Hillsdale Guest Houses

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Our top choices for Hillsdale guest houses

1. Hideaway Inn Lenox

Lenox

Leonardo

includes taxes & fees

9 Aug - 10 Aug

2. The Harlow House

Rhinebeck

Lauren

includes taxes & fees

10 Aug - 11 Aug

3. The Central Downtown Inn & Suites

Pittsfield

Rena

includes taxes & fees

3 Sept - 4 Sept

4. Berkshire Village Carriage House - Super Private!!

Lanesborough

Adam J

includes taxes & fees

31 Aug - 1 Sept

5. 9 Academy

Salisbury

Gina

includes taxes & fees

10 Aug - 11 Aug

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Top Hillsdale Hotel Reviews

Berkshire Mountain Lodge

8/10 Good

"We would come back here, even though there are quirky aspects to it that make it less than ideal. Overall, it's a good spot that seems like it was built in the fifties (has an old school vibe of a classic lodge), though it's only 20 years old.. What we liked: super clean, very spacious, a full kitchen, a comfortable bed, free parking, and a relatively reasonable rate. What needs improvement: We requested a quiet room and were put on the side where there is a noisy street. It was ok with earplugs. There is no housekeeping during the stay, which was fine for 3 nights, but would get old for longer. The door between the bedroom and living room needs to be fixed and didn't close fully. The toilet made a loud, running noise for 2 minutes with each flush. The handle on the fridge door broke off with normal use. We reported all of these, and none were addressed while we were there. The staff said they would send maintenance, but didn't, and didn't mention that they couldn't fix these items. Finally, we were charged a $22 resort fee that was supposed to include coffee. While they have a lovely espresso machine, no decaf was offered. As mentioned, even with the minor drawbacks, and knowing that it's more of a time share kind of place, where there's no sort of concierge service, it has many positive qualities that make it an overall good spot."

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

8/10 Good

"Stayed for two nights in a 2 bedroom villa. The place was very clean, beds and bedding were comfortable. The place could stand a refresh - more so the kitchen and bathrooms but not terribly awful by any means. The area of the property where we stayed was quiet and peaceful."

The Red Lion Inn

10/10 Excellent

"Escaped into another world on each floor's hallway-the memorabilia and artwork spoke of an honest, New England history. The atmosphere was perfect for a genuine, original immersion into New England's past and LOVED going up and down the 150yr old elevator! Meals delicious w/excellent service. Only one issue we had: the AC in the room was difficult to adjust and were quite chilled even w/turning the thermostat up to 80 deg!!!!!!!!! as suggested by the front desk. Shall make this a yearly visit!"

Quality Inn Great Barrington

10/10 Excellent

"Very nice front desk staff-courteous, upbeat, helpful. Room was clean but leftover trash in bin and no ice tray in refrigerator. VERY comfortable bed. Train in middle of the night was a throwback experience to a different age-i liked it but some would be frightened of the noise. Excellent location."

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