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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, (131 reviews)
"The room is clean, exactly how you see it in the picture. Staff is very responsive, we enjoyed our stay and will definitely consider staying there again. "
United States
Michael
The Brooks Motel

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (19 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is CA $190
CA $213 total
includes taxes & fees
Mar 16 - Mar 17
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, (1,005 reviews)
"Very friendly and good Breakfast."
United States
Jesse
The price is CA $131
CA $147 total
includes taxes & fees
Mar 16 - Mar 17
Best Western Plus Berkshire Hills Inn & Suites

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (824 reviews)
"The room was clean, and the staff was friendly and helpful. "
United States
Damien
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, (159 reviews)
"The cabin was very clean and cozy"
United States
Azma
The price is CA $149
CA $220 total
includes taxes & fees
Feb 26 - Feb 27
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (415 reviews)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is CA $144
CA $165 total
includes taxes & fees
Feb 26 - Feb 27
Locust Tree Bed and Breakfast LLC

Spark by Hilton West Coxsackie

Spark by Hilton West Coxsackie
2.5 star property
West Coxsackie
7.8 out of 10, Good, (96 reviews)
"Thanksgiving stay, we’ll accommodating for the family. "
United States
Richard
The price is CA $101
CA $109 total
includes taxes & fees
Mar 20 - Mar 21
Spark by Hilton West Coxsackie

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very good, (1,001 reviews)
"Clean room, great location"
United States
Andrea
The price is CA $91
CA $101 total
includes taxes & fees
Mar 23 - Mar 24
Quality Inn Great Barrington

Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (113 reviews)
"Great experience, looking forward to staying again."
United States
Greg
The price is CA $205
CA $230 total
includes taxes & fees
Feb 26 - Feb 27
Changing Times Boutique Country Lodging

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (864 reviews)
"This place was lovely. I travel a lot for my 2 college athletes and I wish I could have spent more time here. Great place! "
United States
Melissa
Berkshires Untold

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (572 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is CA $103
CA $115 total
includes taxes & fees
Mar 12 - Mar 13
Travelodge by Wyndham Great Barrington Berkshires

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.2 out of 10, Very good, (16 reviews)
"Antonia was wonderful and made our stay special. She was kind and warm and when we were initially unhappy with our room immediately rectified the situation and in the end our stay was perfect! It’s a charming hotel, clean and centrally located, walking distance to all the local shops in town."
United States
Jamie
The price is CA $210
CA $238 total
includes taxes & fees
Mar 21 - Mar 22
The Millerton Inn

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is CA $80
CA $88 total
includes taxes & fees
Mar 12 - Mar 13
Pleasant Valley Motel West Stockbridge

Howard Hotel

Howard Hotel
2.0 star property
Hudson
10.0 out of 10, Exceptional, (118 reviews)
"Awesome hotel!"
United States
michael
Howard Hotel

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (202 reviews)
"Nice room and reasonable prices! Will recommend."
United States
Jianyang
The price is CA $164
CA $184 total
includes taxes & fees
Feb 26 - Feb 27
the Alander

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (446 reviews)
"Had everything we needed. Very thoughtful touches. "
United States
Mark
The price is CA $130
CA $143 total
includes taxes & fees
Mar 3 - Mar 4
Shaker Mill Inn

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (834 reviews)
"Clean room and the bed was very comfortable "
United States
Arlan
The price is CA $95
CA $106 total
includes taxes & fees
Feb 26 - Feb 27
Howard Johnson by Wyndham Lenox

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,005 reviews)
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is CA $119
CA $133 total
includes taxes & fees
Mar 22 - Mar 23
Quality Inn Lee - Lenox South

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (863 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is CA $152
CA $201 total
includes taxes & fees
Mar 10 - Mar 11
Berkshire Mountain Lodge

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,017 reviews)
"Very friendly staff comfy beds!"
United States
Giselle
The price is CA $127
CA $142 total
includes taxes & fees
Mar 4 - Mar 5
The Yankee, Trademark Collection by Wyndham
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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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

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Find out more about Hillsdale

Top reasons to visit Hillsdale

  • Thrilling Ski Adventures: Hillsdale offers excellent skiing options with local resorts and ski lifts, perfect for winter sports enthusiasts.
  • Breathtaking Landscapes: Nestled in the scenic Harlem Valley, visitors can enjoy stunning natural beauty and outdoor activities.
  • Family-Friendly Atmosphere: Hillsdale provides a welcoming environment, ideal for both romantic getaways and family vacations.
  • Diverse Accommodation Options: With a range of hotels from cozy motels to luxurious stays, there's something for every budget.
  • Proximity to Nature Reserves: Explore nearby national and state parks, offering serene spots for relaxation and adventure.

Find great hotels in Hillsdale

Discover the charm of Hillsdale, New York, with a variety of hotel accommodations tailored to suit every budget and preference. From cozy motels to luxurious stays, this picturesque town offers options ranging from 2 to 4.5 stars. Whether you're seeking pet-friendly services or planning a business trip, Hillsdale has the ideal lodging for your adventure. Explore the best hotels in the area and enjoy a memorable vacation experience.

  • Quality Inn: Perfectly tailored for the adventurous and business-minded traveller, Quality Inn is located a mere 12.9km from Hillsdale. This hotel offers a unique blend of comfort and excitement, with amenities that cater to those seeking adventure sports and business facilities. Guests can enjoy thrilling activities such as hiking, skiing, and snow tubing nearby, making it an ideal base for outdoor enthusiasts. The property also provides essential services for business travellers, ensuring a productive stay with convenient access to essential amenities.
  • Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: Nestled 22.5km from Hillsdale, this 3.5-star resort is a family-friendly haven that embraces both adventure and leisure. With easy access to ski shuttles and lifts, guests can indulge in a variety of winter sports, including snowboarding and skiing lessons. The resort is designed with families in mind, featuring amenities such as an arcade game room, mini-golf, and a playground for children. This makes it a perfect spot for families looking to create lasting memories while enjoying the great outdoors.
  • Holiday Inn Express Hotel & Suites Great Barrington by IHG: Located 16.1km from Hillsdale, this hotel is tailored for the business traveller seeking comfort and convenience. With a range of business amenities including meeting rooms, a 24-hour business centre, and conference space, it's designed to facilitate productivity during your stay. Guests can expect modern accommodations and a complimentary breakfast, ensuring a great start to their busy days. This hotel is an excellent choice for those who need to blend work with leisure in the beautiful surroundings of Great Barrington.

Where to stay in Hillsdale

For a delightful getaway, Hillsdale, New York offers a perfect blend of relaxation and adventure. Nestled in the scenic Harlem Valley, this charming area invites you to explore its breathtaking landscapes and friendly atmosphere. Whether you’re skiing on nearby slopes or enjoying quality time with family, Hillsdale’s immediate vicinity provides a romantic and family-friendly vibe, making it an ideal destination for your next vacation.

  • Great Barrington: Located 12.9km from Hillsdale, Great Barrington is a vibrant city known for its outdoor adventures and cultural charm. It offers a year-round experience for travelers, with peak visits during the summer months. Enjoy skiing at local resorts or partake in various adventure sports. Nature enthusiasts will appreciate the nearby lakes and mountains, while the Great Barrington National State Park offers stunning landscapes for hiking and exploration. The city's lively arts scene and boutique shopping make it a delightful stop on your journey.
  • Stockbridge: Situated 20.9km from Hillsdale, Stockbridge is a picturesque town that captures the essence of New England charm. Renowned for its cultural offerings, visitors flock here from July to September. The town is home to various music concerts, theatres, and art galleries, providing a rich entertainment experience. Don't miss the beautiful lakes and historical monuments, including iconic shrines that add to the town's allure. Whether you’re seeking romance or a cultural getaway, Stockbridge is an enchanting destination.
  • Copake: Just 8.0km from Hillsdale, Copake is perfect for those seeking outdoor adventures and winter sports. The town sees its highest visitor numbers in the spring and summer, making it an ideal time for hiking, skiing, and exploring the surrounding natural wonders. With ski fields and resorts nearby, outdoor enthusiasts will find plenty to keep them engaged. Copake is also near beautiful lakes and mountains, ensuring a backdrop of stunning scenery for your adventures.

Things to do in Hillsdale

Hillsdale, New York, is an ideal destination for those seeking a thrilling ski and adventure vacation. Visitors can enjoy skiing at local resorts and stations, complete with ski lifts and a minor ski area. The region also offers picnic spots for relaxation after an exhilarating day on the slopes. With its beautiful landscapes, Hillsdale promises an unforgettable outdoor experience for sports enthusiasts and nature lovers alike.

Shopping

In Hillsdale, you can shop at local gems like Charles H. Baldwin & Sons, Hoffman's Pottery, and Ebenezer II Gifts and Antiques, each about 20.9km away. If you're up for a drive, these stores offer unique gifts and souvenirs for your vacation.

Recreation

Tanglewood Music Center offers a vibrant atmosphere with enriching concerts, located 25.7km from Hillsdale. For relaxation, Lake Mansfield Park, just 12.9km away, provides serene walking trails and peaceful lakeside spots. If you're into sports, Greenock Country Club, also 25.7km away, boasts beautiful golf courses amidst nature.

Adventure

At Catamount Ski Area, located 3.2km from Hillsdale, experience thrilling skiing on varied terrain amidst stunning winter landscapes. For a unique adventure, visit Catamount Aerial Adventure Park in Hillsdale for an exciting zipline and ropes course. Alternatively, hike the scenic Housatonic River Walk, situated 14.5km from town.

Nightlife

For a lively evening in Hillsdale, catch a show at the Mahaiwe Performing Arts Center, just 12.9km away, or enjoy the vibrant atmosphere at the Mac-Haydn Theatre, 20.9km away. If you're feeling lucky, visit Magnolia Bluffs Casino, located 13.2km from Hillsdale.

Booking tips and Expedia advantages for Hillsdale

Traveling to Hillsdale on a budget is quite feasible with several cost-saving options. Enjoy free activities such as Bash Bish Falls State Park and the Housatonic River Walk. To save on accommodation, consider visiting in January or March to April, and aim for stays on Tuesdays for the lowest rates. Utilize Expedia to find eco-friendly hotels and package deals that combine flights and activities for additional savings. Sorting by price can help you uncover the best deals, ensuring you get the most value for your trip.

  • 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 choices based on your budget, desired location, and preferred hotel type. For instance, selecting the "Eco-certified" filter will showcase sustainable and environmentally friendly accommodations available at the moment. To uncover the best prices and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save some money by combining your Hillsdale hotel reservation with your flights and activities through an Expedia package.

Find the best attractions in Hillsdale

Hillsdale, New York, is perfect for a ski or adventure getaway, offering a blend of outdoor and cultural experiences. Visitors can explore nearby attractions such as national and state parks, picturesque lakes, and serene nature reserves. Whether you're seeking an adrenaline rush or a peaceful retreat, Hillsdale caters to all types of adventurers, making it an ideal destination for those looking to connect with nature while enjoying local culture.

  • Taconic State Park: Located 6.4km from Hillsdale, Taconic State Park offers breathtaking scenery and a variety of outdoor adventures. Whether you're hiking, biking, or picnicking, the park's natural beauty provides a perfect escape into nature.
  • National Shrine of the Divine Mercy: About 20.9km away, this serene shrine invites visitors to explore its spiritual atmosphere and cultural significance. It’s a peaceful retreat that encourages reflection and appreciation of its divine artistry.
  • Norman Rockwell Museum: Situated 19.3km from Hillsdale, this art museum showcases the iconic works of American illustrator Norman Rockwell. Experience the rich cultural heritage through his storytelling art that captures the essence of everyday life.

Best time to go to Hillsdale

Visitor numbers in Hillsdale is generally unchanged in popularity throughout the year. The best time to visit Hillsdale can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Hillsdale falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Hillsdale falls in January, visitor numbers are slightly high and weather is mostly cloudy with light rain.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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

For your visit to Hillsdale, New York, you have several airport options. Bradley International Airport (BDL) in Hartford, CT, is situated 74.0km away, with nearby hotels such as the DoubleTree by Hilton Hartford - Bradley Airport, 1.6km from the airport, and the Marriott Hartford Downtown, 19.3km away. Albany International Airport (ALB) is 67.6km from Hillsdale, offering accommodations like The Landing Hotel at Rivers Casino & Resort, 12.9km away. Stewart International Airport (SWF) in Newburgh, NY, is 88.5km from Hillsdale, with options like The Dutchess Inn and Spa at Beacon, 9.7km away. All these airports provide convenient access to Hillsdale.

Frequently asked questions

What is the best area to stay in Hillsdale?
The best area to stay in Hillsdale is in and around the town centre, particularly near the intersection of Routes 23 and 22.

This area is the heart of Hillsdale, where you'll find the majority of the town's shops, eateries, and local services. It's quite walkable, making it easy to pop into a cafe, browse a boutique, or pick up essentials. The general layout is a classic small-town main street, with buildings lining the roads and a few side streets branching off.

Couples looking for a relaxing getaway often find this area ideal. It offers easy access to local establishments for dining and drinks, and many accommodations in this central zone provide a comfortable base for exploring the surrounding countryside or simply enjoying a quiet weekend.

For those seeking a more secluded experience but still wanting to be close to amenities, staying slightly outside the immediate town centre, perhaps a short drive along Route 23 towards Catamount Mountain, can be a good option.
What are the best hotels in Hillsdale that travellers recommend?
For a highly recommended hotel in Hillsdale, consider The Brooks Motel.

The Brooks Motel has a review rating of 7.4. Guests frequently mention the super comfy and clean beds, along with the modern and clean rooms. The customer service also receives excellent remarks. For those interested in outdoor activities, the motel is conveniently located near a ski area and Catamount Aerial Adventure Park, which is just 2.0 km away. The rooms feature premium bedding, Egyptian cotton sheets, and air conditioning, with some even offering a fireplace.
What are the best budget hotels in Hillsdale?
For a highly-rated budget hotel in Hillsdale, consider The Brooks Motel.

The Brooks Motel has a review rating of 7.4. Guests frequently mention the super comfy and clean beds, along with modern and clean rooms. The customer service also receives excellent feedback. This motel offers useful amenities such as free WiFi and complimentary toiletries. For those interested in winter sports, there are ski areas, ski lifts, ski runs, and cross-country skiing all conveniently located nearby. Pets are also welcome to stay free of charge, and free self-parking is available. View all budget hotels in Hillsdale
What are the best hotels in Hillsdale near Catamount Aerial Adventure Park?
For a well-located hotel near Catamount Aerial Adventure Park in Hillsdale, The Brooks Motel is a highly-rated option.

The Brooks Motel, with a 7.4 rating, is conveniently situated just 2.0 km from Catamount Aerial Adventure Park. This motel is particularly suitable for families and offers a range of amenities including free WiFi, free self-parking, and complimentary toiletries. Guests frequently praise the super comfy and clean beds, the modern and clean rooms, and the excellent customer service. For those interested in winter sports, the motel is also very close to various ski facilities, including ski areas, lifts, runs, downhill, and cross-country options. Additionally, it features kitchens in its rooms and welcomes pets at no extra charge.
When is the best time to go to Hillsdale?
The best time to visit Hillsdale is during the summer (June to August) for outdoor activities and autumn (September to October) for the stunning fall foliage.

Summer in Hillsdale offers warm, sunny days superb for enjoying the natural beauty of the region. This is an ideal time for couples and families who want to explore hiking trails, visit local farms, or enjoy swimming in nearby lakes. The weather is generally pleasant for outdoor dining and wandering through the small town centre.

Autumn transforms Hillsdale into a picturesque landscape, with the surrounding hills ablaze with red, orange, and gold leaves. This season is particularly popular with couples seeking a romantic getaway and anyone who appreciates scenic drives and photography.
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?
Members always get our best prices. Find our best Hillsdale hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
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 CA $97 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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