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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 684 South Egremont Rd., Great Barrington, MA 01230 ~6.42 miles southeast of Hillsdale
  • Midscale Mountain property
  • Check-in: 2:00PM
From$185
Excellent 5.0 /5 Latest Reviews Call BookMore Details
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Quality Inn Great Barrington : 372 Main St. 372 Main St., Great Barrington, MA 01230 Website ~7.68 miles east of Hillsdale
  • Two star Rural hotel
  • Check in time: 3:00pm
From$100
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi 249 Stockbridge Rd., Great Barrington, MA 01230 Website ~8.43 miles east of Hillsdale
  • Mid-scale Resort hotel
  • Check-in time: 3:00pm
From$109
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Travelodge by Wyndham Great Barrington Berkshires : 400 Stockbridge Rd. 400 Stockbridge Rd., Great Barrington, MA 01230 ~8.50 miles east of Hillsdale
  • Economical Resort property
  • Free comp. breakfast
From$47
Average 3.0 /5 Read Reviews Call BookMore Details
Holiday Inn Express Great Barrington in Great Barrington 415 Stockbridge Rd., Great Barrington, MA 01230 ~8.51 miles east of Hillsdale
  • 3 star Mountain hotel
  • 6 suites 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 ~10.68 miles northeast of Hillsdale
  • Inexpensive property
  • Check in: 13:00
From$60
Average 3.0 /5 Guest Reviews Call BookMore Details
The Red Lion Inn in Stockbridge 30 Main St., Stockbridge, MA 01262 ~11.09 miles east of Hillsdale
  • Mid-scale Rural hotel
  • 35 suites in hotel
From$120
Average 3.0 /5 Read Reviews Call BookMore Details
Holiday Inn Club Vacations Oak N Spruce Resort : 190 Meadow St. 190 Meadow St., South Lee, MA 01260 ~12.73 miles east of Hillsdale
  • Affordable Mountain property
  • 334 rooms in hotel
From$89
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Econo Lodge Lee - Great Barrington 980 Pleasant St., Lee, MA 01238 ~13.40 miles east of Hillsdale
  • Low priced property
  • Check-in: 11:00
From$48
Average 3.0 /5 Read Reviews Call BookMore Details
Wheatleigh : Hawthorne Rd. Hawthorne Rd., Lenox, MA 01240 ~13.68 miles northeast of Hillsdale
  • Affordable hotel
  • 2 floors in hotel
From$400
Very Good 4.0 /5 Read Reviews Call BookMore Details
Apple Tree Inn - Lenox 10 Richmond Mountain Rd., Lenox, MA 01240 ~13.71 miles northeast of Hillsdale
  • Four-star Mountain hotel
  • Check in: 4:00 PM
From$100
Average 3.0 /5 Review Score Call BookMore Details
St. Charles Hotel in Hudson 16 Park Place, Hudson, NY 12534 ~14.04 miles west of Hillsdale
  • Low-priced Downtown property
  • 3 floors in property
From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Hudson Whaler 542 Warren St., Hudson, NY 12534 ~14.18 miles west of Hillsdale
  • 3-star Downtown property
  • Access to gym on-site
From$75
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Seven Hills Inn : 40 Plunkett St. 40 Plunkett St., Lenox, MA 01240 ~14.34 miles northeast of Hillsdale
  • High end Resort hotel
  • 57 rooms in hotel
From$184
Very Good 4.5 /5 Hotel Reviews Call BookMore Details
Applegate Inn 279 West Park St., Lee, MA 01238 ~14.46 miles east of Hillsdale
  • 3-star Rural hotel
  • 11 rooms in property
From$160
Very Good 4.0 /5 Read Reviews Call BookMore Details
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The Nest Hudson Hotel in Hudson 330 Union St., Hudson, NY 12534 ~14.51 miles west of Hillsdale
  • High-end Downtown hotel
  • 6 suites in property
From$200
Very Good 4.5 /5 Read Reviews Call BookMore Details
33 Main - Lenox 33 Main St., Lenox, MA 01238 ~14.67 miles east of Hillsdale
  • Luxurious Five Star hotel
From$200
Average 3.0 /5 Latest Reviews Call BookMore Details
Rodeway Inn in Lee 200 Laurel St., Lee, MA 01238 ~14.68 miles east of Hillsdale
  • Inexpensive property
  • Hotel has 23 rooms
From$60
Average 3.0 /5 Recent Reviews Call BookMore Details
Chambery Inn : 199 Main St. 199 Main St., Lee, 01238 ~14.69 miles east of Hillsdale
  • 3 star property
  • Hotel has 9 rooms
From$90
Very Good 4.5 /5 Reviews Call BookMore Details
Brook Farm Inn 15 Hawthorne St., Lenox, MA 01240 ~14.71 miles northeast of Hillsdale
  • 4-star Rural property
  • 15 rooms in hotel
From$120
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Black Swan Lee Lenox An Ascend Collection Hotel 435 Laurel St., Lee, MA 01238 ~14.72 miles east of Hillsdale
  • Mid-scale Lake property
  • Free breakfast
From$60
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Canyon Ranch Lenox 165 Kemble St., Lenox, MA 01240 ~14.74 miles northeast of Hillsdale
  • Midscale property
  • Fitness + Health Center
From$90
Average 3.0 /5 Guest Reviews Call BookMore Details
Quality Inn - Lee 170 Housatonic St., Lee, MA 01238 ~14.85 miles east of Hillsdale
  • Economical Lake property
  • Check in time: 11:00 AM
From$47
Average 3.0 /5 Hotel Reviews Call BookMore Details
Pilgrim Inn 165 Housatonic St., Lee, MA 01238 ~14.89 miles east of Hillsdale
  • Three Star hotel
From$80
Average 3.0 /5 Reviews Call BookMore Details
The Constance by The Lenox Collection 11 Old Stockbridge Rd., Lenox, MA 01240 ~14.99 miles northeast of Hillsdale
  • Four-star hotel
  • 3 floors in hotel
From$225
Average 3.0 /5 Guest Reviews Call BookMore Details
Kemble Inn - Lenox 2 Kemble St., Lenox, MA 01240 ~15.04 miles northeast of Hillsdale
  • 3-star Mountain hotel
  • Hotel has 12 suites
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 ~15.08 miles northeast of Hillsdale
  • Midscale property
  • Check-in time: 14:00
From$200
Average 3.0 /5 Latest Reviews Call BookMore Details
Tiara Equest (The Inn at Richmond & Berkshire Equestrian Center in Richmond 802 State Rd., Richmond, MA 01254 ~15.28 miles northeast of Hillsdale
  • Affordable Rural property
  • Hotel has 3 meeting rooms
From$150
Very Good 4.5 /5 Reviews Call BookMore Details
The Dewey by The Lenox Collection : 7 Hubbard St. 7 Hubbard St., Lenox, MA 01240 ~15.43 miles northeast of Hillsdale
  • Expensive hotel
  • 12 sleeping rooms in hotel
From$75
Average 3.0 /5 Review Score Call BookMore Details
The Cornell Inn, Lenox & The Berkshires 203 Main St., Lenox, MA 01240 ~15.59 miles northeast of Hillsdale
  • Mid-scale Mountain hotel
  • Free comp. breakfast
From$60
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Element Lenox Berkshires in Lenox 130 Pittsfield Rd., Lenox, MA 01240 ~16.56 miles northeast of Hillsdale
  • Midscale Mountain hotel
  • Comp. Breakfast
From$50
Average 3.0 /5 Guest Reviews Call BookMore Details
Eastover Estate & Retreat - Lenox 430 East St., Lenox, MA 01240 ~16.64 miles northeast of Hillsdale
  • High-end Mountain property
  • Hotel has 2 floors
From$109
Average 3.5 /5 Hotel Reviews Call BookMore Details
Life House Berkshires - Lenox 194 Pittsfield Rd., Lenox, MA 01240 ~16.83 miles northeast of Hillsdale
  • Low priced Suburban hotel
  • Free breakfast
From$49
Average 3.0 /5 Hotel Reviews Call BookMore Details
Howard Johnson by Wyndham Lenox 462 Pittsfield Rd., Lenox, MA 01240 ~16.98 miles northeast of Hillsdale
  • Low priced Resort property
  • Check-in: 2:00 PM
From$65
Average 3.0 /5 Guest Reviews Call BookMore Details
James Newbury Hotel & Spa in Coxsackie 60 South River St., Coxsackie, NY 12051 ~17.18 miles northwest of Hillsdale
  • 3 star Riverfront hotel
  • Check-in: 04:00pm
From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Miraval Berkshires Resort & Spa - All Inclusive Adults Only 55 Lee Rd., Lenox, MA 01240 ~17.60 miles northeast of Hillsdale
  • 4 star Resort property
  • 105 sleeping rooms in hotel
From$138
Average 3.0 /5 Recent Reviews Call BookMore Details
Hampton Inn & Suites Lenox Berkshires 445 Pittsfield Rd., Lenox, MA 01240 ~17.82 miles northeast of Hillsdale
  • Three Star Mountain property
  • Free complimentary breakfast
From$80
Average 3.0 /5 Review Score Call BookMore Details
The Yankee Inn - Lenox 461 Pittsfield Rd., Lenox, MA 01240 ~17.88 miles northeast of Hillsdale
  • 2 star property
  • Hotel has 9 suites
From$145
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Knights Inn Lenox 474 Pittsfield Rd., Lenox, MA 01240 ~17.97 miles northeast of Hillsdale
  • Economical Downtown property
  • 16 rooms in property
Best Western Plus Berkshire Hills Inn & Suites 1350 West Housatonic St., Pittsfield, MA 01201 ~18.11 miles northeast of Hillsdale
  • 3 star Rural property
  • Check in time: 03:00
From$85
Very Good 4.5 /5 Recent Reviews Call BookMore Details
Lenox Inn in Lenox 525 Pittsfield Rd., Lenox, MA 01240 ~18.16 miles northeast of Hillsdale
  • Two-star property
  • 18 rooms in hotel
Hilton Garden Inn Lenox Pittsfield - Pittsfield 1032 South St., Pittsfield, MA 01201 ~18.18 miles northeast of Hillsdale
  • Midscale Suburban property
  • 2 meeting rooms in property
From$95
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Wake Robin Inn - Lakeville 106 Sharon Rd., Lakeville, CT 06039 ~18.22 miles south of Hillsdale
  • 3 star Rural hotel
  • Hotel has 3 meeting rooms
From$89
Average 3.0 /5 Review Score Call BookMore Details
Holiday Inn Express Pittsfield Lenox Berkshires : 1055 South St. 1055 South St., Pittsfield, MA 01201 ~18.26 miles northeast of Hillsdale
  • Affordable Suburban property
  • Free breakfast
From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Berkshire Mountain Lodge in Pittsfield 8 Dan Fox Dr., Pittsfield, MA 01201 ~18.48 miles northeast of Hillsdale
  • Low Cost Mountain property
  • Hotel has 146 suites
From$125
Very Good 4.5 /5 Hotel Reviews Call BookMore Details
Interlaken Inn - Lakeville 74 Interlaken Rd., Lakeville, CT 06039 ~18.85 miles south of Hillsdale
  • Mid-scale Resort property
  • 86 rooms in property
From$179
Very Good 4.0 /5 Read Reviews Call BookMore Details
Holiday Inn Express Hotel & Suites West Coxsackie by IHG - West Coxsackie 12740 Route 9 West, West Coxsackie, NY 12192 ~18.92 miles west of Hillsdale
  • Affordable Highway property
  • Free breakfast available
From$119
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Blackberry River Inn - Norfolk 538 Greenwoods Rd. West, Norfolk, CT 06058 ~20.05 miles southeast of Hillsdale
  • Mid-scale hotel
  • Check-in: 15:00
From$109
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Spark by Hilton West Coxsackie 12600 State Route 9w, West Coxsackie, NY 12192 ~20.08 miles northwest of Hillsdale
  • 3-star Rural hotel
  • 63 rooms in hotel
From$75
Average 3.0 /5 Recent Reviews Call BookMore Details
Berkshire Inn - Pittsfield 150 West Housatonic St., Pittsfield, MA 01201 ~20.17 miles northeast of Hillsdale
  • Economical Downtown hotel
  • Free breakfast available
From$90
Average 3.0 /5 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: $259.50

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, Seven Hills Inn and The Nest Hudson Hotel 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 Great Barrington, 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 $259.50 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, Seven Hills Inn and The Nest Hudson Hotel 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 Great Barrington, Black Swan Lee Lenox An Ascend Collection Hotel and Econo Lodge Lee - Great Barrington are the best rated Choice Hotels branded hotels (based on HotelPlanner reviews score).

What are the best IHG hotels in Hillsdale?

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

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