Book Hotels in Hillsdale, NY

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Top Hillsdale hotels

Postcard Cabins Eastern Catskills

Postcard Cabins Eastern Catskills

2 out of 5
282 Cairo Junction Rd, Catskill, NY
$184 nightly
The price is $199 total per night from Sep 29 to Sep 30
$199 total
Sep 29 - Sep 30
Total with taxes and fees
This cabin features a virtual front desk. Take advantage of the free self parking.
Quiet and quaint
"Nice little stay and was pleasantly surprised by the cabin. Would recommend"

Reviewed on Sep 20, 2025

Opens in a new windowPostcard Cabins Eastern Catskills
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street, South Lee, MA
Fully refundableReserve now, pay when you stay
$138 nightly
The price is $154 total per night from Sep 28 to Sep 29
$154 total
Sep 28 - Sep 29
Total with taxes and fees
This hotel features 2 outdoor pools, 2 indoor pools, and a poolside bar. There's fun for all ages with mini golf and a playground, and families will appreciate ...
"The room was fantastic - lots of space and well laid out. Having a kitchen is always very helpful. The property was well kept and clean. I love the rustic vibe. The amenities were awesome - the kids spent all day in the large outdoor pool. We also enjoyed the arcade and mini-golf. The whole area ..."

Reviewed on Sep 22, 2025

Opens in a new windowHoliday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $143 total per night from Sep 29 to Sep 30
$143 total
Sep 29 - Sep 30
Total with taxes and fees
A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a lobby ...
"Ggg"

Reviewed on Sep 20, 2025

Opens in a new windowBerkshires Untold
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St, Lee, MA
$115 nightly
The price is $128 total per night from Oct 27 to Oct 28
$128 total
Oct 27 - Oct 28
Total with taxes and fees
A restaurant and a 24-hour gym are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self ...
"great location. so nice to wake up to the view of the lake and have kayaks on property to rent. within a short drive of everything. staff was very nice and informative. downsides are you can hear everything through the front door. it’s hard to stay quiet enough for your neighbors. also no water pressure ..."

Reviewed on Sep 22, 2025

Opens in a new windowThe Black Swan Lee - Lenox, an Ascend Collection Hotel
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $126 total per night from Sep 28 to Sep 29
$126 total
Sep 28 - Sep 29
Total with taxes and fees
This lodge features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, ...
"Clean and spacious one bedroom suite with well stocked kitchen. Large indoor pool and outdoor year round Jacuzzi are wonderful. Also very affordable. Second time staying here and will stay here again."

Reviewed on Sep 25, 2025

Opens in a new windowBerkshire Mountain Lodge
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
$217 nightly
The price is $243 total per night from Sep 29 to Sep 30
$243 total
Sep 29 - Sep 30
Total with taxes and fees
This smoke-free hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi ...
"A great place if you appreciate and like history. The lobby is filled with antiques and the porch is great to rock in a chair and sip some wine. Parking is no issue and you can walk to local restaurants and shops."

Reviewed on Sep 16, 2025

Opens in a new windowThe Red Lion Inn
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $104 total per night from Oct 13 to Oct 14
$104 total
Oct 13 - Oct 14
Total with taxes and fees
A gym, free self parking, and free newspapers are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. ...
"Very good"

Reviewed on Sep 22, 2025

Opens in a new windowQuality Inn
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
Fully refundable
$109 nightly
The price is $122 total per night from Sep 29 to Sep 30
$122 total
Sep 29 - Sep 30
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public ...
"Valerie at the front desk and who checked me in was above and beyond in customer service. She checked to see if I had a IGH account—which I did but had forgotten, and reminded me about the points and promotions. This Holiday Inn is a well managed property. Thank you"

Reviewed on Sep 18, 2025

Opens in a new windowHoliday Inn & Suites Pittsfield-Berkshires by IHG
The Brooks Motel

The Brooks Motel

2 out of 5
2871 New York 23, Hillsdale, NY
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $133 total per night from Sep 29 to Sep 30
$133 total
Sep 29 - Sep 30
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A virtual front desk are provided for your convenience.
"Clean, stylish and simple. Exactly what I was hoping for."

Reviewed on Sep 1, 2025

Opens in a new windowThe Brooks Motel
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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.

  1. 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.
  2. 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.
  3. 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.

  1. 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.
  2. 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.
  3. 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.

Best times to go to Hillsdale

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 iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationcloud iconCloudiness
January25.0°F (-3.9°C)Light RainMostly Cloudy
February26.6°F (-3.0°C)Light RainMostly Cloudy
March34.5°F (1.4°C)Light RainMostly Cloudy
April46.2°F (7.9°C)Light RainMostly Cloudy
May57.9°F (14.4°C)Light RainMostly Sunny
June65.7°F (18.7°C)Light RainMostly Sunny
July72.0°F (22.2°C)Light RainMostly Sunny
August70.0°F (21.1°C)Light RainMostly Sunny
September62.8°F (17.1°C)Light RainMostly Sunny
October51.6°F (10.9°C)Light RainMostly Sunny
November39.4°F (4.1°C)Light RainMostly Sunny
December31.3°F (-0.4°C)Light RainMostly 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

What are the top kid-friendly hotels in Hillsdale?
From fun amenities to bigger rooms, kid-friendly hotels come with features that can help turn an everyday family vacation into an amazing one. These Hillsdale properties make traveling with little ones child's play: Ideal location for summer and winter activities with plenty of outdoor space. will help make your trip the best one yet. It comes with a range of conveniences aimed at families, such as a travel crib and a firepit. Alternatively, spend your Hillsdale escape at Holiday House Motel Hillsdale. Make the most of pet-friendly facilities, express check-out services and more here.
Where can I find cheap hotels in Hillsdale?
At Travelocity you'll find really nice hotels in Hillsdale at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Hillsdale rather than in Hillsdale. We may find you even better rates, too.
How do I find the best Hillsdale hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Hillsdale then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Hillsdale?
The cheapest hotel in Hillsdale is $104. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Hillsdale?
There are 1,805 hotels in Hillsdale on Travelocity.
What are the best hotels in Hillsdale?
Hillsdale has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Hillsdale for you!
When is the best time to visit Hillsdale?
If you want the joy of a fun-filled trip in peak season, visit Hillsdale during February, May and September. If you'd prefer the peace of off-season, book a stay during quieter months, such as March, June and December.
When is the cheapest time to stay in Hillsdale?
Based on historic data is usually the cheapest month to visit Hillsdale. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Hillsdale?
There are multiple hotels in Hillsdale that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Hillsdale. We have plenty of kid-friendly hotels in Hillsdale to choose from on Travelocity!
Why book a hotel in Hillsdale through Travelocity?
Because we have the top hotels in Hillsdale! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Hillsdale on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

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