Find hotels in Hillsdale, NY from $76

Top reasons to visit Hillsdale

• Outdoor Adventures: Enjoy skiing, hiking, and fishing in the scenic Berkshire Mountains, making Hillsdale a paradise for adventure seekers.
• Charming Small Town: Experience the welcoming atmosphere and friendly locals, perfect for families looking to relax and unwind.
• Historical Attractions: Explore unique historic landmarks and houses that offer a glimpse into the region's rich history.
• Diverse Accommodations: Choose from cozy bed and breakfasts to luxurious hotels, catering to every traveler's needs.
• Proximity to Great Barrington: Visit the nearby town for additional activities, dining, and shopping opportunities.

Find great hotels in Hillsdale

Hillsdale, New York, offers a diverse selection of accommodations to suit every traveler's preferences, ranging from cozy bed and breakfasts to luxurious hotels. With options spanning from 1 to 4.5 stars, visitors can find the perfect lodging for their stay. Whether you're seeking pet-friendly facilities, adventure-themed experiences, or a business-friendly environment, Hillsdale has something for everyone. Discover the best hotels and comfortable rooms to make your vacation memorable.

• The Yankee, Trademark Collection by Wyndham: Experience a business-oriented stay at The Yankee, Trademark Collection by Wyndham, located 20 miles from Hillsdale. This hotel is perfect for business travelers, offering extensive amenities such as a 24-hour business center, multiple meeting rooms, and versatile conference spaces. Its modern design and professional atmosphere make it an ideal choice for those looking to blend work and leisure seamlessly during their vacation.
• Howard Johnson by Wyndham Saugerties: Situated 24 miles from Hillsdale, Howard Johnson by Wyndham Saugerties caters to family and business travelers alike. This welcoming hotel features a range of family-friendly amenities such as free cribs and window guards for children, ensuring a safe and comfortable environment for families. Additionally, it offers essential business facilities including a business center and meeting rooms, making it a balanced option for your travels.
• The Black Swan Lee - Lenox, Ascend Hotel Collection: Nestled 17 miles from Hillsdale, The Black Swan Lee - Lenox invites adventure seekers, families, and pet lovers to indulge in a variety of outdoor activities. With skiing, fishing, and mountain climbing nearby, there’s no shortage of excitement. The hotel accommodates pets under specific policies, and offers family amenities like cribs and child safety features, allowing everyone to enjoy a memorable getaway together.

Discover the best areas to stay in Hillsdale

Hillsdale, New York, offers a delightful blend of outdoor adventure and family-friendly charm. Nestled in the scenic Berkshire Mountains, visitors can enjoy activities like skiing and hiking at nearby destinations such as Callicoon Hills and Beautypeakscutt Hill. This small town is perfect for families seeking relaxation amidst stunning landscapes, friendly locals, and a welcoming atmosphere, making it an ideal vacation spot for those looking to unwind and explore the beauty of the region.

• Hudson: Located 15 miles from Hillsdale, Hudson is a charming city known for its vibrant arts scene and stunning natural landscapes. The travel experience here is marked by outdoor adventures, particularly during the peak summer months from July to September. Outdoor enthusiasts will enjoy skiing, as the nearby ski fields and resorts offer thrilling winter sports. Hudson is surrounded by beautiful lakes, mountains, and parks, making it an ideal destination for those seeking scenic views and recreational activities.
• Lenox: Situated 17 miles from Hillsdale, Lenox is a picturesque city that strikes a perfect balance between entertainment and romance. With visitor numbers peaking from June to August, the city is a hub for cultural experiences including music concerts and theater performances. Lenox is also close to stunning parks and lakes, providing a delightful backdrop for family outings or romantic getaways. The area's ski resorts offer winter sports, adding an adventurous twist to your visit.
• Great Barrington: Just 8 miles away from Hillsdale, Great Barrington is a lively city that attracts visitors year-round, with a slight peak in the summer months. This destination is a favorite for ski enthusiasts and adventure seekers, as it boasts excellent ski fields and resorts. Like its neighbors, Great Barrington is surrounded by breathtaking mountains and serene lakes, perfect for outdoor exploration. The vibrant local community also offers a range of shops and eateries, making it a great spot to unwind after a day of adventure.

Things to do in Hillsdale

Hillsdale, New York, offers a fantastic vacation for ski enthusiasts and adventure seekers alike. You can enjoy skiing at local resorts and explore beautiful hiking spots and fishing holes. Be sure to check out Hillsdale's top tips for maximizing your outdoor experience. Whether you're hitting the slopes or enjoying the natural scenery, there's something for everyone in this charming destination.

Food and drinks

Visit the charming Rose's Cafe for a delightful breakfast or lunch with local flavors. For a cozy evening, check out the Irish pub for classic dishes and drinks. Don't miss the alpine-styled restaurant for a unique dining experience that captures the essence of Hillsdale's culinary scene.

Shopping

In Hillsdale, check out Hoffman's Pottery for unique gifts and souvenirs. If you're up for a drive, the Lee Premium Outlets and Berkshire Mountain Country Store, both 17 miles away, offer a variety of shopping experiences, from fashion to local crafts.

Recreation

Lake Mansfield Park offers a tranquil setting for relaxation and leisurely strolls, perfect for rejuvenation. For golf enthusiasts, Wyndhurst Golf & Club provides a scenic outdoor experience with well-maintained greens. Tyringham Cobble invites visitors to explore its serene trails, surrounded by nature, ideal for mindfulness and calm.

Adventure

Experience thrilling winter sports at Catamount Ski Area, located 2 miles from Hillsdale, offering excellent skiing and snowboarding opportunities. For an exhilarating outdoor challenge, visit Catamount Aerial Adventure Park, featuring zip lines and rope courses right in Hillsdale. Enjoy scenic hikes along the Housatonic River Walk, about 9 miles away.

Nightlife

Experience a night out at the Mahaiwe Performing Arts Center for a captivating show, or try your luck at the Magnolia Bluffs Casino, known for its lively atmosphere. For a family-friendly option, catch a performance at The Mac-Haydn Theatre, perfect for a romantic evening or entertainment with loved ones.

Booking tips and Expedia advantages for Hillsdale

To save money during your visit to Hillsdale, consider exploring popular free attractions like Bash Bish Falls State Park and Mount Everett State Reservation. The best time to travel is from November to January when hotel prices are lower. Book accommodations about a month in advance or check Expedia for last-minute deals. Utilize filters to find eco-friendly hotels and sort by price to find the best rates. Combining hotel and flight bookings through Expedia packages can also lead to savings, and joining their One Key membership offers additional discounts and future cash rewards.

• The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Hillsdale are November to January, where the prices are slightly lower. This is in comparison to June to August, where prices are slightly higher.
• The best time to book a hotel: The cheapest time to book a hotel in Hillsdale is usually 1 month out from when you are planning to stay. If you're a little more spontaneous, you could also peruse Expedia's last minute deals which could secure you a cheaper stay. Look out for the green banner below the price to spot the deals.
• Find cheap hotels on Expedia: Utilize Expedia’s search tool to customize your options based on your budget, desired location, and preferred hotel type. For instance, selecting the "Eco-certified" filter will showcase sustainable and environmentally friendly hotels currently available. To find the best prices and deals, simply sort the price filter from low to high.
• Consider bundling your trip: You can save money by combining your Hillsdale hotel reservation with your flights and activities through an Expedia package.
• Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions in Hillsdale

Hillsdale, New York, is a fantastic destination for ski, adventure, and sports enthusiasts. Explore popular attractions like national and state parks, serene lakes, and historic houses that offer a blend of outdoor fun and cultural experiences. Nearby, you can visit unique historic landmarks and the charming town of Great Barrington for even more activities. Whether you seek adventure or a taste of history, Hillsdale has something for every traveler.

• Taconic State Park: Just 4 miles from Hillsdale, Taconic State Park offers stunning natural beauty and outdoor adventures. Hike scenic trails, enjoy picnicking by pristine lakes, or explore the diverse wildlife. It's a perfect spot for nature lovers and those seeking a peaceful escape.
• National Shrine of the Divine Mercy: Located 13 miles away, this serene shrine is a place of worship and reflection. Immerse yourself in its rich culture, beautiful grounds, and inspiring architecture, making it a unique spiritual experience for visitors.
• Norman Rockwell Museum: Situated 12 miles from Hillsdale, this museum showcases the iconic artwork of Norman Rockwell. Dive into American culture and history through his charming illustrations, providing a delightful experience for art enthusiasts and families alike.

Best time to go to Hillsdale

Visitor numbers in Hillsdale is generally unchanged in popularity throughout the year. The best time to visit Hillsdale can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Hillsdale falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Hillsdale falls in January, visitor numbers are slightly high and weather is mostly cloudy with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	25.0°F (-3.9°C)	Light Rain	Mostly Cloudy	Slightly High	Slightly Low
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	Average
April	46.2°F (7.9°C)	Light Rain	Mostly Cloudy	Average	Average
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	Slightly High
July	72.0°F (22.2°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
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	Average
November	39.4°F (4.1°C)	Light Rain	Mostly Sunny	Average	Slightly Low
December	31.3°F (-0.4°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly Low

The nearest major airports for your trip to Hillsdale

When planning your trip to Hillsdale, New York, consider flying into nearby airports for convenience. Hartford, CT (BDL-Bradley Intl.) is 46 miles away, with excellent hotel options like the 4-star DoubleTree by Hilton Hartford - Bradley Airport, just 1 mile from the airport. Albany, NY (ALB-Albany Intl.) is 42 miles away, offering stays at the Park Manor Hotel, 8 miles from the airport. Lastly, Newburgh, NY (SWF-Stewart Intl.) is 55 miles from Hillsdale, with the 3.5-star Dutchess Inn and Spa at Beacon located 6 miles away. Each airport features accessible transportation to these hotels, ensuring a smooth arrival experience.