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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
  • Three Star Mountain property
  • Free breakfast
From£138
Excellent 5.0 /5 Latest Reviews Call BookMore Details
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Quality Inn Great Barrington 372 Main St., Great Barrington, MA 01230 Website ~7.68 miles east of Hillsdale
  • 2-star Rural hotel
  • 2 floors in hotel
From£74
Very good 4.0 /5 Review Score 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
  • 3 star Resort hotel
  • Hotel has 60 rooms
From£81
Very good 4.0 /5 Latest Reviews Call BookMore Details
Travelodge by Wyndham Great Barrington Berkshires 400 Stockbridge Rd., Great Barrington, MA 01230 ~8.50 miles east of Hillsdale
  • Two star Resort hotel
  • Free breakfast available
From£35
Average 3.0 /5 Reviews Call BookMore Details
Holiday Inn Express Great Barrington 415 Stockbridge Rd., Great Barrington, MA 01230 ~8.51 miles east of Hillsdale
  • Three Star Mountain hotel
  • Check-in time: 3:00pm
From£66
Very good 4.0 /5 Read Reviews Call BookMore Details
Pleasant Valley Motel West Stockbridge - West Stockbridge 42 Stockbridge Rd., West Stockbridge, MA 01266 ~10.68 miles northeast of Hillsdale
  • Cheap property
  • Check in time: 13:00
From£44
Average 3.0 /5 Read Reviews Call BookMore Details
The Red Lion Inn - Stockbridge 30 Main St., Stockbridge, MA 01262 ~11.09 miles east of Hillsdale
  • 3-star Rural property
  • 8 meeting rooms in hotel
From£89
Average 3.0 /5 Read Reviews Call BookMore Details
Holiday Inn Club Vacations Oak N Spruce Resort 190 Meadow St., South Lee, MA 01260 ~12.73 miles east of Hillsdale
  • 3 star Mountain property
  • Check-in: 4:00pm
From£66
Very good 4.0 /5 Review Score Call BookMore Details
Econo Lodge Lee - Great Barrington in Lee 980 Pleasant St., Lee, MA 01238 ~13.40 miles east of Hillsdale
  • Inexpensive hotel
  • Check in: 11:00
From£35
Average 3.0 /5 Latest Reviews Call BookMore Details
Wheatleigh Hawthorne Rd., Lenox, MA 01240 ~13.68 miles northeast of Hillsdale
  • 3-star property
  • Hotel has 9 suites
From£299
Very good 4.0 /5 Recent Reviews Call BookMore Details
Apple Tree Inn in Lenox 10 Richmond Mountain Rd., Lenox, MA 01240 ~13.71 miles northeast of Hillsdale
  • 4 star Mountain property
  • 3 floors in hotel
From£74
Average 3.0 /5 Recent Reviews Call BookMore Details
St. Charles Hotel 16 Park Place, Hudson, NY 12534 ~14.04 miles west of Hillsdale
  • Two star Downtown hotel
  • 6 suites in hotel
From£59
Average 3.0 /5 Reviews Call BookMore Details
Hudson Whaler 542 Warren St., Hudson, NY 12534 ~14.18 miles west of Hillsdale
  • Three Star Downtown hotel
  • Gym is available on property
From£56
Very good 4.0 /5 Guest Reviews Call BookMore Details
Seven Hills Inn 40 Plunkett St., Lenox, MA 01240 ~14.34 miles northeast of Hillsdale
  • Expensive Resort property
  • Check in time: 3 pm
From£137
Very good 4.5 /5 Reviews Call BookMore Details
Applegate Inn in Lee 279 West Park St., Lee, MA 01238 ~14.46 miles east of Hillsdale
  • 3 star Rural hotel
  • 3 floors in property
From£119
Very good 4.0 /5 Read Reviews Call BookMore Details
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The Nest Hudson Hotel 330 Union St., Hudson, NY 12534 ~14.51 miles west of Hillsdale
  • High end Downtown property
  • Hotel has 6 rooms
From£149
Very good 4.5 /5 Reviews Call BookMore Details
33 Main - Lenox 33 Main St., Lenox, MA 01238 ~14.67 miles east of Hillsdale
  • Luxurious 5-star hotel
From£149
Average 3.0 /5 Latest Reviews Call BookMore Details
Rodeway Inn - Lee 200 Laurel St., Lee, MA 01238 ~14.68 miles east of Hillsdale
  • Cheap property
  • Check in: 11:00
From£44
Average 3.0 /5 Review Score Call BookMore Details
Chambery Inn 199 Main St., Lee, 01238 ~14.69 miles east of Hillsdale
  • Three Star hotel
  • Check in: 14:00
From£67
Very good 4.5 /5 Review Score Call BookMore Details
Brook Farm Inn - Lenox 15 Hawthorne St., Lenox, MA 01240 ~14.71 miles northeast of Hillsdale
  • High end Rural property
  • Free comp. breakfast
From£89
Very good 4.0 /5 Recent Reviews Call BookMore Details
The Black Swan Lee Lenox An Ascend Collection Hotel in Lee 435 Laurel St., Lee, MA 01238 Website ~14.73 miles east of Hillsdale
  • 3-star Lake hotel
  • Hotel has 52 rooms
From£48
Very good 4.0 /5 Latest Reviews Call BookMore Details
Canyon Ranch Lenox : 165 Kemble St. 165 Kemble St., Lenox, MA 01240 ~14.74 miles northeast of Hillsdale
  • Midscale hotel
  • 2 floors in hotel
From£67
Average 3.0 /5 Read Reviews Call BookMore Details
Quality Inn in Lee 170 Housatonic St., Lee, MA 01238 ~14.85 miles east of Hillsdale
  • Economical Lake hotel
  • Check-in time: 11:00 AM
From£35
Average 3.0 /5 Read Reviews Call BookMore Details
Pilgrim Inn 165 Housatonic St., Lee, MA 01238 ~14.89 miles east of Hillsdale
  • Mid-scale property
From£59
Average 3.0 /5 Latest Reviews Call BookMore Details
The Constance by The Lenox Collection 11 Old Stockbridge Rd., Lenox, MA 01240 ~14.99 miles northeast of Hillsdale
  • High-end property
  • Comp. Breakfast
From£168
Average 3.0 /5 Latest Reviews Call BookMore Details
Kemble Inn - Lenox 2 Kemble St., Lenox, MA 01240 ~15.04 miles northeast of Hillsdale
  • 3 star Mountain hotel
  • Check in: 3:00 PM
From£198
Very good 4.0 /5 Guest Reviews Call BookMore Details
The Whitlock by The Lenox Collection in Lenox 16 Church St., Lenox, MA 01240 ~15.08 miles northeast of Hillsdale
  • Affordable hotel
  • 2 floors in property
From£149
Average 3.0 /5 Read 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
  • Three Star Rural hotel
  • Check-in: 3:00 p.m.
From£112
Very good 4.5 /5 Guest Reviews Call BookMore Details
The Dewey by The Lenox Collection 7 Hubbard St., Lenox, MA 01240 ~15.43 miles northeast of Hillsdale
  • Expensive property
  • Hotel has 12 rooms
From£56
Average 3.0 /5 Guest Reviews 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 breakfast
From£44
Very good 4.0 /5 Review Score Call BookMore Details
Element Lenox Berkshires 130 Pittsfield Rd., Lenox, MA 01240 ~16.56 miles northeast of Hillsdale
  • 3 star Mountain hotel
  • 2 floors in property
From£37
Average 3.0 /5 Review Score Call BookMore Details
Eastover Estate & Retreat 430 East St., Lenox, MA 01240 ~16.64 miles northeast of Hillsdale
  • 4 star Mountain hotel
  • Check-in time: 4:00PM
From£81
Average 3.5 /5 Review Score Call BookMore Details
Life House Berkshires 194 Pittsfield Rd., Lenox, MA 01240 ~16.83 miles northeast of Hillsdale
  • Low-priced Suburban hotel
  • Check in time: 2pm
From£36
Average 3.0 /5 Recent Reviews Call BookMore Details
Howard Johnson by Wyndham Lenox : 462 Pittsfield Rd. 462 Pittsfield Rd., Lenox, MA 01240 ~16.98 miles northeast of Hillsdale
  • Economical Resort property
  • 44 rooms in property
From£48
Average 3.0 /5 Hotel Reviews Call BookMore Details
James Newbury Hotel & Spa - Coxsackie 60 South River St., Coxsackie, NY 12051 ~17.18 miles northwest of Hillsdale
  • Midscale Riverfront property
  • Free comp. breakfast
From£59
Average 3.0 /5 Review Score Call BookMore Details
Miraval Berkshires Resort & Spa - All Inclusive Adults Only : 55 Lee Rd. 55 Lee Rd., Lenox, MA 01240 ~17.60 miles northeast of Hillsdale
  • Four star Resort property
  • Check in time: 3PM
From£103
Average 3.0 /5 Latest Reviews Call BookMore Details
Hampton Inn & Suites Lenox Berkshires : 445 Pittsfield Rd. 445 Pittsfield Rd., Lenox, MA 01240 ~17.82 miles northeast of Hillsdale
  • 3 star Mountain hotel
  • Access to gym on-site
From£59
Average 3.0 /5 Reviews Call BookMore Details
The Yankee, Trademark Collection by Wyndham : 461 Pittsfield Rd. 461 Pittsfield Rd., Lenox, MA 01240 ~17.88 miles northeast of Hillsdale
  • Economy property
  • 9 suites in property
From£108
Very good 4.0 /5 Review Score Call BookMore Details
Knights Inn Lenox - Lenox 474 Pittsfield Rd., Lenox, MA 01240 ~17.97 miles northeast of Hillsdale
  • 2 star Downtown hotel
  • Check in: 2.00 pm
From£27
Poor 2.0 /5 Reviews Call BookMore Details
Best Western Plus Berkshire Hills Inn & Suites in Pittsfield 1350 West Housatonic St., Pittsfield, MA 01201 ~18.11 miles northeast of Hillsdale
  • Midscale Rural property
  • Complimentary breakfast is offered
From£63
Very good 4.5 /5 Recent Reviews Call BookMore Details
Lenox Inn 525 Pittsfield Rd., Lenox, MA 01240 ~18.16 miles northeast of Hillsdale
  • Economy property
  • 18 rooms in property
From£44
Poor 2.0 /5 Read Reviews Call BookMore Details
Hilton Garden Inn Lenox Pittsfield in Pittsfield 1032 South St., Pittsfield, MA 01201 ~18.18 miles northeast of Hillsdale
  • Three Star Suburban property
  • 4 floors in hotel
From£71
Very good 4.0 /5 Guest Reviews Call BookMore Details
Wake Robin Inn : 106 Sharon Rd. 106 Sharon Rd., Lakeville, CT 06039 ~18.22 miles south of Hillsdale
  • Mid-scale Rural hotel
  • Free breakfast available
From£66
Average 3.0 /5 Read Reviews Call BookMore Details
Holiday Inn Express Pittsfield Lenox Berkshires - Pittsfield 1055 South St., Pittsfield, MA 01201 ~18.26 miles northeast of Hillsdale
  • Midscale Suburban hotel
  • 4 floors in hotel
From£59
Average 3.0 /5 Recent Reviews Call BookMore Details
Berkshire Mountain Lodge 8 Dan Fox Dr., Pittsfield, MA 01201 ~18.48 miles northeast of Hillsdale
  • Cheap Mountain property
  • Check-in: 4:00PM
From£93
Very good 4.5 /5 Guest Reviews Call BookMore Details
Interlaken Inn : 74 Interlaken Rd. 74 Interlaken Rd., Lakeville, CT 06039 ~18.85 miles south of Hillsdale
  • 3 star Resort property
  • Gym is available on property
From£133
Very good 4.0 /5 Review Score Call BookMore Details
Holiday Inn Express Hotel & Suites West Coxsackie by IHG in West Coxsackie 12740 Route 9 West, West Coxsackie, NY 12192 ~18.92 miles west of Hillsdale
  • 3 star Highway property
  • 3 floors in property
From£88
Very good 4.0 /5 Read Reviews Call BookMore Details
Blackberry River Inn in Norfolk 538 Greenwoods Rd. West, Norfolk, CT 06058 ~20.05 miles southeast of Hillsdale
  • 3-star property
  • 17 rooms in property
From£81
Very good 4.0 /5 Read Reviews Call BookMore Details
Spark by Hilton West Coxsackie in West Coxsackie 12600 State Route 9w, West Coxsackie, NY 12192 ~20.08 miles northwest of Hillsdale
  • Midscale Rural property
  • Check in: 3:00 pm
From£56
Average 3.0 /5 Review Score Call BookMore Details
Berkshire Inn : 150 West Housatonic St. 150 West Housatonic St., Pittsfield, MA 01201 ~20.17 miles northeast of Hillsdale
  • Economical Downtown hotel
  • 2 floors in hotel
From£67
Average 3.0 /5 Review Score 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: £156.61

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: £187.14

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.

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 best Marriott hotels in Hillsdale?

Fairfield Inn & Suites by Marriott Great Barrington Lenox and The Yankee, Trademark Collection by Wyndham are the best rated Marriott/Starwood branded hotels (based on customer reviews score).

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

Quality Inn Great Barrington, The 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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