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.
+1-888-389-4121
684 South Egremont Rd., Great Barrington, MA 01230 +1-888-389-4121 ~6.42 miles southeast of Hillsdale
  • Affordable Mountain property
  • 13 sleeping rooms in hotel
From$185
Excellent 5.0 /5 Review Score Call BookMore Details
Quality Inn : 372 Main St.
+1-888-675-2083
372 Main St., Great Barrington, MA 01230 Website +1-888-675-2083 ~7.68 miles east of Hillsdale
  • Two-star 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
+1-800-716-8490
249 Stockbridge Rd., Great Barrington, MA 01230 Website +1-800-716-8490 ~8.43 miles east of Hillsdale
  • Affordable Resort hotel
  • Check-in: 3:00pm
From$109
Very Good 4.0 /5 Review Score Call BookMore Details
Travelodge by Wyndham Great Barrington Berkshires - Great Barrington
+1-800-805-5223
400 Stockbridge Rd., Great Barrington, MA 01230 +1-800-805-5223 ~8.50 miles east of Hillsdale
  • Two-star Resort property
  • Comp. Breakfast
From$47
Average 3.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Express Great Barrington : 415 Stockbridge Rd.
+1-888-965-1860
415 Stockbridge Rd., Great Barrington, MA 01230 +1-888-965-1860 ~8.51 miles east of Hillsdale
  • Mid-scale Mountain hotel
  • Hotel has an eco-friendly policy Read more
From$89
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Pleasant Valley Motel West Stockbridge
+1-888-788-5576
42 Stockbridge Rd., West Stockbridge, MA 01266 +1-888-788-5576 ~10.68 miles northeast of Hillsdale
  • 2 star property
  • 16 sleeping rooms in hotel
From$60
Average 3.0 /5 Guest Reviews Call BookMore Details
The Red Lion Inn : 30 Main St.
+1-888-897-9207
30 Main St., Stockbridge, MA 01262 +1-888-897-9207 ~11.09 miles east of Hillsdale
  • 3-star Rural property
  • Hotel has 35 suites
From$80
Average 3.0 /5 Read Reviews Call BookMore Details
Holiday Inn Club Vacations Oak N Spruce Resort : 190 Meadow St.
+1-888-311-4278
190 Meadow St., South Lee, MA 01260 +1-888-311-4278 ~12.73 miles east of Hillsdale
  • 3 star Mountain hotel
  • 3 floors in hotel
From$89
Very Good 4.0 /5 Review Score 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 ~13.40 miles east of Hillsdale
  • Low priced hotel
  • Free breakfast
From$48
Average 3.0 /5 Hotel Reviews Call BookMore Details
Wheatleigh
+1-888-734-9421
Hawthorne Rd., Lenox, MA 01240 +1-888-734-9421 ~13.68 miles northeast of Hillsdale
  • Mid-scale property
  • 9 suites in hotel
From$400
Very Good 4.0 /5 Reviews Call BookMore Details
Apple Tree Inn
+1-888-841-5292
10 Richmond Mountain Rd., Lenox, MA 01240 +1-888-841-5292 ~13.71 miles northeast of Hillsdale
  • 4-star Mountain hotel
  • 3 suites in property
From$100
Average 3.0 /5 Reviews Call BookMore Details
St. Charles Hotel
+1-888-455-5160
16 Park Place, Hudson, NY 12534 +1-888-455-5160 ~14.04 miles west of Hillsdale
  • Economical Downtown hotel
  • 6 suites in property
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Hudson Whaler : 542 Warren St.
+1-888-965-8297
542 Warren St., Hudson, NY 12534 +1-888-965-8297 ~14.18 miles west of Hillsdale
  • Three Star Downtown property
  • Hotel has 3 floors
From$75
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 ~14.34 miles northeast of Hillsdale
  • High-end Resort property
  • Hotel has 2 floors
From$184
Very Good 4.5 /5 Reviews Call BookMore Details
Applegate Inn in Lee
+1-888-749-6785
279 West Park St., Lee, MA 01238 +1-888-749-6785 ~14.46 miles east of Hillsdale
  • Affordable Rural property
  • Check-in time: 2 pm
From$160
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
The Nest Hudson Hotel
+1-888-878-9982
330 Union St., Hudson, NY 12534 +1-888-878-9982 ~14.51 miles west of Hillsdale
  • 4-star Downtown property
  • Hotel has 6 rooms
From$200
Very Good 4.5 /5 Review Score Call BookMore Details
33 Main - Lenox
+1-888-389-4485
33 Main St., Lenox, MA 01238 +1-888-389-4485 ~14.67 miles east of Hillsdale
  • Luxury 5-star hotel
From$200
Average 3.0 /5 Read Reviews Call BookMore Details
Rodeway Inn : 200 Laurel St.
+1-888-389-4121
200 Laurel St., Lee, MA 01238 +1-888-389-4121 ~14.68 miles east of Hillsdale
  • Inexpensive property
  • Check in time: 11:00
From$60
Average 3.0 /5 Latest Reviews Call BookMore Details
Chambery Inn
+1-888-675-2083
199 Main St., Lee, 01238 +1-888-675-2083 ~14.69 miles east of Hillsdale
  • 3-star hotel
  • Check-in time: 14:00
From$90
Very Good 4.5 /5 Latest Reviews Call BookMore Details
Brook Farm Inn - Lenox
+1-800-716-8490
15 Hawthorne St., Lenox, MA 01240 +1-800-716-8490 ~14.71 miles northeast of Hillsdale
  • 4 star Rural property
  • Has environment-friendly policy Learn more
From$120
Very Good 4.0 /5 Read 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 ~14.72 miles east of Hillsdale
  • Midscale Lake property
  • Check-in: 3:00PM
From$60
Very Good 4.0 /5 Read Reviews Call BookMore Details
Quality Inn : 435 Laurel St.
+1-888-965-1860
435 Laurel St., Lee, MA 01238 Website +1-888-965-1860 ~14.73 miles east of Hillsdale
  • 3-star Lake property
  • Fitness / Gym is on-site
From$65
Very Good 4.0 /5 Review Score Call BookMore Details
Canyon Ranch Lenox
+1-888-788-5576
165 Kemble St., Lenox, MA 01240 +1-888-788-5576 ~14.74 miles northeast of Hillsdale
  • 3-star hotel
  • 2 floors in hotel
From$90
Average 3.0 /5 Review Score Call BookMore Details
Pilgrim Inn - Lee
+1-888-897-9207
165 Housatonic St., Lee, MA 01238 +1-888-897-9207 ~14.89 miles east of Hillsdale
  • Affordable property
  • Check-in time: 3:00 PM
From$80
Average 3.0 /5 Read Reviews Call BookMore Details
The Constance by The Lenox Collection
+1-888-311-4278
11 Old Stockbridge Rd., Lenox, MA 01240 +1-888-311-4278 ~14.99 miles northeast of Hillsdale
  • 4-star property
  • Free breakfast available
From$225
Average 3.0 /5 Reviews Call BookMore Details
Kemble Inn - Lenox
+1-888-469-4795
2 Kemble St., Lenox, MA 01240 +1-888-469-4795 ~15.04 miles northeast of Hillsdale
  • Mid-scale Mountain property
  • Check-in: 3:00 PM
From$265
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
The Whitlock by The Lenox Collection in Lenox
+1-888-734-9421
16 Church St., Lenox, MA 01240 +1-888-734-9421 ~15.08 miles northeast of Hillsdale
  • Three Star property
  • 30 rooms in property
From$200
Average 3.0 /5 Read 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 ~15.28 miles northeast of Hillsdale
  • Affordable Rural property
  • Check-in time: 3:00 p.m.
From$150
Very Good 4.5 /5 Read Reviews Call BookMore Details
The Dewey by The Lenox Collection in Lenox
+1-888-455-5160
7 Hubbard St., Lenox, MA 01240 +1-888-455-5160 ~15.43 miles northeast of Hillsdale
  • Four star hotel
  • 2 floors in hotel
From$75
Average 3.0 /5 Recent Reviews Call BookMore Details
The Cornell Inn, Lenox & The Berkshires
+1-888-965-8297
203 Main St., Lenox, MA 01240 +1-888-965-8297 ~15.59 miles northeast of Hillsdale
  • Midscale Mountain property
  • 3 suites in property
From$60
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Element Lenox Berkshires - Lenox
+1-888-906-6358
130 Pittsfield Rd., Lenox, MA 01240 +1-888-906-6358 ~16.56 miles northeast of Hillsdale
  • Affordable Mountain hotel
  • 2 meeting rooms in property
From$50
Average 3.0 /5 Review Score Call BookMore Details
Eastover Estate & Retreat - Lenox
+1-888-749-6785
430 East St., Lenox, MA 01240 +1-888-749-6785 ~16.64 miles northeast of Hillsdale
  • Four-star Mountain hotel
  • 90 sleeping rooms in hotel
From$109
Average 3.5 /5 Recent Reviews Call BookMore Details
Life House Berkshires : 194 Pittsfield Rd.
+1-888-878-9982
194 Pittsfield Rd., Lenox, MA 01240 +1-888-878-9982 ~16.83 miles northeast of Hillsdale
  • Low priced Suburban hotel
  • Check-in: 2pm
From$49
Average 3.0 /5 Read Reviews Call BookMore Details
Howard Johnson by Wyndham Lenox
+1-888-389-4485
462 Pittsfield Rd., Lenox, MA 01240 +1-888-389-4485 ~16.98 miles northeast of Hillsdale
  • Low Cost Resort hotel
  • Free breakfast available
From$65
Average 3.0 /5 Read Reviews Call BookMore Details
James Newbury Hotel & Spa - Coxsackie
+1-888-389-4121
60 South River St., Coxsackie, NY 12051 +1-888-389-4121 ~17.18 miles northwest of Hillsdale
  • 3-star Riverfront hotel
  • Free complimentary breakfast
From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Miraval Berkshires Resort & Spa - All Inclusive Adults Only - Lenox
+1-888-675-2083
55 Lee Rd., Lenox, MA 01240 +1-888-675-2083 ~17.60 miles northeast of Hillsdale
  • Four-star Resort hotel
  • Check in: 3PM
From$138
Average 3.0 /5 Guest Reviews Call BookMore Details
Hampton Inn & Suites Berkshires-Lenox in Lenox
+1-800-716-8490
445 Pittsfield Rd., Lenox, MA 01240 +1-800-716-8490 ~17.82 miles northeast of Hillsdale
  • Three Star Mountain property
  • Check-in time: 3:00 pm
From$109
Average 3.0 /5 Guest Reviews Call BookMore Details
Yankee Inn in Lenox
+1-800-805-5223
461 Pittsfield Rd., Lenox, MA 01240 +1-800-805-5223 ~17.88 miles northeast of Hillsdale
  • Economy hotel
  • Gym is available on property
From$145
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Knights Inn Lenox : 474 Pittsfield Rd.
+1-888-965-1860
474 Pittsfield Rd., Lenox, MA 01240 +1-888-965-1860 ~17.97 miles northeast of Hillsdale
  • 2-star Downtown property
  • Check-in: 2.00 pm
Best Western Plus Berkshire Hills Inn & Suites
+1-888-788-5576
1350 West Housatonic St., Pittsfield, MA 01201 +1-888-788-5576 ~18.11 miles northeast of Hillsdale
  • Three Star Rural property
  • Hotel has 3 floors
From$85
Very Good 4.5 /5 Recent Reviews Call BookMore Details
Lenox Inn : 525 Pittsfield Rd.
+1-888-897-9207
525 Pittsfield Rd., Lenox, MA 01240 +1-888-897-9207 ~18.16 miles northeast of Hillsdale
  • 2-star property
  • 18 rooms in hotel
Hilton Garden Inn Lenox Pittsfield : 1032 South St.
+1-888-311-4278
1032 South St., Pittsfield, MA 01201 +1-888-311-4278 ~18.18 miles northeast of Hillsdale
  • Midscale Suburban property
  • Hotel has 2 meeting rooms
From$95
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Wake Robin Inn in Lakeville
+1-888-469-4795
106 Sharon Rd., Lakeville, CT 06039 +1-888-469-4795 ~18.22 miles south of Hillsdale
  • Three Star Rural property
  • 3 suites in property
From$89
Average 3.0 /5 Hotel Reviews Call BookMore Details
Berkshire Mountain Lodge - Pittsfield
+1-888-734-9421
8 Dan Fox Dr., Pittsfield, MA 01201 +1-888-734-9421 ~18.48 miles northeast of Hillsdale
  • Economy Mountain hotel
  • 146 rooms in property
From$125
Very Good 4.5 /5 Reviews Call BookMore Details
Interlaken Inn in Lakeville
+1-888-841-5292
74 Interlaken Rd., Lakeville, CT 06039 +1-888-841-5292 ~18.85 miles south of Hillsdale
  • 3-star Resort hotel
  • 13 suites in hotel
From$179
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Express Hotel & Suites West Coxsackie by IHG
+1-888-455-5160
12740 Route 9 West, West Coxsackie, NY 12192 +1-888-455-5160 ~18.92 miles west of Hillsdale
  • Three Star Highway property
  • Hotel has 21 suites
From$119
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Blackberry River Inn - Norfolk
+1-888-965-8297
538 Greenwoods Rd. West, Norfolk, CT 06058 +1-888-965-8297 ~20.05 miles southeast of Hillsdale
  • Mid-scale hotel
  • Hotel has 17 rooms
From$109
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Spark by Hilton West Coxsackie
+1-888-906-6358
12600 State Route 9w, West Coxsackie, NY 12192 +1-888-906-6358 ~20.08 miles northwest of Hillsdale
  • Midscale Rural property
  • 7 suites in property
From$75
Average 3.0 /5 Read Reviews Call BookMore Details
Berkshire Inn
+1-888-749-6785
150 West Housatonic St., Pittsfield, MA 01201 +1-888-749-6785 ~20.17 miles northeast of Hillsdale
  • Inexpensive Downtown property
  • Check in time: 1500
From$90
Average 3.0 /5 Recent Reviews Call BookMore Details
Oyo Hotel Coxsackie I 87 North
+1-888-878-9982
12800 Rte 9w, Albany, NY 12192 +1-888-878-9982 ~20.27 miles northwest of Hillsdale
  • 3 star hotel
  • 28 rooms in property
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.

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