Pleasant Valley vacation rentals

We found 128 vacation rentals — enter your dates for availability

Discover a selection of 7 homes and other vacation rentals in Pleasant Valley that are perfect for your trip. Vacation homes provide the best amenities for your stay with friends, family, or just your pet, like air conditioning and WiFi. At the end of the day, you'll find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

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Find out more about Pleasant Valley

Why visit Pleasant Valley

  • Outdoor Adventures: Pleasant Valley is perfect for nature lovers, offering activities like hiking and tranquil walks along Wappinger Creek.
  • Rich History: Explore historic bridges and significant sites that showcase the area's cultural heritage.
  • Family-Friendly Vibes: A welcoming atmosphere makes it ideal for family vacations with plenty of activities for all ages.
  • Diverse Accommodations: Choose from cozy cottages, vacation homes, and comfortable apartments to suit your needs.
  • Proximity to Urban Areas: Enjoy a peaceful retreat while being a short drive from bustling cities.

Popular types of accommodation in Pleasant Valley

Planning a getaway to Pleasant Valley? You're in for a treat. This charming destination offers a variety of accommodations to suit your needs, including houses, cozy cottages, and comfortable apartments. Whether you're searching for affordable rentals, a studio apartment, or an apartment for rent, you'll find the perfect spot to unwind and enjoy your stay. Explore your options and make your vacation memorable in Pleasant Valley.

  • Houses: The top choice for visitors to Pleasant Valley, these homes offer ample space and amenities, perfect for families or groups.
  • Cottages: A charming option that provides a cozy atmosphere, ideal for couples or those seeking a quaint retreat.
  • Apartments: Convenient and versatile, these rentals are great for solo travelers or small groups looking for a central location.
  • Cabins: Embrace the outdoors with rustic cabins, perfect for those who want to experience nature up close.
  • Chalets: These unique structures offer a blend of comfort and mountain charm, great for a memorable getaway.**

Top attractions near Pleasant Valley

Pleasant Valley, New York, is an ideal destination for outdoor enthusiasts and adventure seekers. Visitors can explore a variety of attractions, including a modern college, historic bridges, and significant sites that offer a glimpse into the area's rich culture. Whether you're traveling with family or seeking a scenic getaway, Pleasant Valley has something for everyone, making it a perfect spot for a memorable vacation experience.

  • Vassar College: A beautiful blend of historic architecture and modern facilities, Vassar College offers a vibrant campus atmosphere with art galleries, lush gardens, and cultural events that reflect city vibes.
  • Culinary Institute of America: Renowned for its culinary excellence, this historic institution features stunning buildings, offers cooking demonstrations, and provides a taste of rich culinary culture, making it a must-visit for food enthusiasts.
  • Omega Institute: A serene retreat with a focus on wellness and self-discovery, Omega Institute combines historical significance with urban vibes, offering workshops, nature trails, and an opportunity for personal growth.

Things to do recommended for couples

Planning a romantic getaway in Pleasant Valley? Enjoy a wine tasting at Millbrook Vineyards and Winery or Clinton Vineyards, both offering enchanting atmospheres. For live music, head to Live At The Falcon for an entertaining evening. These experiences promise to create unforgettable memories together.

Things to do recommended for families

Families visiting Pleasant Valley can have a splashing good time at SplashDown Beach, just 14 miles away, or enjoy relaxation at the Richard L. Skimin Memorial Baseball Field, located 5 miles away. Bowdoin Park, 12 miles away, offers more recreational fun for everyone.

Things to do recommended for groups

Your group can enjoy a movie night under the stars at Overlook Drive-In Theater, explore shopping and dining options at Poughkeepsie Galleria, or catch a live performance at Chance Theater, all providing memorable local experiences in 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 a group, family, pets, or looking for extended stays, be sure to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Pleasant Valley with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Pleasant Valley with young kids: Traveling with little ones can be a bit tricky. It's important to prioritize 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 attractions that are enjoyable for families.
  • Taking your pets with you to Pleasant Valley: For many families, a getaway isn't truly satisfying unless their furry companion is along for the adventure. If this resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Pleasant Valley: If you're in search of vacation rentals that offer discounts for month-long stays, 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 include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Pleasant Valley

Discover the charm of Pleasant Valley, New York, where outdoor adventures and breathtaking scenery await. Explore the nearby Wappinger Creek for tranquil walks or enjoy the friendly atmosphere of nearby cities. With a perfect blend of family-friendly vibes and historical sites, your vacation promises to be memorable. Whether you're seeking adventure or relaxation, Pleasant Valley offers a delightful escape just a short drive from bustling urban areas.

  • Poughkeepsie: Located 6 miles from Pleasant Valley, Poughkeepsie is a vibrant city that offers a delightful mix of outdoor and urban experiences. Known for its picturesque Hudson River views, this city attracts visitors looking for family-friendly activities. You can explore the scenic Walkway Over the Hudson, a pedestrian bridge that offers breathtaking vistas. Poughkeepsie also features a variety of shopping areas and local markets, providing ample opportunities for retail therapy. Notable landmarks include the historic Marist College and the beautiful Vassar College campus, along with nearby lakes and mountains that make for great day trips.
  • Hyde Park: Just 4 miles from Pleasant Valley, Hyde Park is renowned for its rich cultural heritage and outdoor attractions. Visitors flock to this charming city to enjoy its lush parks and the scenic beauty of the Hudson River. Hyde Park is home to several educational institutions, including the Franklin D. Roosevelt Presidential Library and Museum, which offers a glimpse into American history. The area also features shopping venues and opportunities for skiing in the winter months. With its blend of historical sites and natural beauty, Hyde Park is perfect for families and culture enthusiasts alike.
  • Rhinebeck: Situated 13 miles from Pleasant Valley, Rhinebeck is a quaint town that promises adventure and stunning scenery. This picturesque locale is known for its outdoor activities, including hiking and skiing in the surrounding mountains. Rhinebeck boasts beautiful lakes and scenic vistas, perfect for a day of exploration or relaxation. Visitors can enjoy a variety of educational venues and participate in seasonal festivals that celebrate local arts and culture. The charming downtown area is filled with boutique shops, restaurants, and galleries, making it a delightful destination for a day trip.

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. Peak season runs in April, July and September, while off-peak times, like October to December tend to have fewer bookings and better deals.

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

Booking with Vrbo is simple

Want to save on your upcoming trip? Try being flexible with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To help you find the perfect Vrbo property that fits your budget, use our filters to sort by price, location, and type of vacation rental. We're here to support you in finding the best options for your travel needs.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan exciting new adventures, pick up right where you left off, or easily view and manage your travel arrangements. You can find properties you've previously saved or booked categorized under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Book a vacation 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 vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Pleasant Valley

Are you hoping to discover things to do in the city? Venture out of your cozy vacation rental and experience everything that Pleasant Valley has to offer. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Clinton Vineyards (7.6 mi / 12.2 km)

Exploring the natural landscape of Pleasant Valley

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Pleasant Valley is a great place to spend some time outside. Here are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city center:

  • Walkway Over the Hudson State Historic Park (7.1 mi / 11.4 km)
  • Northern Dutchess Botanical Gardens (14.3 mi / 23 km)
  • Kingston Point Beach (14.8 mi / 23.8 km)
  • Esopus Creek (16.8 mi / 27.1 km)
  • Forsyth Park (16.8 mi / 27.1 km)
  • Fishkill Ridge (17.3 mi / 27.9 km)

Traveling to and around Pleasant Valley

The nearest airport is in Stewart Intl. Airport (SWF), located 21.7 mi (35 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to Danbury, CT (DXR-Danbury Municipal), which is 31 mi (49.9 km) away.

Frequently asked questions

What is the best area to stay in Pleasant Valley, New York, United States of America when booking a vacation rental?
When considering the best area to stay in Pleasant Valley, New York, a great choice is the vicinity around the charming town center. This neighborhood offers a delightful blend of local shops, cozy cafes, and easy access to beautiful parks, making it great for visitors who enjoy a quaint, community-oriented atmosphere.

For those looking to explore, the nearby Walkway Over the Hudson State Historic Park is a must-visit. This stunning pedestrian bridge offers breathtaking views of the Hudson River and is great for walking, biking, or simply soaking in the natural beauty of the area. Additionally, the scenic Vassar Farm and Ecological Preserve provides a serene setting for hiking and enjoying the local flora and fauna.

In terms of vacation rentals, this area has a variety of properties available, from charming cottages to spacious homes, allowing visitors to find the great fit for their stay.
How much does it cost to rent a vacation home in Pleasant Valley?
Prices for vacation rentals in Pleasant Valley vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Pleasant Valley to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Pleasant Valley vacation house rentals?
You can find great discounts on house rentals in Pleasant Valley on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Pleasant Valley ski resort rentals?
For skiing near Pleasant Valley, travelers should consider the nearby area of Poughkeepsie, which is approximately a 30-minute drive from ski resorts like Catamount, located in Massachusetts. In Poughkeepsie, you can find a variety of vacation rentals that cater to winter sports enthusiasts. Many properties feature cozy living spaces, fireplaces, and kitchens or kitchenettes for convenient meal preparation after a day on the slopes.

Additionally, nearby towns like Rhinebeck and Hyde Park offer charming accommodations, including historic homes and modern cabins, often equipped with amenities like hot tubs, outdoor patios, and easy access to local shops and restaurants. These areas not only provide proximity to ski resorts but also to the beautiful Hudson Valley, where visitors can enjoy hiking trails and scenic views.
What is the most popular type of vacation rental accomodation in Pleasant Valley?
In Pleasant Valley, vacation houses are particularly popular, with several available throughout the area. These homes typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and outdoor spaces like decks or patios, making them ideal for families or groups seeking a comfortable stay. Additionally, several apartments and cottages can be found, offering guests a cozy, home-like atmosphere. Apartments often come with modern amenities and convenient locations, while cottages provide a charming retreat, great for those wanting a more rustic experience.
Are there any family house rentals in Pleasant Valley?
In Pleasant Valley, New York, there are several family-friendly house rentals available, making it a great destination for families. Visitors can find homes that feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces for children to play and explore. Many properties also include amenities like Wi-Fi and air conditioning to enhance comfort during your stay.

The locale is situated near natural attractions, such as the scenic Hudson River and nearby parks, which offer opportunities for hiking, picnicking, and enjoying the outdoors. Additionally, charming local shops and family-friendly restaurants can be found in the area, ensuring that families have everything they need for a memorable getaway.
Can I rent a vacation home with a pool or hot tub in Pleasant Valley?
In Pleasant Valley, New York, there are several vacation homes available for rent that feature pools and hot tubs. This scenic area, located in the Hudson Valley, offers a range of properties set against picturesque landscapes. Travelers can expect amenities such as private outdoor pools, hot tubs, spacious patios for lounging, and well-equipped kitchens for preparing meals. Many rentals are situated in tranquil neighborhoods, providing a peaceful retreat while still being conveniently located near local attractions and outdoor activities.
Can I find long-stay vacation rentals in Pleasant Valley?
A long-stay vacation rental in Pleasant Valley is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any remote work vacation rentals in Pleasant Valley?
In Pleasant Valley, New York, there are several vacation rentals suitable for remote work. Many of these properties come equipped with essential amenities such as reliable Wi-Fi, desk spaces, and comfortable seating to facilitate a productive work environment. Travelers can expect to find homes with generous living areas that allow for both relaxation and work, ensuring a good balance during their stay.

The area itself offers a serene setting, superb for those looking to mix work with leisure. Nearby attractions include beautiful parks and trails for outdoor activities, making it easy to unwind after a day of remote work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Pleasant Valley vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Pleasant Valley with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Pleasant Valley?
In Pleasant Valley, popular vacation rental amenities include spacious decks or patios, great for enjoying the surrounding natural beauty. Most rentals also come equipped with kitchens, allowing travelers to prepare their own meals. A blender is often provided for those who enjoy making smoothies or other blended drinks. Many properties feature inviting fireplaces, adding a cozy touch for cooler evenings. Additionally, onsite parking is typically available, making it convenient for guests traveling by car.
When is the best time to visit Pleasant Valley for a vacation rental?
The best time to visit Pleasant Valley for a vacation rental is during the peak season from July to September. July, in particular, is the most popular month, attracting travelers eager to enjoy the warm summer weather and the vibrant local culture. During this time, visitors can partake in outdoor activities like hiking and biking through the stunning natural landscapes, as well as exploring local farmers' markets and festivals that showcase the area's unique offerings.

Temperatures in July typically range from the mid-60s to the low 80s Fahrenheit, providing a comfortable climate for outdoor exploration and sightseeing. This is an ideal opportunity to immerse yourself in the beauty of the Hudson Valley, with its picturesque views and charming small-town atmosphere.

For those looking for a more budget-friendly option, consider visiting in October. This month offers a different charm, with the fall foliage painting the landscape in vibrant hues of red, orange, and yellow. It's a quieter time, superb for leisurely walks and enjoying the serene ambiance, making it a delightful experience for travelers seeking tranquility.
How early should I book a Pleasant Valley vacation rental?
Book your Pleasant Valley vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Pleasant Valley, New York, United States of America?
In Pleasant Valley, visitors can enjoy a mix of outdoor activities and local charm. The nearby Staatsburg State Historic Site offers a glimpse into the Gilded Age with its historic mansion and beautiful grounds, making it a popular spot for history enthusiasts. The area also features the scenic Dutchess Rail Trail, superb for walking, running, or biking, which connects Pleasant Valley to neighboring towns and provides lovely views of the surrounding landscape.

For those interested in nature, the nearby Ferncliff Forest provides trails and opportunities for birdwatching amidst its wooded areas. Additionally, the local farmers' market is a great place to experience the community's agricultural bounty and sample fresh produce and homemade goods.
Can I change or cancel my Pleasant Valley home rental booking on Vrbo?
To find Pleasant Valley vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Pleasant Valley vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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