Hillsdale New York Accommodations

Only hotels in Hillsdale are listed below. Search for cheap and discounted hotel and motel rates in or near Hillsdale, NY for your business or personal leisure travel. Discover the most popular Hillsdale New York hotel rooms. Review the Hillsdale hotel list below to find the perfect lodging. We also have a map of the Hillsdale hotels. Group booking? Search Hillsdale Group Hotel Deals

The Hillsdale center point is approximately 13 miles southwest of Tanglewood and 14 miles east of Hudson Amtrak Station.

Located amidst the rolling hills of Columbia County, Hillsdale, NY is a charming destination that embodies the rustic allure of the American countryside. Bursting with history, natural beauty, and small-town vibes, Hillsdale is a treasure trove of exciting sights and attractions. From the enchanting Roeliff Jansen Park, with its sprawling meadows and fishing spots, to the Catamount Mountain Resort, which offers thrilling year-round activities, the town never ceases to surprise. It is also home to the Hillsdale Farmers Market, which showcases the best of local produce and handcrafted goods. As for accommodations, visitors will be pleased to find a range of options available. From cozy inns, motels and family-friendly hotels to luxury suites and resorts, the destination has it all, ensuring a comfortable stay for every traveler. These lodgings provide comfortable rooms, attentive service, and convenient amenities such as free Wi-Fi, complimentary breakfast, and on-site parking. They are also conveniently located near popular attractions, outdoor activities, and dining options, making them the perfect base for exploring the area. Whether you're seeking a peaceful retreat, a fun family getaway, or a romantic escape, the availability of accommodations in Hillsdale ensures a memorable and enjoyable rest for all visitors. More from this guide...

Hillsdale Hotels/Motels & Accommodations

The Windflower Inn 684 South Egremont Rd., Great Barrington, MA 01230 Call ~6.42 miles southeast of Hillsdale
  • Mid-scale Mountain hotel
  • 2 floors in property
From£138
Excellent 5.0 /5 Hotel Reviews Call BookMore Details
Quality Inn Great Barrington 372 Main St., Great Barrington, MA 01230 Website Call ~7.68 miles east of Hillsdale
  • Cheap Rural hotel
  • 2 floors in hotel
From£75
Very good 4.0 /5 Guest Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi - Great Barrington 249 Stockbridge Rd., Great Barrington, MA 01230 Website Call ~8.43 miles east of Hillsdale
  • 3-star Resort hotel
  • 5 suites in hotel
From£81
Very good 4.0 /5 Latest Reviews Call BookMore Details
Travelodge by Wyndham Great Barrington Berkshires - Great Barrington 400 Stockbridge Rd., Great Barrington, MA 01230 Call ~8.50 miles east of Hillsdale
  • Two-star Resort hotel
  • Check in: 11:00 AM
From£35
Average 3.0 /5 Read Reviews Call BookMore Details
Holiday Inn Express Great Barrington : 415 Stockbridge Rd. 415 Stockbridge Rd., Great Barrington, MA 01230 Call ~8.51 miles east of Hillsdale
  • Midscale Mountain property
  • 3 floors in property
From£66
Very good 4.0 /5 Latest Reviews Call BookMore Details
Pleasant Valley Motel West Stockbridge 42 Stockbridge Rd., West Stockbridge, MA 01266 Call ~10.68 miles northeast of Hillsdale
  • Economical property
  • Check-in time: 13:00
From£45
Average 3.0 /5 Review Score Call BookMore Details
The Red Lion Inn - Stockbridge 30 Main St., Stockbridge, MA 01262 Call ~11.09 miles east of Hillsdale
  • 3 star Rural hotel
  • Check-in: 4:00
From£90
Average 3.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Club Vacations Oak N Spruce Resort - South Lee 190 Meadow St., South Lee, MA 01260 Call ~12.73 miles east of Hillsdale
  • 3 star Mountain property
  • 3 floors in property
From£66
Very good 4.0 /5 Recent Reviews Call BookMore Details
Econo Lodge Lee - Great Barrington : 980 Pleasant St. 980 Pleasant St., Lee, MA 01238 Call ~13.40 miles east of Hillsdale
  • Economy property
  • Hotel has 28 rooms
From£36
Average 3.0 /5 Guest Reviews Call BookMore Details
Wheatleigh Hawthorne Rd., Lenox, MA 01240 Call ~13.68 miles northeast of Hillsdale
  • Midscale property
  • Hotel has 2 floors
From£300
Very good 4.0 /5 Reviews Call BookMore Details
Apple Tree Inn - Lenox 10 Richmond Mountain Rd., Lenox, MA 01240 Call ~13.71 miles northeast of Hillsdale
  • Expensive Mountain hotel
  • 6 conference rooms in property
From£75
Average 3.0 /5 Guest Reviews Call BookMore Details
St. Charles Hotel - Hudson 16 Park Place, Hudson, NY 12534 Call ~14.04 miles west of Hillsdale
  • Cheap Downtown hotel
  • 34 rooms in property
From£60
Average 3.0 /5 Hotel Reviews Call BookMore Details
Hudson Whaler - Hudson 542 Warren St., Hudson, NY 12534 Call ~14.18 miles west of Hillsdale
  • Affordable Downtown hotel
  • Gym / Fitness Center Available
From£56
Very good 4.0 /5 Read Reviews Call BookMore Details
Seven Hills Inn 40 Plunkett St., Lenox, MA 01240 Call ~14.34 miles northeast of Hillsdale
  • Expensive Resort hotel
  • 2 floors in property
From£138
Very good 4.5 /5 Latest Reviews Call BookMore Details
Applegate Inn 279 West Park St., Lee, MA 01238 Call ~14.46 miles east of Hillsdale
  • 3-star Rural property
  • Check-in time: 2 pm
From£120
Very good 4.0 /5 Hotel Reviews Call BookMore Details
The Nest Hudson Hotel in Hudson 330 Union St., Hudson, NY 12534 Call ~14.51 miles west of Hillsdale
  • High end Downtown hotel
  • 6 suites in hotel
From£150
Very good 4.5 /5 Latest Reviews Call BookMore Details
33 Main 33 Main St., Lenox, MA 01238 Call ~14.67 miles east of Hillsdale
  • Luxurious Five Star hotel
From£150
Average 3.0 /5 Latest Reviews Call BookMore Details
Rodeway Inn in Lee 200 Laurel St., Lee, MA 01238 Call ~14.68 miles east of Hillsdale
  • 2-star property
  • Check-in: 11:00
From£45
Average 3.0 /5 Read Reviews Call BookMore Details
Chambery Inn 199 Main St., Lee, 01238 Call ~14.69 miles east of Hillsdale
  • Mid-scale property
  • Check in time: 14:00
From£67
Very good 4.5 /5 Latest Reviews Call BookMore Details
Brook Farm Inn : 15 Hawthorne St. 15 Hawthorne St., Lenox, MA 01240 Call ~14.71 miles northeast of Hillsdale
  • 4 star Rural property
  • Hotel has 15 rooms
From£90
Very good 4.0 /5 Hotel Reviews Call BookMore Details
The Black Swan Lee Lenox An Ascend Collection Hotel - Lee 435 Laurel St., Lee, MA 01238 Website Call ~14.73 miles east of Hillsdale
  • Mid-scale Lake hotel
  • 52 rooms in hotel
From£48
Very good 4.0 /5 Read Reviews Call BookMore Details
Canyon Ranch Lenox : 165 Kemble St. 165 Kemble St., Lenox, MA 01240 Call ~14.74 miles northeast of Hillsdale
  • 3-star property
  • Hotel has 2 floors
From£67
Average 3.0 /5 Reviews Call BookMore Details
Quality Inn - Lee 170 Housatonic St., Lee, MA 01238 Call ~14.85 miles east of Hillsdale
  • Low Cost Lake property
  • Check in time: 11:00 AM
From£35
Average 3.0 /5 Recent Reviews Call BookMore Details
Pilgrim Inn - Lee 165 Housatonic St., Lee, MA 01238 Call ~14.89 miles east of Hillsdale
  • Midscale hotel
From£60
Average 3.0 /5 Read Reviews Call BookMore Details
The Constance by The Lenox Collection 11 Old Stockbridge Rd., Lenox, MA 01240 Call ~14.99 miles northeast of Hillsdale
  • Four-star hotel
  • 24 sleeping rooms in hotel
From£169
Average 3.0 /5 Read Reviews Call BookMore Details
Kemble Inn : 2 Kemble St. 2 Kemble St., Lenox, MA 01240 Call ~15.04 miles northeast of Hillsdale
  • 3-star Mountain hotel
  • 12 rooms in hotel
From£199
Very good 4.0 /5 Guest Reviews Call BookMore Details
The Whitlock by The Lenox Collection - Lenox 16 Church St., Lenox, MA 01240 Call ~15.08 miles northeast of Hillsdale
  • Mid-scale hotel
  • 2 floors in hotel
From£150
Average 3.0 /5 Recent Reviews Call BookMore Details
Tiara Equest (The Inn at Richmond & Berkshire Equestrian Center in Richmond 802 State Rd., Richmond, MA 01254 Call ~15.28 miles northeast of Hillsdale
  • Mid-scale Rural property
  • Hotel has 3 floors
From£112
Very good 4.5 /5 Reviews Call BookMore Details
The Dewey by The Lenox Collection in Lenox 7 Hubbard St., Lenox, MA 01240 Call ~15.43 miles northeast of Hillsdale
  • High end property
  • Free breakfast available
From£56
Average 3.0 /5 Guest Reviews Call BookMore Details
The Cornell Inn, Lenox & The Berkshires 203 Main St., Lenox, MA 01240 Call ~15.59 miles northeast of Hillsdale
  • Midscale Mountain property
  • 28 sleeping rooms in hotel
From£45
Very good 4.0 /5 Guest Reviews Call BookMore Details
Element Lenox Berkshires - Lenox 130 Pittsfield Rd., Lenox, MA 01240 Call ~16.56 miles northeast of Hillsdale
  • Mid-scale Mountain hotel
  • Hotel has 118 rooms
From£37
Average 3.0 /5 Reviews Call BookMore Details
Eastover Estate & Retreat 430 East St., Lenox, MA 01240 Call ~16.64 miles northeast of Hillsdale
  • 4-star Mountain property
  • Hotel has a green policy See policy
From£81
Average 3.5 /5 Hotel Reviews Call BookMore Details
Life House Berkshires 194 Pittsfield Rd., Lenox, MA 01240 Call ~16.83 miles northeast of Hillsdale
  • Two star Suburban hotel
  • Free complimentary breakfast
From£36
Average 3.0 /5 Guest Reviews Call BookMore Details
Howard Johnson by Wyndham Lenox 462 Pittsfield Rd., Lenox, MA 01240 Call ~16.98 miles northeast of Hillsdale
  • 2 star Resort hotel
  • Check in: 2:00 PM
From£48
Average 3.0 /5 Read Reviews Call BookMore Details
James Newbury Hotel & Spa : 60 South River St. 60 South River St., Coxsackie, NY 12051 Call ~17.18 miles northwest of Hillsdale
  • Three Star Riverfront hotel
  • Free complimentary breakfast
From£60
Average 3.0 /5 Reviews Call BookMore Details
Miraval Berkshires Resort & Spa - All Inclusive Adults Only - Lenox 55 Lee Rd., Lenox, MA 01240 Call ~17.60 miles northeast of Hillsdale
  • High-end Resort property
  • Gym is available on property
From£103
Average 3.0 /5 Read Reviews Call BookMore Details
Hampton Inn & Suites Berkshires-Lenox in Lenox 445 Pittsfield Rd., Lenox, MA 01240 Call ~17.82 miles northeast of Hillsdale
  • 3-star Mountain hotel
  • 24 suites in hotel
From£81
Average 3.0 /5 Reviews Call BookMore Details
The Yankee, Trademark Collection by Wyndham 461 Pittsfield Rd., Lenox, MA 01240 Call ~17.88 miles northeast of Hillsdale
  • Economy hotel
  • Free breakfast
From£108
Very good 4.0 /5 Recent Reviews Call BookMore Details
Knights Inn Lenox 474 Pittsfield Rd., Lenox, MA 01240 Call ~17.97 miles northeast of Hillsdale
  • Low Cost Downtown hotel
  • Check-in: 2.00 pm
From£27
Poor 2.0 /5 Read Reviews Call BookMore Details
Best Western Plus Berkshire Hills Inn & Suites 1350 West Housatonic St., Pittsfield, MA 01201 Call ~18.11 miles northeast of Hillsdale
  • Three Star Rural hotel
  • 3 floors in property
From£63
Very good 4.5 /5 Guest Reviews Call BookMore Details
Lenox Inn - Lenox 525 Pittsfield Rd., Lenox, MA 01240 Call ~18.16 miles northeast of Hillsdale
  • Cheap hotel
  • Check-in time: 15:00
Hilton Garden Inn Lenox Pittsfield in Pittsfield 1032 South St., Pittsfield, MA 01201 Call ~18.18 miles northeast of Hillsdale
  • Three Star Suburban hotel
  • Check in: 03:00PM
From£71
Very good 4.0 /5 Latest Reviews Call BookMore Details
Wake Robin Inn in Lakeville 106 Sharon Rd., Lakeville, CT 06039 Call ~18.22 miles south of Hillsdale
  • 3 star Rural property
  • Hotel has 3 suites
From£66
Average 3.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Express Pittsfield Lenox Berkshires in Pittsfield 1055 South St., Pittsfield, MA 01201 Call ~18.26 miles northeast of Hillsdale
  • Midscale Suburban property
  • 4 floors in hotel
From£60
Average 3.0 /5 Recent Reviews Call BookMore Details
Berkshire Mountain Lodge in Pittsfield 8 Dan Fox Dr., Pittsfield, MA 01201 Call ~18.48 miles northeast of Hillsdale
  • Low priced Mountain hotel
  • Check-in: 4:00PM
From£93
Very good 4.5 /5 Latest Reviews Call BookMore Details
Interlaken Inn in Lakeville 74 Interlaken Rd., Lakeville, CT 06039 Call ~18.85 miles south of Hillsdale
  • Mid-scale Resort hotel
  • Gym is available on property
From£134
Very good 4.0 /5 Read Reviews Call BookMore Details
Holiday Inn Express Hotel & Suites West Coxsackie by IHG 12740 Route 9 West, West Coxsackie, NY 12192 Call ~18.92 miles west of Hillsdale
  • Mid-scale Highway hotel
  • Hotel has 66 rooms
From£89
Very good 4.0 /5 Read Reviews Call BookMore Details
Blackberry River Inn : 538 Greenwoods Rd. West 538 Greenwoods Rd. West, Norfolk, CT 06058 Call ~20.05 miles southeast of Hillsdale
  • 3-star hotel
  • 17 rooms in property
From£81
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Spark by Hilton West Coxsackie 12600 State Route 9w, West Coxsackie, NY 12192 Call ~20.08 miles northwest of Hillsdale
  • Affordable Rural hotel
  • Check-in time: 3:00 pm
From£56
Average 3.0 /5 Latest Reviews Call BookMore Details
Berkshire Inn 150 West Housatonic St., Pittsfield, MA 01201 Call ~20.17 miles northeast of Hillsdale
  • Low priced Downtown hotel
  • Gym is available on property
From£67
Average 3.0 /5 Guest Reviews Call BookMore Details

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Discover the Perfect Time to Visit Hillsdale, NY: Uncover the Best Season for Outdoor Adventure and Cultural Experiences

Hillsdale boasts a humid continental climate with distinct seasonal variations, from hot summers to chilly winters. During the warm summer months, temperatures can reach highs in the 80s °F, creating perfect conditions for outdoor activities. Visitors can explore the beautiful natural surroundings by hiking or biking through the nearby Taconic State Park or enjoy a day of fishing or boating on the picturesque Queechy Lake. As autumn arrives, Hillsdale transforms into a breathtaking display of vibrant fall colors, making it an ideal time for scenic drives through the countryside or attending the annual Arts & Crafts Festival at Berkshire South. Winter brings cold weather and occasional snowfall, providing opportunities for winter sports enthusiasts to enjoy skiing or snowboarding at nearby resorts. In spring, the area comes alive with blossoming flowers and milder temperatures, making it a great time to stroll along the town's charming streets. With its diverse climate and seasonal attractions, Hillsdale, NY offers something for everyone throughout the year.

Unbeatable Hotel Discounts in Picturesque Hillsdale, NY

When it comes to securing the best deals on accommodations in Hillsdale, NY, HotelPlanner is a trusted partner. This renowned platform specializes in providing significant savings with discounts that cater to a wide array of travelers. For instance, solo travelers may enjoy price cuts and receive additional benefits such as complimentary breakfast, access to fitness centers or pools, and discounts for local attractions or dining options. HotelPlanner also offers group booking price cuts, which are ideal for families, friends, or colleagues journeying together. This lowers the cost per person and ensures everyone stays together, further enhancing the trip experience. Whether you're planning a last-minute trip or booking well in advance, it's worth checking the platform for the latest offers. By leveraging the deals available via HotelPlanner, travelers can enjoy a memorable stay in Hillsdale, NY, without straining their budget.

Discover the Best Attractions near Hillsdale, NY

Hillsdale, NY, is a veritable playground for nature enthusiasts and adventure seekers. One of the prime attractions is the Catamount Aerial Adventure Park, an exhilarating treetop course boasting superb views of the area's stunning landscapes. With a variety of aerial trails ranging from easy to challenging, the park caters to adventurers of all ages and skill levels. Just a stone's throw away is the Catamount Mountain Resort, a year-round destination that transforms with the seasons. In winter, its slopes become a haven for skiers and snowboarders, while in summer, it offers mountain biking, zip-lining, and scenic chairlift rides. The resort is also home to the longest zip line in the USA, making it a must-visit for thrill-seekers. For a more tranquil experience, head to the Taconic State Park, renowned for its breathtaking scenery and abundant recreational opportunities. Here, you can hike along miles of trails, explore the South Taconic Range, or simply relax by the picturesque Bash Bish Falls. For those interested in history and culture, the nearby Olana State Historic Site is a must-see. This picturesque estate was once the home of renowned Hudson River School artist Frederic Edwin Church. The site features a stunning Persian-inspired house, beautifully landscaped gardens, and panoramic views of the Hudson River Valley. Visitors can take guided tours of the house, explore the grounds, and even participate in art workshops and events. These attractions, along with many others, make Hillsdale a fascinating and diverse destination, offering something for every type of traveler.

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