Hillside Lake vacation rentals

We found 106 vacation rentals — enter your dates for availability

Nestled amidst the stunning hills and shimmering waters, Hillside Lake is a haven for nature lovers and adventure seekers alike. With its breathtaking vistas, charming local neighborhoods, and a plethora of outdoor activities—from hiking to fishing—this destination is perfect for families and groups looking to create unforgettable memories together. Choose from a variety of cozy hillside homes or spacious lakefront mansions, each offering the comforts and amenities of a home, ensuring a truly enriching getaway.

Holiday rentals with weekly discounts - Hillside Lake

Showing deals for:Jan 15 - Jan 22

Interior
Interior
Living area
Interior
Exceptional
(5 reviews)

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

Poughkeepsie

7% off
$339
$2,376 for 7 nights
All fees included
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Interior
Outdoor dining
Living area
Room
Exceptional
(21 reviews)

Beautiful lake view home on Whaley Lake in Holmes, NY.

Holmes

8% off
$625
$4,378 for 7 nights
All fees included
Beautiful lake view home on Whaley Lake in Holmes, NY.
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!
This sitting area is another great space to gather around the faux fireplace.
Our home sits on 5 partially-wooded acres. Welcome to the country!
Exceptional
(20 reviews)

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

Milton

17% off
$333
$2,328 for 7 nights
All fees included
Historic 4 BR Family Home Near Buttermilk Falls & Hudson River, on 5 Acres
Interior
Exterior
Property grounds
Property grounds
Exceptional
(13 reviews)

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Hopewell Junction

9% off
$179
$1,253 for 7 nights
All fees included
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Dining
Main house. Apt is downstairs to the left.
Second bedroom with two full size beds and large walk-in closet.
Private kitchen
Exceptional
(22 reviews)

Lower level unit in Spectacular Log Home Estate

Marlboro

13% off
$195
$1,365 for 7 nights
All fees included
Lower level unit in Spectacular Log Home Estate
Property grounds
Property grounds
Private kitchen
Private kitchen
Excellent
(62 reviews)

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

Hopewell Junction

9% off
$314
$2,199 for 7 nights
All fees included
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

Find the best place to stay - Hillside Lake

Terrace/patio
Premier Host
10
Exceptional
42 reviews
Wappinger Cottage - Scandinavian retreat on a creek
Relax in our beautiful deck with comfortable chaise lounges, bbq & gas firepit.
Premier Host
9.0
Wonderful
12 reviews
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
Exterior
Premier Host
10
Exceptional
45 reviews
Apartment in scenic Hudson Valley New York
Interior
10
Exceptional
13 reviews
Tranquil Tree-House on the beautiful Hudson River
Interior
Premier Host
10
Exceptional
6 reviews
Hudson Pond · Garden Queen Suite · GF Breakfast
Exterior
10
Exceptional
4 reviews
Hudson Pond · Hideaway King Suite · GF Breakfast

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Find out more about Hillside Lake

Why visit Hillside Lake

  • Scenic Lake Views: Enjoy breathtaking vistas of Hillside Lake, perfect for relaxation and photography.
  • Outdoor Adventures: Engage in a variety of activities such as hiking, fishing, and boating in the surrounding state parks.
  • Charming Accommodations: Choose from cozy cottages, spacious apartments, and hillside lake houses for a memorable stay.
  • Cultural Experiences: Explore nearby modern colleges and historic bridges that offer a glimpse into the area's rich heritage.
  • Family-Friendly Activities: Discover numerous attractions and events designed for visitors of all ages, ensuring fun for everyone.

Popular types of accommodation in Hillside Lake

If you’re wondering about the types of vacation rentals available in Hillside Lake, we’ve got you covered. Here, you'll find an array of popular accommodations, including charming houses, cozy cottages, and spacious apartments. Whether you’re seeking a hillside lake house, a family-friendly home, a custom retreat, or a rustic getaway, Hillside Lake offers the perfect backdrop for your next adventure.

  • Houses: The most sought-after option in Hillside Lake, perfect for families or groups seeking comfort and privacy during their stay.
  • Cottages: Charming and cozy, these rentals provide a quaint retreat for couples or small families wanting a peaceful getaway.
  • Apartments: Convenient and versatile, ideal for travelers looking for a central location with home-like amenities.
  • Cabins: Rustic and inviting, these options offer a unique experience surrounded by nature, perfect for outdoor enthusiasts.
  • Agritourism: A distinctive choice allowing visitors to immerse themselves in rural life, often featuring farm stays and fresh local produce.**

Top attractions near Hillside Lake

Hillside Lake, New York, offers a perfect blend of romance and outdoor adventure, making it an ideal vacation spot. Visitors can explore modern colleges, historic bridges, and nearby state parks, all while enjoying breathtaking water views and the area's scenic lake elevation. Whether you're seeking cultural experiences or family-friendly activities, Hillside Lake has something for everyone, ensuring a memorable getaway in this picturesque setting.

  • Vassar College: A prestigious liberal arts college known for its beautiful campus and modern architecture. With city vibes, it offers a vibrant atmosphere filled with art galleries, student events, and lush green spaces for leisurely strolls.
  • Culinary Institute of America: A renowned culinary school steeped in history, showcasing exceptional cooking techniques and diverse cuisines. The culture vibes here are enhanced by gourmet dining experiences and cooking demonstrations that elevate your appreciation for food.
  • James Baird State Park: A beautiful national park perfect for outdoor enthusiasts, featuring scenic hiking trails, picnic areas, and stunning views. Experience adventure and nature as you explore its lush landscapes and various recreational activities.

Things to do recommended for couples

For a romantic getaway in Hillside Lake, visit Benmarl Vineyards and Winery for a cozy tasting experience, or hit the slopes at Thunder Ridge Ski Resort for some thrilling skiing. Don’t miss Live At The Falcon for a delightful evening of music and entertainment, just a short drive away.

Things to do recommended for families

Your family will have a blast at SplashDown Beach, a fun waterpark 8 miles away, or enjoy arcade games at Fun Central, located 6 miles away. For some relaxation, visit Bowdoin Park, also 8 miles from Hillside Lake, perfect for unwinding together.

Things to do recommended for groups

Explore the vibrant Stormville Airport Antique Show & Flea Market, just 4 miles away, for unique finds. Enjoy a round of golf with your group at Beekman Golf Course, 2 miles from Hillside Lake. Don't miss shopping and entertainment at Poughkeepsie Galleria, 7 miles away.

*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 Hillside Lake

When planning your trip—whether you're traveling with a group, your family, or pets, or if you're considering an extended stay—be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Hillside Lake with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Hillside Lake with young kids: Traveling with young kids can be a bit tough. It's important to prioritize their comfort and safety, along with finding amenities that are suitable for their age, like a private pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Hillside Lake: For many families, a vacation isn't truly complete without their furry companion. If this resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly properties offer amenities like feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Hillside Lake: If you're searching for vacation rentals that offer discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Hillside Lake

Hillside Lake, New York, offers a delightful escape for romantic getaways and outdoor adventures. Nestled in a picturesque setting, visitors can enjoy breathtaking lake views and charming vacation homes. The friendly atmosphere, combined with family-friendly activities and scenic landscapes, makes it an ideal destination for relaxation and exploration. Nearby, you’ll find great lake houses and perfect hillsides that enhance your travel experience, ensuring unforgettable memories in this enchanting region.

  • Poughkeepsie: Located 9 miles from Hillside Lake, Poughkeepsie is a vibrant city that offers a blend of outdoor adventures and urban experiences. This city is known for its stunning river views, particularly along the Walkway Over the Hudson, a scenic pedestrian bridge that provides breathtaking vistas of the Hudson River and surrounding landscapes. Families can enjoy educational visits to local colleges, explore charming shopping areas, or relax at nearby parks. The city's modern university and the scenic beauty of both the lake and mountains make Poughkeepsie a must-visit.
  • Fishkill: Just 8 miles away from Hillside Lake, Fishkill is a family-friendly city that boasts a delightful mix of outdoor fun and shopping opportunities. Visitors can explore the symbolic landmarks and enjoy thrilling rides at the local theme park, making it a perfect spot for families. The city is also home to various shopping centers and malls, offering everything from retail therapy to dining options. The inviting visitor center provides insights into local attractions, ensuring you make the most of your trip.
  • Newburgh: Situated 14 miles from Hillside Lake, Newburgh is a city rich in history and natural beauty. This area attracts families and outdoor enthusiasts alike, with its picturesque lakeside views and numerous parks. Visitors can explore the historic sites that tell the story of the region while enjoying the shopping centers and malls that cater to every need. The local visitor center offers valuable information to help you uncover the hidden gems of Newburgh, making it a rewarding stop on your vacation.

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can change significantly. Also, booking a longer stay can lead to substantial savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to narrow down your search by price, location, and type of vacation rental. We’re here to help you find the perfect getaway.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers an easy-to-use platform for planning your next adventure. You can create new trips, resume planning from where you left off, or organize your existing plans all in one place. Your saved or booked properties will be neatly categorized under Potential, Upcoming, or Current Trips for your convenience. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Book a vacation rental for your Hillside Lake getaway

Learn about the unique charm of Hillside Lake with a stay in a private vacation home. This city has something for everyone. With a vacation rental, you get a home away from home. Many rentals offer full kitchens and outdoor grills for some home cooking.

Sightseeing in and around Hillside Lake

Do you want to discover attractions to visit in the area? Venture out of your vacation home and experience everything that makes Hillside Lake a fun spot to vacation. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • SplashDown Beach (7.6 mi / 12.2 km)
  • Benmarl Vineyards and Winery (9.9 mi / 15.9 km)
  • Thunder Ridge Ski Resort (13.4 mi / 21.6 km)
  • Putnam County Golf Course (16.1 mi / 25.9 km)
  • Millbrook Vineyards and Winery (16.3 mi / 26.2 km)
  • Beekman Golf Course (2 mi / 3.3 km)

Exploring the natural landscape of Hillside Lake

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Hillside Lake is a great place to spend some time outside. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • Bowdoin Park (7.6 mi / 12.3 km)
  • Whaley Lake (8 mi / 12.8 km)
  • Walkway Over the Hudson State Historic Park (10.3 mi / 16.5 km)
  • Hudson Highlands State Park (14.8 mi / 23.8 km)
  • Algonquin Park (15.2 mi / 24.4 km)
  • Lake Mahopac (16.6 mi / 26.7 km)

Traveling to and around Hillside Lake

The nearest airport is in Stewart Intl. Airport (SWF), located 17.2 mi (27.7 km) from the city center. If you're unable to find a flight that fits your schedule, you could also fly into Danbury, CT (DXR-Danbury Municipal), which is 23.3 mi (37.5 km) away.

Frequently asked questions

What is the best area to stay in Hillside Lake, New York, United States of America when booking a vacation rental?
When considering a vacation rental in Hillside Lake, New York, the area surrounding the lake itself is a wonderful choice. This picturesque neighborhood is known for its serene environment and beautiful natural surroundings, making it an ideal spot for relaxation and outdoor activities. The lake offers opportunities for swimming, fishing, and kayaking, allowing visitors to fully immerse themselves in the tranquil atmosphere.In addition to the stunning lake, nearby attractions include scenic parks where you can enjoy hiking and picnicking, as well as charming local shops and eateries that showcase the area's unique character. The combination of natural beauty and local culture makes this neighborhood a superb base for exploring Hillside Lake and its surrounding areas.
How much does it cost to rent a vacation home in Hillside Lake?
Prices for vacation rentals in Hillside Lake 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 Hillside Lake 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 Hillside Lake vacation house rentals?
You can find great discounts on house rentals in Hillside Lake 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.
Can I find long-stay vacation rentals in Hillside Lake?
A long-stay vacation rental in Hillside Lake 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 Hillside Lake vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Hillside Lake 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.
How early should I book a Hillside Lake vacation rental?
Book your Hillside Lake 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 Hillside Lake, New York, United States of America?
In Hillside Lake, New York, visitors can enjoy the serene beauty of the lake itself, which is superb for activities like kayaking, fishing, and swimming during the warmer months. The surrounding area features picturesque trails for hiking and nature walks, ideal for those looking to explore the outdoors.The nearby town of Warwick offers charming shops, local eateries, and the historic Warwick Valley Winery & Distillery, where guests can sample local wines and spirits. Just a short drive away, the Appalachian Trail provides extensive hiking opportunities for outdoor enthusiasts.
Can I change or cancel my Hillside Lake home rental booking on Vrbo?
To find Hillside Lake 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 Hillside Lake 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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