Hillsdale vacation rentals

We found 571 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

Image gallery for Best of the Berkshires & Hudson Valley

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

Best of the Berkshires & Hudson Valley

Canaan

10% off
Price is CA $580
CA $5,387 total
includes taxes & fees
Best of the Berkshires & Hudson Valley

Find spaces that suit your style

  • 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, yards and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Hillsdale

Why visit Hillsdale

  • Outdoor Activities: Enjoy skiing, hiking, and exploring the stunning natural landscapes of Hillsdale and its surrounding national parks.
  • Charming Local Culture: Experience the warmth of friendly locals and the romantic vibe in the picturesque small hamlets.
  • Hillsdale Farmers Market: Immerse yourself in local offerings at this vibrant market, showcasing fresh produce and artisanal goods.
  • Cozy Accommodations: Choose from charming private homes, cozy condos, and delightful cottages, many featuring inviting outdoor spaces.
  • Serene Lakes: Relax by the tranquil lakes, perfect for quiet moments in nature or family-friendly activities.

Popular types of accommodation in Hillsdale

If you're wondering what types of vacation rentals await you in Hillsdale, look no further. Our most popular options include charming houses, cozy condos, and delightful cottages. Many of these accommodations feature inviting back decks, private patios, and seasonal pools for your enjoyment. Plus, dog runs are available for your furry companions, ensuring everyone has a fantastic stay. Discover the perfect getaway in Hillsdale today.

  • Houses: The top choice for visitors to Hillsdale, these homes offer ample space and comfort, perfect for families or groups seeking a home-like atmosphere.
  • Condos: A popular option, condos provide modern amenities and often come with added conveniences like pools or fitness centres.
  • Cottages: These charming retreats provide a quaint and cozy experience, ideal for those wanting a peaceful getaway.
  • Apartments: A practical choice, apartments offer a homey feel with the benefit of self-catering facilities.
  • Cabins: For a rustic experience, cabins are a favourite among nature enthusiasts looking for a serene escape.**

Top attractions near Hillsdale

Hillsdale, New York, is a fantastic destination for skiing, adventure, and sports vacations, offering a range of attractions like national parks, nature reserves, and serene lakes. Whether you're seeking outdoor activities, cultural experiences, or thrilling adventures, Hillsdale has it all. Don't miss the local highlights such as the charming city of Hillsdale and the vibrant Hillsdale Farmers Market, perfect for immersing yourself in the area's unique offerings.

  • Bash Bish Falls State Park: Experience the natural beauty of this national park, featuring breathtaking waterfalls and scenic hiking trails. Perfect for outdoor enthusiasts seeking adventure and tranquility, it’s a must-visit for nature lovers.
  • National Shrine of the Divine Mercy: This serene shrine offers a unique cultural experience, inviting visitors to reflect and appreciate its beautiful architecture and spiritual ambiance, along with the stunning gardens.
  • Norman Rockwell Museum: Celebrate American art and culture at this museum, showcasing Norman Rockwell's iconic works. It’s a delightful destination for art lovers and those interested in storytelling through visuals.

Things to do recommended for couples

Hillsdale offers a delightful romantic getaway. Enjoy skiing at Catamount Ski Area, just 3.2km away, or indulge in a wine tasting at Hudson Chatham Winery, 17.7km from town. For a night of entertainment, don’t miss the Tanglewood Music Center, located 25.7km from Hillsdale.

Things to do recommended for families

Your family will love exploring Lake Mansfield Park, only 12.9km from Hillsdale, perfect for relaxation and wellness. Tyringham Cobble and Stissing Lake Park, both 25.7km away, also offer serene environments for outdoor fun and family bonding amidst nature.

Things to do recommended for groups

Groups visiting Hillsdale can experience the thrill of the Catamount Aerial Adventure Park with its zipline ropes course, enjoy a captivating show at the Mahaiwe Performing Arts Center, and play a round of golf at the scenic Greenock Country Club nearby.

*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 extended stays, it’s important to prioritize your filters accordingly. 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 full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Hillsdale with young kids: Traveling with young kids can be quite the adventure. 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 family-friendly attractions.
  • 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, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Hillsdale: If you're in search of vacation rentals that offer great deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can conveniently discover and save on monthly rentals. Don't forget to include options like parking, a well-equipped kitchen, or even a private pool in your search.

Where to stay near Hillsdale

Hillsdale, New York, is a hidden gem in the Hudson Valley, perfect for a relaxing adventure. Explore charming small hamlets amidst hilly landscapes, where you can ski or immerse yourself in the local scenery. Experience the warmth of friendly locals and the romantic vibe of this picturesque region. Whether you're seeking family-friendly activities or quiet moments in nature, Hillsdale offers a delightful escape for every traveller.

  • Great Barrington: Located 12.9km from Hillsdale, Great Barrington is a vibrant city that beckons adventure seekers and outdoor enthusiasts. Known for its excellent skiing facilities, visitors can enjoy activities at local ski resorts and fields, making it a popular winter destination. Beyond winter sports, the area boasts beautiful lakes and scenic mountains, perfect for hiking and exploring during the warmer months. Great Barrington's charming downtown features local shops, cafes, and a lively arts scene, providing a well-rounded experience for travelers.
  • Stockbridge: Situated 20.9km from Hillsdale, Stockbridge offers a rich cultural experience in a picturesque setting. This charming city is famous for its artistic heritage, with numerous galleries and theaters showcasing local talent. Visitors can enjoy music concerts and theatrical performances, making it an ideal spot for a romantic getaway or cultural exploration. The area is also home to lovely lakes and notable landmarks, including monuments and shrines, inviting travelers to immerse themselves in the history and beauty of this iconic New England town.
  • Copake: Just 8.0km from Hillsdale, Copake presents a wonderful destination for those seeking outdoor adventures. Known for its skiing opportunities, the city features ski fields and resorts that attract winter sports enthusiasts. During the summer months, visitors can explore the surrounding national state parks and enjoy hiking or picnicking by the scenic lakes and mountains. With its laid-back atmosphere and connection to nature, Copake is perfect for those looking to unwind and embrace the great outdoors.

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

Are you hoping to save on your next getaway? Being open to adjusting your travel dates can really help, as prices tend to vary. Additionally, if you opt for a longer stay, you often unlock significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the ideal spot for your adventure.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers a helpful platform for you to plan your journeys, seamlessly pick up from where you last left off, or review and arrange your travel plans. You can easily find your saved or booked properties organized into categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/en-ca/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 when booking a vacation rental?
When considering a vacation rental in Hillsdale, New York, the best area to stay is the charming Hillsdale village itself. This quaint community offers a delightful mix of rural charm and local amenities, making it a great base for your getaway. The village features a variety of properties, from cosy cottages to more spacious family homes, suiting different preferences and group sizes.

Staying in Hillsdale places you in close proximity to some wonderful attractions. For instance, the nearby Catamount Ski Area is a fantastic destination for winter sports enthusiasts, providing excellent skiing and snowboarding opportunities. In the warmer months, the area is equally inviting, with beautiful hiking trails and scenic spots great for picnicking and enjoying the great outdoors. Additionally, the local farmers' market is a must-visit, where you can sample fresh produce and artisanal goods, giving you a taste of the region's vibrant community spirit.
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 travelling 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.
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 ski resort rentals near Hillsdale, New York, travellers should focus on the nearby Catamount Ski Area, located just over the border in Massachusetts, which is easily accessible from Hillsdale. The town itself offers a range of rental options, including cosy cabins and charming chalets that provide a warm and inviting atmosphere after a day on the slopes. Many of these properties come equipped with amenities such as wood-burning fireplaces, fully stocked kitchens, and spacious living areas, great for both families and groups of friends.

In Hillsdale and the surrounding areas, visitors can find rustic lodges that often feature outdoor spaces for barbecues and relaxation, along with proximity to local attractions such as hiking trails and picturesque views of the Berkshires. Some rentals may also include access to hot tubs, which can be a delightful way to unwind after skiing.

Additionally, the nearby towns like Great Barrington and Stockbridge offer more rental choices, from modern apartments to quaint historic homes. These locations not only provide convenient access to skiing but also a vibrant local scene with shops, restaurants, and cultural attractions, making Hillsdale an excellent base for a winter getaway.
What is the most popular type of vacation rental accomodation in Hillsdale?
In Hillsdale, vacation houses are the most popular type of vacation rental, with around 123 available in the area. These homes are generally spacious and well-suited for families or larger groups, featuring multiple bedrooms, fully equipped kitchens, and often outdoor spaces like decks or gardens for relaxation. Additionally, several chalets, apartments, cabins, and cottages can be found, each offering unique charms and amenities, such as rustic decor in cabins or modern conveniences in apartments.
Are there any family house rentals in Hillsdale?
In Hillsdale, New York, families can choose from a variety of vacation rentals, with around 34 options available in the area. This charming locale is known for its picturesque landscapes and proximity to outdoor activities, making it an excellent choice for family getaways. Many properties feature spacious living areas, fully equipped kitchens great for preparing family meals, and outdoor spaces where children can enjoy themselves.

Visitors might find amenities such as Wi-Fi, laundry facilities, and even game rooms in some rentals, ensuring a comfortable stay. The area is also close to attractions like the Bash Bish Falls State Park, ideal for hiking and picnicking, and the Catamount Ski Area for winter sports enthusiasts.
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. This charming area, located in the scenic Berkshire Mountains, offers a peaceful retreat for those looking to unwind. Many of these properties come equipped with private pools, hot tubs, and spacious outdoor areas, great for enjoying the natural beauty that surrounds the town. Travellers can also expect amenities such as fully equipped kitchens, comfortable living spaces, and, in some cases, access to hiking trails or nearby lakes.
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. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Hillsdale?
In Hillsdale, New York, there are numerous pet-friendly house rentals available, providing a welcoming environment for travellers with pets. Many of these vacation homes offer a variety of amenities, including fully equipped kitchens, spacious living areas, and private outdoor spaces, making them suitable for families or groups.

The rentals are often located near scenic spots, allowing for enjoyable walks and outdoor adventures with your furry companions. The surrounding area features beautiful landscapes and parks, providing ample opportunities for hiking and exploring nature.
Are there any remote work vacation rentals in Hillsdale?
In Hillsdale, New York, there are numerous remote work vacation rentals available, with around 138 options to choose from. This charming area offers a peaceful retreat for those looking to combine work and leisure. Many properties come equipped with essential amenities such as high-speed Wi-Fi, dedicated work desks, and comfortable living spaces, allowing you to maintain productivity while enjoying the serene surroundings.

The town's picturesque landscape, with its rolling hills and proximity to the Berkshires, provides a refreshing backdrop for remote work. Additionally, local attractions such as scenic parks and quaint shops offer opportunities to unwind after a day of work. 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 travellers 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 rental amenities include kitchens, which allow travellers to prepare their own meals, and decks or patios that provide outdoor space for relaxation and enjoying the scenery. Many rentals also feature onsite parking for convenience, as well as fireplaces that add a cosy touch during cooler months. Additionally, some properties permit pets, making it easier for guests to bring their furry friends along for the stay.
When is the best time to visit Hillsdale for a vacation rental?
July is the most popular time to visit Hillsdale, making it an ideal choice for those seeking a vibrant vacation experience. During the peak season, which spans from June to August, visitors flock to this charming town to enjoy a variety of outdoor activities and local events. The warm summer months offer the great climate for exploring the scenic landscapes and engaging in recreational pursuits such as hiking, cycling, and enjoying the beautiful parks.

In July, you can expect pleasant temperatures averaging between 15 to 25 degrees Celsius, providing a comfortable environment for sightseeing and outdoor adventures. Whether you're strolling through the quaint streets, visiting local art galleries, or enjoying a picnic at one of the many nearby lakes, the summer atmosphere is bustling and inviting.

For those looking for a more budget-friendly option, consider visiting in October. This month showcases the stunning autumn foliage, allowing you to experience the breathtaking colours of fall while enjoying a quieter atmosphere. It's a wonderful time for leisurely walks and appreciating the natural beauty of the region.

Ultimately, your choice of when to visit Hillsdale will depend on your preferences for lively summer activities or the serene charm of autumn.
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?
In Hillsdale, New York, visitors can enjoy a variety of attractions that showcase the area's natural beauty and cultural heritage. The picturesque Hillsdale area is surrounded by rolling hills and lush landscapes, making it ideal for outdoor activities such as hiking and birdwatching. Nearby, the Catamount Ski Area offers winter sports enthusiasts a chance to ski and snowboard, while in warmer months, the same area is superb for mountain biking and scenic chairlift rides.

The town itself features charming local shops and eateries where visitors can experience the flavour of the Hudson Valley. For art lovers, the nearby Art Omi International Arts Centre presents a unique outdoor sculpture park, as well as indoor galleries showcasing contemporary art. Additionally, the nearby town of Great Barrington, just a short drive away, offers more dining and shopping options, along with cultural venues like the Mahaiwe Performing Arts Centre, which hosts various performances throughout the year.
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 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 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, Vrbo 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 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.

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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

More Vacation Ideas