Best Vacation Homes in Poughkeepsie
500 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $306/Night
For 7 Nights CA $2,145
16145.86 ft²
7 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
CA $375/Night
For 7 Nights CA $2,624
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
CA $356/Night
For 7 Nights CA $2,491
540 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $323/Night
For 7 Nights CA $2,263
2497.23 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Parking
CA $550/Night
For 7 Nights CA $3,850
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
CA $459/Night
For 7 Nights CA $3,215
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $259/Night
For 7 Nights CA $1,810
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $337/Night
For 7 Nights CA $2,360
Poughkeepsie Luxury Rentals
10763.91 ft²
29 Guests
14 Bedrooms
8 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- View
- Pet Friendly
CA $12,448/Night
For 7 Nights CA $87,136
10764 ft²
29 Guests
14 Bedrooms
8 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
CA $8,892/Night
For 7 Nights CA $62,241
14000 ft²
25 Guests
13 Bedrooms
13 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
CA $8,783/Night
For 7 Nights CA $61,480
30 Guests
13 Bedrooms
13 Bathrooms
Family Friendly
Cabin
- Private Pool
- Spa
- Fireplace/Heating
CA $8,632/Night
For 7 Nights CA $60,423
11840.3 ft²
8 Guests
4 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- Balcony/Terrace
- View
CA $6,840/Night
For 7 Nights CA $47,883
6000 ft²
10 Guests
5 Bedrooms
7 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
CA $6,632/Night
For 7 Nights CA $46,427
10000 ft²
12 Guests
8 Bedrooms
5 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
CA $4,286/Night
For 7 Nights CA $30,001
2690.98 ft²
16 Guests
2 Bedrooms
6 Bathrooms
Free Cancellation
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
CA $3,940/Night
For 7 Nights CA $27,581
Poughkeepsie Pet Friendly Vacation Rentals
1500 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $403/Night
For 7 Nights CA $2,821
1248.61 ft²
7 Guests
3 Bedrooms
1 Bathroom
Free Cancellation
House
- Fireplace/Heating
- View
- Pet Friendly
CA $1,411/Night
For 7 Nights CA $9,879
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Spa
- Fireplace/Heating
- Pool
CA $631/Night
For 7 Nights CA $4,416
1400 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $414/Night
For 7 Nights CA $2,896
1097.92 ft²
6 Guests
2 Bedrooms
1 Bathroom
Ski Chalet
- Breakfast
- Pet Friendly
- Kitchen
CA $326/Night
For 7 Nights CA $2,279
1984 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $380/Night
For 7 Nights CA $2,664
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $312/Night
For 7 Nights CA $2,181
950 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $354/Night
For 7 Nights CA $2,480
Poughkeepsie Large Vacation Homes
12 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Balcony/Terrace
- Kitchen
- Parking
CA $208/Night
For 7 Nights CA $1,453
CA $821/Night
For 7 Nights CA $5,746
3996 ft²
8 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
CA $1,811/Night
For 7 Nights CA $12,678
2002.09 ft²
10 Guests
5 Bedrooms
5 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Balcony/Terrace
- View
CA $533/Night
For 7 Nights CA $3,728
4000 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
CA $1,579/Night
For 7 Nights CA $11,055
2600 ft²
12 Guests
6 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
CA $866/Night
For 7 Nights CA $6,065
16 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $986/Night
For 7 Nights CA $6,905
3500 ft²
12 Guests
6 Bedrooms
3 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
CA $1,134/Night
For 7 Nights CA $7,940
Why Choose Rent By Owner for your Poughkeepsie Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Poughkeepsie
When should you plan your Vacation Rentals stay?
Choosing the ideal time to visit here ensures you can enjoy the region’s local events and favorable weather, making your booking of vacation rentals in this destination a memorable and hassle-free experience.
Peak Season Highlights
Summer (June to August)
During the summer months, this destination experiences warm weather ideal for outdoor activities and exploration.
Average Temperature Daytime: around 80°F - Nighttime: about 60°F
Fall (September to November)
Autumn offers a picturesque setting with colorful foliage, making it a popular time for visitors seeking scenic beauty.
Average Temperature Daytime: approximately 70°F - Nighttime: roughly 45°F
Off-Season Highlights
Winter (December to February)
This quieter period sees cooler temperatures, providing a peaceful atmosphere for those who enjoy winter serenity.
Average Temperature Daytime: around 35°F - Nighttime: about 20°F
Spring (March to May)
Early spring brings mild weather and blooming landscapes, appealing to travelers seeking fewer crowds and fresh scenery.
Average Temperature Daytime: roughly 55°F - Nighttime: about 35°F
Weekly Weather Forecast for Poughkeepsie
How to Book Your Poughkeepsie Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Poughkeepsie
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor seating areas such as patios or decks to unwind and take in the scenic views.
- Take advantage of private gardens or landscaped yards perfect for relaxation or outdoor dining.
- Make use of spacious lawns suitable for outdoor activities or family games.
- Look for properties offering outdoor grilling stations or barbecue facilities to enhance your cooking experience.
- Identify accommodations with pools or hot tubs to add a touch of luxury to your stay in this destination.
- Explore options featuring fire pits or outdoor fireplaces for cozy evenings outdoors.
- Check for access to nearby hiking or nature trails directly from the property for outdoor adventures in the region.
Top Attractions Around Poughkeepsie
What attractions are nearby?
Explore the area's rich natural beauty and cultural attractions, including scenic parks and historic sites just a short drive from your vacation rentals in Poughkeepsie, New York.
Family Activities
- Walkway Over the Hudson State Historic Park: Enjoy a family-friendly stroll across this iconic bridge offering stunning views of the surrounding region and a safe area for kids to explore.
- Vassar College Art Gallery: Explore diverse art exhibitions and engaging programs that provide an educational experience for families interested in culture and creativity.
- Locust Grove Estate: Discover the historic estate featuring scenic gardens, interactive tours, and family-friendly events set against the backdrop of the area's natural beauty.
- Poughkeepsie Galleria Mall: Spend quality leisure time shopping and dining together at this popular regional shopping destination in the town center.
Adult Activities
- Hudson River Cruises: Experience the scenic beauty of the river with a relaxing cruise that offers stunning views and a peaceful ambiance, perfect for unwinding during your stay.
- Poughkeepsie Bridge Walkway: Take a walk across this iconic bridge for breathtaking vistas of the Hudson River and the surrounding landscape, making it an ideal outdoor activity for visitors seeking panoramic sights.
- Vanderbilt Mansion National Historic Site: Tour this grand estate to explore the history and architecture of the region while enjoying the beautifully maintained gardens and grounds.
- Local Wineries and Breweries: Visit nearby wineries and breweries to sample regional flavors and enjoy a leisurely day immersed in the area's vibrant craft beverage scene.
Other Places to Stay in Poughkeepsie, NY
Hudson Valley
Lower Hudson Valley
Dutchess County
New Paltz
Kerhonkson
Fishkill
Highland
Town of Stanford
Philipstown
Rhinebeck
Gardiner
Town of Lloyd
Poughkeepsie Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining and Markets: Immerse yourself in the area's culinary scene by visiting local markets and eateries to experience authentic flavors unique to this destination.
- Plan Outdoor Activities: Take advantage of the region’s natural beauty by scheduling outdoor adventures such as hiking, biking, or relaxing by nearby water bodies.
- Discover Cultural Attractions: Spend time exploring museums, historic sites, or art galleries to gain a deeper appreciation of the area's rich heritage.
- Optimize Your Stay with Local Insights: Connect with community resources or hosts for personalized recommendations, ensuring you make the most of your time here.
Transportation Options
- Car Rentals: Renting a car provides the flexibility to explore the region at your own pace while staying close to your vacation rental here in Poughkeepsie.
- Public Transit (Dutchess County Public Transit): The local bus service offers convenient transportation options for getting around the area without the need for a private vehicle.
- Amtrak Train Service: Connecting this destination to major cities along the Northeast Corridor, Amtrak makes it easy to travel to and from the region in comfort.
- Taxis and Rideshare Services: Taxis and rideshare options like Uber and Lyft are readily available, providing quick and reliable transportation within the area.
Local Customs Options
- Welcoming Hospitality: You’ll notice that local residents are known for their friendly and welcoming nature, making your stay in the area comfortable and inviting.
- Historical Preservation: Respect for the region’s rich history is evident through the community’s pride in maintaining historic buildings and landmarks.
- Community Festivals: Participating in or observing local festivals reveals a tradition of celebrating the area's cultural heritage and fostering neighborhood spirit.
- Artistic Expression: The region boasts a vibrant arts scene, encouraging visitors to appreciate local craftsmanship and creative events during your visit.
Frequently Asked Questions About Poughkeepsie?
1. What are the top vacation rentals in Poughkeepsie?
There are a lot of options in Poughkeepsie. If you plan on staying in the Poughkeepsie area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Poughkeepsie:
- Hudson Valley, the Gunks - Beautiful Cottage
- NEW RENO, HIGH FALLS, near Mohonk preserve, New Paltz, Kingston
- Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC!
- Cozy & Charming Farm House just 85 miles north of NYC
- Charming Brick House -Hudson Valley
- Best of both worlds! Amazing views plus an easy walk into town!
- Mountain View escape
- Splendid Isolation: Private Luxury. Breathtaking Modern Villa On Hudson Bluffs.
- Red Barn Retreat - Shawangunk Mountains Getaway
- Modern Home With Stunning Mountain Views
2. How many vacation rentals have private pools in Poughkeepsie?
There are 160 vacation rentals with private pools near Poughkeepsie. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Poughkeepsie are best for families?
If you are looking for a family-friendly vacation home in Poughkeepsie, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Poughkeepsie:
4. How many Rentbyowner vacation rentals are available in Poughkeepsie?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 1163 in the Poughkeepsie area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Poughkeepsie.
5. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary depending on the individual property listing. You should review the specific rental’s cancellation terms directly on the listing page or contact the property owner for detailed information before booking.
6. Are there any additional fees or deposits required when booking a vacation rental here?
Additional fees such as cleaning, service charges, or security deposits are typically listed with the property details. Check the rental listing carefully or reach out to the host to understand all costs involved before confirming your reservation.
7. How do I ensure my stay adheres to house rules and local regulations?
Each vacation rental has its own set of house rules provided by the owner. It’s important to read these rules on the listing page and communicate with the host if you have any questions about local regulations or property expectations.
8. What amenities are usually included in vacation rentals around this destination?
Amenities can vary from one property to another, but common features include Wi-Fi, parking, kitchen facilities, and linens. Review the amenities section of each listing to find a property that meets your needs in this region.
9. How do I confirm booking availability and secure my reservation in this area?
Availability can be checked through the booking calendar on each listing. Once you find a suitable property, follow the booking process to secure your reservation and receive confirmation directly from the property owner.
Poughkeepsie Top Rated Vacation Rentals
1000 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Other
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $368/Night
For 7 Nights CA $2,575
4100 ft²
8 Guests
4 Bedrooms
5 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Spa
CA $2,634/Night
For 7 Nights CA $18,438
3500 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Ocean View
Cabin
- Private Pool
- Fireplace/Heating
- Pool
CA $2,061/Night
For 7 Nights CA $14,426
2316 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
CA $716/Night
For 7 Nights CA $5,010
2500 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $997/Night
For 7 Nights CA $6,980
2000 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
CA $1,091/Night
For 7 Nights CA $7,635
500 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Hot Tub
- Fireplace/Heating
- Pool
CA $296/Night
For 7 Nights CA $2,073
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Other
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $605/Night
For 7 Nights CA $4,237
