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Top Hillsdale hotels
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Good
Reviewed on Oct 18, 2025
Berkshire Mountain Lodge
Clean room
Reviewed on Oct 23, 2025
Berkshires Untold
Had a lovely stay at the Berkshires Untold! We checked in late and the staff reached out to confirm our arrival time and accommodated us without issue. The lobby was absolutely gorgeous and this renovated motel was very well done. We didn’t get to enjoy the fire pits outside but they looked cozy. ...
Reviewed on Oct 23, 2025
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Our room was clean as a pin and we loved the option of daily maid service. Love that there’s a closet with adequate hangers, extra blanket, clock, and the shampoo, body wash dispensers in the shower. Towels were big and fluffy. LOVE the heat lamp in the bathroom!
Reviewed on Oct 23, 2025
The Red Lion Inn
This is a historical hotel and indeed the history is fabulous, everything appears like it did in 1773. Trouble is the rooms are also like this and the beds felt like they were 200 years old - so very uncomfortable. All part of the experience. Our room faced the street and I was surprised how much ...
Reviewed on Oct 21, 2025
Quality Inn
Clean and convenient. Great front desk help.
Reviewed on Oct 25, 2025
Holiday Inn & Suites Pittsfield-Berkshires by IHG
All was very good at this hotel, our room was modernized and updated. The people at the front desk as well as all the employees were all well trained and pleasant . Pittsfield is in the middle of The Berkshires and so it was a great location to see what we wanted to see.
Reviewed on Oct 22, 2025
The Brooks Motel
The property felt safe and welcoming. The room was comfortable and had everything I wanted or needed. The styles “spare” and I like that.
Reviewed on Oct 19, 2025
Howard Johnson by Wyndham Lenox
Coffee maker looks like it has mold inside
Reviewed on Oct 19, 2025
Hotels in Hillsdale with star-rating
Check Hillsdale Hotels by Star Rating
3 Star Hotels
Hillsdale Hotel & Travel Guide\n
Those thinking about roaming in Hillsdale, should consider booking a room as early as possible, as there is not an abundance of accommodation options in close proximity to the downtown area in Hillsdale.
The Rookwood Inn, Massachusetts, which is the closest accommodation option, sits 17 miles (27 kilometers) from the heart of downtown Hillsdale. Instead, why don't you think about the Gateways Inn & Restaurant, located in Massachusetts, which is 17 miles (27 kilometers) from the city center.
It's worth checking out the Hampton Terrace Inn and also the Birchwood Inn. The Hampton Terrace Inn is located only 17 miles (27 kilometers) from the middle of Hillsdale. The Birchwood Inn, is only 17 miles (27 kilometers) away. The Inn At Richmond and the Stockbridge Country Inn are some alternative accommodation options worth checking out around Hillsdale.
While you are here in Hillsdale, be sure to visit Hudson Valley's other cultural and scenic delights. Nature lovers will appreciate Hudson Valley's rivers, valleys and rolling hills. In addition, you should wind your way through a few of the region's historic bridges and open-air markets. Wise travelers in this part of United States of America can enjoy rock climbing.
55 miles (88 kilometers) to the southwest of Hillsdale, you will find Newburgh, which is where you can enjoy Orange County Choppers and Dia Beacon. If you want to spend any time in Newburgh, check out the rooms at the Econo Lodge Near Stewart Inter and Windsor Motel. 60 miles (97 kilometers) south of Hillsdale, is West Point, which boasts the West Point Motel and FairBridge Inn & Suites at West Point. If you visit West Point, make your way to the United States Military Academy and West Point Museum.
Just because you and your traveling partners are on a break, doesn't mean that you shouldn't expand your obsession with a day watching sports. You will find Times Union Center 30 miles (52 kilometers) to the north of Hillsdale. Modern travelers that want to book Travelocity-listed accommodation near to the action can choose from the Hilton Albany or the TownePlace Suites by Marriott Albany Downtown/Medical Center.
For those travelers planning on flying through Albany International Airport, you may like to book Travelocity-listed rooms at Albany Marriott, or Homewood Suites by Hilton Albany, which are both conveniently close.
Top reasons for your vacation to Hillsdale
- Scenic Skiing and Snowboarding: Enjoy the thrill of skiing and snowboarding on Tory Hill, surrounded by breathtaking hilly landscapes.
- Relaxing Spa Treatments: Unwind and rejuvenate at Cranwell Spa with its luxurious and revitalizing treatments.
- Rich History: Explore Hillsdale's historic places and learn about its fascinating past.
- Horseback Riding: Nature lovers can indulge in horseback riding and immerse themselves in the beautiful surroundings.
- Charming Small-Town Atmosphere: Experience the cozy coffee shops, local library, and friendly vibe that make Hillsdale a perfect destination for a memorable family vacation.
Explore the best activities and sights in Hillsdale
Hillsdale, located in upstate New York, offers a fantastic ski vacation experience for families. With its proximity to scenic hills and mountains, there are plenty of activities to engage in. Families can enjoy skiing and snowboarding on Tory Hill, taking chairlift rides to admire the breathtaking scenery. For those seeking relaxation, Cranwell Spa offers rejuvenating treatments. Additionally, history enthusiasts can explore the area's historic places, while nature lovers can indulge in horseback riding. Hillsdale's charming small-town vibe, cozy coffee shops, and local library make it an ideal destination for a memorable family ski vacation.
- Catamount Aerial Adventure Park: This thrilling adventure park will take your breath away with its exhilarating zipline and ropes course. Immerse yourself in the vibrant colors of the flowers and gardens as you navigate through the various obstacles. The park offers hiking trails that lead to stunning mountain vistas, allowing you to admire the breathtaking scenery. For the adrenaline junkies, there are rock climbing challenges that test your skills and provide an adrenaline rush. If you prefer a more relaxed experience, you can enjoy camping in the serene surroundings or visit the nearby churches for a moment of tranquility. Catamount Aerial Adventure Park is the perfect destination for nature lovers and adventure seekers.
- Community Library: This charming library offers a haven of knowledge and a cozy atmosphere for families. Immerse yourself in the rich culture of Hillsdale as you explore the vast collection of books and resources. The library provides a peaceful environment where you can indulge in a good read or engage in cultural activities. Whether you're looking for a children's storytime session or a book club discussion, the Community Library has something for everyone. Discover new worlds and embark on exciting literary adventures in this community treasure.
- Hillsdale Town Hall: Step back in time and experience the rich history of Hillsdale at the Town Hall. This historic civic government building exudes a sense of grandeur with its architectural beauty. Immerse yourself in the culture and traditions of the town as you explore the halls and corridors. Learn about the significant events that shaped the community and admire the timeless craftsmanship. Hillsdale Town Hall is a must-visit for history enthusiasts and those seeking a deeper understanding of the town's heritage.
Where to stay in Hillsdale
Get ready for an unforgettable ski vacation in the charming town of Hillsdale, New York. With its close proximity to Great Barrington and other nearby cities, you'll have plenty of options for dining and shopping. But the real highlight of Hillsdale is its thrilling ski slopes, where you and your family can enjoy hours of fun and adventure. Imagine the exhilarating views as you glide down the slopes, surrounded by picturesque hilly landscapes. And when you're not skiing, take a leisurely stroll through the town, exploring its coffee shops, libraries, and even some historic ruins. Hillsdale has everything you need for a joyful ski vacation.
- Lenox: Just 17.4 miles away from Hillsdale, Lenox is a charming city that offers a unique blend of cultural experiences and natural beauty. Known for its picturesque gardens, museums, and live music scene, Lenox is the perfect destination for families who appreciate art and entertainment. The city also boasts stunning scenery and architecture, making it a great place for hiking and exploring. With a library and yoga studios, Lenox caters to those seeking relaxation and wellness. Its vibrant atmosphere and diverse activities make it an ideal choice for a ski vacation with your family.
- Hudson: Located just 14.6 miles away from Hillsdale, Hudson is a historical city that offers a range of attractions for families. With its opera house, art galleries, and cathedral, Hudson is a hub for cultural experiences. Families can enjoy scenic boat rides on the river and explore the city's architecture and shopping scene. The city's rich history and vibrant dining options make it an exciting destination for all. For a ski vacation, Hudson's proximity to Hillsdale and its unique blend of history, art, and scenic beauty make it a must-visit for families.
- Saugerties: Saugerties, situated 23.1 miles away from Hillsdale, is a city that offers a mix of outdoor adventures and entertainment. With opportunities for horseback riding, skiing, and hunting, Saugerties is a paradise for those seeking outdoor activities. Families can also enjoy festivals, live music, and dancing in this lively city. Saugerties is home to a university, adding an educational touch to your vacation. Surrounded by mountains and with a vibrant atmosphere, Saugerties is an excellent choice for a ski vacation that offers a unique blend of adventure and entertainment for your family.
The travel seasons of Hillsdale
Trips to Hillsdale show no change in popularity throughout the year. The peak season to visit is from June to August, with July being the highest month. Off-peak season starts from October to December, and October sees the least travelers.
Hillsdale has something in store for you whenever you visit. January is the coldest month of the year, while July is hottest, with average temperatures up to 72.0 degrees Fahrenheit. The wettest month in Hillsdale is October, so pack accordingly.
 Calendar Month |  Temperature |  Precipitation |  Cloudiness |
| January | 25.0°F (-3.9°C) | Light Rain | Mostly Cloudy |
| February | 26.6°F (-3.0°C) | Light Rain | Mostly Cloudy |
| March | 34.5°F (1.4°C) | Light Rain | Mostly Cloudy |
| April | 46.2°F (7.9°C) | Light Rain | Mostly Cloudy |
| May | 57.9°F (14.4°C) | Light Rain | Mostly Sunny |
| June | 65.7°F (18.7°C) | Light Rain | Mostly Sunny |
| July | 72.0°F (22.2°C) | Light Rain | Mostly Sunny |
| August | 70.0°F (21.1°C) | Light Rain | Mostly Sunny |
| September | 62.8°F (17.1°C) | Light Rain | Mostly Sunny |
| October | 51.6°F (10.9°C) | Light Rain | Mostly Sunny |
| November | 39.4°F (4.1°C) | Light Rain | Mostly Sunny |
| December | 31.3°F (-0.4°C) | Light Rain | Mostly Cloudy |
How do I find a great hotel with Travelocity?
Give your entire crew an unforgettable vacation. When looking for the ideal accommodations, utilize the family-friendly badge to find hotels that offer additional amenities for children. Furthermore, our customized filters assist you in narrowing down hotels that are in close proximity to popular attractions, provide enhanced cleaning, and fall within your budget.
Why should I book with Travelocity?
Conference calls, to-do lists and, of course, football practice. Busy lives and packed schedules call for trips that are stress-free. Our aim is to provide worry-free travel every time you and your family book with us so that you can spend less time fretting and more time creating memories. In pursuit of this, we will assist you in finding and organizing your ideal trip, while offering transparent pricing and trustworthy reviews, along with round-the-clock customer support before, during, and after your vacation.
How can I save money on my trip to Hillsdale?
If you're looking to save money on your trip to Hillsdale, New York, consider visiting during the less popular season from October to December. This can help you find cheaper accommodations and avoid crowds. Another way to save is by bundling your flights, hotel, and car bookings together, which often comes at a discounted price. When you're in Hillsdale, be sure to take advantage of the inexpensive attractions nearby, such as visiting the local library, exploring the small town, and enjoying the beautiful scenery.
Frequently asked questions
Recent Hillsdale hotel reviews by fellow wanderers
Quality Inn
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