Hillsdale, NY Guest Houses from AED 406

A rural landscape with snow-covered fields, a winding road, and scattered trees.

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Our top choices for Hillsdale guest houses

1. Hideaway Inn Lenox

Lenox

Jeannie

AED 551 total

includes taxes & fees

8 Sep - 9 Sep

Classic Room, 1 King Bed, Balcony | WiFi (free)

2. The Harlow House

Rhinebeck

Lauren

AED 780 total

includes taxes & fees

8 Sep - 9 Sep

3. The Central Downtown Inn & Suites

Pittsfield

Rena

AED 406 total

includes taxes & fees

9 Sep - 10 Sep

The Garden Suite | 1 bedroom, Egyptian cotton sheets, premium bedding, pillowtop beds

4. 9 Academy

Salisbury

Gina

AED 2,483 total

includes taxes & fees

14 Sep - 15 Sep

5. Berkshire Village Carriage House - Super Private!!

Lanesborough

Maya H.

AED 845 total

includes taxes & fees

17 Sep - 18 Sep

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Top Hillsdale Hotel Reviews

Hotel On North

10/10 Excellent

"Super cool hotel!!"

The Yankee Inn

10/10 Excellent

"On an overpriced holiday weekend in the Berkshires, Yankee Inn was a great balance of price and amenities. The indoor pool was nicer than most, and the hot tub was great. Outdoor pool was a bit oddly placed between the parking lot and the main road, but nice as well. Both very clean. Room was spacious and clean, beds were comfortable, though I think they were doubles rather than queens. The included breakfast was on the very good end of standard - the fruit was fresh and delicious, there were both eggs and waffles, plus cereal, yogurt, bacon/sausage. Meh on the pastries, and the coffee was terribly watery. My true only gripe is that there was truly not a single place to hang wet bathing suits that didn't result in them dripping all over the floor. Had we been on the 2nd floor, we would have had an outside railing, but on the first floor there was none. With 4 people using the pool and hot tub, it was an annoyance. Overall, great place for a quick stay."

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"It’s as beautiful as described online. We love the views and all the stuff provided, even though it’s a very compact cabin setting. Every thing is good. Only one thing scared me is some ants and small insects suddenly came out from no where. Outside has mosquitoes. But if you remember it’s in a nature forest, then they should be normal. Staff are very caring and thoughtful. They provide everything we need, and even more. We are very thankful for this opportunity to be there for enjoy."

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Hillsdale guest houses

1. Hideaway Inn Lenox

2. The Harlow House

3. The Central Downtown Inn & Suites

4. 9 Academy

5. Berkshire Village Carriage House - Super Private!!

Top Hillsdale Hotel Reviews

Hotel On North

Berkshire Mountain Lodge

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Yankee Inn

Berkshires Untold

Quality Inn Lee - Lenox South

The Whitlock

FairBridge Inn Express

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

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Search Guest Houses in Hillsdale

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Hillsdale guest houses

1. Hideaway Inn Lenox

2. The Harlow House

3. The Central Downtown Inn & Suites

4. 9 Academy

5. Berkshire Village Carriage House - Super Private!!

Top Hillsdale Hotel Reviews

Hotel On North

Explore a world of travel with Expedia