Hotels in Hillsdale
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Top Rated Hillsdale Hotels
The Brooks Motel
2871 New York 23, Hillsdale, NY
Free Cancellation
Reserve now, pay when you stay
1.02 mi from city center
$149 nightly
The price is $167 total per night
$167 total
Nov 14 - Nov 15
Total with taxes and fees
Guests of The Brooks Motel have access to free WiFi in public areas. If you decide to drive, there's free parking.
Pet friendly
Parking included
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
20.91 mi from city center
$120 nightly
The price is $135 total per night
$135 total
Nov 13 - Nov 14
Total with taxes and fees
At Berkshire Mountain Lodge, guests have access to an indoor pool, free WiFi in public areas, and a hot tub. If you decide to drive, there's free parking. Front-desk staff can help secure valuables, and provide local restaurant recommendations. Other amenities at this golf lodge include a business center, an arcade/game room, and laundry facilities.
Pool
Hot Tub
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
23.12 mi from city center
$88 nightly
The price is $99 total per night
$99 total
Nov 14 - Nov 15
Total with taxes and fees
Guests of Holiday Inn & Suites Pittsfield-Berkshires by IHG have access to an indoor pool, a gym, and free WiFi in public areas. If you decide to drive, there's free parking. The 24-hour front desk has multilingual staff ready to assist with securing valuables, luggage storage, and dry cleaning/laundry. Additional amenities include a conference center, a 24-hour business center, and a computer station.
Pool
Pet friendly
Berkshires Untold
194 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
19.22 mi from city center
$93 nightly
The price is $104 total per night
$104 total
Nov 17 - Nov 18
Total with taxes and fees
Renovated in 2023, Berkshires Untold offers free WiFi in public areas, coffee in a common area, and express check-in. You can take advantage of free parking if you drive. The front desk is staffed 24/7 to help with concierge services, and answer any questions about the accommodations. Additional amenities include a terrace, a water dispenser, and a fireplace in the lobby.
Pet friendly
Parking included
The Black Swan Lee - Lenox, an Ascend Collection Hotel
435 Laurel St, Lee, MA
Free Cancellation
16.73 mi from city center
$110 nightly
The price is $122 total per night
$122 total
Dec 2 - Dec 3
Total with taxes and fees
Guests of The Black Swan Lee - Lenox, an Ascend Collection Hotel enjoy a 24-hour gym, free WiFi in public areas, and a 24-hour business center. If you plan to drive, free parking is available. Front-desk staff are standing by 24/7 to assist with any requests. Additional amenities include coffee/tea in a common area, a microwave in a common area, and a meeting room.
Breakfast included
Pet friendly
The Red Lion Inn
30 Main Street, Stockbridge, MA
13.01 mi from city center
$183 nightly
The price is $205 total per night
$205 total
Nov 16 - Nov 17
Total with taxes and fees
Guests of The Red Lion Inn have access to an outdoor pool, a gym, and free WiFi in public areas. The 24-hour front desk has multilingual staff ready to assist with concierge services, securing valuables, and dry cleaning/laundry. Other amenities at this historic hotel include meeting rooms, a 24-hour business center, and coffee/tea in a common area.
Pool
Spa
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
20.31 mi from city center
$100 nightly
The price is $112 total per night
$112 total
Dec 7 - Dec 8
Total with taxes and fees
Guests staying at The Yankee, Trademark Collection by Wyndham enjoy an indoor pool, a 24-hour gym, and free WiFi in public areas. Free parking is available if you drive. The 24-hour front desk has multilingual staff ready to help with concierge services, and answer any questions about the area. Additional amenities include a hot tub, a seasonal outdoor pool, and coffee/tea in a common area.
Pool
Hot Tub
Quality Inn
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Free Cancellation
Reserve now, pay when you stay
8.25 mi from city center
$84 nightly
The price is $94 total per night
$94 total
Nov 25 - Nov 26
Total with taxes and fees
Guests of Quality Inn enjoy a gym, free WiFi in public areas, and coffee in a common area. You can put free parking to good use if you drive. Front-desk staff are standing by 24/7 to assist with any requests. Additional amenities include a microwave in a common area, free newspapers, and a water dispenser.
Breakfast included
Parking included
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
Free Cancellation
14.43 mi from city center
$148 nightly
The price is $165 total per night
$165 total
Nov 13 - Nov 14
Total with taxes and fees
Guests staying at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG enjoy features like 2 indoor pools, 2 outdoor pools, and a business center. Front-desk staff can help secure valuables, and provide local restaurant recommendations. Other amenities at this family-friendly hotel include a seasonal outdoor pool, an arcade/game room, and express check-out.
Pool
Air conditioning
St. Charles Hotel
16 Park Place, Hudson, NY
Free Cancellation
13.98 mi from city center
$161 nightly
The price is $182 total per night
$182 total
Nov 16 - Nov 17
Total with taxes and fees
St. Charles Hotel features free WiFi in public areas, a 24-hour business center, and a meeting room. There's free parking if you drive. Staff members are on hand to provide dry cleaning/laundry services, concierge services, and a safe deposit box at the front desk. This hotel also has laundry facilities.
Breakfast included
Pet friendly
Holiday Inn Express Hotel & Suites Great Barrington by IHG
415 Stockbridge Rd, Great Barrington, MA
Free Cancellation
9.49 mi from city center
$107 nightly
The price is $120 total per night
$120 total
Nov 30 - Dec 1
Total with taxes and fees
Guests of Holiday Inn Express Hotel & Suites Great Barrington by IHG have access to an indoor pool, a gym, and free WiFi in public areas. Free parking is available if you drive. The front desk has multilingual staff standing by 24 hours a day to assist with dry cleaning/laundry and securing valuables. Additional amenities include conference space, a 24-hour business center, and coffee/tea in a common area.
Pool
Breakfast included
Hotel On North
297 North Street, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
23.44 mi from city center
$133 nightly
The price is $149 total per night
$149 total
Nov 16 - Nov 17
Total with taxes and fees
Hotel On North features free WiFi in public areas, meeting rooms, and a business center. There's free parking if you drive. Front-desk staff can answer questions 24/7, and assist with luggage storage, tours or tickets, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include coffee/tea in a common area, a banquet hall, and an ATM.
Pet friendly
Parking included
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.
Top reasons to visit Hillsdale
- Outdoor Adventures: Hillsdale's hilly terrain is a playground for outdoor enthusiasts. Skiing, horseback riding, and hiking trails offer thrilling experiences.
- Breathtaking Scenery: Prepare to be awestruck by Hillsdale's stunning sunrise and scenic views. It's a feast for the eyes!
- Historic Ruins: Explore the fascinating historic ruins scattered throughout Hillsdale. They're like stepping back in time!
- Charming Districts: Discover the charm of Hillsdale's districts as you wander through its cozy coffee shops and local library.
- Ski Vacation Paradise: Stay in a cozy hotel and hit the slopes in nearby Great Barrington for an unforgettable ski adventure.
Top things to see and do in Hillsdale
Hillsdale, located in upstate New York, offers a wide range of activities for visitors to enjoy. Whether you're in the mood for a relaxing day at a cozy coffee shop or exploring the local library, this small town has something for everyone. The hilly terrain provides the perfect backdrop for outdoor adventures like skiing and horseback riding, while the breathtaking sunrise and scenic views will leave you in awe. Don't miss the chance to explore the historic ruins scattered throughout the area or take a hike on one of the many beautiful trails. Other area attractions include Tory Hill and lovely gardens to explore.
- Catamount Aerial Adventure Park: Get ready for an adrenaline rush at the Catamount Aerial Adventure Park. This zipline and ropes course will take you soaring through the air, surrounded by breathtaking views of flowers, gardens, and majestic mountains. Whether you're hiking, rock climbing, or camping, this outdoor adventure experience will leave you feeling exhilarated and connected to nature. Don't miss the chance to explore this budget-friendly attraction and unleash your inner adventurer.
- Community Library: Dive into a world of knowledge and imagination at the Community Library. This family-friendly point of interest offers a cultural experience like no other. Immerse yourself in the vast collection of books, explore the various programs and events, and let your curiosity flourish. Whether you're a bookworm or simply seeking a quiet escape, the Community Library is the perfect place to relax, learn, and create lasting memories.
- Hillsdale Town Hall: Step back in time and discover the rich history of Hillsdale at the historic Hillsdale Town Hall. This civic government building is a true gem, showcasing the architectural beauty of the past. Immerse yourself in the culture of the town as you explore the halls adorned with vintage photographs and artifacts. From its intricate details to its storied past, this point of interest offers a unique glimpse into the heritage of Hillsdale and is a must-visit for culture enthusiasts.
Best places to visit in Hillsdale
Hillsdale, New York is the perfect destination for a ski vacation. Stay in one of the cozy hotels in the area and enjoy hitting the slopes in nearby Great Barrington. Explore the charming districts of Hillsdale and take in the breathtaking scenery. Exciting destinations and thrilling ski adventures await!
- Lenox: Just a short drive from Hillsdale, Lenox offers a unique experience for those seeking a ski holiday. This charming city is known for its beautiful gardens, world-class museums, rejuvenating yoga retreats, live music scene, and vibrant entertainment options. Immerse yourself in the breathtaking scenery while exploring the art and architecture that the city has to offer. And if you're feeling adventurous, there are plenty of hiking trails and a library filled with literary treasures. Lenox truly has something for everyone, making it a must-visit destination for a ski vacation.
- Hudson: With its rich history, stunning river views, and thriving art scene, Hudson is an ideal destination for a ski holiday. Explore the city's opera house, immerse yourself in its historical charm, and indulge in delicious dining experiences. Discover the beauty of its cathedrals, go shopping in its unique boutiques, and soak in the picturesque scenery while boating on the river. Hudson's architecture is a visual delight, and there are plenty of opportunities for cultural enrichment. Whether you're a history buff or an art enthusiast, Hudson has something to offer to everyone.
- Saugerties: Nestled amidst mountains, Saugerties is a hidden gem for ski enthusiasts. Enjoy thrilling horseback riding adventures, immerse yourself in lively festivals, and relax in cozy cafes after a day on the slopes. With its proximity to ski resorts, Saugerties is the perfect base for your ski holiday. Experience the thrill of skiing or try your hand at hunting in the breathtaking mountain landscapes. In the evenings, indulge in the local entertainment scene, featuring live music and dancing. And don't forget to explore the nearby university, which adds a youthful energy to the town. Saugerties offers a unique blend of adventure and relaxation, making it a top choice for a ski vacation.
Seasonal travel trends of Hillsdale
The popularity of Hillsdale shows no change throughout the year. The most popular time to visit is between June and August, with a seasonal peak in July. The off-peak tourist season is from October and December, with October typically being the quietest month.
Check out the month-by-month weather chart for Hillsdale to help you plan your next trip. With a monthly average of 72.0 degrees Fahrenheit, you can expect the hottest temperatures in July. The coldest month, on average, is January. The most rainfall typically happens in October. Regardless of when you visit Hillsdale, every season has a reason to stay.
 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 |
Where should you stay in Hillsdale?
What are some of the best hotels for a stay with my pet in Hillsdale?
Hudson valley and The Berkshires Cottage is a pet-friendly guesthouse with free WiFi, in-room kitchens, and laundry facilities.
What are the best hotels in Hillsdale?
Here are some top hotels around Hillsdale:
- Berkshire Mountain Lodge is located 20.9 mi away, and this lodge has free WiFi, free parking, and in-room kitchens.
- Holiday Inn & Suites Pittsfield-Berkshires by IHG is located 23.1 mi away, and this hotel has free WiFi, free parking, and a health club.
- Berkshires Untold is located 19.2 mi away, and this lodge has free WiFi, free parking, and concierge services.
What are the best hotels to stay near Catamount Aerial Adventure Park?
A trip to Hillsdale just wouldn't be complete without a stop at Catamount Aerial Adventure Park. This is a favorite aerial adventure park, and it isn't hard to see why. A Beauty on the Border. Catamount Mountain Resort and ski Trails a Minute Away (0.3 miles away) is a great place to stay if you're planning to be nearby. Holiday House Motel (1 mile away) and Silvanus Lodge (2 miles away) are two other smart choices.
Hillsdale hotels essential information
Accommodation | 1,825 hotels |
|---|---|
Lowest Price | $94 |
Highest Price | $205 |
Popular hotels | The Brooks Motel, Berkshire Mountain Lodge, Holiday Inn & Suites Pittsfield-Berkshires by IHG, Berkshires Untold, The Black Swan Lee - Lenox, an Ascend Collection Hotel, The Red Lion Inn, The Yankee, Trademark Collection by Wyndham, Quality Inn, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, St. Charles Hotel, Holiday Inn Express Hotel & Suites Great Barrington by IHG, Hotel On North |
Booking tips for Hillsdale
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Saving tips for your trip
To save money on your trip to Hillsdale, consider visiting during the less popular season from October to December. You can save even more by bundling your flights, hotel, and car bookings together for a discounted price. While in Hillsdale, take advantage of the inexpensive local affinities such as exploring the small town, enjoying the scenic hilly views, and visiting the local library for some relaxation and quiet time.
Recent Reviews
Holiday Inn & Suites Pittsfield-Berkshires by IHG
5/5 Excellent
"Great stay! Nice quiet room for 2 little “alert “ to outside noise pups!! Comfy beds and central location for the day trips we had planned."
A verified traveler stayed at Holiday Inn & Suites Pittsfield-Berkshires by IHG
Posted 4 days ago
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