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Best Vacation rentals and Airbnb offers in Poughkeepsie, NY
9.2 24 reviews
Poughkeepsie, NY
06/29 – 08/31
$91/nighttotal: $5733 (63 )
Bucolic, Cozy Hudson Valley Studio Near All
1 2
studio , Highland
This Highland studio is located just a short 5-minute drive from the Mid Hudson Bridge and the 87 Thruway, making it easy to explore the surrounding area. The studio has received excellent ratings for its cleanliness, location, and overall experience. The cozy apartment offers a private entrance and patio, perfect for relaxing after a day of exploring. Guests can enjoy amenities like a full kitchen, a fire pit, and access to a 13-acre wetlands lake, making it ideal for nature lovers and those seeking a peaceful retreat.
9.8 14 reviews
Poughkeepsie, NY
07/27 – 12/31
$213/nighttotal: $33441 (157 )
Cabin In The Heart Of The Hudson Valley, Cabin 3
1 2
cabin , Marlboro
This Marlboro cabin is located near the Shawangunk Wine Trail and a short drive from the Walkway Over the Hudson, offering a peaceful escape in a scenic setting. The cabin has received very good user ratings, indicating a comfortable and enjoyable stay. This cozy retreat features a king-size bed, a full kitchen, a private bathroom, and a shared grill and picnic table. Guests can enjoy the quiet ambiance, relax by the electric fireplace, and explore the nearby attractions, local farm stands, breweries, and wineries.
9.9 398 reviews
Poughkeepsie, NY
08/28 – 08/29
$309/nightfor 1 night
Charming Home Near Walkway Over The Hudson
1 2
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.
Poughkeepsie, NY
06/29 – 08/31
$142/nighttotal: $8946 (63 )
Night And Armor
3 2
apartment , Poughkeepsie
This 3-bedroom, 1-bathroom apartment in Poughkeepsie offers ample space for up to 4 guests and is conveniently located for exploring local attractions and the Hudson Valley region. This family-friendly rental includes internet, air conditioning, and a kitchen, with a fitness center available on-site for your convenience.
Poughkeepsie, NY
08/22 – 08/28
$624/nighttotal: $3744 (6 )
Black Walnut Farm: 50-acres + Private Pond
1 5
apartment , Clintondale
This 50-acre Highland, NY farmhouse, near New Paltz and Poughkeepsie, offers a tranquil escape with easy access to area attractions. The property boasts a chef's kitchen, four bedrooms sleeping eight, three bathrooms, a swimming pond, fire pit, and gas grill, plus all-risk damage protection up to $1,500.
9.5 234 reviews
Poughkeepsie, NY
06/26 – 06/28
$742/nighttotal: $1484 (2 )
Historic 4br 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, less than a 10-minute drive from Walkway Over The Hudson and Downtown Poughkeepsie. The property has earned excellent ratings for location, cleanliness, and overall user experience. This 4-bedroom, 2-bathroom house can comfortably accommodate up to 10 guests. Enjoy modern amenities, a spacious kitchen, a cozy living room, and a private garden with a fire pit, all within a charming and historic setting.
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 1 review
Poughkeepsie, NY
06/26 – 06/28
$511/nighttotal: $1022 (2 )
Bridgeview Escape
1 2
apartment , Poughkeepsie
This Poughkeepsie apartment rental is located in a renovated winery building, minutes from restaurants, bars, and public transportation. The one-bedroom, one-bathroom unit sleeps two guests and features an on-site gym, sauna, and wine room, plus secure parking and keyless entry.
10 9 reviews
Poughkeepsie, NY
08/24 – 08/29
$302/nighttotal: $1510 (5 )
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.
9.7 27 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.
9.7 179 reviews
Poughkeepsie, NY
08/24 – 08/29
$202/nighttotal: $1010 (5 )
Lake Side Tiny House
1 2
house , Fairview
This Fairview house is located on a private 5-acre property in the woods, just outside of Fairview, offering a peaceful escape by the lake. The property has received excellent ratings for its location, cleanliness, and overall experience. This cozy cottage has one bedroom and one bathroom, accommodating up to two guests. The house is equipped with a kitchen, air conditioning, and a garden, perfect for enjoying meals, relaxing, and exploring the natural surroundings.
Poughkeepsie, NY
08/24 – 08/29
$277/nighttotal: $1385 (5 )
Industry Style Open Concept Downtown
2 2
apartment , Poughkeepsie
This 2-bedroom, 1-bathroom apartment in Poughkeepsie is located in a district offering easy access to local attractions, including the Walkway Over the Hudson State Historic Park, a significant local landmark. This well-appointed unit accommodates up to 6 guests and includes internet, a kitchen, and air conditioning, with convenient access to downtown Poughkeepsie businesses and transportation routes for exploring the Hudson Valley.
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.
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 10 reviews
Poughkeepsie, NY
07/27 – 12/31
$268/nighttotal: $42076 (157 )
(30+ Days) Relaxing Escape In The Hudson Valley
3 2
apartment , Highland
This Highland apartment is situated in a picturesque location, with stunning views of the surrounding countryside and easy access to outdoor activities. It has excellent user, location, and cleanliness ratings. The apartment features a spacious and open layout, with 3 bedrooms, 2 bathrooms, and a guest capacity of 6. Guests can enjoy a private outdoor space with a BBQ and a swimming pool (seasonal), as well as a fully equipped kitchen and amenities such as a TV and access to a shared laundry room.
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
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.
Best Poughkeepsie, NY vacation rentals with parking
9.4 3 reviews
Poughkeepsie, NY
08/24 – 08/29
$369/nighttotal: $1845 (5 )
Scenic Hudson Valley Getaway Farms & Vineyards
2 2
cottage , Marlboro
This Marlboro, NY cabin rental boasts a secluded 10+ acre setting near top-rated Hudson Valley vineyards, a 90-minute drive from New York City, and close to attractions like the Walkway Over the Hudson State Historic Park and Franny Reese State Park. This two-bedroom, one-bathroom cottage sleeps four, offering air conditioning, internet access, and pet-friendly accommodations; nearby activities include winery tours, McCann Ice Arena, and exploring Marlboro's local breweries and restaurants.
9.8 54 reviews
Poughkeepsie, NY
08/22 – 08/28
$423/nighttotal: $2538 (6 )
Summit Sanctuary: Ev Ready Mountain Views
4 5
apartment , Haviland
This Haviland bed and breakfast is in a family-friendly neighborhood with stunning mountain views. Guests consistently rate the location, cleanliness, and overall experience as excellent. The cozy inn has one bathroom and can accommodate up to six guests. Amenities include a full kitchen with a fridge, freezer, microwave, and dishwasher, as well as air conditioning, a garden, parking, and internet access. Pets are welcome, making this a great option for families.
10 32 reviews
Poughkeepsie, NY
07/27 – 12/31
$213/nighttotal: $33441 (157 )
Cabin In The Heart Of The Hudson Valley, Cabin 1
1 2
cabin , Marlboro
This cozy cabin is located in Newburgh, just a short drive from Marlboro, and is near popular attractions like the Shawangunk Wine Trail, Minnewaska State Park Preserve, and Angry Orchard. It has consistently received excellent user ratings, making it a popular choice for travelers. This charming cottage offers 150 square feet of space, comfortably accommodating up to 2 guests, and features a fully equipped kitchen, a private garden, and a shared grill for outdoor dining. The cabin is also equipped with central air conditioning and heating, a comfortable queen-size bed, and a small electric fireplace for ambiance, ensuring a relaxing and enjoyable stay.
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.
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?
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?
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.
Destinations nearby
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.
Poughkeepsie, NY
06/27 – 06/28
$1031/nightfor 1 night
Luxury 4br Home With Mountain Views
1 5
house , Clintondale
This luxury house in Highland offers mountain views and is located approximately 9 miles from Loren Campbell Baseball Field and Bardavon Opera House, with SUNY New Paltz just under 9 miles away. This air-conditioned accommodation features 1 bedroom, 3 bathrooms, a full kitchen, free WiFi, and accommodates up to 15 guests, with a terrace providing garden views and direct access to balconies.
10 6 reviews
Poughkeepsie, NY
08/22 – 08/28
$373/nighttotal: $2238 (6 )
Beautiful Home With Hudson River Views & Adjacent Rushing Waterfall In Hyde Park
3 5
apartment , Hyde Park
This Hyde Park cottage offers direct Hudson River views across from the Vanderbilt Mansion's Lower Gate and is within walking distance to FDR's Home & Library, providing a scenic and historically rich setting. This 3-bedroom vacation rental accommodates up to 7 guests with a fully equipped kitchen, a wood-burning fireplace, a 55" TV, and direct access to hiking trails, all within a short drive to Norrie Point for kayaking.
8.8 7 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 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.
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.
10 1 review
Poughkeepsie, NY
06/27 – 06/28
$2863/nightfor 1 night
The New Paltz Moondance Ridge
1 5
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.
Poughkeepsie, NY
08/22 – 08/28
$296/nighttotal: $1776 (6 )
Bright Highland Home Near New Paltz And Walkway
1 5
apartment , Highland
This Highland rental home is located minutes from New Paltz, the Walkway Over the Hudson, Mohonk, Minnewaska, local orchards, wineries, and hiking trails. This updated, open-concept apartment accommodates up to 6 guests with 3 bedrooms, featuring a king, queen, and twin bed, a kitchen with a fridge and microwave, air conditioning, internet, and a smart TV.
Poughkeepsie, NY
06/26 – 06/27
$1094/nightfor 1 night
Gindelle Suite Buttermilkfalls
1 4
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.
9.9 146 reviews
Poughkeepsie, NY
06/27 – 06/28
$383/nightfor 1 night
2br|1 King 1 Queen Bed|balcony|parking|strong Wifi
1 5
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.