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

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29 Sep - 30 Sep
Tomorrow
30 Sep - 1 Oct
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2 Oct - 4 Oct
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9 Oct - 11 Oct

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Our top choices for Hillsdale hotels

1. The Brooks Motel

The Brooks Motel
Hillsdale
United States
Nelson
AED 503
AED 564 total
includes taxes & fees
12 Oct - 13 Oct
The Brooks Motel

2. Little Cat Lodge

Little Cat Lodge
Copake Falls
United States
Kees
AED 658
AED 737 total
includes taxes & fees
4 Oct - 5 Oct
Little Cat Lodge

3. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
United States
Bruce
AED 715
AED 799 total
includes taxes & fees
4 Oct - 5 Oct
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

4. Quality Inn Great Barrington

Quality Inn Great Barrington
Great Barrington
United States
Joan
AED 372
AED 415 total
includes taxes & fees
20 Oct - 21 Oct
Quality Inn Great Barrington

5. Prospect Berkshires

Prospect Berkshires
Egremont
United States
Conor
AED 1,537
AED 1,840 total
includes taxes & fees
28 Oct - 29 Oct
Prospect Berkshires

6. the Alander

the Alander
Copake
United States
Thomas
AED 531
AED 594 total
includes taxes & fees
4 Oct - 5 Oct
the Alander

7. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
United States
Maria Dulce
AED 437
AED 488 total
includes taxes & fees
19 Oct - 20 Oct
Holiday Inn Express Hotel & Suites Great Barrington by IHG

8. Monument Mountain Motel

Monument Mountain Motel
Great Barrington
United States
Victor
AED 251
AED 281 total
includes taxes & fees
25 Oct - 26 Oct
Monument Mountain Motel

9. Granville House

Granville House
Housatonic
United States
Nicole
AED 1,010
AED 1,128 total
includes taxes & fees
12 Oct - 13 Oct
Granville House

10. Wilder House Berkshires

Wilder House Berkshires
Sheffield
United States
Mark
AED 758
AED 847 total
includes taxes & fees
25 Oct - 26 Oct
Wilder House Berkshires

11. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Stephan
AED 633
AED 890 total
includes taxes & fees
19 Oct - 20 Oct
The Red Lion Inn

12. The Little Lion

The Little Lion
Great Barrington
United States
Lidia
AED 380
AED 425 total
includes taxes & fees
18 Oct - 19 Oct
The Little Lion

13. East Rock Inn

East Rock Inn
Great Barrington
United States
ERIK
AED 525
AED 587 total
includes taxes & fees
19 Oct - 20 Oct
East Rock Inn

14. Shaker Mill Inn

Shaker Mill Inn
West Stockbridge
United States
Mervin
AED 657
AED 721 total
includes taxes & fees
4 Oct - 5 Oct
Shaker Mill Inn

15. Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
Craryville
United States
Thomas
AED 735
AED 823 total
includes taxes & fees
5 Oct - 6 Oct
Changing Times Boutique Country Lodging

16. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
Bob
AED 496
AED 555 total
includes taxes & fees
29 Oct - 30 Oct
The Black Swan Lee - Lenox, an Ascend Collection Hotel

17. Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
Great Barrington
United States
Kevin
AED 290
AED 324 total
includes taxes & fees
25 Oct - 26 Oct
Travelodge by Wyndham Great Barrington Berkshires

18. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
United States
Tracy
AED 519
AED 580 total
includes taxes & fees
25 Oct - 26 Oct
Courtyard by Marriott Lenox Berkshires

19. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
Lee
United States
Christine
AED 403
AED 450 total
includes taxes & fees
20 Oct - 21 Oct
Quality Inn Lee - Lenox South

20. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
United States
Jared
AED 430
AED 552 total
includes taxes & fees
18 Oct - 19 Oct
Holiday Inn Club Vacations Oak 'n Spruce Resort
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Stay near popular Hillsdale attractions

Catamount Aerial Adventure Park

6.4/10 (5 reviews)
Scale New England's largest aerial adventure park with over 150 treetop challenges across nine difficulty levels. Glide between zip lines and navigate bridges while surrounded by serene forest scenery.
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Copake Lake

This glacial lake in the Hudson Valley offers pristine waters for boating, fishing, and swimming year-round. Enjoy serene morning kayaking or lively afternoons of water skiing surrounded by picturesque natural scenery.
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Hillsdale Town Hall

This historic former library now serves as Hillsdale's administrative center with distinctive slate-shingled roof and Ionic columns. Visit during town board meetings to experience local governance.
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Community Library

The Roeliff Jansen Community Library serves as a vital cultural hub for Hillsdale, Copake, and Ancram communities. Visitors enjoy book clubs, writing groups, and educational workshops in its welcoming atmosphere.
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Mosquito Island

Commune with nature and explore the great outdoors at Mosquito Island during your travels in Copake Lake.
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Roe Jan Brewing Co.

After visiting Roe Jan Brewing Co., make a plan to see the other sights and activities in Hillsdale. Discover the sunrises while you're in the area.
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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.

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

Top Hillsdale Hotel Reviews

Berkshires Untold

Berkshires Untold

8/10 Good
"A very good place to stay"
Madhavi R 1-night trip
Posted 7 hours ago
Berkshires Untold
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

8/10 Good
"Overall, the cabin was nice. Especially if you're only planning on staying a few days. But for the price you pay for 2 nights, they could have better utensils, pan, a few more cooking utensils and a kettle for the hot water. These are just a few inexpensive amenities that these places should all have! Because most people are probably cooking there own food nowadays either by choice or the fact that there's nothing close by. But aside from the kitchen issues, this was a very nice, enjoyable getaway. I would definitely recommend it to anyone who loves the outdoors!"
Joy 2-night trip
Posted 16 hours ago
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent
"Wonderful resort"
Ofer 2-night trip
Posted 23 hours ago
Holiday Inn Club Vacations Oak 'n Spruce Resort
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"This was a nice clean convenient hidden gem. Situated on the water, a little cool right now , but the beginning of fall follege was very pretty. Staff was polite and helpful. I would return."
Anthony 2-night trip
Posted 1 day ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

10/10 Excellent
"Very sweet desk clerk answered my question about late arrival quickly and cheerfully."
Chris 1-night trip
Posted 1 day ago
Quality Inn Lee - Lenox South
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"I typically do not reserve in motel with parking in front of each space due to security, I was mistaken at this facility. Pleasant neighborhood and the building was situated well off the main street."
Peter 1-night trip
Posted 1 day ago
Quality Inn Great Barrington
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"One of the most unique establishments in the US. It brings one back to time when life was much simpler. Highly recomended."
Michael 1-night trip
Posted 1 day ago
The Red Lion Inn
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Nice room. Exceptionally clean. Great staff"
Daniel 3-night trip
Posted 1 day ago
The Yankee Inn
St. Charles Hotel

St. Charles Hotel

8/10 Good
"The room was clean and modern and the staff were friendly and professional. Parking was close and ample."
Virginia 1-night trip
Posted 2 days ago
St. Charles Hotel

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 20.9 mi (33.7 km) from the heart of Hillsdale, Berkshire Mountain Lodge is a top choice for your stay based on our traveler data. Two other choices for your visit to the area are Quality Inn Great Barrington 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?
Modern Luxurious Cabin, Catskills - The Tiny Nook: This vacation home rental outside of Hillsdale is located in a rural location and offers a patio, air-conditioning, and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. 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 Hotchkiss Mobile Studio and Stoddard Corner 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. 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: Features free self parking, an indoor pool, and complimentary wireless internet access. Pocketbook Hotel and Bath and The Yankee 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 59 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.