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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/Accommodations

The Windflower Inn
+1-888-389-4121
684 South Egremont Rd., Great Barrington, MA 01230 ~6.43 miles southeast of Hillsdale
  • Mid-scale Mountain hotel
  • Check in time: 2:00PM
From$185
Excellent 5.0 /5 Latest Reviews Call BookMore Details
Tired of clicking around? Talk to an expert Hotel Planner: (855) 276-7561 or say...
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Quality Inn : 372 Main St.
+1-888-675-2083
372 Main St., Great Barrington, MA 01230 Website ~7.69 miles east of Hillsdale
  • Cheap Rural hotel
  • Hotel has 2 floors
From$100
Very Good 4.0 /5 Recent 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 ~8.44 miles east of Hillsdale
  • Midscale Resort property
  • Free breakfast
From$109
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
+1-800-805-5223
415 Stockbridge Road41, Great Barrington, MA 01230 ~8.48 miles east of Hillsdale
  • 3 star Mountain hotel
  • 78 rooms in hotel
From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
Travelodge by Wyndham Great Barrington Berkshires - Great Barrington
+1-888-965-1860
400 Stockbridge Rd., Great Barrington, MA 01230 ~8.51 miles east of Hillsdale
  • Two star Resort hotel
  • Check in time: 11:00 AM
From$47
Average 3.0 /5 Read Reviews Call BookMore Details
Pleasant Valley Motel West Stockbridge - West Stockbridge
+1-888-788-5576
42 Stockbridge Rd., West Stockbridge, MA 01266 ~10.69 miles northeast of Hillsdale
  • Two-star property
  • 16 sleeping rooms in hotel
From$60
Average 3.0 /5 Review Score Call BookMore Details
The Red Lion Inn : 30 Main St.
+1-888-897-9207
30 Main St., Stockbridge, MA 01262 ~11.12 miles east of Hillsdale
  • Affordable Rural property
  • 108 rooms in hotel
From$229
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Club Vacations Oak N Spruce Resort
+1-888-311-4278
190 Meadow St., South Lee, MA 01260 ~12.75 miles east of Hillsdale
  • 3-star Mountain property
  • Hotel has an eco-friendly policy Learn more
From$89
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Econo Lodge Lee - Great Barrington
+1-888-469-4795
980 Pleasant St., Lee, MA 01238 ~13.41 miles east of Hillsdale
  • Low Cost hotel
  • Check-in: 11:00
From$48
Average 3.0 /5 Read Reviews Call BookMore Details
Wheatleigh
+1-888-734-9421
Hawthorne Rd., Lenox, MA 01240 ~13.69 miles northeast of Hillsdale
  • Mid-scale property
  • Free breakfast
From$400
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Apple Tree Inn : 10 Richmond Mountain Rd.
+1-888-841-5292
10 Richmond Mountain Rd., Lenox, MA 01240 ~13.73 miles northeast of Hillsdale
  • Expensive Mountain property
  • 3 suites in property
From$100
Average 3.0 /5 Review Score Call BookMore Details
St. Charles Hotel : 16 Park Place
+1-888-455-5160
16 Park Place, Hudson, NY 12534 ~14.06 miles west of Hillsdale
  • Cheap Downtown property
  • Check in time: 4:00 PM
From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
Hudson Whaler
+1-888-965-8297
542 Warren St., Hudson, NY 12534 ~14.20 miles west of Hillsdale
  • Midscale Downtown property
  • 3 floors in 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
  • 4 star Resort property
  • 57 rooms in hotel
From$184
Very Good 4.5 /5 Guest Reviews Call BookMore Details
Applegate Inn
+1-888-749-6785
279 West Park St., Lee, MA 01238 ~14.47 miles east of Hillsdale
  • 3 star Rural property
  • Check-in time: 2 pm
From$160
Very Good 4.0 /5 Read Reviews Call BookMore Details
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The Nest Hudson Hotel : 330 Union St.
+1-888-878-9982
330 Union St., Hudson, NY 12534 ~14.53 miles west of Hillsdale
  • High-end Downtown hotel
  • Check in: 3:00
From$200
Very Good 4.5 /5 Hotel 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 property
From$200
Average 3.0 /5 Read Reviews Call BookMore Details
Rodeway Inn
+1-888-389-4121
200 Laurel St., Lee, MA 01238 ~14.69 miles east of Hillsdale
  • 2-star hotel
  • Hotel has 23 rooms
From$60
Average 3.0 /5 Hotel Reviews Call BookMore Details
Chambery Inn - Lee
+1-888-675-2083
199 Main St., Lee, 01238 ~14.71 miles east of Hillsdale
  • Mid-scale property
  • 9 rooms in property
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 ~14.72 miles northeast of Hillsdale
  • Expensive Rural hotel
  • 15 rooms in property
From$120
Very Good 4.0 /5 Review Score Call BookMore Details
Black Swan Inn Lee Lenox An Ascend Hotel
+1-800-805-5223
435 Laurel St., Lee, MA 01238 Website ~14.73 miles east of Hillsdale
  • Midscale Lake hotel
  • 52 rooms in property
From$60
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Canyon Ranch Lenox : 165 Kemble St.
+1-888-965-1860
165 Kemble St., Lenox, MA 01240 ~14.76 miles northeast of Hillsdale
  • 3 star property
  • 2 floors in property
From$90
Average 3.0 /5 Latest Reviews Call BookMore Details
Quality Inn : 170 Housatonic St.
+1-888-788-5576
170 Housatonic St., Lee, MA 01238 ~14.86 miles east of Hillsdale
  • Cheap hotel
  • Check in: 11:00 AM
From$47
Average 3.0 /5 Recent Reviews Call BookMore Details
Pilgrim Inn in Lee
+1-888-897-9207
165 Housatonic St., Lee, MA 01238 ~14.90 miles east of Hillsdale
  • Midscale hotel
  • Check in: 3:00 PM
From$80
Average 3.0 /5 Reviews Call BookMore Details
The Constance : 11 Old Stockbridge Rd.
+1-888-311-4278
11 Old Stockbridge Rd., Lenox, MA 01240 ~15.00 miles northeast of Hillsdale
  • 4-star hotel
From$225
Average 3.0 /5 Recent Reviews Call BookMore Details
Kemble Inn in Lenox
+1-888-469-4795
2 Kemble St., Lenox, MA 01240 ~15.05 miles northeast of Hillsdale
  • Mid-scale Mountain hotel
  • Hotel has an eco-friendly policy See more
From$265
Very Good 4.0 /5 Latest Reviews Call BookMore Details
The Whitlock - Lenox
+1-888-734-9421
16 Church St., Lenox, MA 01240 ~15.09 miles northeast of Hillsdale
  • Three Star property
  • Check-in time: 14:00
From$200
Average 3.0 /5 Guest Reviews Call BookMore Details
Tiara Equest (The Inn at Richmond & Berkshire Equestrian Center : 802 State Rd.
+1-888-841-5292
802 State Rd., Richmond, MA 01254 ~15.29 miles northeast of Hillsdale
  • 3 star Rural hotel
  • Comp. Breakfast
From$150
Very Good 4.5 /5 Read Reviews Call BookMore Details
The Dewey - Lenox
+1-888-455-5160
7 Hubbard St., Lenox, MA 01240 ~15.44 miles northeast of Hillsdale
  • Four-star property
From$75
Average 3.0 /5 Recent 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
  • 3-star Mountain property
  • Check-in: 3:00 PM-8PM
From$60
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Eastover Estate & Retreat - Lenox
+1-888-906-6358
430 East St., Lenox, MA 01240 ~16.65 miles northeast of Hillsdale
  • Expensive Mountain hotel
  • Hotel has 90 rooms
From$109
Average 3.5 /5 Latest Reviews Call BookMore Details
Life House Berkshires in Lenox
+1-888-749-6785
194 Pittsfield Rd., Lenox, MA 01240 ~16.85 miles northeast of Hillsdale
  • Inexpensive Suburban property
  • Complimentary breakfast is offered
From$49
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 ~16.99 miles northeast of Hillsdale
  • Low Cost Resort hotel
  • Free breakfast
From$65
Average 3.0 /5 Guest Reviews Call BookMore Details
Miraval Berkshires Resort & Spa - All Inclusive Adults Only : 55 Lee Rd.
+1-888-389-4485
55 Lee Rd., Lenox, MA 01240 ~17.62 miles northeast of Hillsdale
  • High-end Resort property
  • 19 suites in hotel
From$138
Average 3.0 /5 Recent Reviews Call BookMore Details
Hampton Inn & Suites Berkshires Lenox : 445 Pittsfield Rd.
+1-888-389-4121
445 Pittsfield Rd., Lenox, MA 01240 ~17.84 miles northeast of Hillsdale
  • Mid-scale Mountain hotel
  • Free breakfast
From$109
Average 3.0 /5 Read Reviews Call BookMore Details
The Yankee, Trademark Collection by Wyndham - Lenox
+1-888-675-2083
461 Pittsfield Rd., Lenox, MA 01240 ~17.90 miles northeast of Hillsdale
  • 2 star hotel
  • 3 floors in property
From$65
Very Good 4.0 /5 Reviews Call BookMore Details
Knights Inn Lenox : 474 Pittsfield Rd.
+1-800-716-8490
474 Pittsfield Rd., Lenox, MA 01240 ~17.99 miles northeast of Hillsdale
  • 2 star Downtown property
  • Check-in: 2.00 pm
Best Western Plus Berkshire Hills Inn & Suites
+1-800-805-5223
1350 West Housatonic St., Pittsfield, MA 01201 ~18.12 miles northeast of Hillsdale
  • Three Star Rural hotel
  • 3 floors in property
From$79
Very Good 4.0 /5 Review Score Call BookMore Details
Lenox Inn
+1-888-965-1860
525 Pittsfield Rd., Lenox, MA 01240 ~18.17 miles northeast of Hillsdale
  • Two-star property
  • 18 rooms in hotel
Hilton Garden Inn Lenox Pittsfield
+1-888-788-5576
1032 South St., Pittsfield, MA 01201 ~18.20 miles northeast of Hillsdale
  • Mid-scale Suburban property
  • Check-in: 03:00PM
From$95
Very Good 4.0 /5 Reviews Call BookMore Details
Wake Robin Inn : 106 Sharon Rd.
+1-888-897-9207
106 Sharon Rd., Lakeville, CT 06039 ~18.25 miles south of Hillsdale
  • Affordable Rural property
  • Complimentary breakfast is offered
From$89
Average 3.0 /5 Review Score Call BookMore Details
Interlaken Inn & Resort in Lakeville
+1-888-311-4278
74 Interlaken Rd., Lakeville, CT 06039 ~18.85 miles south of Hillsdale
  • Midscale Resort hotel
  • Hotel has a green policy See policy
From$209
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Express Hotel & Suites West Coxsackie, an IHG Hotel : 12740 Route 9 West
+1-888-469-4795
12740 Route 9 West, West Coxsackie, NY 12192 ~18.93 miles west of Hillsdale
  • Affordable Highway property
  • Hotel has 3 floors
From$119
Very Good 4.0 /5 Reviews Call BookMore Details
Best Western New Baltimore Inn - West Coxsackie
+1-888-734-9421
12600 State Route 9w, West Coxsackie, NY 12192 ~20.09 miles northwest of Hillsdale
  • 3 star Rural property
  • 2 floors in hotel
From$75
Average 3.0 /5 Reviews Call BookMore Details
Blackberry River Inn : 538 Greenwoods Rd. West
+1-888-841-5292
538 Greenwoods Rd. West, Norfolk, CT 06058 ~20.10 miles southeast of Hillsdale
  • Affordable property
  • Check in: 15:00
From$109
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Berkshire Inn : 150 West Housatonic St.
+1-888-455-5160
150 West Housatonic St., Pittsfield, MA 01201 ~20.18 miles northeast of Hillsdale
  • Two star Downtown hotel
  • 2 floors in hotel
From$90
Average 3.0 /5 Read Reviews Call BookMore Details
Oyo Hotel Coxsackie I 87 North
+1-888-965-8297
12800 Rte 9w, Albany, NY 12192 ~20.28 miles northwest of Hillsdale
  • Affordable property
  • 28 sleeping rooms in hotel
From$90
Average 3.0 /5 Recent Reviews Call BookMore Details
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
+1-888-906-6358
1 West St., Pittsfield, MA 01201 ~20.64 miles northeast of Hillsdale
  • Three Star Downtown property
  • 170 rooms in property
From$80
Average 3.0 /5 Review Score Call BookMore Details
Hotel on North
+1-888-749-6785
297 North St., Pittsfield, MA 01201 ~20.94 miles northeast of Hillsdale
  • Expensive Downtown property
  • 6 suites in property
From$150
Excellent 5.0 /5 Read Reviews Call BookMore Details
Manor House Inn
+1-888-878-9982
69 Maple Ave., Norfolk, CT 06058 ~22.39 miles southeast of Hillsdale
  • Affordable Rural hotel
  • Hotel has 3 floors
From$240
Very Good 4.0 /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: $217.56

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 $217.56 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 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, Black Swan Inn Lee Lenox An Ascend Hotel and Econo Lodge Lee - Great Barrington 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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