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Featured Hillsdale 3 Star hotels

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Feb 1 to Feb 2
CA $135
CA $182 total
Feb 1 - Feb 2
includes taxes & fees
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (818 reviews)
Great kitchen! Helpful staff, very convenient location.

Reviewed on Jan 21, 2026

Opens in a new windowBerkshire Mountain Lodge
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Fully refundable
The price is CA $134 per night from Jan 30 to Jan 31
CA $134
CA $150 total
Jan 30 - Jan 31
includes taxes & fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (1,001 reviews)
generally good

Reviewed on Jan 19, 2026

Opens in a new windowHoliday Inn & Suites Pittsfield-Berkshires by IHG
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is CA $121 per night from Jan 27 to Jan 28
CA $121
CA $135 total
Jan 27 - Jan 28
includes taxes & fees
Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
9/10 Wonderful! (842 reviews)
Loved everything about our stay, the hotel and staff! From the body lotion to the room decor, the quiet to the ease of check in and out, it was all really lovely with perfect chill vibes and warm atmosphere. Looking forward to our next visit.

Reviewed on Jan 20, 2026

Opens in a new windowBerkshires Untold
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street South Lee MA
Fully refundable
The price is CA $165 per night from Jan 28 to Jan 29
CA $165
CA $211 total
Jan 28 - Jan 29
includes taxes & fees
Book a stay at this family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in ...
9/10 Wonderful! (824 reviews)
Staff was wonderful. Rooms were very well stocked The kids loved the game room and dvd borrowing

Reviewed on Jan 19, 2026

Opens in a new windowHoliday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from Jan 28 to Jan 29
CA $208
CA $294 total
Jan 28 - Jan 29
includes taxes & fees
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
8.6/10 Excellent! (1,003 reviews)
The room was spotless. There was everything we needed in the hotel. Our dinner at the tavern was incredible and then we went down to the Lion’s Den and had a great time. Every staff member was polite and helpful. The cleaning staff were great.

Reviewed on Jan 19, 2026

Opens in a new windowThe Red Lion Inn
Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is CA $204 per night from Jan 27 to Jan 28
CA $204
CA $228 total
Jan 27 - Jan 28
includes taxes & fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (819 reviews)
It can be hard trying to choose a place to stay lately, especially since AI has blown up. I'm so happy I gave this place a chance. The staff was extremely friendly and helpful. Not once did I feel like they didn't want to be there. When we checked out at noon (which is an amazing checkout time), ...

Reviewed on Jan 18, 2026

Opens in a new windowHotel On North
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St Lee MA
Fully refundable
The price is CA $139 per night from Feb 4 to Feb 5
CA $139
CA $155 total
Feb 4 - Feb 5
includes taxes & fees
Stay at this hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions ...
9/10 Wonderful! (1,001 reviews)
The staff is super friendly and accommodating. The location is quiet. We stayed during the winter, but the lake view from the restaurant and breakfast area were really nice. The hotel was well kept and clean. We’ll definitely stay there again.

Reviewed on Jan 19, 2026

Opens in a new windowThe Black Swan Lee - Lenox, an Ascend Collection Hotel
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3 out of 5
70 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is CA $201 per night from Feb 1 to Feb 2
CA $201
CA $225 total
Feb 1 - Feb 2
includes taxes & fees
Book a stay at this business-friendly hotel in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (598 reviews)
Large clean room and bathroom

Reviewed on Jan 12, 2026

Opens in a new windowCourtyard by Marriott Lenox Berkshires
Interlaken Inn & Resort

Interlaken Inn & Resort

3.5 out of 5
74 Interlaken Road Lakeville CT
The price is CA $245 per night from Jan 27 to Jan 28
CA $245
CA $282 total
Jan 27 - Jan 28
includes taxes & fees
Book a stay at this spa hotel in Lakeville. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Holley-Williams House Museum and Harney and ...
8/10 Very Good! (276 reviews)
Quiet and beautiful environment. Room is clean. Friendly and helpful front desk staff.

Reviewed on Jan 18, 2026

Opens in a new windowInterlaken Inn & Resort
 Diamond Mills Resort

Diamond Mills Resort

3.5 out of 5
25 South Partition Street Saugerties NY
The price is CA $368 per night from Feb 1 to Feb 2
CA $368
CA $447 total
Feb 1 - Feb 2
includes taxes & fees
Book a stay at this spa hotel in Saugerties. Enjoy free WiFi, a full-service spa, and room service. Our guests praise the helpful staff in our reviews. Popular ...
9.2/10 Wonderful! (354 reviews)
The view can’t be beaten.

Reviewed on Jan 16, 2026

Opens in a new window Diamond Mills Resort
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3 Star Hotels Hillsdale

Maybe you’ve got to travel for work, or perhaps you’re finally ready to book that much-deserved vacation—regardless, it’s time for you to get on a plane and you’re going to make the most of it. You’ve traveled enough to know how important a comfy bed and room service can be, so booking a hotel with all the amenities you need is a priority.

You can find 3 star hotels in Hillsdale that keep you close to all the great sightseeing and activities around the area, or even book a place that’s a bit more secluded, if that’s what you prefer. No matter what you’re looking for—whether you’re all about the location or are invested in on-site perks--Travelocity will help you find the accommodation that works best for you.

When it comes to options, you’ll have them. The Hillsdale 3 star hotels give you plenty of choices as far as access to the best areas, and many also offer a breakfast buffet, as well as plenty of other amenities like high-speed Wi-Fi and an on-site pool or spa.

Whatever you’re looking for on your next getaway, browse Travelocity’s big selection of hotels to ensure you get the best possible deal. Book one of the best 3 star hotels in Hillsdale today!

Recent Hillsdale hotel reviews by fellow wanderers