Pleasant Valley holiday homes

We found 136 holiday rentals — enter your dates for availability
Discover a selection of 7 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:4 Dec - 11 Dec

Dining
Private kitchen
Outdoor dining
Room
Exceptional
(16 reviews)

Modern Hudson Valley Creekside Retreat + Hot Tub!

Hyde Park

16% off
NZ$6,458
for 7 nights, 1 cottage
NZ$923 per night
includes taxes & fees
Modern Hudson Valley Creekside Retreat + Hot Tub!
A Special Place for Your Special Times!  4 bedroom, 3.5 baths, Full Kitchen, Kitchenette, 2 Living Areas, 2 Dining Areas, Full access to backyard with dining area, fire pit with adirondack chairs, BBQ grill, hammock on 2 acres of land.
Dining
A cozy bedroom boasts a unique charm with its stone wall and wide plank flooring.  Queen size bed with luxury linens you'll find it hard to leave. For your comfort we installed a MiniSplit system for heating and AC.  Creating warm ambiance to enjoy.
For those moments when you prefer a more private escape, we've created a tranquil area in the front yard.
Exceptional
(25 reviews)

Spacious 4BD Country Gem - Fire Pit & Chill Vibes

Highland

7% off
NZ$5,273
for 7 nights, 1 home
NZ$753 per night
includes taxes & fees
Spacious 4BD Country Gem - Fire Pit & Chill Vibes
Exterior
Living area
Property grounds
Interior
Exceptional
(35 reviews)

Hidden Charm in Hudson Valley In Dutchess County

Salt Point

8% off
NZ$7,285
for 7 nights, 1 home
NZ$1,041 per night
includes taxes & fees
Hidden Charm in Hudson Valley In Dutchess County
Settle into the many comfy seats in the Family Room.
Whip up delicious meals in the spacious, bright kitchen with ample counter space
Comfortably seats 8 and also doubles as a large board game table.
View of valley and lush evergreens. Queen bed. Spacious closet
Exceptional
(40 reviews)

Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz

Highland

8% off
NZ$7,501
for 7 nights, 1 home
NZ$1,072 per night
includes taxes & fees
Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz
Private kitchen
Living area
Outdoor dining
Property grounds
Exceptional
(8 reviews)

6 Acre Private Hudson Valley Estate

Highland

8% off
NZ$18,402
for 7 nights, 1 home
NZ$2,629 per night
includes taxes & fees
6 Acre Private Hudson Valley Estate
The Enchanted Forest beckons!
Feel the awe of the 20 foot vaulted ceilings and windows onto the woods
It's mesmerizing to watch and hear the roaring waterfall from this bridge.
Sitting in the living room area, you feel nestled in the woods.
Exceptional
(20 reviews)

Hudson Valley stunning lake side modern barn in an Enchanted Forest

Clinton Corners

8% off
NZ$6,349
for 7 nights, 1 home
NZ$907 per night
includes taxes & fees
Hudson Valley stunning lake side modern barn in an Enchanted Forest
Here's the spacious farmhouse kitchen. A leaf expands the table to seat 6.
George Washington was president when these original hardwood floors were made!
Our home sits on 5 partially-wooded acres. Welcome to the country!
This sitting area is another great space to gather around the faux fireplace.
Exceptional
(19 reviews)

Historic 4 BR Family Home Near Buttermilk Falls & Hudson River, on 5 Acres

Milton

16% off
NZ$4,352
for 7 nights, 1 home
NZ$622 per night
includes taxes & fees
Historic 4 BR Family Home Near Buttermilk Falls & Hudson River, on 5 Acres
Main bedroom with king bed and private full bath and walk in closet.
Exterior
Dinning room & Kitchen. Original exposed beams.
View from front lawn
Exceptional
(11 reviews)

Cheerful Circa 1700 3 Bedroom Farmhouse

Hyde Park

30% off
NZ$5,280
for 7 nights, 1 home
NZ$754 per night
includes taxes & fees
Cheerful Circa 1700 3 Bedroom Farmhouse
Interior
Interior
Interior
Interior
Exceptional
(5 reviews)

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Poughkeepsie

6% off
NZ$6,082
for 7 nights, 1 home
NZ$869 per night
includes taxes & fees
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Do you enjoy cooking/baking? High-end kitchen with everything you need.
Open floor plan is great for groups
Plenty of space for outdoor dining and hanging out
Front entrance is a sun room in the 
winter and porch in the summer.
Exceptional
(6 reviews)

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Millbrook

8% off
NZ$6,247
for 7 nights, 1 home
NZ$892 per night
includes taxes & fees
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

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)
  • New Paltz Golf Course (13.6 mi / 21.9 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)

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:

  • Walkway Over the Hudson State Historic Park (7.1 mi / 11.4 km)
  • Bowdoin Park (11.7 mi / 18.9 km)
  • Whaley Lake (15.3 mi / 24.5 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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