Top 10 Hotels in Hillsdale, NY from ₩112,764 - Competitive Prices

Our top choices for Hillsdale hotels

Egyptian cotton sheets, premium bedding, memory foam beds, desk

The Brooks Motel

Hillsdale

Daljit

₩239,441 total

includes taxes & fees

Jun 7 - Jun 8

Superior Room, 1 King Bed, Jetted Tub | Jetted tub

The Yankee Inn

Lenox

Mark

₩336,896 total

includes taxes & fees

Jun 19 - Jun 20

Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

Great Barrington

Mark

₩131,736 total

includes taxes & fees

Jun 8 - Jun 9

Shaker Mill Inn

West Stockbridge

Mervin

₩253,858 total

includes taxes & fees

Jun 10 - Jun 11

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Catskill

Sherwin

₩362,474 total

includes taxes & fees

Jun 16 - Jun 17

Quality Inn Great Barrington

Great Barrington

Braynd

₩160,992 total

includes taxes & fees

Jun 9 - Jun 10

The Little Lion

Great Barrington

Mia

₩150,641 total

includes taxes & fees

Jun 7 - Jun 8

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk

Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Anandaraja

₩190,355 total

includes taxes & fees

Jun 8 - Jun 9

Pleasant Valley Motel West Stockbridge

West Stockbridge

Olga V

₩107,595 total

includes taxes & fees

Jun 7 - Jun 8

Berkshire Travel Lodge

Austerlitz

Stacy

₩112,764 total

includes taxes & fees

Jun 6 - Jun 7

Berkshire Lake Lodge

Lee

₩228,788 total

includes taxes & fees

Jun 7 - Jun 8

In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Lenox

robert

₩135,236 total

includes taxes & fees

Jun 7 - Jun 8

Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

Pittsfield

Elie

₩121,714 total

includes taxes & fees

Jun 21 - Jun 22

Locust Tree Bed and Breakfast LLC

East Canaan

page

₩185,053 total

includes taxes & fees

Jun 9 - Jun 10

In-room safe, desk, free cribs/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Heather

₩135,236 total

includes taxes & fees

Jun 7 - Jun 8

Wilder House Berkshires

Sheffield

Allison

₩330,007 total

includes taxes & fees

Jun 7 - Jun 8

Berkshires Untold

Lenox

Thomas

₩213,751 total

includes taxes & fees

Jun 8 - Jun 9

Berkshire Inn

Pittsfield

Brian

₩147,199 total

includes taxes & fees

Jun 8 - Jun 9

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

Pittsfield

Kathleen

₩231,106 total

includes taxes & fees

Jun 14 - Jun 15

The Red Lion Inn

Stockbridge

molly

₩347,845 total

includes taxes & fees

Jun 22 - Jun 23

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Stay near popular Hillsdale attractions

Catamount Aerial Adventure Park

3.2/5 (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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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

Red and Green Norway Maple Trees and Wood Fence

Top Hillsdale Hotel Reviews

Howard Johnson by Wyndham Saugerties

8/10 Good

"Rooms were clean property was dated."

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"I went on a solo cabin trip and it was so relaxed and peaceful! The condition of the cabin was better than I expected it to be and the staff were super friendly and accommodating. Definitely plan to go again next year! The cabin had so many supplies from cooking material, mini fridge (no freezer portion), lighters, books, games, stereo! I will say if you're able to rent a car, please do so. It was easy to Uber from New York City to the property, but to get an Uber back into the city was very hard. I ended up calling a taxi service. Lesson learned lol"

The Whitlock

8/10 Good

"We had a late arrival, which worked out with self checkout. Left the next morning after 9am, didn't see a single staff member during our whole stay, Was a bit of a challenge getting luggage up to the top floor without an elevator but we probably should have realized that when we booked. Nice property, nice big room with separate area for visiting. TV channel choices, which included streaming services, was excellent. Overall a good experience, just didn't see anyone there."

Berkshires Untold

8/10 Good

"Here’s what we liked: If we were just reviewing BERKSHIRES UNTOLD based on the staff, we’d be giving it a 5. The staff were extremely friendly, helpful and gracious. When we asked for extra towels and requested a room change, they accommodated those requests immediately. After we switched rooms they checked to see if we were happier. This is exactly the kind of service you want in a hotel or inn. Other good things - The bed was comfortable and there was enough counter space in the bathroom and at the desk area. We also liked that there was a breakfast seating area, bar and small indoor seating area plus outdoor seating with gas fire pits. So, why are we giving the place a 3 overall? It really needed more attention to detail. The carpet in our original room was not in good shape and the fitted bed sheet had a small rip on my side. Some of the room furniture was dinged up and a sofa in the common seating area had some shredded fabric. One thing we didn’t like (that they couldn’t exactly help) was that we were there on a late spring wedding weekend, so there were buses idling in front of our room with loud talkers and smokers nearby. It felt like they were in our room along with the smoke and fumes. The trend of turning motels into better motels is interesting. They’re less expensive and are sometimes more original. But you’re still in a motel. If you value soundproofing and consistently better quality, a mid range chain may be a better choice."

Berkshire Mountain Lodge

10/10 Excellent

"We love the Bershire Mountain Lodge. We've stayed here five other times but this time we do have a few very minor negatives. 1) The cabinet door under the kitchenette sink had a loose hinge. We messaged the staff and requested that they wait until after we checked out to repair the hinge. We hope the hinge was repaired before the next guest checked in. 2) The toilet flush handle was slightly cracked but still functional. We forgot to notify the staff; it was barely noticeable. 3) The guest or owner in the room above our room walked very loudly. We were used to hearing noises from people walking in the hall but this was our first time hearing footsteps through the ceiling. Other than those three items, our stay was excellent. The front desk staff were courteous and helpful. The housekeeping crew were unobtrusive. The long driveway to the ample parking lot gives enough distance from the busy"

More cheap stays in Hillsdale

Quality Inn Great Barrington

372 Main Street Great Barrington MA

₩144,134

₩160,992 total

Jun 9 - Jun 10

includes taxes & fees

8.6/10 Excellent! (1,001 reviews)

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 Berkshires Untold and The Yankee Inn. 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. The Yankee Inn 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 67 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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Our top choices for Hillsdale hotels

The Brooks Motel

The Yankee Inn

Monument Mountain Motel

Shaker Mill Inn

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Quality Inn Great Barrington

The Little Lion

Best Western Plus Berkshire Hills Inn & Suites

Pleasant Valley Motel West Stockbridge

Berkshire Travel Lodge

Berkshire Lake Lodge

Howard Johnson by Wyndham Lenox

FairBridge Inn Express

Locust Tree Bed and Breakfast LLC

Travelodge by Wyndham Great Barrington Berkshires

Wilder House Berkshires

Berkshires Untold

Berkshire Inn

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

The Red Lion Inn

Stay near popular Hillsdale attractions

Catamount Aerial Adventure Park

Learn more about Hillsdale

Top Hillsdale Hotel Reviews

Howard Johnson by Wyndham Saugerties

More cheap stays in Hillsdale

Quality Inn Great Barrington

Frequently asked questions

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