Pleasant Valley holiday rentals

We found 133 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:11 Dec - 18 Dec

Outdoor dining
Living area
Property grounds
Exterior
Exceptional
(9 reviews)

6 Acre Private Hudson Valley Estate

Highland

8% off
AU$13,992
for 7 nights, 1 home
AU$1,999 per night
includes taxes & fees
6 Acre Private Hudson Valley Estate
Interior
Private kitchen
Dining
Room
Exceptional
(17 reviews)

Modern Hudson Valley Creekside Retreat + Hot Tub!

Hyde Park

16% off
AU$5,234
for 7 nights, 1 cottage
AU$748 per night
includes taxes & fees
Modern Hudson Valley Creekside Retreat + Hot Tub!
For those moments when you prefer a more private escape, we've created a tranquil area in the front yard.
Dining
French Doors leading to a veranda offer a wonderful connection to the outdoors, making it the perfect spot to start your day with a cup of morning coffee or tea.
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.
Exceptional
(25 reviews)

Spacious 4BD Country Gem - Fire Pit & Chill Vibes

Highland

7% off
AU$4,383
for 7 nights, 1 home
AU$626 per night
includes taxes & fees
Spacious 4BD Country Gem - Fire Pit & Chill Vibes
Comfortably seats 8 and also doubles as a large board game table.
Whip up delicious meals in the spacious, bright kitchen with ample counter space
Settle into the many comfy seats in the Family Room.
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
AU$6,060
for 7 nights, 1 home
AU$866 per night
includes taxes & fees
Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz
The Enchanted Forest beckons!
Feel the awe of the 20 foot vaulted ceilings and windows onto the woods
Outdoor showers on a hot summer day are the best!
It's mesmerizing to watch and hear the roaring waterfall from this bridge.
Exceptional
(20 reviews)

Hudson Valley stunning lake side modern barn in an Enchanted Forest

Clinton Corners

8% off
AU$5,144
for 7 nights, 1 home
AU$735 per night
includes taxes & fees
Hudson Valley stunning lake side modern barn in an Enchanted Forest
Main bedroom with king bed and private full bath and walk in closet.
Exterior
View from front lawn
Dinning room & Kitchen. Original exposed beams.
Exceptional
(11 reviews)

Cheerful Circa 1700 3 Bedroom Farmhouse

Hyde Park

30% off
AU$4,249
for 7 nights, 1 home
AU$607 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
AU$3,780
for 7 nights, 1 home
AU$540 per night
includes taxes & fees
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Front entrance is a sun room in the winter and porch in the summer.
Open floor plan is great for groups
Interior
Do you enjoy cooking/baking? High-end kitchen with everything you need.
Exceptional
(6 reviews)

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Millbrook

8% off
AU$5,062
for 7 nights, 1 home
AU$723 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

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)
  • Casperkill Golf Club (8.6 mi / 13.8 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)
  • Kingston Point Beach (14.8 mi / 23.8 km)
  • Whaley Lake (15.3 mi / 24.5 km)
  • Esopus Creek (16.8 mi / 27.1 km)
  • Mohonk Lake (17.4 mi / 28 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

What is the best area to stay in Pleasant Valley when booking a holiday rental?
When considering a holiday rental in Pleasant Valley, New York, the area surrounding the town centre is an excellent choice. This charming neighbourhood offers a delightful blend of tranquillity and accessibility, making it appealing for visitors seeking a relaxing getaway. In this area, you can find a variety of properties, ranging from quaint cottages to more spacious homes, suiting different group sizes and preferences.One of the highlights of staying in this part of Pleasant Valley is the proximity to the scenic Walkway Over the Hudson, a stunning elevated walkway that provides breathtaking views of the Hudson River and surrounding landscapes. Additionally, the charming local parks, such as the Pleasant Valley Town Park, offer lovely spots for picnics and leisurely strolls.The town centre also features a selection of quaint shops and local eateries, where you can enjoy a taste of the community.
Where are the best Pleasant Valley ski resort rentals?
For ski resort rentals near Pleasant Valley, the closest area is the Catskill Mountains, particularly around towns like Kingston and Woodstock, which are within a reasonable driving distance. In Kingston, visitors can find a variety of rental options, including charming cabins and modern chalets equipped with amenities such as hot tubs, fireplaces, and spacious decks that offer stunning views of the surrounding mountains.In Woodstock, the atmosphere is artsy and laid-back, with accommodations ranging from cosy cottages to larger homes suitable for families or groups. Many of these properties come with fully equipped kitchens, allowing for easy meal preparation, as well as proximity to local shops and restaurants that celebrate the region's culinary scene.For those who enjoy skiing, rentals in these areas provide access to nearby ski resorts like Hunter Mountain and Belleayre Ski Resort, both of which offer a variety of slopes for different skill levels. After a day on the slopes, guests can unwind in accommodations that often feature amenities such as game rooms, outdoor fire pits, and access to nature trails for hiking or snowshoeing in winter.
What is the most popular type of holiday rental accomodation in Pleasant Valley?
In Pleasant Valley, holiday houses are the most popular type of holiday rental, with several available throughout the area. These properties typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, providing a comfortable setting for families or groups. Many also include outdoor spaces such as patios or gardens, great for relaxing after a day of exploring the scenic surroundings. Additionally, there are several apartments and cottages that cater to different preferences, offering a range of amenities to ensure a pleasant stay.
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 wonderful choice for those travelling with children. This charming area offers spacious properties, often featuring amenities such as full kitchens for preparing family meals, and outdoor spaces superb for kids to play. Many homes include comfortable living rooms and dining areas, providing ample room for everyone to relax together after a day of exploring.Visitors will find that Pleasant Valley is conveniently located near various attractions, including local parks and nature trails, ideal for family outings. The nearby Hudson River offers opportunities for scenic walks and picnics, while the surrounding countryside invites outdoor activities like hiking and biking.
Can I rent a holiday home with a pool or hot tub in Pleasant Valley?
In Pleasant Valley, there are several holiday homes available for rent that feature pools and hot tubs, making it a delightful choice for those seeking relaxation and recreation. This charming area, located in the scenic Hudson Valley, offers a variety of properties, including spacious houses that often come with private pools, outdoor seating areas, and well-equipped kitchens.Travellers can expect amenities such as air conditioning, Wi-Fi, and expansive gardens, great for enjoying sunny days. The tranquil surroundings also provide opportunities for outdoor activities like hiking and exploring local parks, adding to the appeal for families or groups looking to unwind and enjoy nature.
Are there any remote work holiday rentals in Pleasant Valley?
In Pleasant Valley, New York, there are some remote work holiday rentals available, with around 12 options to choose from. This charming town offers a serene environment, ideal for those looking to balance work and leisure. Many properties come equipped with essential amenities for remote work, including reliable Wi-Fi, dedicated desk spaces, and comfortable chairs.Travellers can expect a variety of accommodations, ranging from cozy cottages to spacious homes. Some rentals also feature outdoor areas, making it easy to take breaks in a tranquil setting. The local area is rich in natural beauty, with nearby parks and trails for leisurely strolls or invigorating hikes after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Pleasant Valley?
In Pleasant Valley, popular holiday rental amenities include decks or patios, which provide a great space for outdoor relaxation and enjoying the surroundings. Most properties feature fully equipped kitchens, allowing guests to prepare their own meals comfortably. Additionally, many rentals come with a blender for easy meal prep and smoothies. A fireplace is also a common amenity, offering a cosy atmosphere during cooler evenings. Onsite parking is typically available, making it convenient for those travelling with vehicles.
When is the best time to visit Pleasant Valley for a holiday rental?
The peak season in Pleasant Valley runs from July to September, making it the most popular time for holiday rentals in the area. During these summer months, visitors can bask in warm temperatures, typically ranging from 15 to 30 degrees Celsius, great for outdoor activities and exploring the scenic beauty of the Hudson Valley. Whether you're hiking the nearby trails, enjoying a leisurely picnic by the river, or partaking in local festivals, the vibrant setting is sure to enhance your holiday experience.July stands out as the most sought-after month, with lively events and a bustling community vibe. Families and friends flock to the area to enjoy the sunshine and partake in various outdoor adventures, creating a welcoming environment for everyone.For those looking to travel on a budget, October can be an excellent alternative. As the summer crowds disperse, you can enjoy the tranquil beauty of the fall foliage, with the stunning autumn colours providing a picturesque backdrop for leisurely walks and scenic drives. This quieter time of year allows for a more relaxed experience, great for unwinding and soaking in the charm of Pleasant Valley.
What are the top attractions in Pleasant Valley?
In Pleasant Valley, visitors can enjoy a range of attractions that showcase the area's natural beauty and local charm. One of the main highlights is the beautiful Sprout Creek Farm, where guests can tour the farm, enjoy artisanal cheese tastings, and participate in seasonal events. The nearby Norrie Point State Park offers stunning views of the Hudson River and features walking trails, picnic areas, and opportunities for fishing.For those interested in history, the Pleasant Valley Museum provides insights into the local heritage and hosts various exhibitions throughout the year. The scenic landscapes of the Harlem Valley Rail Trail are superb for outdoor enthusiasts, offering a peaceful setting for walking, cycling, and enjoying the surrounding nature.
Are all fees included in the Pleasant Valley holiday homes prices shown on Stayz?
Stayz 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.
Are there any Pleasant Valley holiday homes with parking?
Stayz offers a wide selection of holiday homes in Pleasant Valley with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details 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.
Are there any discounts for Pleasant Valley holiday homes?
You can find great discounts on holiday homes in Pleasant Valley on Stayz, 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.
Can I change or cancel my Pleasant Valley holiday home booking on Stayz?
To find Pleasant Valley holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Pleasant Valley?
A long-stay holiday home in Pleasant Valley is the best way to experience local living. Plus, you can make the most of long-stay discounts. 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.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a Pleasant Valley holiday home?
Book your Pleasant Valley holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Pleasant Valley?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Pleasant Valley to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.