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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 SAR 401
SAR 449 total
includes taxes & fees
5 Apr - 6 Apr
The Brooks Motel

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (881 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 SAR 262
SAR 293 total
includes taxes & fees
30 Mar - 31 Mar
Berkshires Untold

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (835 reviews)
"Nice place and very reasonable for great location "
United States
Raymond
The price is SAR 225
SAR 251 total
includes taxes & fees
31 Mar - 1 Apr
Monument Mountain Motel

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 SAR 376
SAR 413 total
includes taxes & fees
31 Mar - 1 Apr
Shaker Mill Inn

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, (184 reviews)
"We had the best time! "
United States
Eric
The price is SAR 522
SAR 726 total
includes taxes & fees
1 Apr - 2 Apr
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1,002 reviews)
"Great location, friendly staff"
United States
James
The price is SAR 252
SAR 281 total
includes taxes & fees
13 Apr - 14 Apr
Quality Inn Great Barrington

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, (1,000 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 SAR 400
SAR 447 total
includes taxes & fees
31 Mar - 1 Apr
Best Western Plus Berkshire Hills Inn & Suites

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (24 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is SAR 522
SAR 583 total
includes taxes & fees
5 Apr - 6 Apr
Element Lenox 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 SAR 220
SAR 241 total
includes taxes & fees
31 Mar - 1 Apr
Pleasant Valley Motel West Stockbridge

Chatham Travel Lodge

Chatham Travel Lodge
2.5 star property
Old Chatham
7.8 out of 10, Good, (218 reviews)
"Great friendly personable person at the front desk!!"
United States
Carolyn
The price is SAR 360
SAR 403 total
includes taxes & fees
31 Mar - 1 Apr
Chatham Travel Lodge

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (43 reviews)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is SAR 537
SAR 600 total
includes taxes & fees
19 Apr - 20 Apr
Wilder House Berkshires

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
10.0 out of 10, Exceptional, (3 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 SAR 563
SAR 629 total
includes taxes & fees
30 Mar - 31 Mar
The Berkshire Mountain Inn

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (574 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is SAR 281
SAR 314 total
includes taxes & fees
6 Apr - 7 Apr
Travelodge by Wyndham Great Barrington Berkshires

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 Place!!!"
United States
page
The price is SAR 394
SAR 453 total
includes taxes & fees
6 Apr - 7 Apr
Locust Tree Bed and Breakfast LLC

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,001 reviews)
"Room was spotless, staff was very kind!"
United States
Ilia
The price is SAR 367
SAR 409 total
includes taxes & fees
5 Apr - 6 Apr
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,001 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 SAR 316
SAR 353 total
includes taxes & fees
19 Apr - 20 Apr
Quality Inn Lee - Lenox South

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
"Great place to stay and close to shops and restaurants will be back!"
United States
Marie-Pascale
The price is SAR 368
SAR 411 total
includes taxes & fees
29 Mar - 30 Mar
The Yankee, Trademark Collection by Wyndham

Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Taghkanic
10.0 out of 10, Exceptional, (113 reviews)
"Great experience, looking forward to staying again."
United States
Greg
The price is SAR 563
SAR 630 total
includes taxes & fees
9 Apr - 10 Apr
Changing Times Boutique Country Lodging

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 SAR 413
SAR 461 total
includes taxes & fees
6 Apr - 7 Apr
The Little Lion

Spark by Hilton West Coxsackie

Spark by Hilton West Coxsackie
2.5 star property
West Coxsackie
7.8 out of 10, Good, (101 reviews)
"Thanksgiving stay, we’ll accommodating for the family. "
United States
Richard
The price is SAR 326
SAR 352 total
includes taxes & fees
9 Apr - 10 Apr
Spark by Hilton West Coxsackie
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

More cheap stays in Hillsdale

Find out more about Hillsdale

Top reasons to visit Hillsdale

  • Thrilling Ski Resorts: Hillsdale is ideal for ski enthusiasts, offering scenic ski fields and resorts for an exciting winter getaway.
  • Outdoor Adventures: Explore nearby state parks, nature reserves, and lakes, perfect for hiking, fishing, and relaxation.
  • Vibrant Local Scene: Enjoy live music events and a lively atmosphere that enhances your vacation experience.
  • Charming Accommodations: Choose from cozy agritourism properties and welcoming bed & breakfasts for a unique stay.
  • Friendly Community: Experience the warmth of local hospitality and discover charming spots perfect for families and couples.

Find great hotels near Hillsdale

Discover the charm of Hillsdale, New York, where a variety of lodging options await you, including cozy agritourism properties and welcoming bed & breakfasts. Perfect for families and pet-friendly travelers, these accommodations offer unique experiences for adventure seekers. With numerous hotels boasting positive reviews and exceptional amenities, you’re sure to find the ideal place to unwind and explore the beauty of the region.

  • Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: Nestled in the scenic Berkshires, this 3.5-star resort is perfect for families and ski enthusiasts. Located 22.5km from Hillsdale, it offers a range of family-oriented amenities, including an arcade game room, mini-golf, and a playground for children. The resort's proximity to ski shuttles and lifts makes it an ideal base for winter sports lovers, ensuring a memorable family vacation experience.
  • Quality Inn: Situated 12.9km from Hillsdale, Quality Inn caters to business travelers and adventure seekers alike. With a strong emphasis on outdoor activities, guests can enjoy nearby skiing lessons, downhill skiing, snowboarding, and hiking or biking trails. The hotel's focus on adventure sports ensures that your stay will be filled with excitement and opportunities to explore the beautiful surroundings.
  • Holiday Inn Express Hotel & Suites Great Barrington by IHG: Located 14.5km from Hillsdale, this hotel proudly welcomes LGBTQIA travelers and offers a comfortable atmosphere for business trips. With its affiliation to LGBTQI travel guides, the property ensures an inclusive environment. Guests will appreciate modern accommodations and convenient access to local attractions, making it a great choice for both business and leisure stays.

Where to stay near Hillsdale

Hillsdale, New York, is a gem for those seeking adventure and relaxation. Nestled in a scenic area, it offers easy access to ski resorts and outdoor activities. Just a short walk from the city center, you’ll find friendly locals and charming spots perfect for families and couples alike. Enjoy a peaceful atmosphere while exploring the beautiful surroundings, making your stay truly memorable.

  • Great Barrington: Located 12.9km from Hillsdale, Great Barrington is a vibrant city renowned for its outdoor adventures and cultural experiences. Visitors flock to this area primarily between June and August for its skiing and sports offerings. The nearby ski resorts provide ample opportunities for winter sports enthusiasts. Beyond winter activities, the scenic landscapes featuring lakes, mountains, and parks promise a memorable escape into nature. Great Barrington also boasts charming shops and eateries, making it a delightful destination for those seeking both adventure and relaxation.
  • Stockbridge: Just 20.9km away from Hillsdale, Stockbridge is a city steeped in romance and culture. Peak visitor arrivals occur between July and September, as tourists are drawn to its rich arts scene, including music concerts and theater performances. The city's picturesque lakes and historical monuments offer serene spots for leisurely strolls. Additionally, visitors can find places of worship that reflect the town's cultural heritage. Stockbridge is perfect for couples and families looking to immerse themselves in a blend of entertainment and natural beauty.
  • Craryville: Only 4.8km from Hillsdale, Craryville is a charming city that captivates outdoor enthusiasts year-round. With a peak travel season running throughout the year, visitors are attracted to its adventure-filled options, including skiing at the local resorts. The stunning proximity to lakes, mountains, and national state parks provides endless opportunities for hiking, fishing, and exploring the great outdoors. Craryville is an ideal base for those who crave adventure while enjoying the natural splendor of the region.

Things to do in and around Hillsdale

Hillsdale offers a perfect getaway for ski enthusiasts and adventure seekers with its scenic ski fields and resorts. Visitors can enjoy thrilling outdoor activities while soaking in the beautiful landscape. Additionally, the vibrant local scene features live music events, providing a lively atmosphere to enhance your vacation experience.

Shopping

In Hillsdale, you can explore Hoffman's Pottery, Charles H. Baldwin & Sons, and Ebenezer II Gifts and Antiques, all offering unique gifts and souvenirs. If you're up for a drive, these stores are located 20.9km away from Hillsdale, providing even more shopping options.

Recreation

Tanglewood Music Center offers an enriching experience with captivating concerts, just 25.7km from Hillsdale. For relaxation, Lake Mansfield Park provides a tranquil setting for leisurely walks and picnics, located 12.9km away. Alternatively, enjoy outdoor sports at Greenock Country Club, also 25.7km from Hillsdale.

Adventure

Experience thrilling skiing at Catamount Ski Area, located 3.2km from Hillsdale, where you can enjoy exhilarating slopes and sports vibes. For an adventurous day, visit Catamount Aerial Adventure Park, offering ziplining and ropes courses right in Hillsdale. Don’t miss the scenic Housatonic River Walk, 14.5km away, perfect for hiking.

Nightlife

Experience the vibrant nightlife in Hillsdale by visiting the Mahaiwe Performing Arts Center for a mix of romance and culture, just 12.9km away. The Mac-Haydn Theatre, located 20.9km away, offers more entertainment options, while the Ancram Opera House, 17.7km away, showcases local talent and charm.

*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 cheaper months of January, March, or April, as hotel prices are lower compared to peak months like July or October. Booking your stay on a Tuesday can also help you snag better rates. Use Expedia to compare room rates and find exclusive discounts by filtering for the best deals. Additionally, consider booking a package that combines flights, hotels, and activities to maximize your savings. Enjoy free local attractions and take advantage of public transport options for an economical travel experience.

  • 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 customize your options based on your budget, desired location, and preferred hotel type. To find the best prices and deals, 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.

Find the best attractions near Hillsdale

Hillsdale, New York, is perfect for outdoor and adventure enthusiasts, offering a range of activities for all types of travelers. Explore the stunning natural beauty of the nearby state parks, nature reserves, and lakes. Whether you're looking for thrilling ski experiences or a relaxing nature getaway, Hillsdale caters to those seeking adventure and cultural experiences in a picturesque setting.

  • Taconic State Park: Located 6.4km from Hillsdale, Taconic State Park offers breathtaking scenery and countless outdoor adventures. Hike through lush forests, picnic by serene lakes, or explore miles of trails that cater to all skill levels, making it a perfect spot for nature lovers.
  • National Shrine of the Divine Mercy: Situated 20.9km away, this serene shrine is a cultural gem that invites visitors to reflect and connect with their spirituality. The beautiful grounds and peaceful atmosphere provide a unique experience for those seeking solace and inspiration.
  • Norman Rockwell Museum: Just 19.3km from Hillsdale, this art museum showcases the iconic works of Norman Rockwell. Enjoy a deep dive into American culture through his captivating illustrations that tell stories of everyday life.

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

If you're planning a visit to Hillsdale, New York, you have several airport options. Hartford, CT (BDL-Bradley Intl.) is located 74.0km away, with nearby hotels like the DoubleTree by Hilton Hartford - Bradley Airport, just 1.6km from the airport. ALBany, NY (ALB-Albany Intl.) is 67.6km away, and offers accommodations such as the Park Manor Hotel, 12.9km from the airport. Newburgh, NY (SWF-Stewart Intl.) is 88.5km from Hillsdale, with options including The Dutchess Inn and Spa at Beacon, 9.7km away. Each hotel provides convenient transportation services to their respective airports for easy access during your stay.

Frequently asked questions

Where is the best place to stay in Hillsdale?
Based on Expedia's traveler preferences, The Brooks Motel is a top place to stay in Hillsdale. Two other choices for your visit to the area are Berkshire Mountain Lodge and Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy. See all available top hotels, or vacation rentals in Hillsdale.
What's the top vacation rental in Hillsdale?
Cozy Riverside Berkshires Retreat: This vacation home rental outside of Hillsdale is located on a river and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and kitchenware, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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! You'll find that most room reservations are fully refundable if cancelled before the hotel's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If your reservation is non-refundable, it may still be possible to cancel it and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Hillsdale.
Where can I learn more about changing or cancelling my trip to Hillsdale?
To access more information about changing or cancelling your trip to Hillsdale, head over to our customer service page.
What's the best pet-friendly accommodation in Hillsdale?
The Brooks Motel is a top pet-friendly option for your stay. Hudson valley and The Berkshires Cottage is another option for a stay with your pet. See more pet-friendly hotel accommodations in Hillsdale.
Where is the best hotel to stay close to Catamount Aerial Adventure Park?
Catamount Lodging is one of the top choices for your stay based on our traveler data, and this aparthotel offers private balconies and free WiFi. It's located just a short 0.3 mi (0.5 km) from Catamount Aerial Adventure Park. Another good option is Holiday House Motel, located 1.2 mi (2 km) away.
What are some accommodations 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 Holiday Inn & Suites Pittsfield-Berkshires by IHG are a couple of other choices with an onsite pool. View all hotels with pools in Hillsdale.
What is the best hotel near Albany International Airport (ALB)?
Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.
What's it like staying in Hillsdale?
Visitors can enjoy all that Hillsdale has to offer including the coffeehouses and ski areas. This city also attracts tourists with its relaxing and quaint setting. In Hillsdale, there are 64 hotels and other accommodations to choose from. Find out more about Hillsdale.
What should I do while I'm visiting 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 agenda are Catamount Aerial Adventure Park and Catamount Ski Area. Check out what more to see and do in Expedia's Hillsdale guide.
What's the weather like in Hillsdale?
The hottest months are usually July and August with an average temp of 68°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Hillsdale are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.