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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.

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.
Historic Spacious Home 5 Bed/2 Bath - Poughkeepsie, NY
9.7 26 reviews

Historic Spacious Home 5 Bed/2 Bath

apartment, Poughkeepsie
This five-bedroom house, located in a quiet, central Poughkeepsie neighborhood near local universities and restaurants, offers easy access to the Hudson Valley's attractions.
The spacious home features a fully equipped kitchen with a fridge, microwave, and dishwasher, accommodating up to ten guests with access to a Peloton bike, screened porch, and upstairs deck.
The House In Highland- Secluded Retreat - Poughkeepsie, NY
9.8 28 reviews

The House In Highland- Secluded Retreat

apartment, Highland
This Highland house rental boasts three bedrooms and three bathrooms, comfortably accommodating six guests, and is minutes from the Walkway Over the Hudson State Park and the hamlet of Highland, providing easy access to New Paltz and Poughkeepsie.
The property features a well-equipped kitchen with appliances like a pasta maker and ice cream maker, multiple entertaining areas including a multi-level deck, hot tub, fire pit, 85-inch TV, arcade machines, and one gigabit internet speed.
Charming Townhouse In Historic District - Poughkeepsie, NY
9.8 56 reviews

Charming Townhouse In Historic District

apartment, Poughkeepsie
This charming five-bedroom townhouse is located in the Poughkeepsie Historic District, just a short walk from the city's attractions, restaurants, and shops. The apartment consistently receives excellent ratings for cleanliness, location, and overall user experience.
The spacious home offers ample room for families or groups of friends, accommodating up to eight guests. Enjoy modern conveniences like air conditioning, a dishwasher, and a garden, perfect for relaxing or dining outdoors.

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.
Hudson Valley Estate 90 Min From Nyc Pool&gameroom - Poughkeepsie, NY
10 53 reviews

Hudson Valley Estate 90 Min From Nyc Pool&gameroom

apartment, Highland
This spacious waterfront estate is located in Highland, just 90 minutes from New York City, offering a peaceful escape from the hustle and bustle of the city. The property has earned excellent ratings for its cleanliness, location, and overall experience.
This 6-acre property features a large home with four bedrooms and two bathrooms, comfortably accommodating up to 10 guests. The estate boasts a private pool, a wood-fired pizza oven, a gas grill, a basketball court, a soccer net, a fire pit, and a deck with seating for 12, making it ideal for families and groups seeking a memorable vacation.
Hamptons On The Hudson: Pool, Spa, Bbq, Views! - Poughkeepsie, NY
9.8 50 reviews

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

apartment, Milton
This waterfront vacation rental in Milton is located just 0.1 miles from the Hudson River and within a 3-mile radius of attractions like Live At The Falcon and the Marlboro Free Library. It boasts excellent user, location, and cleanliness ratings, making it a great choice for travelers. This 5-bedroom home spans 5010 square feet and comfortably accommodates up to 10 guests. Amenities include a private pool, spa tub, outdoor barbecue, and a fully equipped kitchen, offering a relaxing and enjoyable stay.
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.

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.

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

Splendid Isolation @ Extraordinary Country Retreat

apartment, Highland
This stunning villa sits on a peninsula overlooking the Hudson River in Highland, just 1.5 hours from New York City and a short drive from FDR's Birthplace & Summer White House. The villa has received excellent ratings for location, cleanliness, and user experience, making it a top choice for travelers seeking a luxurious and comfortable stay.
This 4,100 square foot home features four bedrooms and can accommodate up to eight guests. The villa offers a range of amenities, including a heated saltwater pool, a tennis court, a hot tub, a gourmet kitchen, a sauna, a fitness center, and a variety of games and activities.
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.

Best Poughkeepsie, NY vacation rentals with parking

Nature's Serenity Retreat - Poughkeepsie, NY
No reviews

Nature's Serenity Retreat

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

Historic 4br Family Home Near Buttermilk Falls

apartment, 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.

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.

Zen Peaks Retreat - Poughkeepsie, NY
9.9 19 reviews

Zen Peaks Retreat

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

Hudson Valley Duplex: Hike, Sip + Explore!

house, Highland
Summit Sanctuary With Ev Ready Mountain Views - Poughkeepsie, NY
8.2 9 reviews

Summit Sanctuary With Ev Ready Mountain Views

house, Haviland
Wildflower Creekside | 4br + Suite | Pool & Sauna - Poughkeepsie, NY
9.5 4 reviews

Wildflower Creekside | 4br + Suite | Pool & Sauna

apartment, Marlboro

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.

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

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

apartment, Milton
Wildflower Creekside | 4br + Suite | Pool & Sauna - Poughkeepsie, NY
9.5 4 reviews

Wildflower Creekside | 4br + Suite | Pool & Sauna

apartment, Marlboro
Highland Mansion - Poughkeepsie, NY
8.2 12 reviews

Highland Mansion

house, Milton
Hudson Valley Estate 90 Min From Nyc Pool&gameroom - Poughkeepsie, NY
10 53 reviews

Hudson Valley Estate 90 Min From Nyc Pool&gameroom

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.

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

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

apartment, Milton
The House In Highland- Secluded Retreat - Poughkeepsie, NY
9.8 28 reviews

The House In Highland- Secluded Retreat

apartment, Highland
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