A rural landscape with snow-covered fields, a winding road, and scattered trees.

Find hotels in Hillsdale, NY from AEDĀ 278

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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, (139 reviews)
"Nice "
United States
Daljit
The price is AEDĀ 458
AEDĀ 512 total
includes taxes & fees
6 Jul - 7 Jul
The Brooks Motel

Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
10.0 out of 10, Exceptional, (2 reviews)
"Everything was perfect!!"
United States
Grzegorz
The price is AEDĀ 569
AEDĀ 636 total
includes taxes & fees
1 Jul - 2 Jul
Berkshire Lake Lodge

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (190 reviews)
"beautiful inn"
United States
Maura
The price is AEDĀ 519
AEDĀ 597 total
includes taxes & fees
30 Jun - 1 Jul
Blackberry River Inn

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (137 reviews)
"Had a great stay. Beautiful location."
United States
Joan
The price is AEDĀ 631
AEDĀ 692 total
includes taxes & fees
30 Jun - 1 Jul
Gedney Farm

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (91 reviews)
"Beautiful Inn and outstanding chef"
United States
Catherine
The price is AEDĀ 1,212
AEDĀ 1,463 total
includes taxes & fees
30 Jun - 1 Jul
The Old Inn On The Green

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (427 reviews)
"Below average B&B"
United States
Larry
The price is AEDĀ 386
AEDĀ 444 total
includes taxes & fees
5 Jul - 6 Jul
Locust Tree Bed and Breakfast LLC

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,004 reviews)
"It was a clean, friendly hotel."
United States
Cheri
The price is AEDĀ 544
AEDĀ 608 total
includes taxes & fees
7 Jul - 8 Jul
Quality Inn Lee - Lenox South

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (418 reviews)
"Nice place for a stay"
United States
Jay
The price is AEDĀ 345
AEDĀ 386 total
includes taxes & fees
6 Jul - 7 Jul
Sunset Inn

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (835 reviews)
"Plenty of parking. Staff was friendly"
United States
William
The price is AEDĀ 210
AEDĀ 234 total
includes taxes & fees
14 Jul - 15 Jul
FairBridge Inn Express

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (380 reviews)
"Yes the room was spotless and always the staff is ready to answer any questions that we might have. We have been enjoying the Chambery Inn for many years always had a great stay and again looking for our next visit. Vincent Farricielli and Roibert Modena. "
United States
robert
The price is AEDĀ 992
AEDĀ 1,108 total
includes taxes & fees
30 Jun - 1 Jul
Chambery Inn

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (670 reviews)
"Decent place.friendly, quiet"
United States
William
The price is AEDĀ 306
AEDĀ 342 total
includes taxes & fees
13 Jul - 14 Jul
Econo Lodge Lee - Great Barrington

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (138 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is AEDĀ 1,539
AEDĀ 1,719 total
includes taxes & fees
30 Jun - 1 Jul
Devonfield Inn B&B

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,004 reviews)
"Great breakfast and coffe is available 24 hours. Nice location to near by restaurants and great view by water."
United States
andrew
The price is AEDĀ 632
AEDĀ 705 total
includes taxes & fees
7 Jul - 8 Jul
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.2 out of 10, Wonderful, (918 reviews)
"Wonderful stay for families."
United States
Kimberly
The price is AEDĀ 602
AEDĀ 744 total
includes taxes & fees
29 Jul - 30 Jul
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Great spot close to town. Cozy, tasteful, comfortable room. Nice breakfasts and pleasant interaction with the staff. We love the Berkshires and we’ll definitely stay here again."
United States
Stephen
The price is AEDĀ 1,373
AEDĀ 1,610 total
includes taxes & fees
30 Jun - 1 Jul
The Inn at Stockbridge

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (118 reviews)
"Most comfortable hotel bed I've ever slept in"
United States
Matthew
The price is AEDĀ 628
AEDĀ 702 total
includes taxes & fees
6 Jul - 7 Jul
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (685 reviews)
"Five Star stay!"
United States
Adeline
The price is AEDĀ 672
AEDĀ 751 total
includes taxes & fees
5 Jul - 6 Jul
Hilton Garden Inn Lenox Pittsfield

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (874 reviews)
"Hotel was ok. Great for the price. But the bed was terrible. Old and soft. "
United States
robert
The price is AEDĀ 327
AEDĀ 365 total
includes taxes & fees
30 Jun - 1 Jul
Howard Johnson by Wyndham Lenox

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,008 reviews)
"The staff was very helpful. It was very clean and the bed was comfortable. We would stay there again."
United States
Andrew
The price is AEDĀ 515
AEDĀ 658 total
includes taxes & fees
29 Jul - 30 Jul
Berkshire Mountain Lodge

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,005 reviews)
"Good location and great breakfast."
United States
Linda
The price is AEDĀ 614
AEDĀ 686 total
includes taxes & fees
6 Jul - 7 Jul
Hampton Inn & Suites Berkshires-Lenox
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.

A landscape with a row of trees in autumn colors, a wooden fence, and a hilly background.

Top Hillsdale Hotel Reviews

More cheap stays in Hillsdale

Find out more about Hillsdale

Top reasons to visit Hillsdale

  • Skiing Adventures: Hillsdale is a haven for ski enthusiasts, with nearby resorts offering thrilling slopes and scenic ski fields.
  • Outdoor Exploration: Surrounding national and state parks provide ample opportunities for hiking, boating, and enjoying nature.
  • Vibrant Live Music Scene: After a day outdoors, unwind with the local live music offerings that enhance the Hillsdale experience.
  • Charming Neighborhoods: Explore friendly neighborhoods with stunning scenery, perfect for leisurely strolls.
  • Diverse Accommodations: Enjoy a range of lodging options, from cozy bed and breakfasts to unique agritourism stays.

Find great hotels near Hillsdale

Experience the charm of Hillsdale, New York, with a range of hotel accommodations that cater to every traveler's needs. From cozy bed and breakfasts to unique agritourism properties, you'll find family-friendly and pet-friendly options perfect for adventure seekers. Discover the best hotels in the area and read reviews to ensure a memorable stay in this picturesque destination.

  • Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: This 3.5-star resort is a family-friendly haven located 22.5km from Hillsdale, perfect for those seeking adventure and leisure. The resort features a variety of outdoor activities, including nearby snow tubing, skiing, and hiking, ideal for thrill-seekers. Families will appreciate the on-site amenities like an arcade game room, a shared playground, and mini-golf, ensuring fun for guests of all ages. With a focus on creating memorable experiences, this resort is perfect for both business travelers and vacationers looking for an adventurous getaway.
  • Quality Inn: Situated 12.9km from Hillsdale, Quality Inn is an excellent choice for adventure and business travelers alike. This hotel offers easy access to nearby recreational activities, including skiing, snow tubing, and hiking. Guests can enjoy comfortable accommodations with essential amenities, making it a suitable base for exploring the great outdoors. Whether you're here for business or to experience the thrill of winter sports, Quality Inn provides a welcoming environment for all.
  • Holiday Inn Express Hotel & Suites Great Barrington by IHG: Located 14.5km from Hillsdale, this hotel caters to both business travelers and the LGBTQIA community, making it a welcoming space for everyone. With its modern accommodations and commitment to inclusivity, guests can enjoy a comfortable stay while being part of a diverse environment. The hotel offers essential amenities and is conveniently situated for exploring local attractions, ensuring a pleasant experience for all visitors.

Where to stay near Hillsdale

Hillsdale, New York, offers a delightful blend of adventure and relaxation, perfect for ski enthusiasts and families alike. Explore the charming neighborhoods full of friendly faces and stunning scenery, all within walking distance of the city center. Whether you're seeking a romantic getaway or a family-friendly retreat, you'll find the ideal atmosphere to unwind and enjoy. Discover the convenience and beauty of the Hillsdale area for an unforgettable vacation experience.

  • Great Barrington: Nestled 12.9km from Hillsdale, Great Barrington is a vibrant city renowned for its outdoor adventures and winter sports. The town's appeal peaks in the summer months from June to August, drawing visitors eager to experience its skiing opportunities, including ski resorts and fields. Nature lovers will appreciate the nearby lakes, mountains, and parks, perfect for hiking, picnicking, and enjoying the stunning landscapes. With a charming downtown area filled with eclectic shops and eateries, Great Barrington promises a delightful travel experience year-round.
  • Stockbridge: Located 20.9km from Hillsdale, Stockbridge is a charming city that captivates travelers with its romantic atmosphere and cultural richness. Popular from July to September, visitors flock here to enjoy music concerts, theater performances, and other entertainment-themed events. The town is home to significant landmarks, including beautiful lakes, monuments, and places of worship, all contributing to its unique character. Stockbridge is the perfect destination for those looking to immerse themselves in art and culture while enjoying the picturesque surroundings.
  • Craryville: Just 4.8km away from Hillsdale, Craryville is a hidden gem for outdoor enthusiasts and adventure seekers. With a moderate seasonal influx of visitors, particularly from January to December, this city offers thrilling skiing experiences, including access to ski fields and resorts. Nature lovers will find bliss in the nearby lakes, majestic mountains, and the national state park, making it an ideal spot for hiking, camping, and appreciating the great outdoors. Craryville's close-knit community and tranquil environment provide a refreshing escape from the hustle and bustle.

Things to do in and around Hillsdale

Hillsdale, New York, is a fantastic destination for ski enthusiasts and adventure seekers. Visitors can enjoy a variety of activities including skiing at nearby resorts and exploring scenic ski fields. Additionally, the area offers a vibrant live music scene, enhancing the overall experience for those looking to relax and unwind after a day of outdoor fun. Hillsdale promises an exciting getaway filled with sports and entertainment.

Shopping

In Hillsdale, you can find unique gifts at Hoffman's Pottery, Charles H. Baldwin & Sons, and Ebenezer II Gifts and Antiques, all located 20.9km away. If you're up for a drive, these charming stores offer a delightful shopping experience filled with local craftsmanship and treasures.

Recreation

Tanglewood Music Center offers a vibrant atmosphere with world-class performances, perfect for music lovers. For relaxation, Lake Mansfield Park provides a tranquil setting with scenic views and peaceful walking paths. Meanwhile, Greenock Country Club invites outdoor enthusiasts to enjoy a round of golf in a stunning natural landscape.

Adventure

Experience thrilling skiing at Catamount Ski Area, located 3.2km from Hillsdale, perfect for snow enthusiasts. For an adrenaline rush, try the Catamount Aerial Adventure Park, an exciting zipline and ropes course in town. Enjoy scenic hiking along the Housatonic River Walk, located 14.5km away.

Nightlife

Experience the vibrant nightlife by catching a show at the Mahaiwe Performing Arts Center, just 12.9km away, or enjoy a performance at the Mac-Haydn Theatre, located 20.9km from Hillsdale. Don’t miss the Ancram Opera House, 17.7km away, for a unique cultural experience.

*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 or March to April, with Tuesdays being the least expensive days for accommodation. Use Expedia to compare hotel rates and find great deals, especially by selecting Eco-certified options for sustainable stays. Look for package deals that combine flights and activities for additional savings. Additionally, explore free activities in the area to enhance your experience without breaking the bank.

  • 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 preferences, such as your budget, desired location, and type of hotel you’re looking for. For instance, selecting the Eco-certified option will showcase sustainable and environmentally friendly hotels that are currently available. 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 hotel stay in Hillsdale with your flights and activities through an Expedia package deal.

Find the best attractions near Hillsdale

Hillsdale, New York, is an ideal destination for ski enthusiasts and adventure seekers. Surrounded by stunning natural landscapes, visitors can explore national and state parks, nature reserves, and serene lakes. The area offers a variety of outdoor activities and cultural experiences, making it perfect for travelers looking to immerse themselves in nature and adventure.

  • Taconic State Park: Located 6.4km from Hillsdale, Taconic State Park offers breathtaking scenery and outdoor adventure. Explore hiking trails, serene lakes, and picnic areas surrounded by lush forests, making it perfect for nature enthusiasts and families alike.
  • National Shrine of the Divine Mercy: Situated 20.9km away, this serene shrine is a place of spiritual reflection and cultural significance. Visitors can experience tranquil gardens, beautiful chapels, and various religious events, promoting a sense of peace and community.
  • Norman Rockwell Museum: Just 19.3km from Hillsdale, this art museum showcases the iconic works of Norman Rockwell. Dive into American culture through stunning illustrations, exhibits, and interactive displays that celebrate storytelling through art.

Best time to go to Hillsdale

The best time to visit Hillsdale is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, 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 to visit Hillsdale, New York, there are several major airports to consider. Bradley International Airport (BDL) in Hartford, CT, is 74.0km away, with nearby hotels like the DoubleTree by Hilton Hartford - Bradley Airport, just 1.6km from the airport, and the Marriott Hartford Downtown, 19.3km away. Albany International Airport (ALB) is 67.6km from Hillsdale, with options such as the Park Manor Hotel and The Landing Hotel, both 12.9km away. Lastly, Stewart International Airport (SWF) in Newburgh, NY, is 88.5km away, with hotels like The Dutchess Inn and Spa at Beacon, only 9.7km from the airport. Transportation services are available from these hotels to their respective airports.

Frequently asked questions

Where is the best place to stay in Hillsdale?
Located 20.3 mi (32.7 km) from the heart of Hillsdale, The Yankee Inn is a top choice for your stay based on our traveler data. Two other choices for your visit to the area are Berkshire Mountain Lodge and Quality Inn Great Barrington. 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 an electric kettle, 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 accommodation for a family vacation in Hillsdale?
Farm House Getaway on beautiful horse farm! is a country house with in-room kitchens and laundry facilities, and it's a top choice on Expedia for families. Attractions in the area like Harney and Sons Tea Tasting Room and The Bookstore are also fun for kids of all ages. Find more child-friendly accommodations in Hillsdale.
What's the best accommodation for a romantic getaway to Hillsdale?
Farm House Getaway on beautiful horse farm! is a favorite country house for couples, and features in-room fireplaces and a garden. See all romantic hotels in Hillsdale.
What's the best pet-friendly accommodation in Hillsdale?
The Brooks Motel is a top pet-friendly option for your stay. 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?
The Yankee Inn: Features a seasonal outdoor pool, an indoor pool, and buffet. Berkshire Mountain Lodge and The Red Lion Inn 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.