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

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Oct 22 - Oct 23
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Oct 23 - Oct 24
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Oct 23 - Oct 25
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Our top choices for Hillsdale hotels

A modern bedroom with a large bed, two bedside tables, and a textured wall behind the bed.
A dining area with a wooden table, chairs, and a colorful striped rug.
A compact kitchen with a wooden countertop, a coffee machine, and a small shelf with a hair dryer and cups.
A living room with a sofa, a coffee table, a fireplace, and a ceiling fan.

1. The Brooks Motel

The Brooks Motel
Hillsdale
United States
Nelson
₩193,258
₩216,448 total
includes taxes & fees
Oct 25 - Oct 26
The Brooks Motel
A house with a stone patio and wooden stools.
A wooden fire pit surrounded by six Adirondack chairs in a forested area.
A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.
A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.

2. Little Cat Lodge

Little Cat Lodge
Copake Falls
United States
Stacy
₩201,609
₩225,804 total
includes taxes & fees
Nov 4 - Nov 5
Little Cat Lodge
A wooden boat on calm water with a house in the background.
A wooden wall with a white pendant light fixture.
A wooden cabin with a staircase leading to a deck, surrounded by trees and a gravel path.
A wooden deck with a dog silhouette against a backdrop of autumn foliage.

3. Prospect Berkshires

Prospect Berkshires
Egremont
United States
Conor
₩375,779
₩464,163 total
includes taxes & fees
Nov 9 - Nov 10
Prospect Berkshires
A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.
A hotel room with a bathroom, a bed, a desk, and a nightstand.
A hotel reception area with framed artwork, a coffee machine, and a sign indicating 'Quality by Choice Hotels'.
A Quality Inn sign, a brick building, and a parking lot with cars.

4. Quality Inn Great Barrington

Quality Inn Great Barrington
Downtown Great Barrington
United States
Scott Patterson
₩100,274
₩112,005 total
includes taxes & fees
Nov 12 - Nov 13
Quality Inn Great Barrington
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.
A modern hotel lobby with a seating area, a sofa, and a large window with curtains.
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

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

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
United States
Md
₩190,408
₩212,686 total
includes taxes & fees
Nov 4 - Nov 5
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A modern hotel lobby with seating areas, tables, and a reception desk.
A breakfast area with a counter, coffee machine, and a display of pastries.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A kitchenette with a microwave, coffee maker, and coffee cups.

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

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
United States
Cynthia
₩119,295
₩133,253 total
includes taxes & fees
Nov 12 - Nov 13
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A modern building with a dark exterior, outdoor seating area with wooden chairs, and string lights.
A dining table set with plates of food, wine glasses, and bottles, with a chandelier above and shelves above holding glasses and bottles.
A bar area with a green counter, two pendant lights, and shelves stocked with bottles.
A modern living room with a sofa, armchair, and coffee table. There is a bed with a headboard and pillows, a lamp, and a shelf with items.

7. the Alander

the Alander
Copake
United States
Luis
₩198,825
₩222,684 total
includes taxes & fees
Oct 30 - Oct 31
the Alander
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.
A hotel room with a wooden dresser, a television, a microwave, and a mirror.
A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.
A row of white plastic chairs on a covered outdoor area with a white building in the background.

8. Monument Mountain Motel

Monument Mountain Motel
Great Barrington
United States
Andrea
₩79,331
₩88,610 total
includes taxes & fees
Nov 1 - Nov 2
Monument Mountain Motel
A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A grassy outdoor area with four blue Adirondack chairs arranged in a circle.
A sign for East Rock Inn with a mountainous logo, surrounded by lush greenery and a gravel path leading to a building.

9. East Rock Inn

East Rock Inn
Great Barrington
United States
Sharon
₩179,257
₩200,229 total
includes taxes & fees
Nov 5 - Nov 6
East Rock Inn
A straw hat, sunglasses, and two drinks on a striped towel by a body of water.
A bar with wooden floors and shelves filled with bottles.
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A covered porch with wicker furniture and hanging flower baskets.

10. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Mallory
₩208,794
₩299,074 total
includes taxes & fees
Nov 4 - Nov 5
The Red Lion Inn
A large house with a balcony and a grassy yard.
A two-story building with a gabled roof and a chimney.
A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.
A room with a white desk, two floral chairs, a small round table with a plant, a hanging lamp, and two framed artworks on the wall.

11. The Little Lion

The Little Lion
Great Barrington
United States
David
₩137,189
₩153,241 total
includes taxes & fees
Nov 4 - Nov 5
The Little Lion
A dining area with a round table and four chairs, a radiator, and a window with a view of greenery.
A small cabin with two Adirondack chairs in a grassy field, surrounded by trees and a mountain in the background.
A bedroom with a wooden bed, bedside tables, a desk, and a chair.
A pool table in a room with a patterned rug, a shelf with decorative items, and a window with a view of greenery.

12. Granville House

Granville House
Housatonic
United States
Cynthia
₩336,677
₩376,071 total
includes taxes & fees
Oct 25 - Oct 26
Granville House
Interior detail
A room with a wooden floor, two red armchairs, a small table, and a window with a view of trees.
A bedroom with a large bed, a dresser, a chair, and a mirror.
A cozy living room with a fireplace, a bookshelf, a coffee table with a book, and a plaid sofa.

13. Wilder House Berkshires

Wilder House Berkshires
Sheffield
United States
Liliana
₩217,201
₩242,613 total
includes taxes & fees
Oct 28 - Oct 29
Wilder House Berkshires
A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.
A motel with a two-story structure, multiple rooms with red doors, and a central staircase.
A living room with a patterned carpet, two sofas, a dining table, and chairs.
A hotel room with a sofa, a wooden table, a lamp, a telephone, and a painting on the wall.

14. Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
Great Barrington
United States
Ramakrishnan
₩104,715
₩116,965 total
includes taxes & fees
Oct 28 - Oct 29
Travelodge by Wyndham Great Barrington Berkshires
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

15. The Yankee Inn

The Yankee Inn
Lenox
United States
Basil
₩140,625
₩157,079 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
A reception area with a fireplace, seating, and a doormat with the logo "Quality".
A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.
A hotel room with a sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.
A hotel room with a bed, a desk, a television, a microwave, and a sofa.

16. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
Lee
United States
Lucinda
₩122,808
₩137,178 total
includes taxes & fees
Nov 12 - Nov 13
Quality Inn Lee - Lenox South
A lodge with a large building and a dock by a lake, surrounded by forest.
A lakeside lodge with a dock, fishing rods, and outdoor seating.
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A lakeside dock with kayaks and a covered boat ramp.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
Gustavo
₩152,101
₩169,897 total
includes taxes & fees
Nov 15 - Nov 16
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A balcony with a table featuring a bottle, glasses, and binoculars, overlooking a river, greenery, and a house.
A historic hotel with a prominent tower and a brick facade.
A bar with a patterned floor, bar stools, and a bar counter with taps.
A dining area with a brick fireplace, wooden beams, and a chandelier.

18. Diamond Mills Resort

Diamond Mills Resort
Saugerties
United States
luping
₩352,291
₩427,699 total
includes taxes & fees
Oct 29 - Oct 30
Diamond Mills Resort
A Holiday Inn Express hotel with a covered entrance, multiple floors, and a brick facade.
A Holiday Inn Express & Suites sign with a clear view of the hotel building in the background.
A hotel lobby with a reception desk, seating area, and a corridor leading to other rooms.
A modern lobby with a reception desk, seating area, and a dining section.

19. Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG
Saugerties
United States
Eleanor
₩163,037
₩182,600 total
includes taxes & fees
Nov 22 - Nov 23
Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.
A cozy library with bookshelves, a fireplace, and comfortable seating.
An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".
A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.

20. Berkshires Untold

Berkshires Untold
Lenox
United States
Madhavi R
₩172,566
₩192,756 total
includes taxes & fees
Nov 22 - Nov 23
Berkshires Untold
View all properties

Hotels recommended for families in Hillsdale

A modern bedroom with a large bed, two bedside tables, and a textured wall behind the bed.
A dining area with a wooden table, chairs, and a colorful striped rug.
A compact kitchen with a wooden countertop, a coffee machine, and a small shelf with a hair dryer and cups.
A living room with a sofa, a coffee table, a fireplace, and a ceiling fan.

The Brooks Motel

The Brooks Motel
Hillsdale
₩193,258
₩216,448 total
includes taxes & fees
Oct 25 - Oct 26
The Brooks Motel
A modern hotel lobby with seating areas, tables, and a reception desk.
A breakfast area with a counter, coffee machine, and a display of pastries.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A kitchenette with a microwave, coffee maker, and coffee cups.

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
₩119,295
₩133,253 total
includes taxes & fees
Nov 12 - Nov 13
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.
A hotel room with a wooden dresser, a television, a microwave, and a mirror.
A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.
A row of white plastic chairs on a covered outdoor area with a white building in the background.

Monument Mountain Motel

Monument Mountain Motel
Great Barrington
₩79,331
₩88,610 total
includes taxes & fees
Nov 1 - Nov 2
Monument Mountain Motel
A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.
A motel with a two-story structure, multiple rooms with red doors, and a central staircase.
A living room with a patterned carpet, two sofas, a dining table, and chairs.
A hotel room with a sofa, a wooden table, a lamp, a telephone, and a painting on the wall.

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
Great Barrington
₩104,715
₩116,965 total
includes taxes & fees
Oct 28 - Oct 29
Travelodge by Wyndham Great Barrington Berkshires
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.
A modern hotel lobby with a seating area, a sofa, and a large window with curtains.
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
₩190,408
₩212,686 total
includes taxes & fees
Nov 4 - Nov 5
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A large house with a balcony and a grassy yard.
A two-story building with a gabled roof and a chimney.
A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.
A room with a white desk, two floral chairs, a small round table with a plant, a hanging lamp, and two framed artworks on the wall.

The Little Lion

The Little Lion
Great Barrington
₩137,189
₩153,241 total
includes taxes & fees
Nov 4 - Nov 5
The Little Lion
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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.
See properties

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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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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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.
See properties

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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"We've stayed at Berkshire Mountain Lodge in October a number of times now, and we really enjoy the property. The rooms are well-appointed, very clean, and quite comfortable. We appreciate the free washers and dryers as well as the many other amenities, and you cannot beat the location. There's a supermarket down the driveway and across the street and an excellent specialty grocer--Guido's Market--just down the road. We highly recommend this property. The District Restaurant in Pittsfield is excellent. We've also seen several great plays at Barrington Theatre Company. The area is loaded with historical and cultural activities. We like the proximity to Lenox and the Edith Wharton mansion as well as The Clark art museum in Williamstown, both of which have lovely grounds/gardens typically exhibiting sculptures. There are also abundant outdoor activities and opportunities for hiking and lovely scenic drives. This was a good year for fall color, and the red maples were glorious! It's a short ride to Vermont where we checked out Mt. Equinox for the first time. Highly recommend the drive to the top on a sunny, clear day."
Nancy C 4-night trip
Posted 2 hours ago
Berkshire Mountain Lodge
The Whitlock

The Whitlock

10/10 Excellent
"Nice location."
Beverly 2-night trip
Posted 3 hours ago
The Whitlock
The Yankee Inn

The Yankee Inn

10/10 Excellent
"This is a five star property. Wonderful breakfast. Indoor pool and hot tub. Convenient free parking. Comfortable bedroom with all the amenities. I recommend to anyone visiting the Lenox/Pittsfield area. Good restaurants nearby."
Hall 3-night trip
Posted 3 hours ago
The Yankee Inn
Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

8/10 Good
"The room was clean & the bed was comfortable. The area is very safe. They didn't have breakfast, just coffee. I will definitely stay here again."
Joan 1-night trip
Posted 4 hours ago
Howard Johnson by Wyndham Saugerties
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Unique and very thoughtfully thought through. Welcome bottle of wine, welcome drink, and breakfast were great! Wish the bar was open later and breakfast started earlier, but this is a minor thing. Would definitely stay there again."
Jeffrey 1-night trip
Posted 6 hours ago
The Cornell Inn, Lenox & The Berkshires
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

10/10 Excellent
"nice room"
RICHARD 1-night trip
Posted 8 hours ago
Quality Inn Lee - Lenox South
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent
"Genuinely amazing place run by amazing people. We had a bit of a incident happen while we stayed here which was to no fault of the staff or property. The staff was extremely helpful in getting it resolved, fixing our accomodations, and even offering us a refund. We had an amazing time in the small cozy cabin. The included amenities such as dryfirewood and starters, s'mores packs, tea, and coffee were a wonderful addition and made campfire much more enjoyable . The cabin was equiped with eat, drink, and cookware, and had everything we needed to enjoy our stay comfortably while still feeling like we were camping and enjoying the nature."
Sebastian 3-night trip
Posted 1 day ago
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Hotel On North

Hotel On North

10/10 Excellent
"Staff is awesome and this dog friendly hotel doesn’t feel dirty or different than any other boutique hotel."
Vicki 1-night trip
Posted 2 days ago
Hotel On North
Red Ranch Motel

Red Ranch Motel

8/10 Good
"They need longer curtains to keep the bright lights outside from entering the room, otherwise it was a great stay. Very nice, clean and friendly place."
brynda 1-night trip
Posted 3 days ago
Red Ranch Motel

More cheap stays in Hillsdale

FairBridge Inn Express

FairBridge Inn Express

16 Cheshire Road Pittsfield MA
₩94,243
₩105,270 total
Oct 26 - Oct 27
includes taxes & fees
5.4/10 (925 reviews)
FairBridge Inn Express
Quality Inn Great Barrington

Quality Inn Great Barrington

372 Main Street Great Barrington MA
₩100,274
₩112,005 total
Nov 12 - Nov 13
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
Quality Inn Great Barrington
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA
₩122,808
₩137,178 total
Nov 12 - Nov 13
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
Quality Inn Lee - Lenox South
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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

1055 South Street Pittsfield MA
₩131,225
₩146,578 total
Nov 22 - Nov 23
includes taxes & fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
The Yankee Inn

The Yankee Inn

461 Pittsfield Rd Lenox MA
₩140,625
₩157,079 total
Nov 1 - Nov 2
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
The Yankee Inn
St. Charles Hotel

St. Charles Hotel

16 Park Place Hudson NY
₩169,001
₩190,978 total
Nov 15 - Nov 16
includes taxes & fees
6.6/10 (1,000 reviews)
St. Charles Hotel

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.
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. 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.

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