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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.
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.
Your Own Pied-a-terre "Walkway Over The Hudson"#2 - Poughkeepsie, NY
9.7 112 reviews

Your Own Pied-a-terre "Walkway Over The Hudson"#2

apartment, Poughkeepsie
This charming one-bedroom apartment is located in a central Poughkeepsie neighborhood, just a short drive from Vassar College, Marist College, the Walkway Over the Hudson, and the train station. Guests consistently rate the apartment excellent for its cleanliness, location, and overall experience.
The apartment comfortably sleeps two guests and includes a full-size bed, a kitchen, a living room, and a bathroom. Enjoy amenities like complimentary bicycles, a private entrance with French doors, and a garden, making it the perfect home base for exploring Poughkeepsie.
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.

Best Poughkeepsie, NY vacation rentals with air conditioning

Cozy Escape With Stunning Hudson River Views - Poughkeepsie, NY
10 10 reviews

Cozy Escape With Stunning Hudson River Views

apartment, Milton
This family-friendly apartment in Milton offers sweeping Hudson River views from its location in the scenic Hudson Valley, placing you near wineries, farms, and dining options. This spacious, three-story home accommodates up to 8 guests with 4 bedrooms, 2 bathrooms, air conditioning, internet, a full kitchen, fitness center, garden, and parking, providing exclusive access to the entire residence and an outdoor deck.
Pony's Pad Buttermilkfallsinn - Poughkeepsie, NY
No reviews

Pony's Pad Buttermilkfallsinn

cabin, Milton
Pony's Pad Getaway Suite, a one-bedroom suite in Buttermilk Falls on the Hudson River, offers stunning views of both the Hudson River and a pond on a 75-acre estate in Milton, New York.
This two-story Milton getaway boasts a full kitchen, a luxurious walk-in shower, a California king bed and pull-out couch sleeping four, a wrap-around deck, and on-site access to Henrys at the Farm restaurant, a spa, trails, and Millstone Farm animal rescue.
Gindelle Suite Buttermilkfalls - Poughkeepsie, NY
No reviews

Gindelle Suite Buttermilkfalls

cabin, Milton
The Gindelle getaway suite, a two-bedroom cabin rental located at Buttermilk Falls on the Hudson River in Milton, New York, offers convenient access to Henrys at the Farm restaurant, a spa, and Millstone Farm animal rescue on a 75-acre estate with walking trails.
This Milton, NY getaway boasts a king and queen bedroom, one bathroom with a whirlpool tub, a fully equipped kitchen, two gas fireplaces, stunning garden and pond views, and accommodates up to four guests, providing a relaxing retreat near the Hudson River.
Washington Wonder Big 4bd/2b - Poughkeepsie, NY
9.9 82 reviews

Washington Wonder Big 4bd/2b

apartment, Poughkeepsie
This four-bedroom, two-bathroom Poughkeepsie apartment is conveniently located near the Walkway Over the Hudson and Marist College, a short drive from the Culinary Institute of America and the Franklin D. Roosevelt Presidential Library and Museum.
This rental offers a spacious layout sleeping eight guests, includes amenities such as a front porch, back deck, fire pit, internet, parking, and air conditioning, providing easy access to hiking trails and local restaurants.

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.

Lucious Lagrangeville - Poughkeepsie, NY
1.0 2 reviews

Lucious Lagrangeville

house, Freedom Plains
This spacious vacation home is located in Lucious Lagrangeville, Lagrangeville, offering convenient access to Vassar College (9 miles) and Bardavon Opera House (10 miles).
This 10,760 square foot house accommodates up to 19 guests and features air conditioning, a kitchen, swimming pool, jacuzzi, terrace, balcony, parking, and complimentary WiFi.

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.

Charming 3 Bedroom Home - Near Vassar, Marist - Poughkeepsie, NY
10 85 reviews

Charming 3 Bedroom Home - Near Vassar, Marist

house, 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.

Best Poughkeepsie, NY vacation rentals with parking

Fully Renovated Loft Apartment Permit # 20240329 - Poughkeepsie, NY
10 34 reviews

Fully Renovated Loft Apartment Permit # 20240329

apartment, Fairview
The Hudsy Home - Poughkeepsie, NY
9.8 111 reviews

The Hudsy Home

apartment, Fairview
The Hudson Valley Hideaway - Poughkeepsie, NY
9.9 37 reviews

The Hudson Valley Hideaway

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

Newly Renovated & Comfortable Home-vassar/marist

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.

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

Charming Townhouse In Historic District

apartment, Poughkeepsie

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.

Pony's Pad Buttermilkfallsinn - Poughkeepsie, NY
No reviews

Pony's Pad Buttermilkfallsinn

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

Washington Wonder Big 4bd/2b

apartment, Poughkeepsie
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.

The Hudson Valley Hideaway - Poughkeepsie, NY
9.9 37 reviews

The Hudson Valley Hideaway

apartment, Poughkeepsie
Lucious Lagrangeville - Poughkeepsie, NY
1.0 2 reviews

Lucious Lagrangeville

house, Freedom Plains

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.

Lucious Lagrangeville - Poughkeepsie, NY
1.0 2 reviews

Lucious Lagrangeville

house, Freedom Plains
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