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Top 10 Hillsdale hotels and places to stay

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (400)
"A positively delightful B&B in a beautiful town. "
The price is £90
includes taxes & fees
24 Aug - 25 Aug
Locust Tree Bed and Breakfast LLC

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (585)
"Amazing place to stay. Can’t wait to go again. "
The price is £71
includes taxes & fees
21 Sept - 22 Sept
Berkshire Mountain Lodge

Element Lenox Berkshires

3.0 star property
9.6 out of 10, Exceptional, (4)
"New hotel very nice"
The price is £127
includes taxes & fees
1 Sept - 2 Sept
Element Lenox Berkshires

The Brooks Motel

2.0 star property
7.8 out of 10, Good, (96)
"Basic, clean and good value for the money."
The Brooks Motel

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (117)
"Great stay!"
The price is £108
includes taxes & fees
14 Sept - 15 Sept
Micosta Leisure Inn

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1002)
"nice place"
The price is £77
includes taxes & fees
7 Sept - 8 Sept
Quality Inn

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1002)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is £105
includes taxes & fees
1 Sept - 2 Sept
The Black Swan Lee - Lenox, Ascend Hotel Collection

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (692)
"Great property. Would stay again"
The price is £133
includes taxes & fees
26 Aug - 27 Aug
Berkshires Untold

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
7.4 out of 10, Good, (544)
"Excellent location, friendly service, clean, comfortable room."
The price is £62
includes taxes & fees
4 Sept - 5 Sept
Travelodge by Wyndham Great Barrington Berkshires

Overlook Hotel

2.0 star property
7.8 out of 10, Good, (7)
"设备不齐全"
The price is £178
includes taxes & fees
1 Sept - 2 Sept
Overlook Hotel

Postcard Cabins Eastern Catskills

2.0 star property
9.6 out of 10, Exceptional, (59)
"Really beautiful place to enjoy nature with family!!"
The price is £164
includes taxes & fees
4 Sept - 5 Sept
Postcard Cabins Eastern Catskills

the Alander

2.5 star property
9.0 out of 10, Wonderful, (155)
"Loved our stay, staff very attentive and helpful!! "
The price is £134
includes taxes & fees
24 Aug - 25 Aug
the Alander

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1002)
"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 £135
includes taxes & fees
15 Sept - 16 Sept
The Cornell Inn, Lenox & The Berkshires

Monument Mountain Motel

2.5 star property
8.8 out of 10, Excellent, (740)
"A great mom & pop motel. Clean and friendly "
Monument Mountain Motel

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (786)
"My stay was perfect. I can't wait to stay there again. "
The price is £66
includes taxes & fees
1 Sept - 2 Sept
Howard Johnson by Wyndham Lenox

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (570)
"Fabulous place"
The price is £127
includes taxes & fees
1 Sept - 2 Sept
Courtyard by Marriott Lenox Berkshires

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (20)
"Really enjoyed my stay here, definitely need a car to get around"
The price is £112
includes taxes & fees
18 Sept - 19 Sept
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1000)
"Very clean rooms and excellent staff."
The price is £88
includes taxes & fees
18 Sept - 19 Sept
Best Western Plus Berkshire Hills Inn & Suites

The Nest Hudson

3.5 star property
9.6 out of 10, Exceptional, (200)
"The Nest Hudson is a gem with great amenities and very comfortable bedding. We are riding our bicycles up the state and over to Buffalo, and this place was an oasis that helped us recharge and prep for the next leg of our journey. Food tips: Feast and Floret for an excellent meal and WYLDE Hudson for a morning cafe, both within a short walk. "
The price is £105
includes taxes & fees
25 Aug - 26 Aug
The Nest Hudson

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (127)
"We had a vey clean room with a comfortable bed The breakfast was awesome as was the entire staff. Enjoyed our stay"
The price is £140
includes taxes & fees
18 Sept - 19 Sept
Blackberry River Inn
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Check out pet-friendly hotels in Hillsdale

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.

Learn more about Hillsdale

Quaint Hillsdale is calling! Discover its coffee, library, sunrises and more.

Top Hillsdale Hotel Reviews

Find out more about Hillsdale

Find out more about Hillsdale

Top reasons to visit Hillsdale

  • Thrilling Winter Sports: Hillsdale is a prime destination for skiing and snowboarding enthusiasts, offering exhilarating slopes and winter activities.
  • Stunning Natural Beauty: Explore the picturesque Hudson Valley, serene lakes, and nearby national parks, perfect for outdoor adventures.
  • Charming Accommodations: Choose from delightful bed and breakfasts and unique agritourism properties that cater to various needs.
  • Family-Friendly Atmosphere: Enjoy a welcoming environment with activities suitable for all ages, making it ideal for family holidays.
  • Adventure Parks: Experience exciting activities at local adventure parks, providing fun for thrill-seekers of all ages.

Find great hotels near Hillsdale

Hillsdale, New York, offers a delightful selection of lodging options, from charming bed and breakfasts to unique agritourism properties. Whether you're seeking pet-friendly accommodations, family-friendly amenities, or an adventure-filled getaway, you’ll discover a variety of hotels and resorts that cater to your needs. Explore the inviting rooms in Hillsdale and find the perfect base for your travels in this picturesque region.

  • Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: Nestled 8.7km from Hillsdale, this 3.5-star resort is perfect for families and adventure seekers alike. With a charming mountain lodge theme, guests can indulge in a variety of recreational activities such as snowboarding, tubing, and hiking. The property boasts amenities for children, including an onsite mini-golf course and arcade game room, making it an ideal choice for family vacations. Plus, with convenient ski shuttle access, winter sports enthusiasts will find themselves right at home.
  • Holiday Inn Express Hotel & Suites Great Barrington by IHG: Located 5.6km from Hillsdale, this hotel caters to business travellers and those seeking an inclusive environment. Its modern design and well-equipped business centre, complete with 24-hour access and conference space, ensure that all professional needs are met. The hotel is proudly affiliated with LGBTQI travel guides, promoting a welcoming atmosphere for all guests. With comfortable accommodations and a complimentary breakfast, it strikes a perfect balance between convenience and comfort.
  • Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires: Also situated 5.6km from Hillsdale, this hotel combines a family-friendly environment with business amenities, making it a versatile choice for all types of travellers. The hotel features accessible business facilities, ensuring seamless work experiences. Additionally, it provides amenities for children, such as a free crib service and nearby sledding options. With its affiliation to LGBTQI travel guides, guests can feel assured of an inclusive and warm welcome during their stay.

Where to stay near Hillsdale

Discover the charm of Hillsdale, New York, where adventure and relaxation coexist beautifully. Enjoy thrilling ski trips in the winter and explore the picturesque Hudson Valley in warmer months. With friendly locals and family-friendly atmospheres, you'll uncover hidden gems and breathtaking scenery. Don't miss the chance to experience the unique vibes of this region, from romantic getaways to serene escapes, all while securing the best prices in the Hillsdale area.

  • Great Barrington: Nestled around 5.0km from Hillsdale, Great Barrington is a vibrant city renowned for its outdoor activities and adventure sports. With a steady influx of travellers year-round, the peak season from June to August draws visitors eager to experience skiing and other recreational pursuits. Highlights include the nearby ski fields and resorts, as well as stunning natural attractions like lakes and mountains. The proximity to national and state parks offers ample opportunities for hiking and exploration, making it an ideal destination for those seeking an active getaway.
  • Stockbridge: Approximately 8.1km away from Hillsdale, Stockbridge is a charming city that embodies cultural richness and romantic allure. While visitor numbers peak from July to September, the city maintains a steady flow of guests throughout the year. Art enthusiasts will enjoy the local theatres and music concerts, as well as the picturesque scenery that includes lakes and historic monuments. Stockbridge is perfect for couples looking for a blend of entertainment and relaxation, providing a delightful escape filled with artistic inspiration and natural beauty.
  • Copake: Located just 3.1km from Hillsdale, Copake is a hidden gem for outdoor enthusiasts and adventure seekers. With a consistent stream of visitors, particularly peaking in the spring and summer months, this city is celebrated for its skiing and outdoor activities. The local ski fields and resorts attract thrill-seekers, while the stunning nearby lakes and mountains invite exploration. Copake's proximity to national and state parks enhances its appeal, ensuring a memorable experience for those who love nature and adventure.

Things to do in and around Hillsdale

Hillsdale offers a fantastic getaway for those seeking adventure and winter sports. Visitors can enjoy skiing at local resorts and fields, along with exhilarating activities at adventure parks. Seasonal camping also provides a unique way to experience the area's natural beauty. Whether you are hitting the slopes or exploring the great outdoors, Hillsdale is an ideal destination for an active holiday.

Shopping

For a delightful shopping experience in Hillsdale, visit Charles H. Baldwin & Sons, Hoffman's Pottery, and Ebenezer II Gifts and Antiques, all located 8.1km away. If you're up for a drive, these stores offer unique gifts and charming souvenirs to take home.

Recreation

Experience the enchanting Tanglewood Music Center, where you can immerse yourself in captivating concerts and enjoy the vibrant atmosphere. For a serene retreat, Lake Mansfield Park offers a tranquil setting perfect for relaxation, while Undermountain Golf Course invites you to indulge in outdoor sports and stunning landscapes.

Adventure

At Catamount Ski Area, located 1.2km from Hillsdale, enjoy thrilling ski runs amidst stunning winter scenery. For a different rush, head to Catamount Aerial Adventure Park in Hillsdale for an exhilarating zipline experience. Alternatively, explore the beautiful 9-mile Housatonic River Walk, perfect for hiking enthusiasts.

Nightlife

In Hillsdale, the Mahaiwe Performing Arts Center offers a charming theatre experience just 5.0km away, while the Mac-Haydn Theatre, located 8.1km away, delights with live performances. Ancram Opera House, 6.8km distant, adds to the cultural tapestry, making for an enchanting night out.

Booking tips and Expedia advantages for Hillsdale

To save money on your visit to Hillsdale, consider travelling during the cheaper months of January or March to April, avoiding the pricier summer and autumn periods. Book your stay on a Tuesday for the best rates, and utilise Expedia’s search tool to find affordable hotels that meet your budget, including eco-friendly options. Look for package deals that combine hotels with flights and activities to maximise savings. Lastly, explore free activities in the area to further reduce costs while enjoying 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: Expedia’s search tool enables you to set your budget, choose your desired location, and more. You can arrange your search results to display prices from lowest to highest, allowing you to find the most affordable hotels first. Additionally, you have the option to refine your choices by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels that are available for booking.
  • Consider bundling your trip: You can potentially save money by combining your Hillsdale hotel reservation with your flights and activities by opting for an Expedia package.

Find the best attractions near Hillsdale

Hillsdale, New York, is an ideal destination for ski and adventure enthusiasts, offering a range of outdoor activities. Visitors can explore local attractions such as the nearby national parks, serene lakes, and nature reserves, perfect for those seeking cultural and adventurous experiences. Be sure to discover popular sites in Hillsdale, which provide both thrilling adventures and a taste of the region's natural beauty.

  • Art Omi International Arts Center - Fields Sculpture Park: Discover a stunning outdoor sculpture garden located 8.1km from Hillsdale, where art meets nature. This family-friendly venue features a diverse collection of contemporary sculptures set amidst rolling landscapes, perfect for leisurely walks and family outings.
  • FASNY Museum of Firefighting: Situated 8.7km away, this fascinating museum offers a deep dive into firefighting history and culture. With engaging exhibits and rare artifacts, visitors can learn about the evolution of firefighting and its significance in community safety.
  • Taconic State Park: Just 2.5km from Hillsdale, this national park is an outdoor enthusiast's dream. Experience adventure through hiking, camping, and breathtaking scenery, making it an ideal spot for nature lovers seeking tranquility and exploration.

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

To reach Hillsdale, New York, you have several airport options. Bradley International Airport (BDL) in Hartford, CT, is situated 28.6km away, with nearby hotels like the 4-star DoubleTree by Hilton Hartford - Bradley Airport, just 621m from the airport. Stewart International Airport (SWF) in Newburgh, NY, lies 34.2km from Hillsdale, boasting hotels such as The Dutchess Inn and Spa at Beacon, located 3.7km away. Albany International Airport (ALB) is 26.1km distant, with the 4-star Landing Hotel at Rivers Casino & Resort a mere 5.0km away. Each hotel offers convenient access to their respective airports, ensuring a smooth travel experience.

Frequently asked questions

What are the best budget hotels in Hillsdale?
The Brooks Motel in Hillsdale, NY, is a charming option for travellers 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 best time to visit Hillsdale is during the summer months, particularly July, when the weather is warm and inviting. Average temperatures around 25°C make it great for enjoying outdoor activities and exploring the charming surroundings.

During the peak season from June to August, Hillsdale sees an influx of visitors eager to take advantage of the vibrant atmosphere and numerous local events. This is a fantastic time for sightseeing and engaging with the community through festivals and outdoor markets that showcase local crafts and cuisine.

If you enjoy outdoor adventures, July offers ample opportunities to hike the scenic trails or relax by the tranquil lakes. The long summer days provide plenty of sunlight for your explorations, whether you're biking through picturesque landscapes or enjoying a leisurely picnic in one of the many parks.

For those considering a visit later in the year, October offers a quieter experience. While the temperatures start to dip, averaging around 15°C, it's still a lovely time to enjoy the fall foliage and the peaceful ambiance of the area. Plus, you can take advantage of potentially lower accommodation rates during this time.
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 £59 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.