Search Hillsdale hotels

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Filter by

Guest rating
Guest rating
Star rating

Top hotels and accommodation in Hillsdale

The Brooks Motel

2.0 star property
7.8 out of 10, Good, (103)
"The room was very comfortable & clean. It had a really nice shower, which is very important for us when travelling. Thank you! See you again some time."
The Brooks Motel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
9.0 out of 10, Wonderful, (1003)
"Great Indian restaurant in the hotel!"
The price is AU$180
includes taxes & fees
2 Nov - 3 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (743)
"Great location and very clean. Beautifully decorated and the restaurant is amazing. Just wish it offered a free breakfast with the room. "
The price is AU$148
includes taxes & fees
2 Nov - 3 Nov
Berkshires Untold

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1001)
"Nice area to visit "
The price is AU$227
includes taxes & fees
2 Nov - 3 Nov
The Yankee, Trademark Collection by Wyndham

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1003)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
The price is AU$275
includes taxes & fees
28 Oct - 29 Oct
The Cornell Inn, Lenox & The Berkshires

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1004)
"great place have stayed several times, and hope to return."
The price is AU$339
includes taxes & fees
4 Nov - 5 Nov
The Red Lion Inn

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

3.5 star property
9.0 out of 10, Wonderful, (747)
"The lodging was convenient to all the area attractions."
The price is AU$218
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (889)
"Excellent customer service and great rooms"
The price is AU$174
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (671)
"Very convenient set up of both room and kitchen, resort very easy to navigate. "
The price is AU$191
includes taxes & fees
2 Nov - 3 Nov
Berkshire Mountain Lodge

Catskill Motor Court Motel

2.5 star property
5.8 out of 10, (120)
"We like the playground just in front of the room. The pool is closes. The motel is degraded and used. The owner is kind. We like our stay for the activities nearby in the Catskill region."
The price is AU$167
includes taxes & fees
6 Oct - 7 Oct
Catskill Motor Court Motel

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (777)
"Great property! Very large clean room in a unique hotel! "
The price is AU$211
includes taxes & fees
3 Nov - 4 Nov
Hotel On North

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.4 out of 10, Exceptional, (50)
"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"
The price is AU$243
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

The Constance by the Lenox Collection

3.5 star property
8.4 out of 10, Very good, (548)
"Staff was so friendly and helpful. The room was small and comfortable and the grounds were well kept. "
The price is AU$173
includes taxes & fees
3 Nov - 4 Nov
The Constance by the Lenox Collection

Chatham Travel Lodge

2.5 star property
7.8 out of 10, Good, (202)
"Clean, comfortable room. Check in was easy."
The price is AU$197
includes taxes & fees
6 Oct - 7 Oct
Chatham Travel Lodge

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
7.4 out of 10, Good, (550)
"Excellent location, friendly service, clean, comfortable room."
The price is AU$127
includes taxes & fees
7 Oct - 8 Oct
Travelodge by Wyndham Great Barrington Berkshires

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (635)
"Easy check in"
The price is AU$106
includes taxes & fees
2 Nov - 3 Nov
Econo Lodge Lee - Great Barrington

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (740)
"Thank you for nice hospity. Staff was very friendly and professional."
The price is AU$242
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

St. Charles Hotel

2.0 star property
6.8 out of 10, (811)
"Great location. Staff was super friendly. Rooms were very clean. The hotel is getting a renovation and I can’t wait to see it when it’s done."
The price is AU$275
includes taxes & fees
14 Oct - 15 Oct
St. Charles Hotel

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
8.8 out of 10, Excellent, (667)
"Very Good; Clean, Quiet Motel, Area has many dining options."
The price is AU$188
includes taxes & fees
3 Nov - 4 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG

voco James Newbury Hudson Valley by IHG

3.5 star property
9.2 out of 10, Wonderful, (311)
"Needs better signage on the street side to locate entrance. "
The price is AU$309
includes taxes & fees
9 Oct - 10 Oct
voco James Newbury Hudson Valley by IHG
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.
Save an average of 15% on thousands of hotels when you're signed in

Stay near top Hillsdale attractions

Catamount Aerial Adventure Park

Catamount Aerial Adventure Park

You can take time to visit Catamount Aerial Adventure Park during your travels to Hillsdale. Discover the area's mountain views and seek out the hiking trails.

Top Hillsdale Hotel Reviews

More cheap accommodation in Hillsdale

More cheap accommodation in Hillsdale

Find out more about Hillsdale

Find out more about Hillsdale

Top reasons to visit Hillsdale

  • Thrilling Ski Resorts: Hillsdale is a haven for ski enthusiasts, featuring excellent slopes and resorts for an adrenaline-packed adventure.
  • Picturesque Nature: Explore stunning national parks, serene lakes, and nature reserves, perfect for outdoor adventures and relaxation.
  • Cultural Entertainment: Enjoy a vibrant atmosphere filled with arcade games, live performances, and weekly cultural events.
  • Charming Towns: Wander through friendly local towns that boast beautiful scenery and inviting vibes.
  • Varied Accommodation: Choose from delightful bed and breakfasts or unique agritourism properties tailored for every traveller.

Find great hotels near Hillsdale

Discover the charm of Hillsdale, New York, with a range of delightful accommodation options tailored for every traveller. From inviting bed and breakfasts to unique agritourism properties, Hillsdale's hotels cater to families, pet owners, and adventure seekers alike. Whether you're searching for the best Hillsdale hotels or the cosy ambiance of a hillside retreat, you're sure to find the perfect spot to relax and enjoy your getaway.

  • Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: Nestled 22.5km from Hillsdale, this 3.5-star resort is ideal for families and adventure seekers alike. With a vibrant atmosphere that welcomes LGBTQIA travellers, the property offers a plethora of onsite activities, including mini-golf and an arcade game room for kids. Adventure enthusiasts can explore nearby hiking trails, ski resorts, and snowboarding opportunities, ensuring an action-packed getaway. The resort’s child-friendly amenities, such as free cribs and shared playgrounds, make it a perfect choice for families wishing to create lasting memories.
  • Quality Inn: Located 12.9km from Hillsdale, Quality Inn is a practical choice for business travellers and adventure lovers. The hotel provides essential business amenities, catering to those on a work trip while still wanting to enjoy the great outdoors. Guests can take advantage of nearby skiing, snowboarding, and hiking opportunities, ensuring that there's never a dull moment. The Quality Inn strikes a balance between professional convenience and recreational pursuits, making it an excellent choice for those who want to blend work and play.
  • Holiday Inn Express Hotel & Suites Great Barrington by IHG: Situated 14.5km from Hillsdale, this hotel combines business efficiency with a welcoming vibe for LGBTQIA guests. It features comprehensive business facilities, including a 24-hour business centre, meeting rooms, and conference spaces, making it suitable for corporate travellers. The modern accommodations and convenient amenities ensure a comfortable stay while allowing guests to unwind after a day of meetings. With its strategic location, this hotel is perfect for those who seek a productive visit to the area.

Where to stay near Hillsdale

Hillsdale, New York, offers an enchanting escape for adventure lovers and those seeking a relaxing vibe. Explore nearby ski resorts for thrilling slopes, or wander through charming towns that exude a friendly atmosphere and stunning scenery. Enjoy alfresco dining with a delightful evening breeze, and take in the captivating city views. Whether you’re after a romantic getaway or a family-friendly adventure, Hillsdale and its surroundings promise memorable experiences for every traveller.

  • Great Barrington: Nestled 12.9km from Hillsdale, Great Barrington is a vibrant city renowned for its outdoor adventures. Visitors flock here for skiing, sports activities, and a plethora of thrilling experiences. The peak season runs from June to August, but the area is enchanting year-round. Nature enthusiasts will appreciate the stunning landscapes featuring lakes, mountains, and the nearby national state park, making it a perfect spot for outdoor explorations and relaxation.
  • Stockbridge: Located 20.9km from Hillsdale, Stockbridge is a cultural gem famed for its romantic ambiance and artistic flair. This city draws visitors primarily from July to September, offering a delightful mix of entertainment, including music concerts and theatrical performances. The nearby lakes, historic monuments, and serene shrines provide a picturesque backdrop for leisurely strolls and cultural immersion. Stockbridge is the ideal destination for those seeking an enriching and enchanting experience.
  • Copake: Just 8.0km away from Hillsdale, Copake is a fantastic choice for adventure seekers and outdoor enthusiasts. The city sees increased visitor numbers mainly in March, April, and July, with skiing and outdoor activities at the forefront of its appeal. With its proximity to breathtaking lakes, majestic mountains, and a national state park, Copake offers countless opportunities for exploration and excitement. It’s a perfect base for those eager to embrace both adventure and the beauty of nature.

Things to do in and around Hillsdale

Hillsdale offers a fantastic getaway for adventure lovers, particularly those keen on skiing, with excellent ski resorts and fields. In addition to outdoor activities, you'll find plenty of entertainment options, including arcade games and live performances, alongside a variety of weekly events that showcase the local culture. Whether you're hitting the slopes or enjoying the vibrant atmosphere, Hillsdale has something for everyone.

Shopping

In Hillsdale, you can visit local gems like Charles H. Baldwin & Sons, Hoffman's Pottery, and Ebenezer II Gifts and Antiques, all located 20.9km away. If you're up for a drive, these stores offer unique gifts and souvenirs to take home.

Recreation

At Tanglewood Music Center, immerse yourself in enchanting music concerts that elevate your spirit, located 25.7km from Hillsdale. Experience wellness and tranquillity at Lake Mansfield Park, 12.9km away, or enjoy outdoor activities at the Undermountain Golf Course, also 12.9km from Hillsdale.

Adventure

At Catamount Aerial Adventure Park, soar through the treetops on thrilling ziplines and tackle challenging ropes courses, all while soaking up the outdoor atmosphere. Experience exhilarating skiing at Catamount Ski Area, located 3.2km away, or enjoy a scenic hike along the Housatonic River Walk, situated 14.5km from Hillsdale.

Nightlife

For a vibrant night out near Hillsdale, catch a show at the Mahaiwe Performing Arts Center, just 12.9km away, or enjoy a performance at the Mac-Haydn Theatre, 20.9km down the road. The Ancram Opera House, 17.7km away, offers a charming cultural experience.

Booking tips and Expedia advantages for Hillsdale

To save money during your trip to Hillsdale, consider visiting in January or March to April when accommodation prices are lower. Tuesdays are the most budget-friendly days for stays, while Saturdays tend to be pricier. Use Expedia to search for eco-friendly hotels and sort options by price for the best deals. Additionally, package your hotel with flights and activities for extra savings. Enjoy free outdoor activities like hiking and explore local parks to make the most of your budget while experiencing the beauty of Hillsdale.

  • 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: Utilise Expedia’s search tool to refine your preferences, such as your budget, preferred location, and the type of accommodation you’re after. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels currently available. To find the best prices and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save some cash by combining your Hillsdale hotel reservation with your flights and activities through an Expedia package.

Find the best attractions in and around Hillsdale

Hillsdale, New York, is perfect for ski and adventure enthusiasts, offering a range of outdoor activities. Visitors can explore national and state parks, serene lakes, and nature reserves, making it a great spot for those seeking a mix of adventure and culture. Whether you're hitting the slopes or enjoying the breathtaking scenery, Hillsdale promises a memorable experience for all types of travellers.

  • National Shrine of the Divine Mercy: Located 20.9km from Hillsdale, this serene shrine offers a unique spiritual experience amidst beautiful surroundings. Visitors can engage in prayer, reflection, and admire the stunning architecture that reflects deep cultural significance.
  • Taconic State Park: Just 6.4km away, this national park is perfect for adventure enthusiasts. With its extensive hiking trails and breathtaking views, you can immerse yourself in nature, enjoy outdoor activities, and take in the picturesque scenery.
  • Copake Lake: Situated within Hillsdale, this lovely lake features a beautiful beach area, ideal for relaxation and romance. Enjoy outdoor activities like swimming or picnicking while soaking up the stunning views.

Best time to go to Hillsdale

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.

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

When planning your visit to Hillsdale, New York, you have several major airports to consider. Hartford, CT (BDL-Bradley Intl.) is 74.0km away, with nearby hotels like the 4-star Simsbury 1820 House and the 3.5-star Sheraton Hartford Hotel, both offering convenient access to the airport. Albany, NY (ALB-Albany Intl.) is 67.6km from Hillsdale, featuring quality accommodations such as The Landing Hotel at Rivers Casino & Resort and the DoubleTree by Hilton Schenectady Downtown, both 12.9km from the airport. Lastly, Newburgh, NY (SWF-Stewart Intl.) is 88.5km away, with options like the 3.5-star Thayer Hotel and the Crossroads Hotel, just 3.2km from the airport.

Frequently asked questions

Where is the best place to stay in Hillsdale?

Based on Expedia's traveller preferences, The Brooks Motel is a top place to stay in Hillsdale. Two other options for your trip to the area are Berkshire Mountain Lodge and Postcard Cabins Eastern Catskills. See all available top hotels, or vacation rentals in Hillsdale.

What are some of the best holiday rentals that Hillsdale has to offer?

Lakefront Fall Foliage in New England Just 2 Hours From NYC: This holiday home rental outside Hillsdale is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a private garden and a selection of games. See all vacation rentals in Hillsdale.

If I need to cancel my hotel reservation in Hillsdale, will I receive a refund?

Yes! Most hotel reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before check in. If you have a non-refundable reservation, you might be able to still cancel and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Hillsdale.

What's the best dog-friendly place to stay in Hillsdale?

The Brooks Motel is a top dog-friendly option for your stay. Hudson valley and The Berkshires Cottage is another good option for you and your pet. See more pet-friendly hotel accommodations in Hillsdale.

What are some accommodation options with pools in Hillsdale?

Berkshire Mountain Lodge: Offers free self parking, an indoor pool and complimentary wireless Internet access. Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG and The Red Lion Inn are a couple of other choices that feature an on-site pool. View all hotels with pools in Hillsdale.

What's it like staying in Hillsdale?

Visitors can enjoy all that Hillsdale has to offer, including the coffee shops and ski areas. This city also attracts tourists with its relaxing and quaint setting. In Hillsdale, there are 68 hotels and other accommodation options to choose from. Find out more about Hillsdale.

What should I see while I'm in Hillsdale?

The picturesque setting of Copake Lake and Mosquito Island exemplify the area's natural beauty. A couple of additional sights to add to your itinerary are Catamount Aerial Adventure Park and Catamount Ski Area. Take a look at what more there is to see and do in Expedia's Hillsdale guide.

What's the seasonal weather in Hillsdale?

The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Hillsdale are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

Explore a world of travel with Expedia

Explore a world of travel with Expedia