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Pleasant Valley holiday homes

We found 145 holiday rentals — enter your dates for availability

Discover a selection of 8 homes and other holiday rentals in Pleasant Valley that are perfect for your trip. Holiday homes provide the best amenities for your family, friends or furry companion, such as Wi-Fi and a fireplace. Whatever you're looking for, you'll find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Pleasant Valley

Showing deals for:2 Jan - 9 Jan
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Why visit Pleasant Valley

  • Stunning outdoor adventures: Pleasant Valley boasts beautiful parks and scenic surroundings, perfect for nature lovers and outdoor enthusiasts.
  • Rich cultural experiences: Explore historic sites, charming local attractions, and a welcoming community vibe that enhances your visit.
  • Family-friendly atmosphere: The area is ideal for families, offering a variety of activities and attractions for all ages.
  • Historic bridges and colleges: Discover the unique blend of modern education and historical architecture in the region.
  • Proximity to nearby cities: Enjoy easy access to vibrant business districts and additional historical sites just a short drive away.

Top attractions near Pleasant Valley

Pleasant Valley, New York, offers a delightful mix of outdoor adventures and cultural experiences, making it perfect for holidaymakers. Explore historic sites, beautiful parks, and a local library while enjoying the scenic surroundings. You can also visit modern colleges and historic bridges, ensuring fun for families and solo travellers alike. Don't forget to grab a map of the area to make the most of your visit to this charming destination.

  • Vanderbilt Mansion National Historic Site: This grand historic house offers a glimpse into the opulent life of the Gilded Age, surrounded by stunning gardens and views of the Hudson River, making it a serene cultural retreat.
  • Vassar College: A prestigious modern institution, Vassar boasts beautiful architecture and vibrant campus life, offering a lively atmosphere enriched by art and academic pursuits.
  • Culinary Institute of America: Renowned for its culinary education, this historic college combines rich traditions with innovative techniques, offering delightful dining experiences and cooking demonstrations.

Things to do recommended for couples

For a romantic getaway in Pleasant Valley, explore Millbrook Vineyards and Winery or Clinton Vineyards, both offering delightful wine experiences just a short drive away. Don't miss the live music at The Falcon, perfect for a cozy evening together.

Things to do recommended for families

Your family will love SplashDown Beach, a thrilling waterpark 22.5km from Pleasant Valley. For a more relaxed vibe, visit Richard L. Skimin Memorial Baseball Field, 8.0km away, or enjoy the serene Bowdoin Park, located 19.3km from town, perfect for unwinding together.

Things to do recommended for groups

Enjoy a fun night at the Overlook Drive-In Theater, catch a show at the Chance Theater for a cultural experience, or indulge in shopping and dining at Poughkeepsie Galleria, all within a short drive from Pleasant Valley.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Pleasant Valley

If you're planning a trip with friends, family, or pets, or if you're considering a longer stay, it's important to refine your search based on your priorities. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Pleasant Valley with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group get-togethers. Luckily, you can easily narrow down your options for all of these and more on Vrbo.
  • Traveling to Pleasant Valley with young kids: Navigating travel with young kids can be quite a task. It’s essential to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Pleasant Valley: For many families, a holiday isn't truly fulfilled without their furry companion by their side. If that resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly options come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Pleasant Valley: If you’re in search of holiday rentals with special offers for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay near Pleasant Valley

Pleasant Valley, NY, is a hidden gem in the Hudson Valley, offering stunning outdoor adventures and beautiful scenery. With a family-friendly atmosphere and a warm community vibe, you’ll find plenty to explore, from charming local attractions to breathtaking surroundings. Nearby cities also present a mix of historical sites and vibrant business districts, making it an ideal spot for a well-rounded vacation. Embrace the unique experiences that Pleasant Valley has to offer during your stay.

  • Hyde Park: Nestled just 6.4km from Pleasant Valley, Hyde Park presents a delightful blend of outdoor activities and cultural experiences. Visitors can discover the rich history of the area, including the notable Franklin D. Roosevelt Presidential Library and Museum. The city is perfect for families, offering scenic parks and educational outings. Adventure seekers can indulge in skiing during the winter months or explore the beautiful nearby lakes. With charming shopping areas, Hyde Park is an excellent spot to enjoy both recreation and relaxation.
  • Rhinebeck: Located 20.9km from Pleasant Valley, Rhinebeck is a picturesque town known for its stunning scenery and outdoor adventures. The area is ideal for those looking to connect with nature, with the nearby mountains and lakes providing ample opportunities for hiking, skiing, and photography. Rhinebeck's vibrant arts scene and historic charm make it a perfect destination for a day trip. Don't miss the chance to visit local institutes and explore the quaint shops and eateries that line the streets, offering a taste of the region's culture.
  • Millbrook: Just 11.3km from Pleasant Valley, Millbrook is a charming town that combines romance and adventure in a serene setting. Known for its beautiful landscapes, visitors can enjoy skiing or hiking in the nearby mountains. The area is rich in history, with several historic sites to explore. The lovely lakes provide a perfect backdrop for a romantic picnic or leisurely day out. Millbrook is an ideal destination for those seeking both outdoor thrills and a touch of tranquility during their vacation.

Best time to go to Pleasant Valley

If you're planning a trip to Pleasant Valley, it's a good idea to check both the weather and property rates. The warmest month is July.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January27.5°F (-2.5°C)Light RainMostly SunnyAverage
February29.3°F (-1.5°C)Light RainMostly SunnyAverage
March36.9°F (2.7°C)Light RainMostly SunnyAverage
April48.4°F (9.1°C)Light RainMostly SunnySlightly High
May59.4°F (15.2°C)Light RainMostly SunnyAverage
June67.5°F (19.7°C)Light RainMostly SunnyAverage
July73.8°F (23.2°C)Light RainMostly SunnySlightly High
August71.8°F (22.1°C)Light RainMostly SunnyAverage
September64.6°F (18.1°C)Light RainMostly SunnySlightly High
October53.6°F (12.0°C)Light RainMostly SunnySlightly Low
November41.5°F (5.3°C)Light RainMostly SunnySlightly Low
December33.4°F (0.8°C)Light RainMostly SunnySlightly Low

Booking with Vrbo is simple

Are you keen to save on your upcoming adventure? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can enjoy substantial savings by opting for a longer stay. To discover a Vrbo property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s clever Trip Board offers you a convenient way to plan your adventures, pick up right where you left off, or keep track of your arrangements. You can easily find the properties you’ve saved or booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Book a holiday rental for your Pleasant Valley getaway

The parks and other outdoor surroundings create an inviting atmosphere in Pleasant Valley. This city is well-known for its shopping and restaurants. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Pleasant Valley

Do you want to find attractions to see while you're in town? Venture out of your cosy holiday rental and experience everything that Pleasant Valley has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Millbrook Vineyards and Winery (9.6 mi / 15.4 km)
  • Benmarl Vineyards and Winery (13.4 mi / 21.5 km)
  • SplashDown Beach (14.3 mi / 23 km)
  • Mohonk Golf Course (16.3 mi / 26.3 km)
  • Thunder Ridge Ski Resort (20.5 mi / 33.1 km)
  • McCann Ice Arena (6.2 mi / 10 km)

Exploring the natural landscape of Pleasant Valley

Whether you're an active traveller or just want to take in the scenery, Pleasant Valley is a great place to get out in nature. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Innisfree Garden (3.9 mi / 6.2 km)
  • Walkway Over the Hudson State Historic Park (7.1 mi / 11.4 km)
  • Kingston Point Beach (14.8 mi / 23.8 km)
  • Esopus Creek (16.8 mi / 27.1 km)
  • Mohonk Lake (17.4 mi / 28 km)
  • Hudson Highlands State Park (22 mi / 35.5 km)

Travelling to and around Pleasant Valley

The nearest airport is in Newburgh, NY (SWF-Stewart Intl.), located 21.7 mi (35 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Danbury, CT (DXR-Danbury Municipal), which is 31 mi (49.9 km) away.

Frequently asked questions

How much does it cost to rent a holiday home in Pleasant Valley?
Property type, length of stay and season are some of the conditions that can influence the price of a holiday home. Simply add your travel dates to find your perfect escape. From cosy cabins to plush villas, all Bookabach holiday homes provide unbeatable value.
How much does it cost to rent a beach house in Pleasant Valley?
The average price for a holiday home close to the beach in Pleasant Valley depends on when you're going and the type and size of property you want. Find prices easily on Bookabach by entering the dates you'll be travelling. Then use our filters to pick the number of bedrooms and amenities essential to you, like air conditioning, a pool and WiFi.
What are the top attractions for families in Pleasant Valley?
Keeping the kids amused during your Pleasant Valley holiday is a cinch with these top family-friendly attractions:

  • Hyde Park Historical Society Museum
  • Hyde Park Railroad Station
  • Mid-Hudson Childrens Museum

How old do you have to be to rent a holiday home in Pleasant Valley?
You'll need to check with the Pleasant Valley holiday home you want on Bookabach as the minimum age varies. However, generally it's 16, 18 or 21.
How long can I rent a holiday home in Pleasant Valley for?
How long you can book a holiday home in Pleasant Valley differs according to the property. Simply enter your chosen dates to see a list of options offering extended stays. With loads of features such as air conditioning and kitchens, as well as some offering weekly or monthly discounts, you're sure to discover somewhere perfect to call your home away from home in Pleasant Valley.

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