𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Hillsdale (2026)

Our top choices for Hillsdale hotels

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

The Brooks Motel

Hillsdale

Daljit

₹14,056 total

includes taxes & fees

8 Jun - 9 Jun

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

The Yankee Inn

Lenox

Mark

₹11,898 total

includes taxes & fees

17 Jun - 18 Jun

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

Monument Mountain Motel

Great Barrington

Mark

₹8,234 total

includes taxes & fees

14 Jun - 15 Jun

Shaker Mill Inn

West Stockbridge

Mervin

₹14,427 total

includes taxes & fees

10 Jun - 11 Jun

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Catskill

Sherwin

₹22,657 total

includes taxes & fees

16 Jun - 17 Jun

Quality Inn Great Barrington

Great Barrington

Braynd

₹10,063 total

includes taxes & fees

8 Jun - 9 Jun

The Little Lion

Great Barrington

Mia

₹9,416 total

includes taxes & fees

7 Jun - 8 Jun

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

₹11,888 total

includes taxes & fees

9 Jun - 10 Jun

Pleasant Valley Motel West Stockbridge

West Stockbridge

Olga V

₹6,585 total

includes taxes & fees

17 Jun - 18 Jun

Berkshire Travel Lodge

Austerlitz

Stacy

₹7,042 total

includes taxes & fees

17 Jun - 18 Jun

Berkshire Lake Lodge

Lee

₹13,665 total

includes taxes & fees

7 Jun - 8 Jun

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

Howard Johnson by Wyndham Lenox

Lenox

robert

₹8,453 total

includes taxes & fees

7 Jun - 8 Jun

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

FairBridge Inn Express

Pittsfield

Elie

₹7,303 total

includes taxes & fees

21 Jun - 22 Jun

Locust Tree Bed and Breakfast LLC

East Canaan

page

₹11,567 total

includes taxes & fees

10 Jun - 11 Jun

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

Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Heather

₹8,446 total

includes taxes & fees

8 Jun - 9 Jun

Wilder House Berkshires

Sheffield

Allison

₹20,627 total

includes taxes & fees

7 Jun - 8 Jun

Berkshires Untold

Lenox

Thomas

₹13,361 total

includes taxes & fees

7 Jun - 8 Jun

Berkshire Inn

Pittsfield

Brian

₹8,963 total

includes taxes & fees

17 Jun - 18 Jun

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

Pittsfield

Kathleen

₹14,446 total

includes taxes & fees

14 Jun - 15 Jun

The Red Lion Inn

Stockbridge

molly

₹21,393 total

includes taxes & fees

22 Jun - 23 Jun

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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."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Wonderful hidden gem of a little hotel. Right on lake laurel we had a beautiful lake view. Rooms were very clean. Decent breakfast. Well Located and close to Lee downtown main st, the Lennox Main Street and Stockbridge as well. Looking forward to returning"

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

₹9,009

₹10,063 total

8 Jun - 9 Jun

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 traveller data. Two other options for your trip 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! Most hotel reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before check in. If you have a non-refundable reservation, you might be able to still cancel and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Hillsdale.

What's the best dog-friendly place to stay in Hillsdale?

The Brooks Motel is a top dog-friendly option for your stay. See more pet-friendly hotel accommodations in Hillsdale.

What are some accommodation options 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 that feature an on-site pool. View all hotels with pools in Hillsdale.

What's it like staying in Hillsdale?

Visitors can enjoy all that Hillsdale has to offer, including the coffee shops and ski areas. This city also attracts tourists with its relaxing and quaint setting. In Hillsdale, there are 67 hotels and other accommodation options to choose from. Find out more about Hillsdale.

What should I see while I'm in 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 itinerary are Catamount Aerial Adventure Park and Catamount Ski Area. Take a look at what more there is to see and do in Expedia's Hillsdale guide.

What's the seasonal weather in Hillsdale?

The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Hillsdale are January, March, February and November, with each month seeing an average of 18 cm 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

Explore a world of travel with Expedia

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