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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.

Newly Renovated 1 Bd Apartment - Poughkeepsie, NY
9.3 35 reviews

Newly Renovated 1 Bd Apartment

apartment, Poughkeepsie
This Poughkeepsie apartment is located in a central district, within walking distance of the Walkway Over the Hudson and four nearby colleges. This makes it an excellent choice for travelers who want to explore the city and enjoy the scenic beauty of the Hudson River. The apartment has received excellent ratings for cleanliness and location, and guests have consistently praised its peaceful atmosphere.
The apartment has one bedroom and one bathroom, comfortably accommodating up to four guests. It features modern amenities like air conditioning, internet access, and a fully equipped kitchen with a fridge, freezer, and microwave. Enjoy the convenience of a central location, explore the city's attractions, and relax in the peaceful environment of this well-maintained apartment.
King Bed Garden Retreat - Poughkeepsie, NY
9.5 132 reviews

King Bed Garden Retreat

apartment, Poughkeepsie
This charming apartment is located in the Hudson Valley, just a short drive from Poughkeepsie, offering a peaceful retreat while being close to the city's attractions. It's consistently rated excellent for location, cleanliness, and overall experience.
This one-bedroom apartment comfortably sleeps four guests with a separate sleeping area and a full-size sleeper sofa in the living room. Guests can enjoy a fully equipped kitchen, access to a shared yard with a fire pit, and private porches for relaxing and enjoying the outdoors.
Two Tillson - Poughkeepsie, NY
10 18 reviews

Two Tillson

apartment, Highland
This apartment is located on the grounds of the Inn at Twaalfskill in Highland, adjacent to the Hudson Valley Rail Trail and within minutes of Vassar College, Marist University, and the Culinary Institute of America.
This 2-bedroom, 2-bathroom residence accommodates up to 5 guests and features air conditioning, a kitchen with a fridge and dishwasher, and garden and parking access.
Stunning 5-bedroom House With Ac / Heat In Charming Poughkeepsie Ny - Poughkeepsie, NY
9.6 4 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.

Best Poughkeepsie, NY vacation rentals with air conditioning

Riverbirch Buttermilkfallsinn - Poughkeepsie, NY
No reviews

Riverbirch Buttermilkfallsinn

apartment, Milton
This four-bedroom, four-bathroom residence is located on a 75-acre estate along the Hudson River, part of the Buttermilk Falls property.
This apartment offers accommodation for up to eight guests, featuring a fully equipped kitchen, spacious living and dining areas, and access to Millstone Farm's animal rescues.
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.
Nature's Serenity Retreat - Poughkeepsie, NY
No reviews

Nature's Serenity Retreat

apartment, Milton
This 4-bedroom, 2-bathroom apartment is located in a quiet, nature-filled district of Milton, offering a peaceful retreat from city noise.
This dwelling accommodates up to 12 guests and features a large kitchen, air conditioning, internet, and parking, with spacious living areas ideal for relaxation and socializing.
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.

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.

Riverbirch Buttermilkfallsinn - Poughkeepsie, NY
No reviews

Riverbirch Buttermilkfallsinn

apartment, Milton
This four-bedroom, four-bathroom residence is located on a 75-acre estate along the Hudson River, part of the Buttermilk Falls property.
This apartment offers accommodation for up to eight guests, featuring a fully equipped kitchen, spacious living and dining areas, and access to Millstone Farm's animal rescues.

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.

King Bed Garden Retreat - Poughkeepsie, NY
9.5 132 reviews

King Bed Garden Retreat

apartment, Poughkeepsie
This charming apartment is located in the Hudson Valley, just a short drive from Poughkeepsie, offering a peaceful retreat while being close to the city's attractions. It's consistently rated excellent for location, cleanliness, and overall experience.
This one-bedroom apartment comfortably sleeps four guests with a separate sleeping area and a full-size sleeper sofa in the living room. Guests can enjoy a fully equipped kitchen, access to a shared yard with a fire pit, and private porches for relaxing and enjoying the outdoors.

Best Poughkeepsie, NY vacation rentals with parking

Nature's Serenity Retreat - Poughkeepsie, NY
No reviews

Nature's Serenity Retreat

apartment, Milton
Newly Renovated 1 Bd Apartment - Poughkeepsie, NY
9.3 35 reviews

Newly Renovated 1 Bd Apartment

apartment, Poughkeepsie
Stunning 5-bedroom House With Ac / Heat In Charming Poughkeepsie Ny - Poughkeepsie, NY
9.6 4 reviews

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

apartment, Poughkeepsie
Pony's Pad Buttermilkfallsinn - Poughkeepsie, NY
No reviews

Pony's Pad Buttermilkfallsinn

cabin, Milton

Best 5-Star Vacation Rentals in Poughkeepsie, NY

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

King Bed Garden Retreat - Poughkeepsie, NY
9.5 132 reviews

King Bed Garden Retreat

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.

Stunning 5-bedroom House With Ac / Heat In Charming Poughkeepsie Ny - Poughkeepsie, NY
9.6 4 reviews

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

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

Gindelle Suite Buttermilkfalls

cabin, Milton
Newly Renovated 1 Bd Apartment - Poughkeepsie, NY
9.3 35 reviews

Newly Renovated 1 Bd Apartment

apartment, Poughkeepsie
Pony's Pad Buttermilkfallsinn - Poughkeepsie, NY
No reviews

Pony's Pad Buttermilkfallsinn

cabin, Milton

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.

Riverbirch Buttermilkfallsinn - Poughkeepsie, NY
No reviews

Riverbirch Buttermilkfallsinn

apartment, Milton

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.

Newly Renovated 1 Bd Apartment - Poughkeepsie, NY
9.3 35 reviews

Newly Renovated 1 Bd Apartment

apartment, Poughkeepsie
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