Hotels in Hillsdale

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January 2026

February 2026

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Where to stay in Hillsdale?

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

The Brooks Motel

Hillsdale

Ski lodge convenience near winter sports with comfy rooms and free amenities.

Little Cat Lodge

Copake Falls

Rustic alpine charm by the Catskills with a Nordic-inspired restaurant and sauna.

Prospect Berkshires

Egremont

Relax amid tranquil woods at a Great Barrington retreat with spa services and dining.

CNY1,890 total

includes taxes & fees

Jan 26 - Jan 27

the Alander

Copake

Serene Copake lodge surrounded by natural beauty with American dining onsite.

CNY1,095 total

includes taxes & fees

Jan 19 - Jan 20

Quality Inn Great Barrington

Great Barrington

Explore the serene setting of Great Barrington with hiking trails and ski slopes nearby.

CNY590 total

includes taxes & fees

Jan 21 - Jan 22

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

Monument Mountain Motel

Great Barrington

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

Located in Great Barrington with free breakfast, WiFi, and parking for easy explorations.

CNY765 total

includes taxes & fees

Jan 25 - Jan 26

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

Rest peacefully near Housatonic River with soundproof rooms and complimentary perks.

CNY1,054 total

includes taxes & fees

Jan 25 - Jan 26

Individually decorated, individually furnished, desk, laptop workspace

Granville House

Housatonic

Relax in a cozy Housatonic B&B with complimentary breakfast and nearby attractions.

CNY1,357 total

includes taxes & fees

Jan 20 - Jan 21

Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

East Rock Inn

Great Barrington

Set in Great Barrington with hiking trails and river access just moments away.

CNY1,017 total

includes taxes & fees

Jan 22 - Jan 23

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

Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

CNY585 total

includes taxes & fees

Jan 20 - Jan 21

The Little Lion

Great Barrington

Restful home base near Monument Mountain with easy access to outdoor adventures.

CNY858 total

includes taxes & fees

Jan 20 - Jan 21

Deluxe Room, 1 King Bed, Ensuite (2nd Floor) | Premium bedding, individually decorated, individually furnished, desk

Changing Times Boutique Country Lodging

Craryville

Tranquil B&B near outdoor adventures with easy access to state parks.

CNY1,173 total

includes taxes & fees

Jan 14 - Jan 15

Wilder House Berkshires

Sheffield

Stay at a charming Sheffield B&B with a convenient weekend breakfast service.

Desk, laptop workspace, blackout drapes, iron/ironing board

Pleasant Valley Motel West Stockbridge

West Stockbridge

Charming Berkshires motel near Tanglewood with free WiFi and convenient parking.

CNY498 total

includes taxes & fees

Jan 20 - Jan 21

Shaker Mill Inn

West Stockbridge

Escape to the scenic Berkshires with free breakfast and outdoor activities nearby.

CNY836 total

includes taxes & fees

Jan 13 - Jan 14

Berkshire Travel Lodge

Austerlitz

CNY528 total

includes taxes & fees

Jan 20 - Jan 21

Suite, Private Bathroom (RedBird Suite) | View from room

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Stockbridge

Unwind in a luxurious B&B just minutes from Norman Rockwell Museum.

CNY3,227 total

includes taxes & fees

Jan 21 - Jan 22

The Red Lion Inn

Stockbridge

CNY1,484 total

includes taxes & fees

Jan 14 - Jan 15

Micosta Leisure Inn

Hudson

Relax in Hudson with a garden retreat just minutes from local attractions.

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Budget hotels in Hillsdale and vicinity

Monument Mountain Motel

Great Barrington

Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

CNY585 total

includes taxes & fees

Jan 20 - Jan 21

Suite, Multiple Beds (2 Queen Beds with Sofa bed) | Pillowtop beds, in-room safe, desk, iron/ironing board

Holiday Inn Express Hotel & Suites West Coxsackie by IHG

West Coxsackie

CNY717 total

includes taxes & fees

Jan 25 - Jan 26

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

Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

CNY596 total

includes taxes & fees

Feb 8 - Feb 9

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

CNY765 total

includes taxes & fees

Jan 25 - Jan 26

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

CNY733 total

includes taxes & fees

Jan 10 - Jan 11

The Yankee, Trademark Collection by Wyndham

Lenox

CNY789 total

includes taxes & fees

Jan 15 - Jan 16

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

CNY763 total

includes taxes & fees

Jan 28 - Jan 29

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Go beyond your typical stay in Hillsdale

Spa

Hot tub

Top landmarks in Hillsdale

Catamount Aerial Adventure Park

3.0/5 (2 reviews)

Catamount Aerial Adventure Park is 2.2 mi (3.5 km) from central Hillsdale, why not stop by during your stay.

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Copake Lake

Copake Lake is 0.7 mi (1.2 km) from central Copake Lake, why not stop by during your stay.

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Learn more about Hillsdale

Hillsdale is well-known for its attractions such as Catamount Aerial Adventure Park and Catamount Ski Area. The city has something for everyone including sights like Copake Lake and Hillsdale Town Hall within a small-town setting.

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Red and Green Norway Maple Trees and Wood Fence

Check out reviews of Hillsdale hotels guests love

Berkshire Mountain Lodge

10/10 Excellent

"Great staff, clean comfortable room. "

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"The staff were very nice, the room was clean and generally pleasant. the beds were not bad. They provide a continental-style breakfast, which is something. They are also dog-friendly! And there is a wonderful Indian restaurant that is adjacent to the hotel, and it is good! The only negative was a bit of mold, presumably causing some sinus issues, but that is to be expected in a hotel right on a lake like this. Otherwise, we would certainly stay there again."

Frequently asked questions

How much does a hotel room cost in Hillsdale?

You can discover great hotels in Hillsdale from CNY498 with properties to suit all budgets and needs. To find an affordable hotel in Hillsdale that meets all of your requirements, just apply filters on Hotels.com and sort hotels by "Price: low to high".

How can I find deals and earn rewards at Hillsdale hotels?

Discover great deals on Hillsdale hotel stays with Hotels.com. Take a look at hotel prices mid-week or during the low season as to find those off-peak deals. If it's a spontaneous trip, check out our last-minute deals on Hillsdale hotels.

Can I book Hillsdale hotels with free cancellation?

In order to book a refundable Hillsdale hotel, simply filter hotels by "Property cancellation options" and select "Fully refundable property". Many hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.

What are some popular hotels in central Hillsdale?

If you're looking for hotels in central Hillsdale, check out Prospect Berkshires and The Egremont Village Inn. Travelers love Prospect Berkshires for its location, as well as the outdoor pool, restaurant and bar/lounge this hotel offers. The Egremont Village Inn is another popular central inn with a restaurant, a bar/lounge and a coffee shop/cafe.

What accommodations do travelers recommend in Hillsdale?

The Brooks Motel is an accommodation that is popular with guests.

Can I book a refundable accommodation in Hillsdale?

If you want the flexibility to change your travel plans to Hillsdale, most hotels offer refundable* rates you can book. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.

Where can I stay in Hillsdale if I want a vacation home instead of a traditional hotel?

If you want to find a good alternative to a hotel, review our selection of 51 vacation homes.

What will the weather in Hillsdale be like during my vacation?

The warmest months in Hillsdale are usually July and August with an average temp of 68°F. January and February are the chilliest months when the average temp is 29°F. The rainiest months are October and August.

Why should I book my Hillsdale accommodation with Hotels.com?

There are plenty of reasons to book your Hillsdale travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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