Find hotels in Hillsdale, NY from $74

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Our top choices for Hillsdale hotels

The Brooks Motel

The Brooks Motel
2.0 star property
Hillsdale
7.4 out of 10, Good, (124)
"So peaceful and beautiful. Very clean ! "
United States
Asanda
$126 nightly
The price is $142
Jan 18 - Jan 19
Total with taxes and fees
The Brooks Motel

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (14)
"The room we stayed in was extremely clean and comfy. The whole hotel was very nice and had an awesome breakfast. Will be staying here again for sure. "
United States
Keith
$139 nightly
The price is $155
Jan 19 - Jan 20
Total with taxes and fees
Element Lenox Berkshires

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1002)
"Very friendly and good Breakfast."
United States
Jesse
$76 nightly
The price is $85
Jan 22 - Jan 23
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (1007)
"Room was very comfortable and it was clean. Staff were nice and helpful. Christmas decorations were lovely!"
United States
Clare
$98 nightly
The price is $109
Jan 9 - Jan 10
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1006)
"Simple and straightforward hotel experience. Just needed a clean, dry place to stay and the hotel accomplished this just fine."
United States
Nikki
$76 nightly
The price is $85
Jan 19 - Jan 20
Total with taxes and fees
Quality Inn Great Barrington

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (440)
"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"
United States
Carin
$102 nightly
The price is $112
Jan 6 - Jan 7
Total with taxes and fees
Shaker Mill Inn

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (814)
"Room was very well designed and clean. The woman who worked at the desk was wonderful!"
United States
Cynthia
$67 nightly
The price is $74
Jan 6 - Jan 7
Total with taxes and fees
Monument Mountain Motel

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.0 star property
Catskill
9.6 out of 10, Exceptional, (118)
"The hospitality and making sure our stay was enjoyable most of all our needs during the time being. "
United States
Yessica
$169 nightly
The price is $183
Jan 6 - Jan 7
Total with taxes and fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Holiday Inn Express Hotel & Suites West Coxsackie by IHG

Holiday Inn Express Hotel & Suites West Coxsackie by IHG
2.5 star property
West Coxsackie
8.4 out of 10, Very Good, (986)
"Perfect spot for an overnight stay when coming to the area"
United States
Lisa
$79 nightly
The price is $85
Jan 25 - Jan 26
Total with taxes and fees
Holiday Inn Express Hotel & Suites West Coxsackie by IHG

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (566)
"Excellent location!!"
United States
Abdul Samad
$75 nightly
The price is $84
Jan 6 - Jan 7
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (828)
"Staff was very friendly and helpful."
United States
Pamela
$79 nightly
The price is $88
Jan 6 - Jan 7
Total with taxes and fees
Howard Johnson by Wyndham Lenox

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1010)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
$101 nightly
The price is $113
Jan 19 - Jan 20
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1001)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
$52 nightly
The price is $57
Jan 10 - Jan 11
Total with taxes and fees
Pleasant Valley Motel West Stockbridge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (807)
"great stall and friendly pet friendly place"
United States
bonnie
$108 nightly
The price is $120
Feb 4 - Feb 5
Total with taxes and fees
Berkshire Mountain Lodge

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1003)
"Safe, clean rooms, decent breakfast "
United States
Neil
$82 nightly
The price is $92
Feb 1 - Feb 2
Total with taxes and fees
Quality Inn Lee - Lenox South

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (413)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
$105 nightly
The price is $121
Jan 6 - Jan 7
Total with taxes and fees
Locust Tree Bed and Breakfast LLC

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (18)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
$251 nightly
The price is $280
Jan 6 - Jan 7
Total with taxes and fees
Prospect Berkshires

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1004)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
$104 nightly
The price is $116
Jan 15 - Jan 16
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (716)
"Nice warm pool and hot tub. Good little fitness center. "
United States
Fawn
$98 nightly
The price is $109
Jan 25 - Jan 26
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (816)
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
United States
Stephanie
$130 nightly
The price is $145
Jan 15 - Jan 16
Total with taxes and fees
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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Stay near popular Hillsdale attractions

Learn more about Hillsdale

Tucked in the Hudson Valley, this rural hamlet offers scenic hikes through Taconic State Park and charming farm-to-table dining. Explore nearby art galleries in Copake or visit Catamount Mountain Resort for outdoor adventures in all seasons.

Red and Green Norway Maple Trees and Wood Fence

Top Hillsdale Hotel Reviews

More cheap stays in Hillsdale

Hotels in Hillsdale with star-rating

Find out more about Hillsdale

Top reasons to visit Hillsdale

  • Outdoor Adventure: Hillsdale is a haven for ski enthusiasts and outdoor sports lovers, boasting excellent ski fields and access to national parks and beautiful lakes.
  • Live Music Events: Experience vibrant local music events that enhance the community's lively atmosphere.
  • Scenic Beauty: Enjoy breathtaking landscapes that provide the perfect backdrop for a romantic getaway or family vacation.
  • Diverse Accommodations: Choose from cozy bed and breakfasts to unique agritourism properties, catering to various preferences.
  • Friendly Atmosphere: Hillsdale's welcoming vibe makes it an ideal base for exploring the surrounding regions.

Find great hotels near Hillsdale

Discover the charm of Hillsdale, New York, where a variety of accommodations await to enhance your stay. From cozy bed and breakfasts to unique agritourism properties, there’s something for everyone. Enjoy family-friendly amenities, pet-friendly options, and adventure-filled experiences. Whether you’re looking for the best hotels or detailed reviews, Hillsdale offers a welcoming atmosphere perfect for your next getaway.

  • Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: Nestled in the picturesque Berkshires, this 3.5-star resort is ideal for families and adventure seekers alike. Located 14 miles from Hillsdale, it offers a business-friendly atmosphere with amenities such as a Business Center that includes resort fee inclusivity. Guests can indulge in a variety of outdoor activities, including nearby snowboarding, skiing lessons, and hiking. Families will appreciate the onsite Mini Golf, Arcade Game Room, and shared playground, making it a well-rounded destination for both leisure and work.
  • Quality Inn: Located just 8 miles from Hillsdale, Quality Inn is a great choice for travelers seeking adventure and business facilities. With a focus on providing a comfortable stay, this hotel offers easy access to nearby outdoor activities, including snow tubing, downhill skiing, and hiking. Business travelers will find it convenient with essential amenities for their needs. Quality Inn combines relaxation and functionality, making it an excellent choice for those on the go.
  • Holiday Inn Express Hotel & Suites Great Barrington by IHG: Situated 9 miles from Hillsdale, this hotel welcomes all travelers, including the LGBTQIA community, with open arms. The property features a 24-hour Business Center and meeting rooms, catering to business needs while ensuring a comfortable stay. Guests can enjoy modern amenities and a warm atmosphere, making it a perfect base for exploring the Great Barrington area. This hotel is perfect for those who seek a blend of business convenience and welcoming hospitality.

Where to stay near Hillsdale

Hillsdale, New York, offers an ideal getaway for adventure seekers and relaxation enthusiasts alike. Nestled in a picturesque setting, visitors can enjoy skiing and outdoor sports while soaking in the scenic beauty. The city boasts a friendly atmosphere, perfect for romantic getaways or family vacations. With essential amenities within walking distance and a central location, Hillsdale serves as an awesome base for exploring the surrounding regions and enjoying memorable experiences.

  • Great Barrington: Located 8 miles from Hillsdale, Great Barrington is a vibrant city known for its outdoor adventures and sports experiences. With a year-round influx of travelers, the peak season runs from June to August, making it an ideal time for skiing and other outdoor fun. Visitors can enjoy thrilling activities at local ski resorts and explore the stunning natural landscapes, including nearby lakes and mountains within national state parks. Great Barrington is perfect for adventure enthusiasts looking to immerse themselves in nature.
  • Stockbridge: Just 13 miles away from Hillsdale, Stockbridge is a charming city steeped in culture and romance. Visitors flock here primarily between July and September to enjoy its rich arts scene, including music concerts and theatrical performances. The city's picturesque surroundings feature beautiful lakes, historical monuments, and serene shrines, making it a delightful destination for those seeking entertainment and cultural enrichment. Stockbridge offers a unique blend of relaxation and excitement, perfect for a romantic getaway.
  • Copake: Located 5 miles from Hillsdale, Copake is a small city that promises adventure and outdoor experiences, particularly during its peak seasons in March to April and July. Known for its ski fields and resorts, visitors come here to engage in thrilling activities against a backdrop of breathtaking lakes and mountains. Nature lovers and outdoor enthusiasts will find plenty of opportunities to explore the nearby national state park, making Copake a fantastic base for those looking to enjoy the great outdoors.

Things to do in and around Hillsdale

Hillsdale, New York, is an ideal destination for ski enthusiasts and adventure seekers, featuring excellent ski fields and resorts. In addition to winter sports, visitors can enjoy vibrant live music events that enhance the local atmosphere. Whether you're hitting the slopes or soaking up the local entertainment, Hillsdale offers a fulfilling vacation experience for those looking to combine adventure with relaxation.

Shopping

In Hillsdale, enjoy local shopping at unique spots like Ebenezer II Gifts and Antiques for quaint finds. If you're up for a drive, visit Charles H. Baldwin & Sons and Hoffman's Pottery, both located 13 miles away, for a charming selection of pottery and gifts.

Recreation

Experience the vibrant atmosphere at Tanglewood Music Center, where you can enjoy captivating concerts. For relaxation, visit Lake Mansfield Park, perfect for unwinding in nature. If you prefer outdoor activities, the Greenock Country Club offers an excellent golfing experience amidst scenic landscapes.

Adventure

Experience thrilling adventures at Catamount Ski Area, a ski field located 2 miles from Hillsdale, perfect for winter sports enthusiasts. For an adrenaline rush, visit Catamount Aerial Adventure Park, offering ziplining and ropes courses. Enjoy scenic hikes along the Housatonic River Walk, located 9 miles away, surrounded by nature.

Nightlife

In Hillsdale, you can enjoy the Mahaiwe Performing Arts Center's diverse shows just 8 miles away, or catch a captivating performance at the Mac-Haydn Theatre, located 13 miles away. The Ancram Opera House, 11 miles from Hillsdale, also offers a delightful blend of culture and entertainment.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Hillsdale

To save money on your trip to Hillsdale, consider visiting during the off-peak months of January and March to April, when prices are lower. The best day to book is Tuesday, while Saturday tends to be the most expensive. Use Expedia to compare hotel rates and take advantage of package deals by bundling your hotel, flights, and activities for additional savings. Joining Expedia's One Key membership can unlock exclusive discounts and allow you to earn cash for future stays. Exploring the area on foot can also help you save on transportation costs.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Hillsdale are January and March to April, where the prices are slightly lower. This is in comparison to July to August and October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Hillsdale is Tuesday. The most expensive day to stay in Hillsdale is Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia’s search tool to refine your options based on your budget, desired location, and preferred type of accommodation. To find the best prices and offers, simply arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your Hillsdale hotel reservation with your flights and activities through an Expedia package deal.
  • Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions near Hillsdale

Hillsdale, New York, is perfect for ski and adventure enthusiasts, offering a variety of outdoor activities. Visitors can explore national parks, nature reserves, and beautiful lakes that cater to those seeking adventure and cultural experiences. Whether you're looking for sports or simply enjoying nature, Hillsdale has a range of attractions to make your vacation memorable.

  • Taconic State Park: Located 4 miles from Hillsdale, Taconic State Park offers a stunning blend of adventure and natural beauty. Explore scenic trails, enjoy picnicking by Lake Taghkanic, and immerse yourself in the great outdoors, perfect for hiking, fishing, and wildlife watching.
  • National Shrine of the Divine Mercy: Situated 13 miles away, this serene shrine provides a peaceful atmosphere steeped in spirituality. Visitors can enjoy beautiful gardens, reflection areas, and the opportunity to participate in daily Mass, making it a unique cultural experience.
  • Norman Rockwell Museum: Just 12 miles from Hillsdale, this renowned museum showcases the iconic works of Norman Rockwell. Explore his illustrations that capture American culture and storytelling in a charming setting, perfect for art lovers.

Best time to go to Hillsdale

The best time to visit Hillsdale is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly high and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.0°F (-3.9°C)Light RainMostly CloudySlightly HighSlightly Low
February26.6°F (-3.0°C)Light RainMostly CloudySlightly HighAverage
March34.5°F (1.4°C)Light RainMostly CloudySlightly LowSlightly Low
April46.2°F (7.9°C)Light RainMostly CloudyAverageSlightly Low
May57.9°F (14.4°C)Light RainMostly SunnyAverageAverage
June65.7°F (18.7°C)Light RainMostly SunnyAverageAverage
July72.0°F (22.2°C)Light RainMostly SunnySlightly HighSlightly High
August70.0°F (21.1°C)Light RainMostly SunnyAverageSlightly High
September62.8°F (17.1°C)Light RainMostly SunnyAverageAverage
October51.6°F (10.9°C)Light RainMostly SunnySlightly LowSlightly High
November39.4°F (4.1°C)Light RainMostly SunnyAverageAverage
December31.3°F (-0.4°C)Light RainMostly CloudySlightly LowAverage

The nearest major airports for your trip to Hillsdale

If you're planning to visit Hillsdale, New York, there are several major airports you can fly into. Hartford, CT (BDL-Bradley Intl.) is 46 miles away, with nearby hotels like the 4-star DoubleTree by Hilton Hartford - Bradley Airport, located only 1 mile from the airport. Albany, NY (ALB-Albany Intl.) is 42 miles distant, offering options such as the Park Manor Hotel, which is 8 miles away. Lastly, Newburgh, NY (SWF-Stewart Intl.) is 55 miles from Hillsdale, featuring hotels like The Dutchess Inn and Spa at Beacon, just 6 miles from the airport. Each hotel provides convenient access to its respective airport for travelers.

Frequently asked questions

What are the best budget hotels in Hillsdale?
The Brooks Motel in Hillsdale, NY, is a charming option for travelers seeking budget-friendly accommodations without sacrificing comfort. With a cozy atmosphere and convenient amenities, this motel boasts free Wi-Fi and self-parking, making it a straightforward choice for families or couples on the go. View all budget hotels in Hillsdale.
When is the best time to go to Hillsdale?
The most popular time to visit Hillsdale is during the summer months, particularly July. This time of year is characterized by warm weather, with average temperatures reaching around 75°F, great for enjoying outdoor activities and local events. The town comes alive with festivals, farmers' markets, and vibrant community gatherings that invite visitors to experience the local culture in a relaxed and friendly atmosphere.

During the peak season from June to August, Hillsdale offers a range of outdoor adventures, from hiking in the nearby Berkshire mountains to exploring the charming downtown area filled with boutique shops and artisanal cafés. The long daylight hours allow for ample exploration, whether you're strolling through the scenic parks or enjoying a picnic by the water.

For travelers seeking a peaceful yet engaging experience, September can be an excellent alternative. As the summer crowds begin to thin, you'll find that local attractions are more accessible, and the beautiful fall foliage creates a picturesque backdrop for your adventures. Additionally, prices for accommodations and activities may be slightly lower compared to the peak summer months, allowing you to enjoy the same quality experiences at a better value.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Hillsdale.
How can I save on a Hillsdale hotel booking with Expedia?
One Key™ - Expedia's free travel rewards program - gives you instant access to perks and Member Prices on Hillsdale hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings.

*OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
How much is the nightly rate at a Hillsdale hotel?
Prices for hotels in Hillsdale often vary, but you can find a great deal from $74 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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