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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, (133 reviews)
"Room was clean"
United States
Patrick
The price is CA $156
CA $175 total
includes taxes & fees
Apr 13 - Apr 14
The Brooks Motel

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, (1,003 reviews)
"It was a solid experience at the Best western, staff was super nice, the room was spacious and clean, the breakfast was delicious and the location is superb. Overall it was a great experience and will definitely stay there again "
United States
Kristina
The price is CA $153
CA $171 total
includes taxes & fees
Apr 15 - Apr 16
Best Western Plus Berkshire Hills Inn & Suites

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (895 reviews)
"This was a great stay! The room and hotel itself were up to date and was overall a great location to check out the Berkshires. We ate one night at the hotel too and the dinner was really good! I recommend the mushroom ravioli, would stay again."
United States
Payton
The price is CA $109
CA $121 total
includes taxes & fees
Apr 14 - Apr 15
Berkshires Untold

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (447 reviews)
"Had everything we needed. Very thoughtful touches. "
United States
Mark
The price is CA $151
CA $166 total
includes taxes & fees
Apr 13 - Apr 14
Shaker Mill Inn

Four Seasons Motel

Four Seasons Motel
2.0 star property
Catskill
8.2 out of 10, Very good, (208 reviews)
"It was a joy to be there for it had everything including real cups and saucers with spoons! No paper cups, which I appreciated. Plus live bamboo in the room and more than adequate bathroom products including new tooth brushes. Real art and prints on the wall that gave it a very Asian- European flair. Lovely"
United States
Lynn
The price is CA $138
CA $149 total
includes taxes & fees
Apr 13 - Apr 14
Four Seasons Motel

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,000 reviews)
"Great visit all around. Centrally located to the skiing resorts, lots to do in town, decent breakfast spread, clean room, and for a short stay, housekeeping came when unexpected! "
United States
Amy
The price is CA $128
CA $143 total
includes taxes & fees
Apr 26 - Apr 27
Quality Inn Lee - Lenox South

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, (198 reviews)
"We had the best time! "
United States
Eric
The price is CA $199
CA $275 total
includes taxes & fees
Apr 26 - Apr 27
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is CA $203
CA $227 total
includes taxes & fees
Apr 19 - Apr 20
Element Lenox Berkshires

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (839 reviews)
"Nice place and very reasonable for great location "
United States
Raymond
The price is CA $83
CA $93 total
includes taxes & fees
Apr 19 - Apr 20
Monument Mountain Motel

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (44 reviews)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is CA $223
CA $249 total
includes taxes & fees
Apr 14 - Apr 15
Wilder House Berkshires

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (88 reviews)
"New hotel clean and nice. Heated pool and hot tub a bonus. Timely breakfast for early departures- great on demand coffee. Added bonus they have a car charger."
United States
Charline
The price is CA $163
CA $182 total
includes taxes & fees
Apr 16 - Apr 17
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (846 reviews)
"Staff was super nice! Everything was clean and neat. "
United States
Elizabeth
The price is CA $109
CA $122 total
includes taxes & fees
Apr 13 - Apr 14
Howard Johnson by Wyndham Lenox

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (555 reviews)
"Clean … check in , good location for us .. we’ll be back in Maynn"
United States
Kathleen
The price is CA $152
CA $170 total
includes taxes & fees
Apr 14 - Apr 15
The Little Lion

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (416 reviews)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is CA $145
CA $167 total
includes taxes & fees
Apr 14 - Apr 15
Locust Tree Bed and Breakfast LLC

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
9.6 out of 10, Exceptional, (5 reviews)
"The new owners have done a great job. The place is immaculate, the room was very comfortable and well appointed, the common areas charming. Highly recommended."
United States
Robert
The price is CA $277
CA $309 total
includes taxes & fees
Apr 15 - Apr 16
The Berkshire Mountain Inn

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very good, (1,003 reviews)
"Great location, friendly staff"
United States
James
The price is CA $93
CA $104 total
includes taxes & fees
Apr 26 - Apr 27
Quality Inn Great Barrington

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (576 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is CA $104
CA $116 total
includes taxes & fees
Apr 13 - Apr 14
Travelodge by Wyndham Great Barrington Berkshires

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,000 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is CA $96
CA $106 total
includes taxes & fees
Apr 26 - Apr 27
Pleasant Valley Motel West Stockbridge

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (173 reviews)
"Best host (Lucas) makes all the difference! Great views and delicious breakfasts. "
United States
diane
The price is CA $198
CA $228 total
includes taxes & fees
Apr 13 - Apr 14
Blackberry River Inn

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"Very clean, modern hotel. Would definitely stay here again. "
United States
Debra
The price is CA $154
CA $172 total
includes taxes & fees
Apr 26 - Apr 27
Hampton Inn & Suites Berkshires-Lenox
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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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Hotels in Hillsdale with star rating

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 $104 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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