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 - Great Barrington 684 South Egremont Rd., Great Barrington, MA 01230 Call ~6.42 miles southeast of Hillsdale
  • 3 star Mountain hotel
  • 2 meeting rooms in property
From$185
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 property
  • 2 floors in property
From$100
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi 249 Stockbridge Rd., Great Barrington, MA 01230 Website Call ~8.43 miles east of Hillsdale
  • Affordable Resort hotel
  • 5 suites in hotel
From$109
Very Good 4.0 /5 Reviews Call BookMore Details
Travelodge by Wyndham Great Barrington Berkshires in Great Barrington 400 Stockbridge Rd., Great Barrington, MA 01230 Call ~8.50 miles east of Hillsdale
  • Economy Resort hotel
  • Check in: 11:00 AM
From$47
Average 3.0 /5 Reviews Call BookMore Details
Holiday Inn Express Great Barrington - Great Barrington 415 Stockbridge Rd., Great Barrington, MA 01230 Call ~8.51 miles east of Hillsdale
  • 3-star Mountain hotel
  • 3 floors in hotel
From$89
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Pleasant Valley Motel West Stockbridge 42 Stockbridge Rd., West Stockbridge, MA 01266 Call ~10.68 miles northeast of Hillsdale
  • Low Cost property
  • Check in: 13:00
From$60
Average 3.0 /5 Hotel Reviews 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
  • Hotel has an eco-friendly policy See policy
From$120
Average 3.0 /5 Recent 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
  • Mid-scale Mountain hotel
  • 334 suites in hotel
From$89
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Econo Lodge Lee - Great Barrington in Lee 980 Pleasant St., Lee, MA 01238 Call ~13.40 miles east of Hillsdale
  • Low-priced hotel
  • Check-in time: 11:00
From$48
Average 3.0 /5 Review Score Call BookMore Details
Wheatleigh : Hawthorne Rd. Hawthorne Rd., Lenox, MA 01240 Call ~13.68 miles northeast of Hillsdale
  • Affordable hotel
  • Comp. Breakfast
From$400
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
  • 4-star Mountain hotel
  • Hotel has 3 floors
From$100
Average 3.0 /5 Review Score Call BookMore Details
St. Charles Hotel - Hudson 16 Park Place, Hudson, NY 12534 Call ~14.04 miles west of Hillsdale
  • Economical Downtown property
  • Hotel has 3 floors
From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Hudson Whaler : 542 Warren St. 542 Warren St., Hudson, NY 12534 Call ~14.18 miles west of Hillsdale
  • Mid-scale Downtown hotel
  • Fitness center on property
From$75
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Seven Hills Inn 40 Plunkett St., Lenox, MA 01240 Call ~14.34 miles northeast of Hillsdale
  • Four star Resort hotel
  • Check-in time: 3 pm
From$184
Very Good 4.5 /5 Latest Reviews Call BookMore Details
Applegate Inn in Lee 279 West Park St., Lee, MA 01238 Call ~14.46 miles east of Hillsdale
  • Affordable Rural hotel
  • 6 suites in property
From$160
Very Good 4.0 /5 Read Reviews Call BookMore Details
The Nest Hudson Hotel 330 Union St., Hudson, NY 12534 Call ~14.51 miles west of Hillsdale
  • High-end Downtown property
  • Hotel has 6 suites
From$200
Very Good 4.5 /5 Guest Reviews Call BookMore Details
33 Main - Lenox 33 Main St., Lenox, MA 01238 Call ~14.67 miles east of Hillsdale
  • Luxury 5 star hotel
From$200
Average 3.0 /5 Recent Reviews Call BookMore Details
Rodeway Inn 200 Laurel St., Lee, MA 01238 Call ~14.68 miles east of Hillsdale
  • Economy hotel
  • Check in: 11:00
From$60
Average 3.0 /5 Recent Reviews Call BookMore Details
Chambery Inn - Lee 199 Main St., Lee, 01238 Call ~14.69 miles east of Hillsdale
  • Mid-scale property
  • 9 rooms in property
From$90
Very Good 4.5 /5 Reviews Call BookMore Details
Brook Farm Inn : 15 Hawthorne St. 15 Hawthorne St., Lenox, MA 01240 Call ~14.71 miles northeast of Hillsdale
  • Expensive Rural property
  • Hotel has 3 floors
From$120
Very Good 4.0 /5 Latest Reviews Call BookMore Details
The Black Swan Lee Lenox An Ascend Collection Hotel in Lee 435 Laurel St., Lee, MA 01238 Website Call ~14.73 miles east of Hillsdale
  • Three Star Lake property
  • Access to gym on-site
From$65
Very Good 4.0 /5 Reviews Call BookMore Details
Canyon Ranch Lenox - Lenox 165 Kemble St., Lenox, MA 01240 Call ~14.74 miles northeast of Hillsdale
  • Mid-scale property
  • Shuttle from airport available
From$90
Average 3.0 /5 Hotel Reviews Call BookMore Details
Quality Inn 170 Housatonic St., Lee, MA 01238 Call ~14.85 miles east of Hillsdale
  • Cheap Lake property
  • Check in: 11:00 AM
From$47
Average 3.0 /5 Hotel Reviews Call BookMore Details
Pilgrim Inn - Lee 165 Housatonic St., Lee, MA 01238 Call ~14.89 miles east of Hillsdale
  • 3 star hotel
From$80
Average 3.0 /5 Read Reviews Call BookMore Details
The Constance by The Lenox Collection in Lenox 11 Old Stockbridge Rd., Lenox, MA 01240 Call ~14.99 miles northeast of Hillsdale
  • Four star hotel
  • Hotel has 24 rooms
From$225
Average 3.0 /5 Review Score Call BookMore Details
Kemble Inn : 2 Kemble St. 2 Kemble St., Lenox, MA 01240 Call ~15.04 miles northeast of Hillsdale
  • Midscale Mountain property
  • 3 floors in hotel
From$265
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 property
  • Hotel has 30 rooms
From$200
Average 3.0 /5 Read Reviews Call BookMore Details
Tiara Equest (The Inn at Richmond & Berkshire Equestrian Center - Richmond 802 State Rd., Richmond, MA 01254 Call ~15.28 miles northeast of Hillsdale
  • 3-star Rural hotel
  • 3 floors in property
From$150
Very Good 4.5 /5 Reviews Call BookMore Details
The Dewey by The Lenox Collection 7 Hubbard St., Lenox, MA 01240 Call ~15.43 miles northeast of Hillsdale
  • High-end property
  • Hotel has 2 floors
From$75
Average 3.0 /5 Review Score Call BookMore Details
The Cornell Inn, Lenox & The Berkshires : 203 Main St. 203 Main St., Lenox, MA 01240 Call ~15.59 miles northeast of Hillsdale
  • 3 star Mountain hotel
  • Hotel has 2 floors
From$60
Very Good 4.0 /5 Read Reviews Call BookMore Details
Element Lenox Berkshires : 130 Pittsfield Rd. 130 Pittsfield Rd., Lenox, MA 01240 Call ~16.56 miles northeast of Hillsdale
  • Midscale Mountain hotel
  • 2 meeting rooms in property
From$50
Average 3.0 /5 Guest Reviews Call BookMore Details
Eastover Estate & Retreat in Lenox 430 East St., Lenox, MA 01240 Call ~16.64 miles northeast of Hillsdale
  • Expensive Mountain hotel
  • Check in: 4:00PM
From$109
Average 3.5 /5 Recent Reviews Call BookMore Details
Life House Berkshires 194 Pittsfield Rd., Lenox, MA 01240 Call ~16.83 miles northeast of Hillsdale
  • Inexpensive Suburban hotel
  • Check in: 2pm
From$49
Average 3.0 /5 Latest Reviews Call BookMore Details
Howard Johnson by Wyndham Lenox 462 Pittsfield Rd., Lenox, MA 01240 Call ~16.98 miles northeast of Hillsdale
  • Low-priced Resort hotel
  • Comp. Breakfast
From$65
Average 3.0 /5 Hotel Reviews Call BookMore Details
James Newbury Hotel & Spa - Coxsackie 60 South River St., Coxsackie, NY 12051 Call ~17.18 miles northwest of Hillsdale
  • 3 star Riverfront hotel
  • Hotel has a green policy See more
From$80
Average 3.0 /5 Guest 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
  • High end Resort property
  • Gym is available on property
From$138
Average 3.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn & Suites Berkshires-Lenox 445 Pittsfield Rd., Lenox, MA 01240 Call ~17.82 miles northeast of Hillsdale
  • Midscale Mountain hotel
  • Hotel has 79 rooms
From$109
Average 3.0 /5 Hotel Reviews Call BookMore Details
The Yankee, Trademark Collection by Wyndham in Lenox 461 Pittsfield Rd., Lenox, MA 01240 Call ~17.88 miles northeast of Hillsdale
  • Low-priced hotel
  • Free complimentary breakfast
From$145
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Knights Inn Lenox 474 Pittsfield Rd., Lenox, MA 01240 Call ~17.97 miles northeast of Hillsdale
  • Economy Downtown hotel
  • 16 sleeping rooms in hotel
Best Western Plus Berkshire Hills Inn & Suites 1350 West Housatonic St., Pittsfield, MA 01201 Call ~18.11 miles northeast of Hillsdale
  • 3-star Rural hotel
  • 59 rooms in property
From$85
Very Good 4.5 /5 Read Reviews Call BookMore Details
Lenox Inn - Lenox 525 Pittsfield Rd., Lenox, MA 01240 Call ~18.16 miles northeast of Hillsdale
  • Low priced hotel
  • 18 rooms in hotel
Hilton Garden Inn Lenox Pittsfield in Pittsfield 1032 South St., Pittsfield, MA 01201 Call ~18.18 miles northeast of Hillsdale
  • 3 star Suburban hotel
  • 95 rooms in hotel
From$95
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Wake Robin Inn - Lakeville 106 Sharon Rd., Lakeville, CT 06039 Call ~18.22 miles south of Hillsdale
  • 3-star Rural property
  • 3 meeting rooms in hotel
From$89
Average 3.0 /5 Latest 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
  • 3 star Suburban property
  • Hotel has 28 suites
From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
Berkshire Mountain Lodge in Pittsfield 8 Dan Fox Dr., Pittsfield, MA 01201 Call ~18.48 miles northeast of Hillsdale
  • Two star Mountain hotel
  • Check-in: 4:00PM
From$125
Very Good 4.5 /5 Latest Reviews Call BookMore Details
Interlaken Inn 74 Interlaken Rd., Lakeville, CT 06039 Call ~18.85 miles south of Hillsdale
  • 3 star Resort hotel
  • Check in: 4:00pm
From$179
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Express Hotel & Suites West Coxsackie by IHG : 12740 Route 9 West 12740 Route 9 West, West Coxsackie, NY 12192 Call ~18.92 miles west of Hillsdale
  • 3-star Highway hotel
  • 3 floors in hotel
From$119
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Blackberry River Inn in Norfolk 538 Greenwoods Rd. West, Norfolk, CT 06058 Call ~20.05 miles southeast of Hillsdale
  • 3 star hotel
  • 2 floors in property
From$109
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
  • Check in time: 3:00 pm
From$75
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 Cost Downtown property
  • Free breakfast available
From$90
Average 3.0 /5 Latest Reviews Call BookMore Details

Next: See My Hillsdale Hotels with Pricing

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.

Back to Top