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Find hotels in Hillsdale, NY from CA $85

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    Check prices for these dates, December 15–16, 2026

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    Our top choices for Hillsdale hotels

    1. The Brooks Motel

    A living room with a sofa, a coffee table, a fireplace, and a ceiling fan.

    2. Little Cat Lodge

    A wooden fire pit surrounded by six Adirondack chairs in a forested area.

    3. The Cozy Cat Motel

    A wooden cabin with a deck, large windows, and outdoor seating.

    4. Quality Inn Great Barrington

    A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

    5. Holiday Inn Express Hotel & Suites Great Barrington by IHG

    An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.

    6. Prospect Berkshires

    A wooden house with a porch, surrounded by trees and a body of water.

    7. Monument Mountain Motel

    A neatly made bed with white linens, two bedside lamps, a nightstand with a telephone, and a painting on the wall.

    8. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

    A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

    9. the Alander

    A modern building with a dark exterior, outdoor seating area with wooden chairs, and string lights.

    10. Travelodge by Wyndham Great Barrington Berkshires

    A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.

    11. The Black Swan Lee - Lenox, an Ascend Collection Hotel

    A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

    12. East Rock Inn

    A sign for East Rock Inn with a mountainous logo, surrounded by lush greenery and a gravel path leading to a building.

    13. The Little Lion

    A bedroom with two beds, a wall-mounted clock, and framed pictures.

    14. Quality Inn Lee - Lenox South

    A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.

    15. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

    An indoor swimming pool with clear water, tiled floors, and a blue wall.

    16. Granville House

    A dining table with pastries, a coffee pot, and a vase of sunflowers.

    17. Micosta Leisure Inn

    A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

    18. Courtyard by Marriott Lenox Berkshires

    An outdoor patio area with a circular fire pit surrounded by wicker furniture and a stone fire table.

    19. The Yankee Inn

    Two Adirondack chairs facing a river with a forested hill in the background.

    20. Berkshire Mountain Lodge

    A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

    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.

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    Stay near popular Hillsdale attractions

    Catamount Aerial Adventure Park

    Rating: 6.4/10 (5 reviews)

    You can take time to visit Catamount Aerial Adventure Park during your travels to Hillsdale. Discover the area's mountain views and seek out the hiking trails.

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    Copake Lake

    Commune with nature and explore the great outdoors at Copake Lake during your travels in Copake Lake.

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    Hillsdale Town Hall

    Hillsdale Town Hall is just one of the places to see in Hillsdale, so why not enjoy the other things to explore during your travels? Discover the sunrises while you're in the area.

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    Roe Jan Brewing Co.

    After visiting Roe Jan Brewing Co., make a plan to see the other sights and activities in Hillsdale. Discover the sunrises while you're in the area.

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    Community Library

    Community Library is just one of the places to see in Hillsdale, so why not enjoy the other things to explore during your travels? Discover the sunrises while you're in the area.

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    Mosquito Island

    Commune with nature and explore the great outdoors at Mosquito Island during your travels in Copake Lake.

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    Learn more about Hillsdale

    Tucked in the Hudson Valley, this rural hamlet offers scenic hikes through Taconic State Park and charming farm-to-table dining. Explore nearby art galleries in Copake or visit Catamount Mountain Resort for outdoor adventures in all seasons.

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    A landscape with a row of trees in autumn colors, a wooden fence, and a hilly background.

    Top Hillsdale Hotel Reviews

    Monument Mountain Motel

    A neatly made bed with white linens, two bedside lamps, a nightstand with a telephone, and a painting on the wall.

    Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

    A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

    Granville House

    A dining table with pastries, a coffee pot, and a vase of sunflowers.

    the Alander

    A modern building with a dark exterior, outdoor seating area with wooden chairs, and string lights.

    Micosta Leisure Inn

    A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

    Howard Hotel

    A hallway with a staircase, a framed painting, a mirror, and a potted plant.

    Inn at Silver Maple Farm

    A spacious kitchen with wooden beams, a dining area with a large table and chairs, and a view of the outdoors through large windows.

    The Black Swan Lee - Lenox, an Ascend Collection Hotel

    A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

    Shaker Mill Inn

    A red building with a sign reading "Shaker Mill Inn".

    The Nest Hudson

    A window with a gold-framed shelf containing a potted plant, a white bowl, and two gold pitchers.

    Hotel On North

    A multi-story hotel with a classic facade, large windows, and a prominent entrance.

    Find out more about Hillsdale

    Top reasons to visit Hillsdale

    Find great hotels near Hillsdale

    Discover a range of charming accommodations in Hillsdale, New York, perfect for your getaway. From cozy bed and breakfasts to welcoming agritourism properties, you'll find options that cater to families and pet owners alike. Whether you're seeking a quaint motel or a comfortable inn, Hillsdale offers a variety of hotels designed to enhance your adventure vacation experience.

    Where to stay near Hillsdale

    Hillsdale, New York, offers a refreshing getaway for adventure lovers and those seeking scenic relaxation. Explore the charming hamlet of Hillsdale, where friendly locals and unique shops enhance your experience. Just a short drive away, discover picturesque landscapes perfect for skiing or outdoor activities. Enjoy a romantic atmosphere with family-friendly options, making it an ideal destination for all. Embrace the vibrant community and breathtaking scenery that Hillsdale has to offer.

    Things to do in Hillsdale

    Hillsdale, New York, is an excellent destination for outdoor enthusiasts, offering skiing at various resorts and ski fields. Visitors can also enjoy leisurely strolls, explore shopping malls, and participate in themed nights. Don't miss the Hillsdale Community Fair for local festivities and live music, making it a vibrant spot for adventure and relaxation alike.

    Shopping

    In Hillsdale, you can explore local shops that offer unique gifts and souvenirs. If you're up for a drive, visit the nearby Great Barrington, where you'll find a variety of boutiques and specialty stores showcasing artisan goods and local crafts.

    Recreation

    Hillsdale Wellness Retreat offers rejuvenating spa treatments and meditation sessions amidst tranquil surroundings. Nearby, the Catamount Ski Area provides thrilling outdoor activities year-round, including hiking and skiing, ensuring both relaxation and adventure are at your fingertips during your visit to this charming town.

    Adventure

    Explore the scenic trails at Catamount Mountain Resort for hiking and exhilarating zip-lining experiences. For a thrilling day, visit the nearby Bash Bish Falls State Park to witness stunning waterfalls and enjoy nature walks that offer breathtaking views of the surrounding landscape.

    Nightlife

    For a lively evening in Hillsdale, check out the cozy atmosphere at the Hillsdale Tavern for local brews and friendly conversation. If you're in the mood for live music, the nearby Catskill Music Café offers a mix of genres in a relaxed setting, perfect for unwinding after a day of exploring.

    *Distances are measured in a straight line; actual driving distances may vary depending on the route.

    Booking tips and Expedia advantages for Hillsdale

    Find the best attractions near Hillsdale

    Hillsdale, New York, is a perfect destination for outdoor enthusiasts and adventure seekers. Visitors can explore stunning national and state parks, nature reserves, and picturesque lakes. The area offers a variety of activities that cater to those looking for thrilling adventures as well as cultural experiences, ensuring a memorable vacation for all who visit.

    Best time to go to Hillsdale

    The best time to visit Hillsdale is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly high and weather is mostly cloudy with light rain.

    Calendar MonthTemperaturePrecipitationCloudinessOccupancyPricing
    January25.0°F (-3.9°C)Light RainMostly CloudySlightly HighSlightly Low
    February26.6°F (-3.0°C)Light RainMostly CloudySlightly HighAverage
    March34.5°F (1.4°C)Light RainMostly CloudySlightly LowSlightly Low
    April46.2°F (7.9°C)Light RainMostly CloudyAverageSlightly Low
    May57.9°F (14.4°C)Light RainMostly SunnyAverageAverage
    June65.7°F (18.7°C)Light RainMostly SunnyAverageAverage
    July72.0°F (22.2°C)Light RainMostly SunnySlightly HighSlightly High
    August70.0°F (21.1°C)Light RainMostly SunnyAverageSlightly High
    September62.8°F (17.1°C)Light RainMostly SunnyAverageAverage
    October51.6°F (10.9°C)Light RainMostly SunnySlightly LowSlightly High
    November39.4°F (4.1°C)Light RainMostly SunnyAverageAverage
    December31.3°F (-0.4°C)Light RainMostly CloudySlightly LowAverage

    The nearest major airports for your trip to Hillsdale

    If you're planning a trip to Hillsdale, New York, you have several major airports to choose from. Hartford, CT (BDL-Bradley Intl.) is located 74.0km away, with nearby hotels such as the 4-star DoubleTree by Hilton Hartford - Bradley Airport, just 1.6km from the airport. ALBany, NY (ALB-Albany Intl.) is 67.6km away, offering options like The Landing Hotel at Rivers Casino & Resort, 12.9km from the airport. Lastly, White Plains, NY (HPN-Westchester County) is 123.9km from Hillsdale, with luxury accommodations like The Opus Westchester, only 6.4km from the airport, providing convenient transportation services.

    Frequently Asked Questions

    What is the best area to stay in Hillsdale?

    The best area to stay in Hillsdale is in and around the town centre, particularly near the intersection of Routes 23 and 22.

    This area is the heart of Hillsdale, where you'll find the majority of the town's shops, eateries, and local services. It's quite walkable, making it easy to pop into a cafe, browse a boutique, or pick up essentials. The general layout is a classic small-town main street, with buildings lining the roads and a few side streets branching off.

    Couples looking for a relaxing getaway often find this area ideal. It offers easy access to local establishments for dining and drinks, and many accommodations in this central zone provide a comfortable base for exploring the surrounding countryside or simply enjoying a quiet weekend.

    For those seeking a more secluded experience but still wanting to be close to amenities, staying slightly outside the immediate town centre, perhaps a short drive along Route 23 towards Catamount Mountain, can be a good option.

    What are the best hotels in Hillsdale that travellers recommend?

    For a highly recommended hotel in Hillsdale, consider The Brooks Motel.

    The Brooks Motel has a review rating of 7.4. Guests frequently mention the super comfy and clean beds, along with the modern and clean rooms. The customer service also receives excellent remarks. For those interested in outdoor activities, the motel is conveniently located near a ski area and Catamount Aerial Adventure Park, which is just 2.0 km away. The rooms feature premium bedding, Egyptian cotton sheets, and air conditioning, with some even offering a fireplace.

    What are the best budget hotels in Hillsdale?

    For a highly-rated budget hotel in Hillsdale, consider The Brooks Motel.

    The Brooks Motel has a review rating of 7.4. Guests frequently mention the super comfy and clean beds, along with modern and clean rooms. The customer service also receives excellent feedback. This motel offers useful amenities such as free WiFi and complimentary toiletries. For those interested in winter sports, there are ski areas, ski lifts, ski runs, and cross-country skiing all conveniently located nearby. Pets are also welcome to stay free of charge, and free self-parking is available. View all budget hotels in Hillsdale

    What are the best hotels in Hillsdale near Catamount Aerial Adventure Park?

    For a well-located hotel near Catamount Aerial Adventure Park in Hillsdale, The Brooks Motel is a highly-rated option.

    The Brooks Motel, with a 7.4 rating, is conveniently situated just 2.0 km from Catamount Aerial Adventure Park. This motel is particularly suitable for families and offers a range of amenities including free WiFi, free self-parking, and complimentary toiletries. Guests frequently praise the super comfy and clean beds, the modern and clean rooms, and the excellent customer service. For those interested in winter sports, the motel is also very close to various ski facilities, including ski areas, lifts, runs, downhill, and cross-country options. Additionally, it features kitchens in its rooms and welcomes pets at no extra charge.

    When is the best time to go to Hillsdale?

    The best time to visit Hillsdale is during the summer (June to August) for outdoor activities and autumn (September to October) for the stunning fall foliage.

    Summer in Hillsdale offers warm, sunny days superb for enjoying the natural beauty of the region. This is an ideal time for couples and families who want to explore hiking trails, visit local farms, or enjoy swimming in nearby lakes. The weather is generally pleasant for outdoor dining and wandering through the small town centre.

    Autumn transforms Hillsdale into a picturesque landscape, with the surrounding hills ablaze with red, orange, and gold leaves. This season is particularly popular with couples seeking a romantic getaway and anyone who appreciates scenic drives and photography.

    Can I cancel my hotel reservation on Expedia?

    You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Hillsdale.

    How much is the nightly rate at a Hillsdale hotel?

    Prices for hotels in Hillsdale often vary, but you can find a great deal from CA $85 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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