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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
+1-888-389-4121
684 South Egremont Rd., Great Barrington, MA 01230 ~6.43 miles southeast of Hillsdale
  • 3-star Mountain hotel
  • 2 meeting rooms in hotel
From$185
Excellent 5.0 /5 Guest Reviews Call BookMore Details
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Quality Inn
+1-888-675-2083
372 Main St., Great Barrington, MA 01230 Website ~7.69 miles east of Hillsdale
  • 2-star Rural property
  • Hotel has 2 floors
From$100
Very Good 4.0 /5 Hotel 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 ~8.44 miles east of Hillsdale
  • Three Star Resort property
  • Fitness + Health Center
From$109
Very Good 4.0 /5 Reviews Call BookMore Details
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel : 415 Stockbridge Road41
+1-800-805-5223
415 Stockbridge Road41, Great Barrington, MA 01230 ~8.48 miles east of Hillsdale
  • 3 star Mountain property
  • Hotel has an eco-friendly policy See policy
From$80
Average 3.0 /5 Review Score Call BookMore Details
Travelodge by Wyndham Great Barrington Berkshires in Great Barrington
+1-888-965-1860
400 Stockbridge Rd., Great Barrington, MA 01230 ~8.51 miles east of Hillsdale
  • Cheap Resort property
  • Check in time: 11:00 AM
From$47
Average 3.0 /5 Guest Reviews Call BookMore Details
Pleasant Valley Motel West Stockbridge : 42 Stockbridge Rd.
+1-888-788-5576
42 Stockbridge Rd., West Stockbridge, MA 01266 ~10.69 miles northeast of Hillsdale
  • Economical hotel
  • Check in time: 13:00
From$60
Average 3.0 /5 Review Score Call BookMore Details
The Red Lion Inn
+1-888-897-9207
30 Main St., Stockbridge, MA 01262 ~11.12 miles east of Hillsdale
  • 3 star Rural hotel
  • Gym is available on property
From$229
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Club Vacations Oak N Spruce Resort - South Lee
+1-888-311-4278
190 Meadow St., South Lee, MA 01260 ~12.75 miles east of Hillsdale
  • 3-star Mountain hotel
  • 334 sleeping rooms in hotel
From$89
Very Good 4.0 /5 Read Reviews Call BookMore Details
Econo Lodge Lee - Great Barrington : 980 Pleasant St.
+1-888-469-4795
980 Pleasant St., Lee, MA 01238 ~13.41 miles east of Hillsdale
  • 2 star hotel
  • Comp. Breakfast
From$48
Average 3.0 /5 Latest Reviews Call BookMore Details
Wheatleigh
+1-888-734-9421
Hawthorne Rd., Lenox, MA 01240 ~13.69 miles northeast of Hillsdale
  • Mid-scale hotel
  • Check in time: 16:00
From$400
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Apple Tree Inn - Lenox
+1-888-841-5292
10 Richmond Mountain Rd., Lenox, MA 01240 ~13.73 miles northeast of Hillsdale
  • 4-star Mountain hotel
  • 34 rooms in hotel
From$100
Average 3.0 /5 Guest Reviews Call BookMore Details
St. Charles Hotel
+1-888-455-5160
16 Park Place, Hudson, NY 12534 ~14.06 miles west of Hillsdale
  • Low priced Downtown hotel
  • 34 sleeping rooms in hotel
From$80
Average 3.0 /5 Reviews Call BookMore Details
Hudson Whaler
+1-888-965-8297
542 Warren St., Hudson, NY 12534 ~14.20 miles west of Hillsdale
  • 3 star Downtown property
  • Fitness center on property
From$75
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Seven Hills Inn
+1-888-906-6358
40 Plunkett St., Lenox, MA 01240 ~14.35 miles northeast of Hillsdale
  • Four star Resort hotel
  • 4 suites in hotel
From$184
Very Good 4.5 /5 Review Score Call BookMore Details
Applegate Inn
+1-888-749-6785
279 West Park St., Lee, MA 01238 ~14.47 miles east of Hillsdale
  • Mid-scale Rural hotel
  • 11 rooms in property
From$160
Very Good 4.0 /5 Reviews Call BookMore Details
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The Nest Hudson Hotel
+1-888-878-9982
330 Union St., Hudson, NY 12534 ~14.53 miles west of Hillsdale
  • Four star Downtown hotel
  • 3 floors in hotel
From$200
Very Good 4.5 /5 Reviews Call BookMore Details
33 Main
+1-888-389-4485
33 Main St., Lenox, MA 01238 ~14.69 miles east of Hillsdale
  • Luxurious 5 Star hotel
From$200
Average 3.0 /5 Guest Reviews Call BookMore Details
Rodeway Inn
+1-888-389-4121
200 Laurel St., Lee, MA 01238 ~14.69 miles east of Hillsdale
  • Economy property
  • Check-in: 11:00
From$60
Average 3.0 /5 Hotel Reviews Call BookMore Details
Chambery Inn : 199 Main St.
+1-888-675-2083
199 Main St., Lee, 01238 ~14.71 miles east of Hillsdale
  • Three Star hotel
From$90
Very Good 4.5 /5 Review Score Call BookMore Details
Brook Farm Inn
+1-800-716-8490
15 Hawthorne St., Lenox, MA 01240 ~14.72 miles northeast of Hillsdale
  • High end Rural property
  • Complimentary breakfast is offered
From$120
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Black Swan Inn Lee Lenox An Ascend Hotel
+1-800-805-5223
435 Laurel St., Lee, MA 01238 ~14.73 miles east of Hillsdale
  • 3-star Lake hotel
  • 2 floors in hotel
From$60
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Quality Inn - Lee
+1-888-965-1860
435 Laurel St., Lee, MA 01238 ~14.74 miles east of Hillsdale
  • Midscale Lake property
  • Gym is available on property
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 ~14.76 miles northeast of Hillsdale
  • Affordable property
  • Hotel has 2 floors
From$90
Average 3.0 /5 Review Score Call BookMore Details
Pilgrim Inn in Lee
+1-888-897-9207
165 Housatonic St., Lee, MA 01238 ~14.90 miles east of Hillsdale
  • 3-star property
  • Check in: 3:00 PM
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
The Constance by The Lenox Collection in Lenox
+1-888-311-4278
11 Old Stockbridge Rd., Lenox, MA 01240 ~15.00 miles northeast of Hillsdale
  • High-end property
  • Hotel has 3 floors
From$225
Average 3.0 /5 Recent Reviews Call BookMore Details
Kemble Inn : 2 Kemble St.
+1-888-469-4795
2 Kemble St., Lenox, MA 01240 ~15.05 miles northeast of Hillsdale
  • Affordable Mountain hotel
  • 12 rooms in property
From$265
Very Good 4.0 /5 Review Score Call BookMore Details
The Whitlock by The Lenox Collection
+1-888-734-9421
16 Church St., Lenox, MA 01240 ~15.09 miles northeast of Hillsdale
  • Affordable hotel
  • Hotel has 2 floors
From$200
Average 3.0 /5 Review Score Call BookMore Details
Tiara Equest (The Inn at Richmond & Berkshire Equestrian Center - Richmond
+1-888-841-5292
802 State Rd., Richmond, MA 01254 ~15.29 miles northeast of Hillsdale
  • Affordable Rural hotel
  • 4 suites in hotel
From$150
Very Good 4.5 /5 Reviews Call BookMore Details
The Dewey by The Lenox Collection in Lenox
+1-888-455-5160
7 Hubbard St., Lenox, MA 01240 ~15.44 miles northeast of Hillsdale
  • 4 star hotel
  • 12 rooms in property
From$75
Average 3.0 /5 Guest Reviews Call BookMore Details
The Cornell Inn, Lenox : 203 Main St.
+1-888-965-8297
203 Main St., Lenox, MA 01240 ~15.60 miles northeast of Hillsdale
  • Midscale Mountain property
  • Check in: 3:00 PM-8PM
From$60
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Eastover Estate & Retreat in Lenox
+1-888-906-6358
430 East St., Lenox, MA 01240 ~16.65 miles northeast of Hillsdale
  • High-end Mountain hotel
  • 90 rooms in hotel
From$109
Average 3.5 /5 Latest Reviews Call BookMore Details
Life House Berkshires : 194 Pittsfield Rd.
+1-888-749-6785
194 Pittsfield Rd., Lenox, MA 01240 ~16.85 miles northeast of Hillsdale
  • Economy Suburban property
  • Check-in: 2pm
From$49
Average 3.0 /5 Read Reviews Call BookMore Details
Howard Johnson by Wyndham Lenox
+1-888-878-9982
462 Pittsfield Rd., Lenox, MA 01240 ~16.99 miles northeast of Hillsdale
  • Low priced Resort hotel
  • 44 sleeping rooms in hotel
From$65
Average 3.0 /5 Recent Reviews Call BookMore Details
James Newbury Hotel & Spa in Coxsackie
+1-888-389-4485
60 South River St., Coxsackie, NY 12051 ~17.20 miles northwest of Hillsdale
  • Three Star Riverfront property
  • Free breakfast
From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Miraval Berkshires Resort & Spa - All Inclusive Adults Only
+1-888-389-4121
55 Lee Rd., Lenox, MA 01240 ~17.62 miles northeast of Hillsdale
  • Four star Resort property
  • Has environment-friendly policy Read more
From$138
Average 3.0 /5 Guest Reviews Call BookMore Details
Hampton Inn & Suites Berkshires-Lenox
+1-888-675-2083
445 Pittsfield Rd., Lenox, MA 01240 ~17.84 miles northeast of Hillsdale
  • 3 star Mountain property
  • 24 suites in hotel
From$109
Average 3.0 /5 Hotel Reviews Call BookMore Details
Yankee Inn - Lenox
+1-800-716-8490
461 Pittsfield Rd., Lenox, MA 01240 ~17.90 miles northeast of Hillsdale
  • Low Cost hotel
  • 3 floors in hotel
From$145
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Knights Inn Lenox - Lenox
+1-800-805-5223
474 Pittsfield Rd., Lenox, MA 01240 ~17.99 miles northeast of Hillsdale
  • Economical Downtown hotel
  • Hotel has 16 rooms
Best Western Plus Berkshire Hills Inn & Suites in Pittsfield
+1-888-965-1860
1350 West Housatonic St., Pittsfield, MA 01201 ~18.12 miles northeast of Hillsdale
  • Mid-scale Rural hotel
  • Gym is available on property
From$79
Very Good 4.0 /5 Read Reviews Call BookMore Details
Lenox Inn
+1-888-788-5576
525 Pittsfield Rd., Lenox, MA 01240 ~18.17 miles northeast of Hillsdale
  • Two star hotel
Hilton Garden Inn Lenox Pittsfield - Pittsfield
+1-888-897-9207
1032 South St., Pittsfield, MA 01201 ~18.20 miles northeast of Hillsdale
  • Affordable Suburban hotel
  • Hotel has 2 meeting rooms
From$95
Very Good 4.0 /5 Read Reviews Call BookMore Details
Wake Robin Inn - Lakeville
+1-888-311-4278
106 Sharon Rd., Lakeville, CT 06039 ~18.25 miles south of Hillsdale
  • Three Star Rural hotel
  • Check in time: 3 pm
From$89
Average 3.0 /5 Guest Reviews Call BookMore Details
Interlaken Inn & Resort
+1-888-469-4795
74 Interlaken Rd., Lakeville, CT 06039 ~18.85 miles south of Hillsdale
  • 3 star Resort property
  • Fitness + Health Center
From$209
Very Good 4.0 /5 Review Score Call BookMore Details
Holiday Inn Express Hotel & Suites West Coxsackie, an IHG Hotel - West Coxsackie
+1-888-734-9421
12740 Route 9 West, West Coxsackie, NY 12192 ~18.93 miles west of Hillsdale
  • Midscale Highway property
  • Gym / Fitness Center Available
From$119
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Best Western New Baltimore Inn
+1-888-841-5292
12600 State Route 9w, West Coxsackie, NY 12192 ~20.09 miles northwest of Hillsdale
  • Mid-scale Rural hotel
  • Gym / Fitness Center Available
From$75
Average 3.0 /5 Review Score Call BookMore Details
Blackberry River Inn : 538 Greenwoods Rd. West
+1-888-455-5160
538 Greenwoods Rd. West, Norfolk, CT 06058 ~20.10 miles southeast of Hillsdale
  • 3-star hotel
  • 17 rooms in property
From$109
Very Good 4.0 /5 Read Reviews Call BookMore Details
Berkshire Inn
+1-888-965-8297
150 West Housatonic St., Pittsfield, MA 01201 ~20.18 miles northeast of Hillsdale
  • Cheap Downtown hotel
  • Hotel has 2 floors
From$90
Average 3.0 /5 Reviews Call BookMore Details
Oyo Hotel Coxsackie I 87 North in Albany
+1-888-906-6358
12800 Rte 9w, Albany, NY 12192 ~20.28 miles northwest of Hillsdale
  • Three Star hotel
  • 28 rooms in hotel
From$90
Average 3.0 /5 Read Reviews Call BookMore Details
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel - Pittsfield
+1-888-749-6785
1 West St., Pittsfield, MA 01201 ~20.64 miles northeast of Hillsdale
  • Midscale Downtown hotel
  • Hotel has 170 rooms
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Hotel on North in Pittsfield
+1-888-878-9982
297 North St., Pittsfield, MA 01201 ~20.94 miles northeast of Hillsdale
  • 4-star Downtown hotel
  • Check-in time: 15:00
From$150
Excellent 5.0 /5 Guest Reviews Call BookMore Details

Next: See My Hillsdale Hotels with Pricing

Graph of Hillsdale, NY Hotel Prices for Next 20 Days

Rates shown are nightly rates before taxes and do not necessarily reflect all Hillsdale, NY discounts available. The chart reflects the cheapest Hillsdale hotel for each day and each star rating category.

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.

Below is a chart of the current pricing seasonality of hotels and motels in Hillsdale, NY:

Hillsdale, NY: Prices by Star Rating Class

Below are 3 charts illustrating avg. rate trends by star rating class in Hillsdale, NY. Browse these charts to evaluate the most cost effective time period to book a room in Hillsdale for any future trips.

Indulge in Luxury: Discover Hotel Gems in Hillsdale, NY

For those seeking a more indulgent stay, Hillsdale, NY, features an array of luxury accommodations. This town is home to high-end hotels, resorts, inns, and suites that provide exceptional services and amenities, promising a truly unforgettable getaway. These establishments often boast well-appointed rooms, fine dining options, rejuvenating spa facilities, and state-of-the-art fitness centers. Many even offer stunning vistas of the surrounding countryside, providing a serene backdrop to your luxurious stay. With such an impressive choice of premium-class properties, Hillsdale, NY proves to be a destination that caters not only to budget travelers but also to those desiring a lavish retreat.

Affordable Accommodation in Hillsdale, NY: Discover Low-Budget Hotel Options for Budget-Conscious Travelers

3 Star Average Prices: $191.57

Hillsdale, NY features an array of reasonably priced accommodations that compromise neither on quality nor comfort. Travelers on a budget can choose from a variety of low-cost hotels, motels, inns, and suites. Despite the lower rates, these establishments still offer clean and cozy rooms, essential amenities, and friendly service. Additionally, many of these pocket-friendly options are located in convenient locations near the town's attractions, shops, and restaurants. With such a wide range of affordable lodgings, a trip to Hillsdale, NY can be both memorable and wallet-friendly.

2 Star Average Prices: $119.00

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.

FAQs about hotels in Hillsdale

What are the most favored hotels in Hillsdale?

The Windflower Inn, Hotel on North and Seven Hills Inn are the best rated hotels based on customer reviews in the last 365 days.

What are the most high-end hotels in Hillsdale?

33 Main, Apple Tree Inn and Seven Hills Inn are the top 3 luxury hotels near Hillsdale city center.

What hotels are closest to the city center of Hillsdale?

The Windflower Inn, Quality Inn, and Fairfield Inn & Suites by Marriott Great Barrington Lenox are the properties closest to Hillsdale city center.

How much does a cheap hotel in Hillsdale cost per night?

In the last year, a 2 star hotel in Hillsdale can be as cheap as $119.00 per night. (based on HotelPlanner prices)

How much does a 3 star hotel in Hillsdale cost per night?

In the last year, the average 3 star hotel in Hillsdale has been $191.57 per night. (based on HotelPlanner prices)

What are the best independent hotels in Hillsdale?

The Windflower Inn, Hotel on North and Seven Hills Inn are the best rated independent hotels (not part of a big brand).

What are the most popular Choice Hotels branded hotels in Hillsdale?

Quality Inn, Black Swan Inn Lee Lenox An Ascend Hotel and Quality Inn are the best rated Choice Hotels branded hotels (based on HotelPlanner reviews score).

What are the best Best Western hotels in Hillsdale?

Best Western Plus Berkshire Hills Inn & Suites and Best Western New Baltimore Inn are the best rated Best Western branded hotels (based on user reviews score).

What are the most popular IHG hotels in Hillsdale?

Holiday Inn Club Vacations Oak N Spruce Resort, Holiday Inn Express Hotel & Suites West Coxsackie, an IHG Hotel and Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel are the best rated Intercontinental Hotel Group (IHG) branded hotels (based on user reviews score).

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