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Choose from 1869 Hillsdale Hotel Deals
The Yankee Inn
"It’s easy to miss driving by. Building, parking area and pool are separated from the highway by a tree landscaped berm. The sign is small, tan-ish orange and partially hidden by trees on the berm. Made finding the entrance difficult. Once there, our stay was very enjoyable."
Reviewed on Jun 27, 2026
Berkshire Mountain Lodge
"The room in lobby were great. The big front porch was actually a nice thing to have, because the fire pit was closed (and the guy worked the front desk at night said he didn’t have a key to start it.) The bar was closed. The boutique was closed and there really wasn’t anywhere else you could go. ..."
Reviewed on Jun 26, 2026
Berkshires Untold
"I usually stay here and yes staff are nice and rooms are decent but I’ve seen a decline in amenities. Maybe the expense of things - bathrobe in room, water and snacks were what I was used to seeing .in the room."
Reviewed on Jun 25, 2026
The Red Lion Inn
"Staff"
Reviewed on Jun 27, 2026
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
"They thought of everything. We traveled with our pup, we had an incredible time."
Reviewed on Jun 25, 2026
Quality Inn Great Barrington
"No frills, great place to stay. Everything seems clean, there's a CVS right next to the hotel which is convenient. I gave them 4 stars because when we arrived (at 4am), no one was there to greet us. We waited around in the parking lot for a bit while we called other places and got on the phone with ..."
Reviewed on Jun 28, 2026
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
"Best hotel breakfast I have had in a long time. The breakfast attendant kept items well stocked. She made sure that vacated tables were cleaned and ready for the next guests to enjoy their meal. The room was kept very clean. I really enjoyed the fresh pancakes that were made to order by a pancake ..."
Reviewed on Jun 26, 2026
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
"Nice people"
Reviewed on Jun 22, 2026
Hotel On North
"Always a great experience at Hotel on North! Great, comfortable room with amazing bathroom. Helpful and friendly staff. Safe parking in the rear secured lot."
Reviewed on Jun 24, 2026
Quality Inn Lee - Lenox South
"All in all, it was a good value, but there was a male employee who was working when I checked in and whose behavior was similar to multiple people. I was ignored for over 10 minutes while he spoke on the phone. He issued me a card without asking for my ID and when I brought multiple packages in on ..."
Reviewed on Jun 27, 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel
"Had a wonderful 4 night stay at the Black Swan Inn. Location was great - close to Lenox and on a beautiful lake - I recommend booking a lakeside room."
Reviewed on Jun 26, 2026
FairBridge Inn Express
"Property definitely needs a facelift. Ground floor room is damp and rust behind toilet."
Reviewed on Jun 28, 2026
Find cheap hotels in Hillsdale
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