Hillsdale vacation rentals

Why visit Hillsdale

1. Stunning natural attractions: Experience breathtaking parks, lakes, and nature reserves ideal for outdoor activities.
2. Thrilling ski and adventure spots: Enjoy skiing and other adrenaline-pumping activities in a picturesque setting.
3. Charming downtown atmosphere: Explore quaint streets filled with friendly locals and unique shops.
4. Historic sites: Discover the rich history and vibrant neighbourhoods that reflect Hillsdale's unique character.
5. Diverse accommodations: Choose from private homes, condos, and cottages tailored to meet every traveler's needs.

Popular types of accommodation in Hillsdale

If you're exploring vacation rentals in Hillsdale, you're in for a treat! Our most sought-after accommodations include Houses, Condos, and Cottages. Whether you're searching for Hillsdale apartments, vacation apartments, or the best Hillsdale hotels, we ensure a transparent and reassuring experience. Enjoy your stay in this charming destination with a variety of options that cater to every traveler's needs!

• Houses: The top choice for visitors to Hillsdale, offering spacious and comfortable living for families or groups.
• Condos: A popular second option, providing modern amenities and often located in vibrant areas.
• Cottages: Our third most sought-after accommodation, perfect for a quaint and picturesque getaway.
• Apartments: A convenient fourth choice, ideal for those seeking a home-like atmosphere in the heart of the town.
• Cabins: Fifth on the list, these rustic retreats are perfect for immersing yourself in nature.**

Top attractions in Hillsdale

Hillsdale, New York, is an ideal destination for travellers seeking ski, adventure, and sports vacations. With stunning natural attractions such as national and state parks, lakes, and nature reserves, visitors can enjoy outdoor activities and immerse themselves in the local culture. Whether you're looking for thrilling adventures or peaceful escapes, Hillsdale has something for everyone to experience and cherish.

1. Taconic State Park: Located 6.4km from Hillsdale, this national park offers stunning outdoor adventures, picturesque scenery, and a true connection to nature, perfect for hiking, picnicking, and enjoying wildlife.
2. National Shrine of the Divine Mercy: Situated 20.9km away, this serene shrine provides a cultural experience, inviting visitors to reflect and appreciate its beautiful architecture and peaceful surroundings.
3. Jug End State Reservation: Just 4.8km from Hillsdale, this reserve features diverse landscapes for outdoor enthusiasts, offering trails for hiking and opportunities for wildlife observation.

Things to do recommended for couples

For a romantic getaway in Hillsdale, enjoy skiing at Catamount Ski Area, just 3.2km away. Explore the enchanting sounds at Tanglewood Music Center, 25.7km distant, or indulge in a wine tasting at Hudson Chatham Winery, located 17.7km away, perfect for a cozy couple's experience.

Things to do recommended for families

During your family vacation in Hillsdale, explore Lake Mansfield Park for a day of relaxation, visit the scenic Tyringham Cobble, and enjoy the recreational fun at Stissing Lake Park, all offering wellness vibes perfect for families seeking outdoor experiences.

Things to do recommended for groups

Groups visiting Hillsdale can experience the thrill of ziplining at Catamount Aerial Adventure Park, hike the scenic trails along the Housatonic River, and enjoy a captivating performance at the Mahaiwe Performing Arts Center, offering a perfect mix of adventure, culture, and entertainment.

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

If you're travelling with a group, family, pets, or planning an extended stay, it's important to set your priorities straight when filtering your options. Here are some helpful Vrbo booking tips for you.

• Traveling to Hillsdale with a group: Think about how many bedrooms you'll require, along with features like a complete 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 children can present its challenges. It's important to prioritize their comfort and safety, along with ensuring access to age-appropriate amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are suitable for families.
• Taking your pets with you to Hillsdale: For many families, a getaway isn’t truly enjoyable without their furry companion by their side. If you can relate, explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that your whole family feels comfortable and at home.
• Planning for a long term stay visiting Hillsdale: If you’re in search of vacation rentals offering discounts for stays of a month or more, you’ve come to the perfect spot. By utilizing the appropriate filters, you can effortlessly discover and save on monthly rental options. Don’t forget to include features like parking, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Hillsdale

Hillsdale, New York, offers a delightful blend of adventure and relaxation for visitors. From thrilling ski spots to charming downtown streets, you'll find a welcoming atmosphere with friendly locals. Explore the scenic beauty of the surrounding areas, perfect for family-friendly outings or romantic getaways. Don't miss the historic sites and vibrant neighbourhoods that showcase the unique character of Hillsdale and its surroundings, ensuring a memorable vacation experience.

• Great Barrington: Situated 12.9km from Hillsdale, Great Barrington is a vibrant city known for its outdoor adventures and local charm. This picturesque locale is a hub for skiing enthusiasts, offering several ski resorts and fields that attract visitors year-round. Beyond skiing, the scenic beauty of nearby lakes and mountains beckons for hiking and exploration. Great Barrington also boasts a lively arts scene, with galleries and theatres that reflect the region's cultural richness, making it an ideal spot for both adventure seekers and art lovers.
• Stockbridge: Located 20.9km from Hillsdale, Stockbridge is a charming city steeped in culture and romance. Visitors are drawn to its artistic heritage, with numerous concerts and theatre performances available throughout the year. The city's serene lakes and historic monuments provide a picturesque backdrop for leisurely strolls or picnics. Notable attractions include the Norman Rockwell Museum, which celebrates the iconic American painter's work, and the beautiful gardens and shrines that enhance the area's enchanting ambiance, making it a perfect getaway for those seeking a blend of entertainment and relaxation.
• Copake: Just 8.0km from Hillsdale, Copake is an outdoor enthusiast's paradise, renowned for its adventure and skiing opportunities. The city features several ski resorts and fields that cater to winter sports lovers, while the surrounding natural landscapes, including lakes and mountains, invite year-round outdoor activities such as hiking and fishing. Copake's close proximity to the Copake Iron Works State Historic Site adds a historical element to your visit, allowing you to explore the rich heritage of the region amidst its breathtaking scenery.

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 Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	25.0°F (-3.9°C)	Light Rain	Mostly Cloudy	Slightly High	Average
February	26.6°F (-3.0°C)	Light Rain	Mostly Cloudy	Slightly High	Average
March	34.5°F (1.4°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly Low
April	46.2°F (7.9°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
May	57.9°F (14.4°C)	Light Rain	Mostly Sunny	Average	Average
June	65.7°F (18.7°C)	Light Rain	Mostly Sunny	Average	Average
July	72.0°F (22.2°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	70.0°F (21.1°C)	Light Rain	Mostly Sunny	Average	Slightly High
September	62.8°F (17.1°C)	Light Rain	Mostly Sunny	Average	Average
October	51.6°F (10.9°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
November	39.4°F (4.1°C)	Light Rain	Mostly Sunny	Average	Slightly High
December	31.3°F (-0.4°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly High

Booking with Vrbo is simple

Are you hoping to save on your next getaway? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, consider booking a longer stay to unlock even greater savings. To discover a Vrbo property that suits your budget, simply utilize our filters to sort by price, location, and type of vacation rental. We're here to support you in finding the perfect escape!

Vrbo Trips: Planning made easy

Vrbo's advanced Trip Board offers you a dedicated area to plan new trips, pick up right where you left off, or view and manage your travel arrangements. You can easily access the properties you’ve saved or booked, now categorized under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.