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. 684 South Egremont Rd., Great Barrington, MA 01230 Call ~6.42 miles southeast of Hillsdale
  • Midscale Mountain property
  • 2 floors in property
From£137
Excellent 5.0 /5 Reviews Call BookMore Details
Quality Inn Great Barrington 372 Main St., Great Barrington, MA 01230 Website Call ~7.68 miles east of Hillsdale
  • 2 star Rural property
  • 63 sleeping rooms in hotel
From£74
Very good 4.0 /5 Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Great Barrington Lenox / Berks in Great Barrington 249 Stockbridge Rd., Great Barrington, MA 01230 Website Call ~8.43 miles east of Hillsdale
  • Mid-scale Resort property
  • Free complimentary breakfast
From£81
Very good 4.0 /5 Latest Reviews Call BookMore Details
Travelodge by Wyndham Great Barrington Berkshires : 400 Stockbridge Rd. 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 Guest Reviews Call BookMore Details
Holiday Inn Express Great Barrington 415 Stockbridge Rd., Great Barrington, MA 01230 Call ~8.51 miles east of Hillsdale
  • 3 star Mountain hotel
  • Hotel has an eco-friendly policy Read more
From£66
Very good 4.0 /5 Guest Reviews Call BookMore Details
Pleasant Valley Motel West Stockbridge : 42 Stockbridge Rd. 42 Stockbridge Rd., West Stockbridge, MA 01266 Call ~10.68 miles northeast of Hillsdale
  • 2 star hotel
  • 16 sleeping rooms in hotel
From£44
Average 3.0 /5 Review Score Call BookMore Details
The Red Lion Inn 30 Main St., Stockbridge, MA 01262 Call ~11.09 miles east of Hillsdale
  • Midscale Rural hotel
  • 35 suites in hotel
From£89
Average 3.0 /5 Read 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
  • Three Star Mountain hotel
  • 2 meeting rooms in property
From£66
Very good 4.0 /5 Reviews Call BookMore Details
Econo Lodge Lee - Great Barrington 980 Pleasant St., Lee, MA 01238 Call ~13.40 miles east of Hillsdale
  • Two star hotel
  • 28 rooms in hotel
From£35
Average 3.0 /5 Hotel Reviews Call BookMore Details
Wheatleigh in Lenox Hawthorne Rd., Lenox, MA 01240 Call ~13.68 miles northeast of Hillsdale
  • Mid-scale property
  • 9 suites in property
From£298
Very good 4.0 /5 Reviews Call BookMore Details
Apple Tree Inn in Lenox 10 Richmond Mountain Rd., Lenox, MA 01240 Call ~13.71 miles northeast of Hillsdale
  • 4-star Mountain hotel
  • Hotel has 3 floors
From£74
Average 3.0 /5 Read Reviews Call BookMore Details
St. Charles Hotel 16 Park Place, Hudson, NY 12534 Call ~14.04 miles west of Hillsdale
  • Low priced Downtown property
  • Free breakfast available
From£59
Average 3.0 /5 Guest Reviews Call BookMore Details
Hudson Whaler 542 Warren St., Hudson, NY 12534 Call ~14.18 miles west of Hillsdale
  • Mid-scale Downtown hotel
  • Fitness + Health Center
From£55
Very good 4.0 /5 Recent Reviews Call BookMore Details
Seven Hills Inn : 40 Plunkett St. 40 Plunkett St., Lenox, MA 01240 Call ~14.34 miles northeast of Hillsdale
  • Expensive Resort property
  • 2 floors in hotel
From£137
Very good 4.5 /5 Reviews Call BookMore Details
Applegate Inn : 279 West Park St. 279 West Park St., Lee, MA 01238 Call ~14.46 miles east of Hillsdale
  • Midscale Rural property
  • 6 suites in property
From£119
Very good 4.0 /5 Latest Reviews Call BookMore Details
The Nest Hudson Hotel : 330 Union St. 330 Union St., Hudson, NY 12534 Call ~14.51 miles west of Hillsdale
  • High-end Downtown property
  • Hotel has 6 rooms
From£149
Very good 4.5 /5 Guest Reviews Call BookMore Details
33 Main : 33 Main St. 33 Main St., Lenox, MA 01238 Call ~14.67 miles east of Hillsdale
  • Luxurious 5-star property
From£149
Average 3.0 /5 Hotel Reviews Call BookMore Details
Rodeway Inn in Lee 200 Laurel St., Lee, MA 01238 Call ~14.68 miles east of Hillsdale
  • Two-star hotel
  • 23 rooms in hotel
From£44
Average 3.0 /5 Read Reviews Call BookMore Details
Chambery Inn in Lee 199 Main St., Lee, 01238 Call ~14.69 miles east of Hillsdale
  • 3-star property
  • Check in: 14:00
From£67
Very good 4.5 /5 Review Score Call BookMore Details
Brook Farm Inn : 15 Hawthorne St. 15 Hawthorne St., Lenox, MA 01240 Call ~14.71 miles northeast of Hillsdale
  • Expensive Rural hotel
  • Hotel has an eco-friendly policy See policy
From£89
Very good 4.0 /5 Guest Reviews Call BookMore Details
Black Swan Lee Lenox An Ascend Collection Hotel 435 Laurel St., Lee, MA 01238 Call ~14.72 miles east of Hillsdale
  • 3-star Lake hotel
  • Check-in time: 3:00PM
From£44
Very good 4.0 /5 Review Score Call BookMore Details
Canyon Ranch Lenox 165 Kemble St., Lenox, MA 01240 Call ~14.74 miles northeast of Hillsdale
  • Mid-scale hotel
  • Airport shuttle available
From£67
Average 3.0 /5 Guest Reviews Call BookMore Details
Quality Inn - Lee 170 Housatonic St., Lee, MA 01238 Call ~14.85 miles east of Hillsdale
  • Economical Lake property
From£35
Average 3.0 /5 Recent Reviews Call BookMore Details
Pilgrim Inn in Lee 165 Housatonic St., Lee, MA 01238 Call ~14.89 miles east of Hillsdale
  • Three Star property
From£59
Average 3.0 /5 Reviews Call BookMore Details
The Constance by The Lenox Collection - Lenox 11 Old Stockbridge Rd., Lenox, MA 01240 Call ~14.99 miles northeast of Hillsdale
  • High-end property
  • 24 sleeping rooms in hotel
From£167
Average 3.0 /5 Guest Reviews Call BookMore Details
Kemble Inn 2 Kemble St., Lenox, MA 01240 Call ~15.04 miles northeast of Hillsdale
  • Mid-scale Mountain hotel
  • 3 floors in property
From£197
Very good 4.0 /5 Hotel Reviews Call BookMore Details
The Whitlock by The Lenox Collection - Lenox 16 Church St., Lenox, MA 01240 Call ~15.08 miles northeast of Hillsdale
  • Affordable hotel
  • 30 rooms in hotel
From£149
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
  • Check-in: 3:00 p.m.
From£111
Very good 4.5 /5 Guest 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
  • Hotel has 2 floors
From£55
Average 3.0 /5 Reviews Call BookMore Details
The Cornell Inn, Lenox & The Berkshires - Lenox 203 Main St., Lenox, MA 01240 Call ~15.59 miles northeast of Hillsdale
  • Affordable Mountain hotel
  • 2 floors in hotel
From£44
Very good 4.0 /5 Reviews Call BookMore Details
Element Lenox Berkshires 130 Pittsfield Rd., Lenox, MA 01240 Call ~16.56 miles northeast of Hillsdale
  • 3-star Mountain property
  • 118 rooms in property
From£37
Average 3.0 /5 Reviews Call BookMore Details
Eastover Estate & Retreat : 430 East St. 430 East St., Lenox, MA 01240 Call ~16.64 miles northeast of Hillsdale
  • 4 star Mountain property
  • Has environment-friendly policy See more
From£81
Average 3.5 /5 Review Score Call BookMore Details
Life House Berkshires 194 Pittsfield Rd., Lenox, MA 01240 Call ~16.83 miles northeast of Hillsdale
  • Economy Suburban property
  • Check-in time: 2pm
From£36
Average 3.0 /5 Latest Reviews Call BookMore Details
Howard Johnson by Wyndham Lenox : 462 Pittsfield Rd. 462 Pittsfield Rd., Lenox, MA 01240 Call ~16.98 miles northeast of Hillsdale
  • Economy Resort hotel
  • 44 rooms in property
From£48
Average 3.0 /5 Reviews Call BookMore Details
James Newbury Hotel & Spa in Coxsackie 60 South River St., Coxsackie, NY 12051 Call ~17.18 miles northwest of Hillsdale
  • 3-star Riverfront hotel
  • Free breakfast available
From£59
Average 3.0 /5 Hotel Reviews Call BookMore Details
Miraval Berkshires Resort & Spa - All Inclusive Adults Only in Lenox 55 Lee Rd., Lenox, MA 01240 Call ~17.60 miles northeast of Hillsdale
  • Four star Resort property
  • Fitness / Gym is on-site
From£102
Average 3.0 /5 Read Reviews Call BookMore Details
Hampton Inn & Suites Lenox Berkshires in Lenox 445 Pittsfield Rd., Lenox, MA 01240 Call ~17.82 miles northeast of Hillsdale
  • 3-star Mountain property
  • Fitness center on property
From£59
Average 3.0 /5 Recent Reviews Call BookMore Details
The Yankee Inn in Lenox 461 Pittsfield Rd., Lenox, MA 01240 Call ~17.88 miles northeast of Hillsdale
  • Inexpensive hotel
  • Fitness center on property
From£108
Very good 4.0 /5 Latest Reviews Call BookMore Details
Knights Inn Lenox : 474 Pittsfield Rd. 474 Pittsfield Rd., Lenox, MA 01240 Call ~17.97 miles northeast of Hillsdale
  • Low Cost Downtown hotel
Best Western Plus Berkshire Hills Inn & Suites 1350 West Housatonic St., Pittsfield, MA 01201 Call ~18.11 miles northeast of Hillsdale
  • Affordable Rural property
  • Hotel has 19 suites
From£63
Very good 4.5 /5 Review Score Call BookMore Details
Lenox Inn 525 Pittsfield Rd., Lenox, MA 01240 Call ~18.16 miles northeast of Hillsdale
  • Low-priced hotel
  • Check-in: 15:00
From£44
Poor 2.0 /5 Read Reviews Call BookMore Details
Hilton Garden Inn Lenox Pittsfield 1032 South St., Pittsfield, MA 01201 Call ~18.18 miles northeast of Hillsdale
  • Midscale Suburban hotel
  • 95 rooms in property
From£70
Very good 4.0 /5 Review Score Call BookMore Details
Wake Robin Inn 106 Sharon Rd., Lakeville, CT 06039 Call ~18.22 miles south of Hillsdale
  • Affordable Rural property
  • Free breakfast available
From£66
Average 3.0 /5 Reviews Call BookMore Details
Holiday Inn Express Pittsfield Lenox Berkshires : 1055 South St. 1055 South St., Pittsfield, MA 01201 Call ~18.26 miles northeast of Hillsdale
  • Midscale Suburban property
  • Hotel has 81 rooms
From£59
Average 3.0 /5 Read Reviews Call BookMore Details
Berkshire Mountain Lodge 8 Dan Fox Dr., Pittsfield, MA 01201 Call ~18.48 miles northeast of Hillsdale
  • Cheap Mountain property
  • 146 suites in property
From£93
Very good 4.5 /5 Review Score Call BookMore Details
Interlaken Inn - Lakeville 74 Interlaken Rd., Lakeville, CT 06039 Call ~18.85 miles south of Hillsdale
  • Midscale Resort property
  • Has environment-friendly policy Learn more
From£133
Very good 4.0 /5 Reviews Call BookMore Details
Holiday Inn Express Hotel & Suites West Coxsackie by IHG - West Coxsackie 12740 Route 9 West, West Coxsackie, NY 12192 Call ~18.92 miles west of Hillsdale
  • Affordable Highway property
  • Check in: 03:00pm
From£88
Very good 4.0 /5 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
  • Three Star property
  • Check-in: 15:00
From£81
Very good 4.0 /5 Recent Reviews Call BookMore Details
Spark by Hilton West Coxsackie 12600 State Route 9w, West Coxsackie, NY 12192 Call ~20.08 miles northwest of Hillsdale
  • 3-star Rural property
  • Fitness + Health Center
From£55
Average 3.0 /5 Recent Reviews Call BookMore Details
Berkshire Inn 150 West Housatonic St., Pittsfield, MA 01201 Call ~20.17 miles northeast of Hillsdale
  • Economical Downtown property
  • Check in time: 1500
From£67
Average 3.0 /5 Latest 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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