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Poughkeepsie, NY vacation rentals
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Best Vacation rentals and Airbnb offers in Poughkeepsie, NY

Browse Vacation Rentals in the Historic District of Poughkeepsie, NY

From vibrant downtown areas to historic streets, these Poughkeepsie, NY vacation rentals put you close to everything worth seeing.

Your Own Pied-a-terre "Walkway Over The Hudson" #4 - Poughkeepsie, NY
9.9 33 reviews

Your Own Pied-a-terre "Walkway Over The Hudson" #4

apartment, Poughkeepsie
This studio apartment is located in a central Poughkeepsie neighborhood, just a short walk from Mansion Square Park and less than 10 minutes from Marist and Vassar Colleges, Vassar Bros. Medical Center, and the Walkway Over The Hudson. This accommodation has excellent user, location, and cleanliness ratings.
The studio features a full-size bed, a full kitchenette, and a tiled bathroom with a shower. Guests can enjoy the landscaped backyard and patio, and the studio is pet-friendly.
Stunning 5-bedroom House With Ac / Heat In Charming Poughkeepsie Ny - Poughkeepsie, NY
9.6 5 reviews

Stunning 5-bedroom House With Ac / Heat In Charming Poughkeepsie Ny

apartment, Poughkeepsie
This Poughkeepsie residence is located near Franny Reese State Park and Vanderbilt Mansion National Historic Site, providing easy access to notable local attractions.
This spacious home accommodates up to 18 guests with five bedrooms and two bathrooms, featuring air conditioning, heating, and an iron for guest convenience.
Spacious And Stylish Entire One Bedroom Apartment. - Poughkeepsie, NY
9.9 387 reviews

Spacious And Stylish Entire One Bedroom Apartment.

apartment, Poughkeepsie
This charming Victorian townhouse is located in downtown Poughkeepsie, within walking distance of the Walkway Over the Hudson, the Bardavon Opera House, the train station, and the waterfront. The apartment has received excellent ratings for cleanliness, location, and user experience.
The home features a spacious, open layout with a private entrance, ideal for groups of up to 4 guests. Modern amenities include air conditioning, parking, a fully equipped kitchen, and a security camera for added peace of mind.
3 Bdrm. Near Hudson Valley Colleges & Attractions - Poughkeepsie, NY
9.9 397 reviews

3 Bdrm. Near Hudson Valley Colleges & Attractions

apartment, Poughkeepsie
This 3-bedroom apartment is located in Poughkeepsie, just a half-mile from the train station and within two miles of Marist and Vassar Colleges. Guests have consistently rated the apartment excellent for location, cleanliness, and overall experience.
The apartment features a spacious layout, comfortably accommodating up to 5 guests with its three bedrooms and pull-out sofa. Enjoy a well-equipped kitchen, two porches, and driveway parking, perfect for exploring the nearby Shawangunk Mountains, Mohonk Preserve, and Minnewaska State Park.

Best Poughkeepsie, NY vacation rentals with air conditioning

Secluded Country Getaway - Poughkeepsie, NY
9.6 27 reviews

Secluded Country Getaway

cottage, Highland
This secluded cottage in Highland, Ulster County, is located just 8 minutes from the Walkway Over the Hudson, 6 minutes from Franny Reese State Park, and under 30 minutes from historic sites in Hyde Park.
This accommodation offers 2 bedrooms, 1 bathroom, and can host up to 6 guests with amenities like air conditioning, a kitchen, and a terrace, while the surrounding area provides opportunities for hiking and exploring nearby towns.
Summit Sanctuary With Ev Ready Mountain Views - Poughkeepsie, NY
8.2 9 reviews

Summit Sanctuary With Ev Ready Mountain Views

house, Haviland
This Poughkeepsie residence offers mountain top views, located 6.7 miles from Vassar College and 10 miles from Marist College.
This 3,400 square foot house accommodates up to 15 guests with 4 bedrooms and 4 bathrooms, featuring a well-equipped kitchen, air conditioning, a terrace, garden, and convenient EV charging.
Charming Home Near Walkway Over The Hudson - Poughkeepsie, NY
9.9 420 reviews

Charming Home Near Walkway Over The Hudson

apartment, Poughkeepsie
This charming 1856 house is located in Poughkeepsie, within walking distance of the train station and a short drive from popular attractions like Marist College, Vassar College, and the Walkway Over the Hudson. Guests consistently rate this home excellent for its location, cleanliness, and overall experience.
The house features two bedrooms and two bathrooms, comfortably accommodating up to four guests. Enjoy modern amenities like a fully equipped kitchen, air conditioning, a private garden, and laundry access, all while experiencing the unique charm of this historic home.
Beautiful Home - 4br/2.5ba - Hot Tub And Patio - Poughkeepsie, NY
9.6 93 reviews

Beautiful Home - 4br/2.5ba - Hot Tub And Patio

apartment, Highland
This family-friendly vacation home is located on a river in Highland, within a 3 km radius of Berean Park Beach and Walkway Over the Hudson State Historic Park. This Highland rental receives excellent ratings for its location, cleanliness, and user experience.
The home has 4 bedrooms and 3 bathrooms, comfortably accommodating up to 8 guests. Enjoy features like a swimming pool, jacuzzi, spa, and a fully equipped kitchen, perfect for relaxing and entertaining.

Frequently Asked Questions about vacation rentals in Poughkeepsie, NY

  • What should a first-time visitor not miss in Poughkeepsie, NY?

    For a first-timer, you absolutely can't miss the Walkway Over the Hudson State Historic Park. It's a 1.28-mile-long pedestrian bridge offering stunning views of the Hudson River and the surrounding area. Another must-see is the Vassar College campus, known for its beautiful architecture and historical significance.
  • What are the best Airbnb and vacation rentals in Poughkeepsie, NY?

    3 Bdrm - Near Hudson Valley Colleges & Attractions, Spacious And Stylish Entire One Bedroom Apartment and Lovely Hudson Valley Guest Cottage are the most popular Airbnb and vacation rentals in Poughkeepsie, NY among travelers.

  • Which neighborhood in Poughkeepsie, NY should you consider for a vacation rental?

    The area around the Walkway Over the Hudson is great for vacation rentals. It's close to the park, restaurants, and shops. You can also consider the historic district, which has charming old homes and is within walking distance of the city center.
  • What are the most popular Airbnbs in Poughkeepsie, NY?

  • What are the top family-friendly attractions in Poughkeepsie, NY?

    The Mid-Hudson Children's Museum is a great place for kids, with interactive exhibits and educational activities. The Poughkeepsie Farm Project also offers family-friendly events, like farm tours and workshops. Don't forget the Dutchess County Fairgrounds, which hosts the annual Dutchess County Fair, a popular event for families.
  • What are the best vacation rentals with a pool in Poughkeepsie, NY?

  • When is the best time to book a vacation rental in Poughkeepsie, NY?

    The best time to book a vacation rental in Poughkeepsie is during the shoulder seasons, from April to May and September to October. You'll avoid the crowds and get better rates compared to the peak summer months.
  • What are the best rentals for families and kids in Poughkeepsie, NY?

  • What are the best budget-friendly activities in Poughkeepsie, NY?

    The Walkway Over the Hudson is free to walk, and offers stunning views. The Poughkeepsie Farmers' Market, held on Saturdays, is a great place to find local produce and crafts at affordable prices. And you can't beat the free concerts at the Walkway Over the Hudson Amphitheater.
  • What are the best rentals or Airbnbs with a jacuzzi in Poughkeepsie, NY?

    The best vacation rentals or Airbnb with a jacuzzi in Poughkeepsie, NY are House In Highland: Secluded Retreat, Beautiful Home - 4br/2 -5ba - Hot Tub And Patio - Minutes From New Paltz and Pentimento.

  • What are the best restaurants with local dishes in Poughkeepsie, NY?

    For local dishes, head to The Dutch, which serves up classic American comfort food with a modern twist. The Red Jug Pub is another great option, known for its traditional Irish fare and lively atmosphere. If you're looking for something more upscale, try The Grandview, which offers a fine dining experience with breathtaking views of the Hudson River.
  • What are the best walking or cycling routes in Poughkeepsie, NY?

    The Walkway Over the Hudson itself is a great walking or cycling route, offering stunning views of the river. The Dutchess Rail Trail is another popular option, a 13-mile paved trail that runs through scenic farmland and forests. For a more challenging ride, try the 30-mile loop around the city, which takes you through the historic district and along the riverfront.
  • Are there pet-friendly attractions in Poughkeepsie, NY?

    The Walkway Over the Hudson is pet-friendly, allowing dogs on leash. The Poughkeepsie Farm Project also welcomes dogs, and they have a dedicated dog park. Many restaurants in the city offer outdoor seating that is dog-friendly.

Popular destinations

Top Vacation Rentals with Balconies in Poughkeepsie, NY

Start your morning right with a vacation rental in Poughkeepsie, NY featuring a private balcony and stunning views.

Hudson Valley Duplex: Hike, Sip + Explore! - Poughkeepsie, NY
No reviews

Hudson Valley Duplex: Hike, Sip + Explore!

house, Highland
This Hudson Valley duplex in Highland is located 3.7 miles from Bardavon Opera House and 6.2 miles from Vassar College, with Stewart International Airport 16 miles away.
This spacious three-bedroom, three-bathroom holiday home offers 1500 square feet of living space, accommodates up to 11 guests, and features a fully equipped kitchen, air conditioning, a garden, terrace, and barbecue, with free on-site parking.
Summit Sanctuary: Ev Ready Mountain Views - Poughkeepsie, NY
9.2 16 reviews

Summit Sanctuary: Ev Ready Mountain Views

apartment, Haviland
This Haviland mountainside home, situated three miles from the Eleanor Roosevelt National Historic Site and Richard L. Skimin Memorial Baseball Field, offers convenient access to local attractions.
This 3400-square-foot vacation rental boasts four bedrooms, four bathrooms, and accommodates eight guests, featuring a private pool, spa, fitness center, and on-site water park.
Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat - Poughkeepsie, NY
10 6 reviews

Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat

apartment, Fairview
This Fairview vacation home offers a peaceful rural setting, conveniently located within three miles of King Street Dog Park, Richard L. Skimin Memorial Baseball Field, Chance Theater, Mid-Hudson Heritage Center, and Walkway Over the Hudson State Historic Park.
This 2300-square-foot house features three bedrooms, three bathrooms, and can comfortably accommodate six guests, boasting amenities such as a fully equipped kitchen, a balcony, fireplace, free WiFi, and air conditioning.

Discover Family-Friendly Vacation Rentals in Poughkeepsie, NY

Booking a family-oriented vacation rental in Poughkeepsie, NY keeps you close to top city attractions for a stress-free getaway.

Highland Mansion - Poughkeepsie, NY
8.2 12 reviews

Highland Mansion

house, Milton
This Milton manor house, sleeping up to 10 guests in 4 bedrooms and 6 bathrooms, offers a family-friendly escape with a swimming pool, and is conveniently located near Milton's major attractions (exact distances and attractions require further details).
The large estate boasts a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, internet access, and ample parking, ensuring a comfortable stay for all.
Charming 3 Bedroom Home - Near Vassar, Marist - Poughkeepsie, NY
10 86 reviews

Charming 3 Bedroom Home - Near Vassar, Marist

apartment, Poughkeepsie
This newly renovated, historic apartment is located in a quiet neighborhood on the south side of Poughkeepsie, just a 5-minute drive from Vassar College and Vassar Brothers Medical Center.
The 3-bedroom apartment sleeps up to 5 guests and features a fully equipped kitchen with black walnut cabinetry, a dedicated workspace, a spacious living room with a 65-inch smart TV, and outdoor relaxation spaces including a front porch and a backyard patio with a gas grill.
The Scenic Mansion With Breathtaking View - Poughkeepsie, NY
8.0 24 reviews

The Scenic Mansion With Breathtaking View

house, Highland
This luxurious Milton mountain villa boasts stunning views, situated 1.1 miles from Franny Reese State Park and within 3 miles of the Hudson River and Walkway Over the Hudson State Historic Park.
The 4-bedroom, 6-bathroom house comfortably sleeps 10 guests and features a private pool, Jacuzzi, tennis court, and fully equipped kitchen with modern appliances, including a dishwasher; enjoy nearby hiking and explore the Hudson Valley.
Zen Peaks Retreat - Poughkeepsie, NY
9.9 19 reviews

Zen Peaks Retreat

apartment, Highland
This refurbished colonial farmhouse near Highland, New York, is a 30-minute drive from the Mohonk Mountains and Lake Minnewaska, and 5 minutes from a rail trail ideal for biking.
This four-bedroom, two-bathroom house sleeps twelve guests and boasts a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, a garden, fitness center, parking, and internet access; nearby attractions include shopping in Poughkeepsie and dining in New Paltz.

Best Poughkeepsie, NY vacation rentals with parking

Hamptons On The Hudson: Pool, Spa, Bbq, Views! - Poughkeepsie, NY
9.8 50 reviews

Hamptons On The Hudson: Pool, Spa, Bbq, Views!

apartment, Milton
Newly Renovated & Comfortable Home-vassar/marist - Poughkeepsie, NY
9.6 152 reviews

Newly Renovated & Comfortable Home-vassar/marist

apartment, Poughkeepsie
Charming Historic District Modern Home - Poughkeepsie, NY
No reviews

Charming Historic District Modern Home

apartment, Poughkeepsie
Under The Walkway Near The Train In Little Italy - Poughkeepsie, NY
9.8 121 reviews

Under The Walkway Near The Train In Little Italy

apartment, Poughkeepsie

Best 5-Star Vacation Rentals in Poughkeepsie, NY

Discover high-end comfort in Poughkeepsie, NY with upscale rentals that prioritize luxury and guest satisfaction.

Lake Side Tiny House - Poughkeepsie, NY
9.7 187 reviews

Lake Side Tiny House

house, Fairview

Find the Best Dog-Friendly Vacation Rentals in Poughkeepsie, NY

Discover pet-friendly vacation rentals in Poughkeepsie, NY that prioritize comfort for both you and your dog.

Historic 4br Family Home Near Buttermilk Falls - Poughkeepsie, NY
9.5 236 reviews

Historic 4br Family Home Near Buttermilk Falls

apartment, Milton
Washington Wonder Big 4bd/2b - Poughkeepsie, NY
9.9 82 reviews

Washington Wonder Big 4bd/2b

apartment, Poughkeepsie
Gindelle Suite Buttermilkfalls - Poughkeepsie, NY
No reviews

Gindelle Suite Buttermilkfalls

cabin, Milton
Charming Townhouse In Historic District - Poughkeepsie, NY
9.8 56 reviews

Charming Townhouse In Historic District

apartment, Poughkeepsie

Search Vacation Rentals with Swimming Pool in Poughkeepsie, NY

Choose a vacation rental in Poughkeepsie, NY with a swimming pool for a proper workout or a leisurely dip right in the heart of the city.

Splendid Isolation @ Extraordinary Country Retreat - Poughkeepsie, NY
9.9 154 reviews

Splendid Isolation @ Extraordinary Country Retreat

apartment, Highland

Top-Rated Vacation Rentals with a Hot Tub in Poughkeepsie, NY

Unwind after exploring the city with a private hot tub in your own Poughkeepsie, NY vacation rental.

The House In Highland- Secluded Retreat - Poughkeepsie, NY
9.8 29 reviews

The House In Highland- Secluded Retreat

apartment, Highland
Hamptons On The Hudson: Pool, Spa, Bbq, Views! - Poughkeepsie, NY
9.8 50 reviews

Hamptons On The Hudson: Pool, Spa, Bbq, Views!

apartment, Milton
Beautiful Home - 4br/2.5ba - Hot Tub And Patio - Poughkeepsie, NY
9.6 93 reviews

Beautiful Home - 4br/2.5ba - Hot Tub And Patio

apartment, Highland
Splendid Isolation @ Extraordinary Country Retreat - Poughkeepsie, NY
9.9 154 reviews

Splendid Isolation @ Extraordinary Country Retreat

apartment, Highland
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