Hillsdale vacation rentals

We found 562 vacation rentals — enter your dates for availability

Discover a selection of 52 homes and other vacation rentals in Hillsdale that are perfect for your trip. Whether you're traveling with your kids or with friends, vacation homes have the amenities you expect for your stay, which might include parking and a fireplace. No matter what you're looking for, you're sure to find a rental to meet everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Hillsdale

Showing deals for:Oct 10 - Oct 17
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home

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

    More space, more privacy, more amenities — more value
  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Hillsdale

Why visit Hillsdale

  1. Outdoor activities: Hillsdale is a haven for adventure seekers with skiing, hiking, and exploring national parks.
  2. Charming neighborhoods: Discover friendly locals and family-friendly activities in picturesque surroundings.
  3. Cultural experiences: Visit historic landmarks like the Hillsdale House and local taverns to immerse in the area's rich history.
  4. Relaxing atmosphere: Enjoy a romantic setting perfect for unwinding, whether in nature or city strolls.
  5. Diverse accommodations: Choose from cozy vacation homes, condos, or unique hotel experiences to suit your needs.

Popular types of accommodation in Hillsdale

If you're exploring vacation rentals in Hillsdale, you're in for a treat! Our most popular accommodations include charming houses, cozy condos, and quaint cottages. Whether you're searching for a spacious Hillsdale house, a comfortable room hotel in Hillsdale, or a unique room hotel experience, we have options that cater to every traveler's needs. Enjoy your stay with transparency, savings, and reassurance!

  • Houses: The top choice for travelers in Hillsdale, these spacious homes offer privacy and comfort for families, groups, or couples seeking a home-away-from-home experience.
  • Condos: A popular option for those looking for modern amenities and a community feel, condos in Hillsdale provide convenience and style.
  • Cottages: Quaint and charming, cottages are ideal for a cozy getaway amidst the scenic beauty of Hillsdale.
  • Apartments: Offering flexibility and ease, apartments are great for solo travelers or couples wanting a convenient base.
  • Cabins: Perfect for nature lovers, cabins provide a rustic experience with close proximity to outdoor adventures.**

Top attractions near Hillsdale

Hillsdale, New York, is an ideal destination for outdoor enthusiasts and adventure seekers, offering a blend of skiing, sports, and cultural experiences. Explore nearby national parks, serene lakes, and nature reserves, while also visiting local landmarks like the historic tavern and Hillsdale House. With its rich history and abundance of outdoor activities, Hillsdale promises a memorable vacation for travelers looking to immerse themselves in nature and adventure.

  1. Taconic State Park: Located 4 miles from Hillsdale, this national park offers stunning scenery and a variety of outdoor adventures, including hiking, fishing, and picnicking amidst beautiful natural landscapes.
  2. National Shrine of the Divine Mercy: Situated 13 miles away, this serene shrine is a place of cultural significance, attracting visitors seeking spiritual reflection and peace in its tranquil environment.
  3. Jug End State Reservation: Just 3 miles from Hillsdale, this preserve features a network of trails perfect for hiking and enjoying the diverse flora and fauna of the region.

Things to do recommended for couples

For a romantic getaway in Hillsdale, indulge in skiing at Catamount Ski Area, just 2 miles away. Enjoy a concert at Tanglewood Music Center, 16 miles from town. Don't miss a wine tasting at Hudson Chatham Winery, 11 miles away, perfect for an intimate evening together.

Things to do recommended for families

Families will love exploring Lake Mansfield Park, only 8 miles away, for relaxation and outdoor fun. Tyringham Cobble and Stissing Lake Park, both 16 miles from Hillsdale, offer beautiful scenery and peaceful vibes, perfect for enjoying nature together.

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

When planning your trip—whether you're traveling with a group, family, or pets, or seeking extended stays—be sure to prioritize your preferences with the right filters. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Hillsdale 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 Hillsdale with young kids: Traveling with young kids can present some challenges. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private swimming pool. Additionally, considering your location in relation to family-friendly attractions can make your trip more enjoyable.
  • Taking your pets with you to Hillsdale: For many families, a vacation just isn't the same without their furry companion. If you can relate to this, explore Vrbo listings that welcome pets. Many of these pet-friendly properties offer amenities like feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Hillsdale: If you’re searching for vacation rentals that offer discounts 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 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 Hillsdale

Hillsdale, New York, offers a delightful blend of adventure and relaxation, making it an ideal destination for tourists. Nestled in the scenic Hudson Valley, visitors can explore charming neighborhoods filled with friendly locals and family-friendly activities. Whether you're hitting the slopes or strolling through the city center, the picturesque surroundings provide a romantic atmosphere perfect for unwinding. With many attractions within walking distance, Hillsdale is a fantastic base for your New York getaway.

  • Great Barrington: Nestled approximately 8 miles from Hillsdale, Great Barrington is a vibrant town renowned for its outdoor adventures and sports experiences. Visitors flock here for exceptional skiing at nearby resorts, making it a winter wonderland for snow enthusiasts. In addition to skiing, the town is surrounded by stunning natural landscapes, including mountains and lakes, perfect for hiking and exploring. Great Barrington also boasts a lively downtown area with unique shops, restaurants, and cultural events, making it an ideal stop for a day of adventure and relaxation.
  • Stockbridge: Located about 13 miles from Hillsdale, Stockbridge is a charming town steeped in culture and romance. This picturesque destination is famous for its art scene, with attractions like the Norman Rockwell Museum and the Berkshire Theatre Festival. Visitors can enjoy live music concerts and theatrical performances throughout the year. The town is also home to beautiful lakes and historic monuments, providing a serene backdrop for a leisurely day of exploration. Stockbridge's quaint downtown area features delightful shops and eateries, perfect for an intimate getaway.
  • Copake: Just 5 miles from Hillsdale, Copake is a haven for outdoor adventurers. Known for its skiing options, including local ski fields and resorts, Copake attracts thrill-seekers year-round. The surrounding landscape offers breathtaking views of mountains and lakes, ideal for hiking, fishing, and enjoying nature. This small town also features a friendly community atmosphere, making it a great place to unwind after a day of outdoor activities. Visitors can explore local parks and take advantage of the scenic beauty that Copake has to offer.

Best time to go to Hillsdale

If you're planning a trip to Hillsdale, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in January to February and July, while off-peak times, like March, October and December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January25.0°F (-3.9°C)Light RainMostly CloudySlightly HighAverage
February26.6°F (-3.0°C)Light RainMostly CloudySlightly HighAverage
March34.5°F (1.4°C)Light RainMostly CloudySlightly LowSlightly Low
April46.2°F (7.9°C)Light RainMostly CloudyAverageSlightly Low
May57.9°F (14.4°C)Light RainMostly SunnyAverageAverage
June65.7°F (18.7°C)Light RainMostly SunnyAverageAverage
July72.0°F (22.2°C)Light RainMostly SunnySlightly HighSlightly High
August70.0°F (21.1°C)Light RainMostly SunnyAverageSlightly High
September62.8°F (17.1°C)Light RainMostly SunnyAverageAverage
October51.6°F (10.9°C)Light RainMostly SunnySlightly LowSlightly Low
November39.4°F (4.1°C)Light RainMostly SunnyAverageAverage
December31.3°F (-0.4°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is a breeze

Are you interested in finding ways to save on your upcoming trip? Keeping a flexible schedule for your travel dates can really pay off, as prices can vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo rental that fits your budget, feel free to utilize our filters to sort by price, location, and type of vacation home. We’re here to help you make the most of your travel experience!

Unlock savings with One Key

Plan your group getaway by booking an eligible Vrbo property and earn OneKeyCash™ on your reservation. Being the planner definitely has its perks! When you join our travel rewards program, One Key, you'll gain immediate access to member discounts and the chance to earn and redeem OneKeyCash™ on qualifying bookings. Sign up today and begin enjoying your savings!

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a dedicated area to plan your upcoming travels, pick up right where you left off, or manage and organize your itinerary. You can easily access the properties you've saved or booked previously, categorized under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/en-us/trips.

**Based on Vrbo properties bookings.

Take in the picturesque beauty of Hillsdale

Learn about the unique charm of Hillsdale with a stay in a private vacation home. This city's coffeehouses, skiing and horseback riding attract many visitors, and its relaxing and scenic location add to the charm. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Hillsdale

Do you want to find things to do while you're in the area? Venture out of your cozy vacation rental and experience everything that Hillsdale has to offer. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Catamount Ski Area (2.5 mi / 4.1 km)
  • Ski Butternut (10.5 mi / 16.9 km)
  • Lake Taghkanic State Park (10.9 mi / 17.6 km)
  • Harney and Sons Tea Tasting Room (15 mi / 24.1 km)
  • Kennedy Park (18.8 mi / 30.2 km)
  • Bousquet Ski Area (20.6 mi / 33.1 km)

Exploring the natural landscape of Hillsdale

Whether you're an adventurous traveler or just want to take in the scenery, Hillsdale is a great place to get outside. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city center:

  • Copake Lake (4.3 mi / 7 km)
  • Lake Mansfield Park (8.3 mi / 13.4 km)
  • Housatonic River Walk (8.5 mi / 13.7 km)
  • Housatonic River (8.5 mi / 13.7 km)
  • Lake Taghkanic State Park (10.9 mi / 17.6 km)
  • Lake Buel (12.8 mi / 20.6 km)

Traveling to and around Hillsdale

The nearest airport is in Hudson, NY (HCC-Columbia County), located 12.5 mi (20.1 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to Pittsfield, MA (PSF-Pittsfield Municipal), which is 20.8 mi (33.4 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Hillsdale?
The most desirable types of vacation rentals in Hillsdale are cottages. Ready for more choices? Vrbo offers a variety of options to match our guests' diverse needs, so you'll see vacation properties in lots of sizes and shapes. The perfect fit is waiting for you --- book yours today.
How much does it cost to rent a vacation rental in Hillsdale?
Property type, length of stay and season are some things that can affect the price of a vacation home. Simply enter your dates of travel to find your ideal fit. From comfy cottages to expansive luxury villas, all Vrbo vacation rentals provide incredible value.
How much does it cost to rent a beach house in Hillsdale?
Prices for beach houses in Hillsdale will vary depending on the size and type of the property and when you plan to travel. All you need to do is enter your travel dates into Vrbo and the number of guests to view available options and prices. From there you can use the filters to narrow your search results by nearby activities, ratings, amenities and more.
Are there pet-friendly vacation rentals in Hillsdale?
Good news. There are. You can choose from 66 vacation homes that allow pets in Hillsdale on Vrbo. Our furry best friends need a getaway too, so simply use our search function for pet-friendly vacation rentals to find a perfect property where your puppy dog can lap up the good times.
Can I rent a house with a pool in Hillsdale?
Tick the "pool" box in our handy filter tool and choose from 15 houses with private pools in Hillsdale on Vrbo. Morning swim, afternoon splash or midnight soak? Leisure time is your call when your Vrbo vacation property boasts a swimming pool.
What are popular rental amenities in Hillsdale?
A fireplace, a lake view and ski-in/ski-out facilities top the list of most popular rental amenities in Hillsdale. Whether you're planning to travel solo, with your spouse or a group of friends, Vrbo can help you find a vacation rental that matches your tastes with all the options you need.
Are there large group vacation rentals in Hillsdale?
Hillsdale has 15 vacation rentals that can accommodate 10 or more people. These properties come with all the space you need to enjoy good times with your favorite people.
Are there vacation rentals in Hillsdale that welcome kids?
Hillsdale has 66 family-friendly vacation rentals to pick from. And securing a stay that welcomes children is a breeze with Vrbo's "Properties good for families" filter. Besides having the entire place to yourselves, you'll get amenities and perks such as bunk beds, yards and private pools.
What are the top attractions for families in Hillsdale?
If you're craving some family-friendly fun close to the heart of Hillsdale, visit Catamount Aerial Adventure Park.
Are there one-bedroom vacation rentals in Hillsdale?
Yes, you'll find 14 one-bedroom properties in Hillsdale to pick from. A one-bedroom vacation rental is a wonderful choice if it's just you and your partner or if you're vacationing alone. Toss in more convenience, space and privacy than a standard hotel, and you've got yourself an unforgettable break.
Can I find two-bedroom vacation rentals in Hillsdale?
Gather your family and relax in total privacy and comfort in one of the nine two-bedroom vacation rentals Hillsdale has to offer.
Are there vacation rentals with WiFi in Hillsdale?
You can pick from 37 vacation rentals with WiFi in Hillsdale. If you'd like to disconnect from daily life during your escape, but still want to be connected to the web, these getaways have what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Hillsdale?
Hillsdale has 61 vacation rentals where you'll be able to spend your days in air-conditioned comfort. To book a stay on Vrbo with this amenity, enter your preferred travel dates and use the convenient filters to select the "air conditioning" box.
How old do you have to be to rent a vacation rental in Hillsdale?
The minimum required age is typically 16, 18 or 21. It can change between properties on Vrbo, so look at the rules of your preferred Hillsdale vacation rental before booking your trip.
How long can I rent a vacation rental in Hillsdale for?
The amount of time you can stay in a Hillsdale vacation home for is up to the property. Simply enter your preferred travel dates to browse available options that offer long-term stays. They feature everything you need to make your extended vacation more enjoyable like kitchens and laundries. Some vacation homes may also offer weekly or monthly discounts, so you can stay even longer for less.
Does Vrbo offer discounts for vacation homes in Hillsdale?
Short stay or a much-needed extended vacation, Vrbo has some great deals and discounted options in Hillsdale to suit your style and your budget. Browse our weekly and monthly discounts on vacation rentals, or see what's just been added with one of our newly listed homes. Whatever it is you're after, you'll find the ideal place to stay --- at an affordable rate.

More Vacation Rentals ideas

People also search for