kitchen
Exceptional
(13 reviews)

"Frank Lloyd Wright" Catskills Mountain Yoga-Spa Retreat on 15 Acres

Mount Tremper

12% off
AU$8,713
for 7 nights, 1 home
AU$1,245 per night
includes taxes & fees
"Frank Lloyd Wright" Catskills Mountain Yoga-Spa Retreat on 15 Acres
Sitting in the living room area, you feel nestled in the woods.
Feel the awe of the 20 foot vaulted ceilings and windows onto the woods
Outdoor showers on a hot summer day are the best!
It's mesmerizing to watch and hear the roaring waterfall from this bridge.
Exceptional
(20 reviews)

Hudson Valley stunning lake side modern barn in an Enchanted Forest

Clinton Corners

8% off
AU$5,158
for 7 nights, 1 home
AU$737 per night
includes taxes & fees
Hudson Valley stunning lake side modern barn in an Enchanted Forest
Our home sweet home!
kitchen island w/reclaimed wood
view from the kitchen window
Swing on our porch!
Exceptional
(26 reviews)

TREEMENDOUS VIEWS COTTAGE

Amenia

8% off
AU$5,540
for 7 nights, 1 home
AU$791 per night
includes taxes & fees
TREEMENDOUS VIEWS COTTAGE
Dining
Room
Interior
Interior
Exceptional
(86 reviews)

for the creative spirit, swimming dock on pond, horses to pet, Fire pit

Ulster Park

8% off
AU$3,215
for 7 nights, 1 home
AU$459 per night
includes taxes & fees
for the creative spirit, swimming dock on pond, horses to pet, Fire pit
Room
Property grounds
Property grounds
Property grounds
Exceptional
(17 reviews)

Hudson Valley’s Private Waterfront Camping Getaway

Lake Katrine

8% off
AU$2,270
for 7 nights, 1 unit
AU$324 per night
includes taxes & fees
Hudson Valley’s Private Waterfront Camping Getaway
Living area
Exterior
Property grounds
Interior
Exceptional
(13 reviews)

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Hopewell Junction

8% off
AU$1,975
for 7 nights, 1 home
AU$282 per night
includes taxes & fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Private kitchen
Exterior
Terrace/patio
Interior
Exceptional
(10 reviews)

Mohonk's Peaceful 5BR-3BA~Jacuzzi~Huge Deck~Right On Coxing Kill~ Private Road

High Falls

16% off
AU$6,791
for 7 nights, 1 home
AU$970 per night
includes taxes & fees
Mohonk's Peaceful 5BR-3BA~Jacuzzi~Huge Deck~Right On Coxing Kill~ Private Road
Living area
Interior
Private kitchen
Welcome!!
Exceptional
(27 reviews)

Beautiful Saugerties Rental -Pool, Fire Pit, close to HITS, Hiking, Festivals

Saugerties

8% off
AU$8,827
for 7 nights, 1 home
AU$1,261 per night
includes taxes & fees
Beautiful Saugerties Rental -Pool, Fire Pit, close to HITS, Hiking, Festivals
Living room through Mahogany pocket doors
View of the dining room
Hallway with pocket doors on main floor
Walk way to back yard from side of the house
Exceptional
(17 reviews)

Stunning historic Victorian house in Newburgh. Pet friendly

Newburgh

21% off
AU$8,083
for 7 nights, 1 home
AU$1,155 per night
includes taxes & fees
Stunning historic Victorian house in Newburgh. Pet friendly
Kitchen with everything you'll need
Private kitchen
Exterior
Great room featuring a wonderful wall of windows
Exceptional
(52 reviews)

Private Woodstock Retreat – Heated Pool, Hot Tub & Fireplace on 5 Secluded Acres

Woodstock

12% off
AU$5,955
for 7 nights, 1 home
AU$851 per night
includes taxes & fees
Private Woodstock Retreat – Heated Pool, Hot Tub & Fireplace on 5 Secluded Acres
Interior
Exterior detail
Exterior detail
Room
Exceptional
(10 reviews)

Heart of the Village Victorian Saugerties NY

Saugerties

6% off
AU$4,684
for 7 nights, 1 home
AU$669 per night
includes taxes & fees
Heart of the Village Victorian Saugerties NY
Kitchen Entrance and dining room
Master bedroom with TV
Stone steps to the pool
Interior
Exceptional
(33 reviews)

HIKE, SWIM, STARGAZE IN WOODS SIDING MINNEWASKA STATE PARK SHAWANGUNK MOUNTAINS

Wallkill

11% off
AU$3,695
for 7 nights, 1 cottage
AU$528 per night
includes taxes & fees
HIKE, SWIM, STARGAZE IN WOODS SIDING MINNEWASKA STATE PARK SHAWANGUNK MOUNTAINS

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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)
  • Bowdoin Park (7.2 mi / 11.6 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)

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.
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.
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 Stayz.
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.
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.
Are all fees included in the Poughkeepsie holiday homes prices shown on Stayz?
Stayz 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.
Are there any Poughkeepsie holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Poughkeepsie holiday homes?
You can find great discounts on holiday homes in Poughkeepsie on Stayz, 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.
Can I change or cancel my Poughkeepsie holiday home booking on Stayz?
To find Poughkeepsie holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Poughkeepsie?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Poughkeepsie holiday home?
Book your Poughkeepsie holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Poughkeepsie?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Poughkeepsie to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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