Hillsdale vacation rentals

We found 569 vacation rentals — enter your dates for availability

Discover a selection of 49 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:May 15 - May 22

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10 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)

Best of the Berkshires & Hudson Valley

Canaan

9% off
Price is $511
$3,575 for 7 nights
All fees included
Best of the Berkshires & Hudson Valley

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Find out more about Hillsdale

Why visit Hillsdale

  • Outdoor Adventures: Enjoy activities like hiking, skiing, and exploring stunning national parks and serene lakes.
  • Charming Downtown: Stroll through picturesque downtown Hillsdale, perfect for summer getaways with a relaxing atmosphere.
  • Lakefront Relaxation: Unwind at the beautiful lakefront, ideal for leisure and family fun during the warmer months.
  • Diverse Accommodations: Choose from cozy cottages to spacious vacation homes that cater to every traveler's needs.
  • Welcoming Community: Experience the friendly locals who ensure a warm and inviting atmosphere throughout your stay.

Popular types of accommodation in Hillsdale

Discover the charm of Hillsdale with a variety of vacation rentals perfect for your getaway. Whether you prefer a cozy cottage, a spacious private vacation home, or a modern condo, Hillsdale has something to suit every traveler’s needs. With options like house rentals and holiday cottages, you'll find the ideal place to unwind and create lasting memories. Explore your options and enjoy a hassle-free vacation experience in this beautiful destination.

  • Houses: These spacious homes are the top choice for travelers seeking comfort and privacy, ideal for families or groups.
  • Condos: Perfect for those wanting a blend of luxury and convenience, these modern units offer great amenities and locations.
  • Cottages: These quaint and charming retreats provide a cozy atmosphere, perfect for a peaceful getaway.
  • Apartments: A practical option for visitors, offering flexibility and often located near local attractions.
  • Cabins: For a rustic experience, these cozy lodgings are nestled in nature, ideal for outdoor enthusiasts.**

Top attractions near Hillsdale

Hillsdale, New York, offers a fantastic vacation for adventure enthusiasts and sports lovers. With its stunning national parks, nature reserves, and serene lakes, the area is perfect for outdoor activities and cultural experiences. Whether you're skiing, hiking, or simply enjoying the beautiful landscapes, Hillsdale has something to offer for every traveler seeking adventure or relaxation in nature.

  • Bash Bish Falls State Park: A breathtaking destination known for its stunning waterfalls and scenic hiking trails, perfect for outdoor enthusiasts seeking adventure and natural beauty.
  • National Shrine of the Divine Mercy: A serene and culturally rich site, this shrine offers a peaceful atmosphere for reflection and spiritual connection, attracting visitors from all backgrounds.
  • Jug End State Reservation: This tranquil preserve features beautiful landscapes and wooded areas, ideal for hiking, wildlife observation, and enjoying the great outdoors.

Things to do recommended for couples

For a romantic getaway in Hillsdale, explore the slopes at Catamount Ski Area, enjoy captivating performances at Tanglewood Music Center, and savor exquisite wines at Hudson Chatham Winery. Each destination offers unique experiences perfect for couples looking to create lasting memories together.

Things to do recommended for families

Families visiting Hillsdale can enjoy a day at Lake Mansfield Park for relaxation and wellness, or explore the scenic trails at Tyringham Cobble. Stissing Lake Park also offers a great spot for recreation and family fun, making it a perfect getaway for everyone.

Things to do recommended for groups

Experience the thrill of ziplining at Catamount Aerial Adventure Park, hike the scenic Housatonic River Walk, or enjoy a show at the Mahaiwe Performing Arts Center for a taste of local culture. These activities promise fun and adventure for your group.

*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 Hillsdale

When traveling with a group, family, pets, or planning for an extended stay, it’s important to prioritize your specific needs. Here are some helpful booking tips for Vrbo to assist you.

  • Traveling to Hillsdale with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Hillsdale with young kids: Traveling with little ones can be quite a task. It's important to prioritize their comfort and safety, along with ensuring access to age-appropriate features, 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 Hillsdale: For many families, a vacation feels incomplete without their furry companions. If you can relate, explore Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone, including your four-legged friend, feels comfortable and at home.
  • Planning for a long term stay visiting Hillsdale: If you're searching for vacation rentals that offer special deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can easily discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Hillsdale

Hillsdale, New York, is a charming destination perfect for outdoor enthusiasts and families alike. Enjoy the stunning scenery and relaxing atmosphere as you explore downtown Hillsdale, ideal for a summer getaway. The picturesque lakefront offers a fun place to unwind during the warmer months, while the friendly locals ensure a welcoming experience. Whether you're seeking adventure or a romantic retreat, Hillsdale has something for everyone to enjoy.

  • Great Barrington: Located 8 miles from Hillsdale, Great Barrington is a vibrant city known for its adventurous spirit and outdoor activities. Visitors flock to this area for a thrilling ski experience at the nearby ski resorts, offering diverse terrain for all skill levels. Beyond skiing, Great Barrington boasts picturesque lakes and stunning mountain views, along with access to national state parks. The combination of breathtaking landscapes and recreational opportunities makes it a perfect destination for adventure seekers.
  • Stockbridge: Situated 13 miles from Hillsdale, Stockbridge offers a unique blend of cultural richness and romantic charm. This city is renowned for its vibrant arts scene, featuring music concerts and theatrical performances throughout the year. Visitors can explore local landmarks such as serene lakes, historical monuments, and peaceful shrines. The enchanting atmosphere of Stockbridge makes it a delightful destination for those seeking entertainment and a romantic getaway, all while soaking in the area's rich history.
  • Copake: Just 5 miles from Hillsdale, Copake is an outdoor lover's paradise, perfect for adventure enthusiasts. This city is well-known for its ski fields and resorts, providing excellent opportunities for winter sports. Beyond skiing, Copake is surrounded by beautiful lakes and mountains, making it an attractive spot for hiking, fishing, and exploring the nearby national state parks. With its emphasis on outdoor activities, Copake is an ideal destination for those looking to immerse themselves in nature and enjoy exhilarating adventures.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.0°F (-3.9°C)Light RainMostly CloudySlightly HighAverage
February26.6°F (-3.0°C)Light RainMostly CloudySlightly HighSlightly Low
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 HighAverage
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 LowAverage
November39.4°F (4.1°C)Light RainMostly SunnyAverageSlightly High
December31.3°F (-0.4°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is a breeze

Looking to save on your next vacation? Consider staying flexible with your travel dates, as this can lead to significant price differences. Furthermore, extending your stay can often unlock additional savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to narrow down your search by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash from your booking. Being the planner definitely has its perks. By enrolling in our travel rewards program, OneKey, you can immediately access member discounts and earn OneKeyCash on eligible reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo's Trip Board feature offers you a convenient way to plan your travels. You can easily create new trips, pick up right where you left off, or organize your existing plans. Any properties you've saved or booked are now neatly categorized under Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply visit: https://www.vrbo.com/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)
  • Hudson Chatham Winery (10.9 mi / 17.5 km)
  • Lake Taghkanic State Park (10.9 mi / 17.6 km)
  • Furnace Brook Winery at Hilltop Orchards (16.5 mi / 26.6 km)
  • Wyndhurst Golf & Club (17.4 mi / 28 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 best area to stay in Hillsdale, New York, United States of America when booking a vacation rental?
When considering a vacation rental in Hillsdale, New York, the area surrounding the picturesque town center is an excellent choice. This neighborhood offers a charming blend of natural beauty and local culture, making it an ideal spot for visitors looking to immerse themselves in the region's serene atmosphere.

One of the top attractions nearby is the scenic Catamount Ski Area, which is great for winter sports enthusiasts and offers year-round outdoor activities like hiking and mountain biking. Additionally, the nearby Olana State Historic Site provides a glimpse into the artistic legacy of Frederic Edwin Church, with stunning views of the Hudson River Valley and beautifully landscaped grounds.

In terms of accommodations, Hillsdale features a variety of properties, from cozy cabins to spacious homes, providing a range of options to suit different preferences and group sizes.
How much does it cost to rent a vacation home in Hillsdale?
Prices for vacation rentals in Hillsdale 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 Hillsdale 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 Hillsdale vacation house rentals?
You can find great discounts on house rentals in Hillsdale 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 Hillsdale ski resort rentals?
For skiing in Hillsdale, the nearby Catamount Mountain Resort is a popular choice for visitors. Travelers seeking rentals should focus on the Hillsdale area and the surrounding towns like Copake and Great Barrington. In Hillsdale, you'll find cozy cabins and rustic chalets that often feature amenities such as wood-burning stoves, fully equipped kitchens, and outdoor spaces for barbecues or enjoying the scenic views. Many properties in this area cater to families or groups, with ample space for relaxation after a day on the slopes.

As you venture towards Copake, there are additional options that blend comfort and convenience, including well-appointed condos and larger homes that can accommodate groups. Some rentals here might offer features like game rooms, hot tubs, and access to hiking trails or nearby lakes for year-round enjoyment.

Great Barrington, slightly further afield, offers a vibrant town atmosphere with shops and dining options, along with a range of rental properties from quaint cottages to modern homes. Many of these accommodations provide amenities such as Wi-Fi, outdoor fire pits, and proximity to both skiing and local attractions, making it a great base for winter sports enthusiasts.
What is the most popular type of vacation rental accomodation in Hillsdale?
In Hillsdale, vacation houses are the most popular type of rental, with about 41 available throughout the area. These properties are often located in serene settings, providing a great escape for families or groups looking to enjoy the beauty of the surrounding countryside. Most vacation houses come equipped with fully furnished kitchens, spacious living areas, and outdoor spaces such as decks or patios for relaxing and taking in the fresh air.

Additionally, several chalets, apartments, cabins, and cottages can be found, each offering great experiences. Chalets often feature rustic decor and cozy atmospheres, while apartments provide convenient access to local attractions. Cabins and cottages typically offer a more secluded experience, great for those wanting to immerse themselves in nature.
Are there any family house rentals in Hillsdale?
In Hillsdale, New York, families will find a good selection of approximately 34 vacation rentals that cater to their needs. Properties in this charming area often feature spacious living rooms, full kitchens for family meals, and outdoor spaces great for kids to play. Many homes also include amenities such as Wi-Fi and cozy fireplaces, ensuring a comfortable and enjoyable stay.

This picturesque region is close to the scenic beauty of the Berkshires, where families can explore trails, visit local farms, and enjoy outdoor activities throughout the year. Additionally, nearby attractions like the Catamount Ski Area provide opportunities for winter sports, while local parks offer playgrounds and picnic areas for daytime outings. See all family-friendly rentals in Hillsdale.
Can I rent a vacation home with a pool or hot tub in Hillsdale?
In Hillsdale, New York, there are several vacation homes available for rent that feature pools and hot tubs, making it a great choice for travelers seeking relaxation and leisure. This charming area is located in the picturesque Berkshire Mountains, offering a tranquil escape while still being close to various outdoor activities.

Many of the rentals in Hillsdale come with desirable amenities such as private pools, hot tubs, spacious outdoor decks, and fully equipped kitchens, which enhance the overall experience for families or groups looking to unwind together. Some properties may also include scenic views of the surrounding countryside, barbecue facilities, and cozy indoor living spaces, great for enjoying the serene atmosphere of the region.
Can I find long-stay vacation rentals in Hillsdale?
A long-stay vacation rental in Hillsdale 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 pet-friendly house rentals in Hillsdale?
In Hillsdale, travelers can find a selection of pet-friendly house rentals, with around 33 options available. These vacation homes often come equipped with amenities such as fully furnished kitchens, spacious living areas, and outdoor spaces like gardens or decks, great for enjoying the surrounding nature. Many rentals also feature cozy fireplaces, making them inviting for relaxation after a day of exploration.

The area itself is known for its beautiful landscapes, offering opportunities for outdoor activities such as hiking and biking. Additionally, Hillsdale is close to parks and natural reserves, providing ample space for pets to roam and enjoy the outdoors.
Are there any remote work vacation rentals in Hillsdale?
In Hillsdale, New York, there are several remote work vacation rentals available, with around 46 options to choose from. This quaint town offers a serene environment ideal for productivity, surrounded by the scenic beauty of the Berkshires. Many of the rentals provide essential amenities for remote work, including free Wi-Fi, dedicated desk spaces, and comfortable seating options.

Travelers can expect cozy accommodations that often feature spacious living areas, fully equipped kitchens, and outdoor spaces to unwind after a day of work. The surrounding area offers recreational opportunities, including hiking trails and nearby lakes, superb for those looking to balance work with relaxation. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Hillsdale vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Hillsdale 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 Hillsdale?
In Hillsdale, popular vacation rental amenities include fully equipped kitchens, which allow travelers to prepare their own meals, and decks or patios that provide outdoor space for relaxation and enjoying the scenic surroundings. Onsite parking is also a common feature, making it convenient for guests with vehicles. Many rentals come with cozy fireplaces, superb for warming up during cooler evenings. Additionally, a number of properties in the area are pet-friendly, accommodating travelers who wish to bring their furry companions along on their getaway.
When is the best time to visit Hillsdale for a vacation rental?
July is the most popular time to visit Hillsdale, attracting travelers looking to enjoy the vibrant summer atmosphere and a variety of outdoor activities. The peak season runs from June through August, offering warm temperatures that typically range from the mid-60s to the low 80s Fahrenheit. This is ideal for those who love hiking, biking, and exploring the beautiful landscapes of the Catskill Mountains, as well as indulging in local festivals and events.

During July, visitors can engage in the lively community spirit, with many outdoor concerts and farmers' markets showcasing the region's rich culture and local produce. The long days and pleasant evenings provide ample opportunities for stargazing or relaxing by a campfire after a day full of adventures.

If you're looking for a more budget-friendly option, consider planning your stay in October. This month presents a unique charm as the fall foliage begins to paint the landscape in stunning shades of red, orange, and gold. Exploring the scenic byways and enjoying the crisp autumn air can be a refreshing experience, great for those who appreciate nature's beauty without the summer crowds.
How early should I book a Hillsdale vacation rental?
Book your Hillsdale 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 Hillsdale, New York, United States of America?
In Hillsdale, New York, visitors can enjoy a variety of attractions that highlight the area's natural beauty and cultural offerings. The town is surrounded by picturesque landscapes, making it ideal for outdoor activities such as hiking and biking. Nearby, the Catamount Ski Area offers winter sports during the colder months, while in the warmer seasons, the Catamount Outdoor Family Center provides trails for mountain biking and hiking.

The nearby Olana State Historic Site, the former home of artist Frederic Edwin Church, features stunning views of the Hudson River and beautiful grounds for leisurely walks. The area is also known for its quaint shops and local restaurants, particularly those showcasing farm-to-table cuisine, enhancing the charming small-town experience.

For art enthusiasts, the nearby town of Great Barrington features galleries and cultural events, while the picturesque towns of Hudson and Stockbridge are within a short drive, offering additional shopping, dining, and historical attractions, such as the Norman Rockwell Museum.
Can I change or cancel my Hillsdale home rental booking on Vrbo?
To find Hillsdale 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 Hillsdale 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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