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Best Vacation rentals and Airbnb offers in Poughkeepsie, NY
10 47 reviews
Poughkeepsie, NY
08/22 – 08/28
$1569/nighttotal: $9414 (6 )
Hudson Valley Estate 90 Min From Nyc Pet Friendly
1 5
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.
9.9 34 reviews
Poughkeepsie, NY
06/29 – 08/31
$347/nighttotal: $21861 (63 )
Monthly Rental: Ridgetop Wooded Retreat
4 2
apartment , Poughkeepsie
This modern, dual-level apartment rental in Poughkeepsie's desirable Spackenhill neighborhood, a 90-minute drive from New York City, offers easy access to the Hudson Valley. The 4,200-square-foot residence boasts a spacious layout sleeping up to eight guests, featuring a saltwater pool (open June 15-October 15), a fully equipped kitchen, a lower-level entertainment area with a pool table, and high-speed internet.
9.6 5 reviews
Poughkeepsie, NY
06/27 – 07/04
$480/nighttotal: $3360 (7 )
Charming 4-bedrm Colonial Farmhouse Amidst The Mountains With Wifi In Highland.
4 8
apartment , Highland
This refurbished colonial farmhouse rental in Highland, New York, is located 30 minutes from the Mohonk Mountains and Lake Minnewaska, and 5 minutes from a rail trail ideal for biking. This four-bedroom, three-bathroom house sleeps ten guests and features WiFi, fitness equipment, air conditioning, and proximity to Apple Greens Golf Course, Mid-Hudson Children's Museum, and other Highland attractions.
Poughkeepsie, NY
06/29 – 08/31
$684/nighttotal: $43092 (63 )
Charming Home In Hudson Valley, With A Seasonal Pool, 2 Hours From Nyc
3 2
apartment , Highland
This 3-bedroom Highland apartment is located about a 2-hour drive from New York City, near the Walkway Over the Hudson State Historic Park and the Mid-Hudson Bridge, offering a peaceful retreat surrounded by trees and greenery. The apartment provides a sense of privacy while being close to many attractions. The apartment features a spacious open layout with two living rooms, a dining area, and a well-equipped kitchen, comfortably accommodating up to 7 guests. The apartment offers amenities such as a pool, dining area, lounge chairs, umbrellas, and a BBQ for outdoor relaxation and entertainment, as well as nearby hiking, kayaking, biking, breweries, wineries, and other upstate attractions.
10 9 reviews
Poughkeepsie, NY
08/28 – 08/29
$350/nightfor 1 night
Bella Woods ~ A Hidden Gem In The Heart Of It All~
1 2
apartment , Highland
This Highland duplex apartment is located less than a mile from the Walkway Over the Hudson, the Hudson Valley Rail Trail, and Highland Landing Park, offering easy access to major attractions and public transportation. This one-bedroom, one-bathroom unit sleeps four guests and features a fully equipped kitchen, air conditioning, swimming pool, parking, and is ideal for exploring the Hudson Valley.
10 78 reviews
Poughkeepsie, NY
08/22 – 08/28
$1469/nighttotal: $8814 (6 )
Luxe Wooded Modern Getaway, Saltwater Pool + Spa
1 5
apartment , Crown Heights
This modern house is located in Wappingers Falls, a 90-minute drive from New York City, offering easy access to the Hudson Valley's natural beauty and cultural attractions. The property has consistently received excellent ratings for its location, cleanliness, and overall experience. The home features three bedrooms and two bathrooms, comfortably accommodating up to six guests. Amenities include a fully equipped kitchen, a private pool and hot tub, a fitness center, and a Peloton bike for a convenient workout.
Poughkeepsie, NY
06/29 – 08/31
$28/nighttotal: $1764 (63 )
Mini Yurt Camping With 2 Cots
1 2
yurt , Fairview
This Fairview yurt rental offers a unique, intimate stay in a small community, providing full access to shared indoor bathroom, kitchen, and living room facilities. The 1-bedroom, 1-bathroom yurt sleeps 2 guests, features a microwave, fridge, freezer, and dishwasher, and includes outdoor stargazing with provided cots and optional bedding.
9.7 7 reviews
Poughkeepsie, NY
08/24 – 08/29
$158/nighttotal: $790 (5 )
View On Vineyard.
1 2
apartment , Highland
This Highland, New York apartment rental is centrally located in the Hudson Valley, minutes from the Walkway Over the Hudson, Mohonk Preserve, and local restaurants. The 500+ square-foot unit features one bedroom, one bathroom, sleeps two, and includes a kitchen with a fridge, freezer, and microwave, air conditioning, a swimming pool, a garden, parking, and internet access; nearby activities include apple picking, wine tasting, and access to numerous hiking trails.
9.6 86 reviews
Poughkeepsie, NY
08/24 – 08/29
$692/nighttotal: $3460 (5 )
Beautiful Home - 4br/2.5ba - Hot Tub And Patio - Minutes From New Paltz
4 2
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.
Poughkeepsie, NY
06/27 – 06/28
$247/nightfor 1 night
Elixir Apartment
2 5
apartment , Clintondale
Elixir Apartment in Highland offers proximity to SUNY New Paltz and Historic Huguenot Street, both 6 miles away, with convenient access to Loren Campbell Baseball Field (6.1 miles) and Bardavon Opera House (8.2 miles). This pet-friendly apartment features air conditioning, complimentary WiFi, free private parking, a fully equipped kitchen, and garden access, located 10 miles from Vassar College and 16 miles from Stewart International Airport.
9.5 191 reviews
Poughkeepsie, NY
06/26 – 06/28
$337/nighttotal: $674 (2 )
Historic 1 Br Family Home Near Buttermilk Falls
1 2
apartment , Milton
This historic home is located in Milton, New York, directly across the street from Buttermilk Falls Resort & Spa and Henry's at the Farm Restaurant, with the Hudson River just a short walk away. It consistently receives excellent ratings for its location, cleanliness, and overall guest experience. The house features a spacious kitchen, a full bath, a living room, a sunroom, and a large garden. It can accommodate up to four guests and allows one well-behaved dog per stay. Guests can enjoy amenities like a fire pit, Adirondack chairs, and Roku Guest Mode for streaming services.
Poughkeepsie, NY
08/24 – 08/29
$715/nighttotal: $3575 (5 )
Hudson Escape W/ Hot Tub + Bridge View
3 2
apartment , Highland
This waterfront apartment in rural Highland offers an idyllic setting, located a 4-minute drive from the Walkway Over the Hudson State Historic Park and a 15-minute walk from the Hudson River. This spacious 18,300 sq ft residence accommodates up to 6 guests with 3 bedrooms and 1.5 bathrooms, featuring a full kitchen, air conditioning, Wi-Fi, a hot tub, and a garden, with on-site parking available.
Top Vacation Rentals for Families in Poughkeepsie, NY
Ideal for family vacations, these Poughkeepsie, NY rentals or Airbnbs offer spacious layouts near top city attractions.
9.7 26 reviews
Poughkeepsie, NY
08/22 – 08/28
$1236/nighttotal: $7416 (6 )
Modern Designer Cabin In Woods W/ 5-star Amenities
1 5
cabin , Highland
This Highland, NY A-frame log cabin boasts a secluded location on two wooded acres, a short 10-minute drive from both New Paltz and Poughkeepsie. This four-bedroom, four-bathroom house sleeps eight guests and features a 100-inch screen theater room, game room, private gym, saltwater pool, cedar barrel sauna, hot tub, and multiple fireplaces.
9.9 356 reviews
Poughkeepsie, NY
08/24 – 08/29
$258/nighttotal: $1290 (5 )
Orchard Views From A Light-filled Tiny Home With A Fire Pit
1 2
cabin , Marlboro
This charming farmhouse is located in the Shawangunk wine trail region, just 20 minutes from the Beacon train station and 90 minutes from New York City, offering a peaceful escape surrounded by vineyards and orchards. It has received excellent ratings for location, cleanliness, and overall user experience. The 276 square foot farmhouse comfortably accommodates up to 4 guests and features a lofted bedroom, a reading nook, and a well-designed layout that maximizes space. Enjoy the farm-fresh eggs from the nearby chicken coop, relax by the fire pit, and take advantage of the luxurious amenities like a king-sized memory foam mattress and high-end toiletries.
10 21 reviews
Poughkeepsie, NY
08/22 – 08/28
$798/nighttotal: $4788 (6 )
The House In Highland-\nsecluded Retreat
3 5
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.
9.8 105 reviews
Poughkeepsie, NY
06/27 – 06/28
$668/nightfor 1 night
Beautiful, Fun, Spacious 5 Acre Family Retreat
1 5
apartment , Fairview
This Fairview home is located just a short distance from the Dutchess Rail Trail, the Walkway Over the Hudson, and Vassar College, making it a convenient base for exploring the area. The apartment has earned excellent ratings for cleanliness, location, and overall user experience. This 3-bedroom, 2-bathroom rental comfortably accommodates up to 11 guests. The home offers a spacious garden room, a modern kitchen, and a balcony with views of the surrounding wildlife, as well as a private garden, parking, and a unique location near a brewery and tasting room.
Best Poughkeepsie, NY vacation rentals with parking
9.4 9 reviews
Poughkeepsie, NY
06/21 – 06/26
$205/nighttotal: $1025 (5 )
Stylist And Spacious Centrally Located One Bedroom Apartment
1 2
apartment , Poughkeepsie
This Poughkeepsie vacation rental is conveniently located within a 10-minute walk of the Mid-Hudson Civic Center, McCann Ice Arena, and the Mid-Hudson Heritage Center, and a short walk from the Poughkeepsie train station. This two-bedroom, one-bathroom house sleeps three guests and offers a fully equipped kitchen, a sofa bed, smart TV, free on-site parking, and Wi-Fi.
8.8 18 reviews
Poughkeepsie, NY
08/24 – 08/29
$1192/nighttotal: $5960 (5 )
The Scenic Mansion With Breathtaking View
4 2
house , Milton
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.
10 5 reviews
Poughkeepsie, NY
06/26 – 06/28
$591/nighttotal: $1182 (2 )
Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat
3 2
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.
10 33 reviews
Poughkeepsie, NY
08/24 – 08/29
$367/nighttotal: $1835 (5 )
The Secret Cottage
A Rare Find In Prime Location
1 2
house , Crown Heights
This charming cottage is located in the Hudson Valley, a short distance from restaurants, a mall, and Metro North. The area offers a peaceful retreat with easy access to amenities and transportation. This private one-bedroom home comfortably accommodates three guests. The open-layout design seamlessly integrates the outdoors with the interior space, creating a spacious and airy feel. The cottage features a fully equipped kitchen, air conditioning, a private garden, and a covered patio with garden views. Enjoy morning coffee or evening relaxation on the patio, watch the magical fireflies, or take advantage of the convenient location for exploring the area.
Frequently Asked Questions about vacation rentals in Poughkeepsie, NY
What are the top family-friendly attractions in Poughkeepsie, NY?
The Mid-Hudson Children's Museum is a fun and educational place for kids. The Poughkeepsie Farm Project is a great place to learn about agriculture and enjoy some fresh air. The Walkway Over the Hudson is also a great family-friendly spot, especially for a bike ride or a walk.
What are the best Airbnb and vacation rentals 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, spring and fall. The weather is still pleasant, but the crowds are smaller and the prices are lower. Avoid peak season, which is summer, as prices are higher and it can be crowded.
What are the most popular Airbnbs in Poughkeepsie, NY?
What are the best budget-friendly activities in Poughkeepsie, NY?
The Walkway Over the Hudson is free to walk or bike. The Poughkeepsie Farm Project offers free tours and events. The Vassar College campus is free to explore, and you can enjoy the beautiful architecture and gardens.
What are the best vacation rentals with a pool in Poughkeepsie, NY?
What are the best restaurants with local dishes in Poughkeepsie, NY?
Try the Hudson Valley Restaurant, they specialize in local dishes with fresh ingredients. The Arlington is a popular spot for a more upscale dining experience. If you're looking for something casual, try the Smokehouse BBQ for some delicious barbecue.
What are the best rentals for families and kids in Poughkeepsie, NY?
What are the best walking or cycling routes in Poughkeepsie, NY?
The Walkway Over the Hudson is a popular spot for walking and biking. The Dutchess Rail Trail is another great option for a scenic bike ride. The Vassar College campus is also a good place to walk around and enjoy the beautiful architecture and gardens.
What are the best rentals or Airbnbs with a jacuzzi in Poughkeepsie, NY?
Are there pet-friendly attractions in Poughkeepsie, NY?
The Walkway Over the Hudson is pet-friendly. The Poughkeepsie Farm Project is also pet-friendly, but it's best to check their website for specific rules.
Destinations nearby
Best 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.
9.0 14 reviews
Poughkeepsie, NY
08/22 – 08/28
$469/nighttotal: $2814 (6 )
Summit Sanctuary: Ev Ready Mountain Views
4 5
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.
Poughkeepsie, NY
06/27 – 06/28
$701/nightfor 1 night
Lucious Lagrangeville
1 5
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.
9.0 6 reviews
Poughkeepsie, NY
08/22 – 08/28
$522/nighttotal: $3132 (6 )
Summit Sanctuary With Ev Ready Mountain Views
4 5
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.
10 1 review
Poughkeepsie, NY
06/27 – 07/04
$2433/nighttotal: $17031 (7 )
The New Paltz Moondance Ridge
1 8
house , New Paltz
This estate is located in a tranquil area offering garden views, providing a peaceful retreat near New Paltz. This 4700 square foot residence accommodates up to 35 guests with 1 bedroom, 5 bathrooms, air conditioning, internet, a kitchen, a swimming pool, jacuzzi, terrace, sauna, and parking.
Our Favorite Pet-Friendly Vacation Rentals in Poughkeepsie, NY
Travel with ease to Poughkeepsie, NY with pet-friendly rentals located near local dog parks and scenic city walks.
9.9 146 reviews
Poughkeepsie, NY
06/29 – 08/31
$212/nighttotal: $13356 (63 )
2br|1 King 1 Queen Bed|balcony|parking|strong Wifi
1 2
apartment , Poughkeepsie
This Poughkeepsie apartment is conveniently located within walking distance of local restaurants, breweries, and the Walkway Over the Hudson, offering easy access to the city's attractions. The apartment consistently receives excellent ratings for its location, cleanliness, and overall user experience. This two-bedroom, one-bathroom rental can comfortably accommodate up to six guests. Enjoy a fully equipped kitchen, two balconies, 125 cable TV channels, a Roku TV, and a relaxing ambiance, perfect for a comfortable and enjoyable stay.
9.8 192 reviews
Poughkeepsie, NY
08/24 – 08/29
$159/nighttotal: $795 (5 )
Your Own Pied-a-terre "Walkway Over The Hudson" #1
1 2
apartment , Poughkeepsie
This studio apartment is conveniently located in central Poughkeepsie, just a short distance from the Dutchess County Civic Center, Marist and Vassar Colleges, Vassar Brothers Medical Center, the Walkway Over the Hudson, the train station, and Hudson River Park. The apartment has received excellent ratings for its cleanliness, location, and overall user experience. The studio has a private entrance and parking, and can accommodate up to two guests. You'll enjoy amenities such as a fully equipped kitchen, air conditioning, a private garden, and complimentary bicycles for exploring the nearby Walkway Over the Hudson and Rail Trails.
10 5 reviews
Poughkeepsie, NY
06/21 – 06/26
$243/nighttotal: $1215 (5 )
Wonderful Washington
1 2
apartment , Poughkeepsie
This 4-bedroom, 2-bathroom apartment in Poughkeepsie offers a prime central location in the Mid-Hudson Valley, within walking distance to Marist University, Walkway Over the Hudson, Mid Hudson Regional Hospital, and Palace Diner. The spacious residence accommodates up to 9 guests and features a full kitchen, air conditioning, and internet, with 30+ day bookings available starting mid-March, making it ideal for those visiting Marist University or working at nearby medical facilities.
8.9 11 reviews
Poughkeepsie, NY
08/28 – 08/29
$543/nightfor 1 night
Quiet Hudson Valley Escape
1 2
apartment , Highland
This Highland, NY apartment is conveniently located near the Mid-Hudson Bridge, offering easy access to Marist College and Vassar College, and the Walkway Over the Hudson. This three-bedroom, three-bathroom rental sleeps six guests and features a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, plus air conditioning, parking, and internet access.