Berkshire County Short-Term Rentals from S$143: Search Holiday Rentals

A historic stone building with a yellow roof, surrounded by a white fence and lush green grass.

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Our top choices for Berkshire County holiday rentals

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

1. Berkshire Mountain Lodge

Pittsfield

Robert

includes taxes & fees

1 Oct - 2 Oct

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

2. Vacation Village in the Berkshires

Williamstown

Alex

includes taxes & fees

2 Sept - 3 Sept

A wooden cabin with a covered deck, a fire pit, and string lights.

3. Huttopia Berkshires

Williamstown

GEORGINA

includes taxes & fees

8 Sept - 9 Sept

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Top Berkshire County Hotel Reviews

Hotel On North

10/10 Excellent

"Location is a bit in the middle of nowhere, but all else is great at this hotel. Would recommend."

Berkshires Untold

10/10 Excellent

"Although an excellent 2-night stay, our comments are intended to make future stays even better. Room temperature: virtually impossible to maintain a comfort level. Basically it was too cold in spite of raising the thermostat temp. At 80 when the heat came on, it was much too hot! Room lighting: too dark; only the bathroom was well lit. Bathroom moisture: in the absence of a ventilation or fan, the bathroom remained damp after a shower and keeping the door open resulted in everything in the bedroom becoming damp. But the positives far outweigh these few items."

The Red Lion Inn

10/10 Excellent

"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"

Room 1

Change your mind

Treat yourself

Be picky

Our top choices for Berkshire County holiday rentals

1. Berkshire Mountain Lodge

2. Vacation Village in the Berkshires

3. Huttopia Berkshires

Find holiday rentals that suit your style

Top Berkshire County Hotel Reviews

Hotel On North

Holiday Inn Club Vacations Oak 'n Spruce Resort

Jiminy Peak Mountain Resort

Berkshire Mountain Lodge

Berkshires Untold

Quality Inn Great Barrington

The Red Lion Inn

Best Western Plus Berkshire Hills Inn & Suites

Hampton Inn & Suites Berkshires-Lenox

Berkshire County Holiday Rentals

Change your mind

Treat yourself

Be picky

Our top choices for Berkshire County holiday rentals

1. Berkshire Mountain Lodge

2. Vacation Village in the Berkshires

3. Huttopia Berkshires

Find holiday rentals that suit your style

Top Berkshire County Hotel Reviews

Hotel On North