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 in Great Barrington 684 South Egremont Rd., Great Barrington, MA 01230 Call ~6.42 miles southeast of Hillsdale
  • Mid-scale Mountain hotel
  • Check in time: 2:00PM
From£137
Excellent 5.0 /5 Latest Reviews Call BookMore Details
Quality Inn Great Barrington : 372 Main St. 372 Main St., Great Barrington, MA 01230 Website Call ~7.68 miles east of Hillsdale
  • Economical Rural hotel
  • Gym / Fitness Center Available
From£74
Very good 4.0 /5 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 property
  • Check in: 3:00pm
From£80
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
  • Low Cost Resort hotel
  • Free breakfast
From£34
Average 3.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Express Great Barrington 415 Stockbridge Rd., Great Barrington, MA 01230 Call ~8.51 miles east of Hillsdale
  • Affordable Mountain property
  • Hotel has an eco-friendly policy Learn more
From£66
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 priced hotel
  • 16 sleeping rooms in hotel
From£44
Average 3.0 /5 Read Reviews Call BookMore Details
The Red Lion Inn 30 Main St., Stockbridge, MA 01262 Call ~11.09 miles east of Hillsdale
  • Affordable Rural property
  • Check-in time: 4:00
From£89
Average 3.0 /5 Read Reviews Call BookMore Details
Holiday Inn Club Vacations Oak N Spruce Resort in South Lee 190 Meadow St., South Lee, MA 01260 Call ~12.73 miles east of Hillsdale
  • Three Star Mountain property
  • Hotel has 334 suites
From£66
Very good 4.0 /5 Latest Reviews Call BookMore Details
Econo Lodge Lee - Great Barrington 980 Pleasant St., Lee, MA 01238 Call ~13.40 miles east of Hillsdale
  • Two-star property
  • Check in time: 11:00
From£35
Average 3.0 /5 Latest Reviews Call BookMore Details
Wheatleigh in Lenox Hawthorne Rd., Lenox, MA 01240 Call ~13.68 miles northeast of Hillsdale
  • Mid-scale hotel
  • Free complimentary breakfast
From£296
Very good 4.0 /5 Latest 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 property
  • 34 rooms in property
From£74
Average 3.0 /5 Guest Reviews Call BookMore Details
St. Charles Hotel 16 Park Place, Hudson, NY 12534 Call ~14.04 miles west of Hillsdale
  • Cheap Downtown property
  • 6 suites in hotel
From£59
Average 3.0 /5 Latest Reviews Call BookMore Details
Hudson Whaler - Hudson 542 Warren St., Hudson, NY 12534 Call ~14.18 miles west of Hillsdale
  • Three Star Downtown hotel
  • 3 floors in hotel
From£55
Very good 4.0 /5 Review Score Call BookMore Details
Seven Hills Inn - Lenox 40 Plunkett St., Lenox, MA 01240 Call ~14.34 miles northeast of Hillsdale
  • 4-star Resort property
  • Check in time: 3 pm
From£136
Very good 4.5 /5 Guest Reviews Call BookMore Details
Applegate Inn 279 West Park St., Lee, MA 01238 Call ~14.46 miles east of Hillsdale
  • 3-star Rural hotel
  • 11 rooms in hotel
From£118
Very good 4.0 /5 Latest Reviews Call BookMore Details
The Nest Hudson Hotel 330 Union St., Hudson, NY 12534 Call ~14.51 miles west of Hillsdale
  • Expensive Downtown hotel
  • 6 suites in property
From£148
Very good 4.5 /5 Recent Reviews Call BookMore Details
33 Main 33 Main St., Lenox, MA 01238 Call ~14.67 miles east of Hillsdale
  • Luxury Five Star hotel
From£148
Average 3.0 /5 Recent Reviews Call BookMore Details
Rodeway Inn 200 Laurel St., Lee, MA 01238 Call ~14.68 miles east of Hillsdale
  • 2 star property
  • Check-in time: 11:00
From£44
Average 3.0 /5 Hotel Reviews Call BookMore Details
Chambery Inn - Lee 199 Main St., Lee, 01238 Call ~14.69 miles east of Hillsdale
  • Three Star property
  • Hotel has 9 rooms
From£66
Very good 4.5 /5 Reviews Call BookMore Details
Brook Farm Inn 15 Hawthorne St., Lenox, MA 01240 Call ~14.71 miles northeast of Hillsdale
  • High end Rural hotel
  • Has environment-friendly policy See more
From£89
Very good 4.0 /5 Reviews Call BookMore Details
The Black Swan Lee Lenox An Ascend Collection Hotel : 435 Laurel St. 435 Laurel St., Lee, MA 01238 Website Call ~14.73 miles east of Hillsdale
  • 3 star Lake hotel
  • 52 rooms in property
From£48
Very good 4.0 /5 Reviews Call BookMore Details
Canyon Ranch Lenox 165 Kemble St., Lenox, MA 01240 Call ~14.74 miles northeast of Hillsdale
  • Mid-scale hotel
  • 2 floors in hotel
From£66
Average 3.0 /5 Read Reviews Call BookMore Details
Quality Inn 170 Housatonic St., Lee, MA 01238 Call ~14.85 miles east of Hillsdale
  • Low Cost Lake hotel
  • Check-in time: 11:00 AM
From£34
Average 3.0 /5 Read Reviews Call BookMore Details
Pilgrim Inn : 165 Housatonic St. 165 Housatonic St., Lee, MA 01238 Call ~14.89 miles east of Hillsdale
  • Three Star property
From£59
Average 3.0 /5 Review Score 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
  • Free comp. breakfast
From£166
Average 3.0 /5 Guest Reviews Call BookMore Details
Kemble Inn - Lenox 2 Kemble St., Lenox, MA 01240 Call ~15.04 miles northeast of Hillsdale
  • Three Star Mountain property
  • Check-in time: 3:00 PM
From£196
Very good 4.0 /5 Reviews Call BookMore Details
The Whitlock by The Lenox Collection 16 Church St., Lenox, MA 01240 Call ~15.08 miles northeast of Hillsdale
  • Mid-scale property
  • Check in: 14:00
From£148
Average 3.0 /5 Recent Reviews Call BookMore Details
Tiara Equest (The Inn at Richmond & Berkshire Equestrian Center : 802 State Rd. 802 State Rd., Richmond, MA 01254 Call ~15.28 miles northeast of Hillsdale
  • 3-star Rural hotel
  • 3 meeting rooms in property
From£111
Very good 4.5 /5 Guest Reviews Call BookMore Details
The Dewey by The Lenox Collection 7 Hubbard St., Lenox, MA 01240 Call ~15.43 miles northeast of Hillsdale
  • Four star hotel
  • 12 sleeping rooms in hotel
From£55
Average 3.0 /5 Guest Reviews 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
  • Three Star Mountain property
  • Check-in: 3:00 PM-8PM
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
  • Midscale Mountain property
  • Check in time: 3:00PM
From£37
Average 3.0 /5 Review Score Call BookMore Details
Eastover Estate & Retreat in Lenox 430 East St., Lenox, MA 01240 Call ~16.64 miles northeast of Hillsdale
  • 4-star Mountain hotel
  • 10 meeting rooms in property
From£80
Average 3.5 /5 Latest Reviews Call BookMore Details
Life House Berkshires - Lenox 194 Pittsfield Rd., Lenox, MA 01240 Call ~16.83 miles northeast of Hillsdale
  • Two star Suburban property
  • Free breakfast
From£36
Average 3.0 /5 Read Reviews Call BookMore Details
Howard Johnson by Wyndham Lenox - Lenox 462 Pittsfield Rd., Lenox, MA 01240 Call ~16.98 miles northeast of Hillsdale
  • Low priced Resort hotel
  • Check-in: 2:00 PM
From£48
Average 3.0 /5 Review Score 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
  • 3-star Riverfront hotel
  • Comp. Breakfast
From£59
Average 3.0 /5 Guest 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
  • Four star Resort property
  • Check in: 3PM
From£102
Average 3.0 /5 Guest Reviews Call BookMore Details
Hampton Inn & Suites Lenox Berkshires 445 Pittsfield Rd., Lenox, MA 01240 Call ~17.82 miles northeast of Hillsdale
  • Affordable Mountain property
  • Check-in time: 3:00 pm
From£59
Average 3.0 /5 Reviews Call BookMore Details
The Yankee Inn : 461 Pittsfield Rd. 461 Pittsfield Rd., Lenox, MA 01240 Call ~17.88 miles northeast of Hillsdale
  • 2 star property
  • 3 floors in property
From£107
Very good 4.0 /5 Guest Reviews Call BookMore Details
Knights Inn Lenox 474 Pittsfield Rd., Lenox, MA 01240 Call ~17.97 miles northeast of Hillsdale
  • 2-star Downtown property
  • Check-in time: 2.00 pm
From£27
Poor 2.0 /5 Review Score Call BookMore Details
Best Western Plus Berkshire Hills Inn & Suites - Pittsfield 1350 West Housatonic St., Pittsfield, MA 01201 Call ~18.11 miles northeast of Hillsdale
  • Three Star Rural hotel
  • 59 rooms in property
From£63
Very good 4.5 /5 Guest Reviews Call BookMore Details
Lenox Inn 525 Pittsfield Rd., Lenox, MA 01240 Call ~18.16 miles northeast of Hillsdale
  • Economy property
  • Check in time: 15:00
From£44
Poor 2.0 /5 Read Reviews Call BookMore Details
Hilton Garden Inn Lenox Pittsfield - Pittsfield 1032 South St., Pittsfield, MA 01201 Call ~18.18 miles northeast of Hillsdale
  • Mid-scale Suburban property
  • 4 floors in property
From£70
Very good 4.0 /5 Read Reviews Call BookMore Details
Wake Robin Inn in Lakeville 106 Sharon Rd., Lakeville, CT 06039 Call ~18.22 miles south of Hillsdale
  • Affordable Rural property
  • 3 floors in property
From£66
Average 3.0 /5 Read Reviews Call BookMore Details
Holiday Inn Express Pittsfield Lenox Berkshires - Pittsfield 1055 South St., Pittsfield, MA 01201 Call ~18.26 miles northeast of Hillsdale
  • Three Star Suburban property
  • 4 floors in hotel
From£59
Average 3.0 /5 Latest Reviews Call BookMore Details
Berkshire Mountain Lodge 8 Dan Fox Dr., Pittsfield, MA 01201 Call ~18.48 miles northeast of Hillsdale
  • Cheap Mountain property
  • 5 floors in property
From£92
Very good 4.5 /5 Guest Reviews Call BookMore Details
Interlaken Inn in Lakeville 74 Interlaken Rd., Lakeville, CT 06039 Call ~18.85 miles south of Hillsdale
  • Midscale Resort hotel
  • Hotel has 13 suites
From£132
Very good 4.0 /5 Recent 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
  • Three Star Highway hotel
  • 3 floors in property
From£88
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Blackberry River Inn in Norfolk 538 Greenwoods Rd. West, Norfolk, CT 06058 Call ~20.05 miles southeast of Hillsdale
  • Affordable property
  • 17 rooms in property
From£80
Very good 4.0 /5 Latest Reviews Call BookMore Details
Spark by Hilton West Coxsackie - West Coxsackie 12600 State Route 9w, West Coxsackie, NY 12192 Call ~20.08 miles northwest of Hillsdale
  • Mid-scale Rural property
  • 7 suites in property
From£55
Average 3.0 /5 Latest Reviews Call BookMore Details
Berkshire Inn in Pittsfield 150 West Housatonic St., Pittsfield, MA 01201 Call ~20.17 miles northeast of Hillsdale
  • Cheap Downtown property
  • Free complimentary breakfast
From£66
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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