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 & Accommodations

The Windflower Inn
+1-888-389-4121
684 South Egremont Rd., Great Barrington, MA 01230 +1-888-389-4121 ~6.43 miles southeast of Hillsdale
  • 3 star Mountain property
  • Free comp. breakfast
From£145
Excellent 5.0 /5 Reviews Call BookMore Details
Quality Inn in Great Barrington
+1-888-675-2083
372 Main St., Great Barrington, MA 01230 Website +1-888-675-2083 ~7.69 miles east of Hillsdale
  • Two-star Rural hotel
  • 63 rooms in hotel
From£78
Very good 4.0 /5 Latest Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi in Great Barrington
+1-800-716-8490
249 Stockbridge Rd., Great Barrington, MA 01230 Website +1-800-716-8490 ~8.44 miles east of Hillsdale
  • Three Star Resort property
  • Free comp. breakfast
From£85
Very good 4.0 /5 Read Reviews Call BookMore Details
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel in Great Barrington
+1-800-805-5223
415 Stockbridge Road41, Great Barrington, MA 01230 +1-800-805-5223 ~8.48 miles east of Hillsdale
  • 3 star Mountain property
  • Check-in: 3:00pm
From£62
Average 3.0 /5 Latest Reviews Call BookMore Details
Travelodge by Wyndham Great Barrington Berkshires
+1-888-965-1860
400 Stockbridge Rd., Great Barrington, MA 01230 +1-888-965-1860 ~8.51 miles east of Hillsdale
  • 2-star Resort hotel
  • Free breakfast
From£36
Average 3.0 /5 Latest Reviews Call BookMore Details
Pleasant Valley Motel West Stockbridge - West Stockbridge
+1-888-788-5576
42 Stockbridge Rd., West Stockbridge, MA 01266 +1-888-788-5576 ~10.69 miles northeast of Hillsdale
  • Economy hotel
  • 16 rooms in property
From£47
Average 3.0 /5 Hotel Reviews Call BookMore Details
The Red Lion Inn in Stockbridge
+1-888-897-9207
30 Main St., Stockbridge, MA 01262 +1-888-897-9207 ~11.11 miles east of Hillsdale
  • Midscale Rural property
  • Check-in: 3:00
From£62
Average 3.0 /5 Read Reviews Call BookMore Details
Holiday Inn Club Vacations Oak N Spruce Resort in South Lee
+1-888-311-4278
190 Meadow St., South Lee, MA 01260 +1-888-311-4278 ~12.75 miles east of Hillsdale
  • 3-star Mountain hotel
  • Has environment-friendly policy See policy
From£70
Very good 4.0 /5 Reviews Call BookMore Details
Econo Lodge Lee - Great Barrington : 980 Pleasant St.
+1-888-469-4795
980 Pleasant St., Lee, MA 01238 +1-888-469-4795 ~13.41 miles east of Hillsdale
  • 2-star property
  • Comp. Breakfast
From£37
Average 3.0 /5 Read Reviews Call BookMore Details
Wheatleigh
+1-888-734-9421
Hawthorne Rd., Lenox, MA 01240 +1-888-734-9421 ~13.69 miles northeast of Hillsdale
  • Mid-scale hotel
  • Check-in time: 16:00
From£314
Very good 4.0 /5 Review Score Call BookMore Details
Apple Tree Inn
+1-888-841-5292
10 Richmond Mountain Rd., Lenox, MA 01240 +1-888-841-5292 ~13.73 miles northeast of Hillsdale
  • High end Mountain hotel
  • Check in time: 4:00 PM
From£78
Average 3.0 /5 Review Score Call BookMore Details
St. Charles Hotel in Hudson
+1-888-455-5160
16 Park Place, Hudson, NY 12534 +1-888-455-5160 ~14.06 miles west of Hillsdale
  • Cheap Downtown hotel
  • 34 rooms in hotel
From£62
Average 3.0 /5 Latest Reviews Call BookMore Details
Hudson Whaler
+1-888-965-8297
542 Warren St., Hudson, NY 12534 +1-888-965-8297 ~14.20 miles west of Hillsdale
  • 3-star Downtown hotel
  • 16 sleeping rooms in hotel
From£59
Very good 4.0 /5 Reviews Call BookMore Details
Seven Hills Inn
+1-888-906-6358
40 Plunkett St., Lenox, MA 01240 +1-888-906-6358 ~14.35 miles northeast of Hillsdale
  • 4 star Resort property
  • 2 floors in hotel
From£144
Very good 4.5 /5 Hotel Reviews Call BookMore Details
Applegate Inn
+1-888-749-6785
279 West Park St., Lee, MA 01238 +1-888-749-6785 ~14.47 miles east of Hillsdale
  • Affordable Rural property
  • Free comp. breakfast
From£125
Very good 4.0 /5 Guest Reviews Call BookMore Details
The Nest Hudson Hotel in Hudson
+1-888-878-9982
330 Union St., Hudson, NY 12534 +1-888-878-9982 ~14.53 miles west of Hillsdale
  • Four star Downtown hotel
  • Hotel has 6 suites
From£157
Very good 4.5 /5 Review Score Call BookMore Details
33 Main : 33 Main St.
+1-888-389-4485
33 Main St., Lenox, MA 01238 +1-888-389-4485 ~14.69 miles east of Hillsdale
  • Luxury 5-star hotel
From£157
Average 3.0 /5 Hotel Reviews Call BookMore Details
Rodeway Inn in Lee
+1-888-389-4121
200 Laurel St., Lee, MA 01238 +1-888-389-4121 ~14.69 miles east of Hillsdale
  • Low-priced property
  • Hotel has 23 rooms
From£47
Average 3.0 /5 Hotel Reviews Call BookMore Details
Chambery Inn
+1-888-675-2083
199 Main St., Lee, 01238 +1-888-675-2083 ~14.71 miles east of Hillsdale
  • Three Star hotel
  • Check-in: 14:00
From£70
Very good 4.5 /5 Hotel Reviews Call BookMore Details
Brook Farm Inn - Lenox
+1-800-716-8490
15 Hawthorne St., Lenox, MA 01240 +1-800-716-8490 ~14.72 miles northeast of Hillsdale
  • High end Rural hotel
  • Free complimentary breakfast
From£94
Very good 4.0 /5 Guest Reviews Call BookMore Details
Black Swan Inn Lee Lenox An Ascend Hotel
+1-800-805-5223
435 Laurel St., Lee, MA 01238 +1-800-805-5223 ~14.73 miles east of Hillsdale
  • Affordable Lake hotel
  • Hotel has 52 rooms
From£47
Very good 4.0 /5 Guest Reviews Call BookMore Details
Quality Inn - Lee
+1-888-965-1860
435 Laurel St., Lee, MA 01238 +1-888-965-1860 ~14.74 miles east of Hillsdale
  • Affordable Lake hotel
  • Check in: 3:00 PM
From£51
Very good 4.0 /5 Latest Reviews Call BookMore Details
Canyon Ranch Lenox - Lenox
+1-888-788-5576
165 Kemble St., Lenox, MA 01240 +1-888-788-5576 ~14.76 miles northeast of Hillsdale
  • Affordable hotel
  • Gym / Fitness Center Available
From£70
Average 3.0 /5 Recent Reviews Call BookMore Details
Pilgrim Inn - Lee
+1-888-897-9207
165 Housatonic St., Lee, MA 01238 +1-888-897-9207 ~14.90 miles east of Hillsdale
  • Midscale hotel
  • Check-in: 3:00 PM
From£62
Average 3.0 /5 Hotel Reviews Call BookMore Details
The Constance by The Lenox Collection - Lenox
+1-888-311-4278
11 Old Stockbridge Rd., Lenox, MA 01240 +1-888-311-4278 ~15.00 miles northeast of Hillsdale
  • 4-star property
  • Hotel has 24 rooms
From£177
Average 3.0 /5 Read Reviews Call BookMore Details
Kemble Inn - Lenox
+1-888-469-4795
2 Kemble St., Lenox, MA 01240 +1-888-469-4795 ~15.05 miles northeast of Hillsdale
  • Mid-scale Mountain property
  • 3 conference rooms in property
From£208
Very good 4.0 /5 Reviews Call BookMore Details
The Whitlock by The Lenox Collection : 16 Church St.
+1-888-734-9421
16 Church St., Lenox, MA 01240 +1-888-734-9421 ~15.09 miles northeast of Hillsdale
  • 3-star property
  • Check in: 14:00
From£157
Average 3.0 /5 Hotel Reviews Call BookMore Details
Tiara Equest (The Inn at Richmond & Berkshire Equestrian Center
+1-888-841-5292
802 State Rd., Richmond, MA 01254 +1-888-841-5292 ~15.29 miles northeast of Hillsdale
  • 3-star Rural property
  • Complimentary breakfast is offered
From£118
Very good 4.5 /5 Guest Reviews Call BookMore Details
The Dewey by The Lenox Collection : 7 Hubbard St.
+1-888-455-5160
7 Hubbard St., Lenox, MA 01240 +1-888-455-5160 ~15.44 miles northeast of Hillsdale
  • Four star hotel
  • Free complimentary breakfast
From£59
Average 3.0 /5 Hotel Reviews Call BookMore Details
The Cornell Inn, Lenox
+1-888-965-8297
203 Main St., Lenox, MA 01240 +1-888-965-8297 ~15.60 miles northeast of Hillsdale
  • Affordable Mountain hotel
  • 2 floors in property
From£47
Very good 4.0 /5 Review Score Call BookMore Details
Eastover Estate & Retreat
+1-888-906-6358
430 East St., Lenox, MA 01240 +1-888-906-6358 ~16.65 miles northeast of Hillsdale
  • Expensive Mountain property
  • 2 floors in hotel
From£85
Average 3.5 /5 Recent Reviews Call BookMore Details
Life House Berkshires
+1-888-749-6785
194 Pittsfield Rd., Lenox, MA 01240 +1-888-749-6785 ~16.85 miles northeast of Hillsdale
  • Low Cost Suburban hotel
  • Check-in: 2pm
From£38
Average 3.0 /5 Read Reviews Call BookMore Details
Howard Johnson by Wyndham Lenox : 462 Pittsfield Rd.
+1-888-878-9982
462 Pittsfield Rd., Lenox, MA 01240 +1-888-878-9982 ~16.99 miles northeast of Hillsdale
  • Inexpensive Resort property
  • Check in time: 2:00 PM
From£51
Average 3.0 /5 Reviews Call BookMore Details
James Newbury Hotel & Spa
+1-888-389-4485
60 South River St., Coxsackie, NY 12051 +1-888-389-4485 ~17.20 miles northwest of Hillsdale
  • Affordable Riverfront hotel
  • 47 rooms in property
From£62
Average 3.0 /5 Reviews Call BookMore Details
Miraval Berkshires Resort & Spa - All Inclusive Adults Only
+1-888-389-4121
55 Lee Rd., Lenox, MA 01240 +1-888-389-4121 ~17.62 miles northeast of Hillsdale
  • 4 star Resort property
  • Hotel has 105 rooms
From£108
Average 3.0 /5 Review Score Call BookMore Details
Hampton Inn & Suites Berkshires-Lenox : 445 Pittsfield Rd.
+1-888-675-2083
445 Pittsfield Rd., Lenox, MA 01240 +1-888-675-2083 ~17.84 miles northeast of Hillsdale
  • 3-star Mountain hotel
  • 24 suites in property
From£85
Average 3.0 /5 Guest Reviews Call BookMore Details
Yankee Inn in Lenox
+1-800-716-8490
461 Pittsfield Rd., Lenox, MA 01240 +1-800-716-8490 ~17.90 miles northeast of Hillsdale
  • Low priced hotel
  • Free complimentary breakfast
From£114
Very good 4.0 /5 Recent Reviews Call BookMore Details
Knights Inn Lenox - Lenox
+1-800-805-5223
474 Pittsfield Rd., Lenox, MA 01240 +1-800-805-5223 ~17.99 miles northeast of Hillsdale
  • 2 star Downtown hotel
  • Hotel has 16 rooms
Best Western Plus Berkshire Hills Inn & Suites
+1-888-965-1860
1350 West Housatonic St., Pittsfield, MA 01201 +1-888-965-1860 ~18.12 miles northeast of Hillsdale
  • Midscale Rural property
  • Free comp. breakfast
From£62
Very good 4.0 /5 Recent Reviews Call BookMore Details
Lenox Inn : 525 Pittsfield Rd.
+1-888-788-5576
525 Pittsfield Rd., Lenox, MA 01240 +1-888-788-5576 ~18.17 miles northeast of Hillsdale
  • Low-priced property
  • Check-in time: 15:00
Hilton Garden Inn Lenox Pittsfield in Pittsfield
+1-888-897-9207
1032 South St., Pittsfield, MA 01201 +1-888-897-9207 ~18.20 miles northeast of Hillsdale
  • 3 star Suburban hotel
  • Hotel has 2 meeting rooms
From£74
Very good 4.0 /5 Guest Reviews Call BookMore Details
Wake Robin Inn : 106 Sharon Rd.
+1-888-311-4278
106 Sharon Rd., Lakeville, CT 06039 +1-888-311-4278 ~18.25 miles south of Hillsdale
  • Three Star Rural property
  • Complimentary breakfast is offered
From£70
Average 3.0 /5 Reviews Call BookMore Details
Interlaken Inn & Resort
+1-888-469-4795
74 Interlaken Rd., Lakeville, CT 06039 +1-888-469-4795 ~18.85 miles south of Hillsdale
  • Three Star Resort hotel
  • Hotel has an eco-friendly policy Learn more
From£164
Very good 4.0 /5 Read Reviews Call BookMore Details
Holiday Inn Express Hotel & Suites West Coxsackie, an IHG Hotel in West Coxsackie
+1-888-734-9421
12740 Route 9 West, West Coxsackie, NY 12192 +1-888-734-9421 ~18.93 miles west of Hillsdale
  • 3-star Highway hotel
  • 21 suites in hotel
From£93
Very good 4.0 /5 Reviews Call BookMore Details
Best Western New Baltimore Inn
+1-888-841-5292
12600 State Route 9w, West Coxsackie, NY 12192 +1-888-841-5292 ~20.09 miles northwest of Hillsdale
  • Three Star Rural hotel
  • Fitness / Gym is on-site
From£59
Average 3.0 /5 Hotel Reviews Call BookMore Details
Blackberry River Inn : 538 Greenwoods Rd. West
+1-888-455-5160
538 Greenwoods Rd. West, Norfolk, CT 06058 +1-888-455-5160 ~20.10 miles southeast of Hillsdale
  • Three Star hotel
  • 2 floors in property
From£85
Very good 4.0 /5 Recent Reviews Call BookMore Details
Berkshire Inn
+1-888-965-8297
150 West Housatonic St., Pittsfield, MA 01201 +1-888-965-8297 ~20.18 miles northeast of Hillsdale
  • Low-priced Downtown property
  • Fitness / Gym is on-site
From£70
Average 3.0 /5 Review Score Call BookMore Details
Oyo Hotel Coxsackie I 87 North
+1-888-906-6358
12800 Rte 9w, Albany, NY 12192 +1-888-906-6358 ~20.28 miles northwest of Hillsdale
  • Three Star hotel
  • 28 rooms in hotel
From£70
Average 3.0 /5 Reviews Call BookMore Details
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel in Pittsfield
+1-888-749-6785
1 West St., Pittsfield, MA 01201 +1-888-749-6785 ~20.64 miles northeast of Hillsdale
  • Three Star Downtown hotel
  • 170 sleeping rooms in hotel
From£62
Average 3.0 /5 Recent Reviews Call BookMore Details
Hotel on North - Pittsfield
+1-888-878-9982
297 North St., Pittsfield, MA 01201 +1-888-878-9982 ~20.94 miles northeast of Hillsdale
  • High-end Downtown property
  • Hotel has 45 rooms
From£118
Excellent 5.0 /5 Read 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