The Berkshires Condo Rentals from CA $133

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Our top choices for The Berkshires condo rentals

A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

1. 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

Hancock

Jim H.

CA $458 total

includes taxes & fees

Sep 1 - Sep 2

Four people seated at a table with food and drinks, wearing winter sports helmets.

2. 2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

Hancock

J S.

CA $495 total

includes taxes & fees

Sep 9 - Sep 10

A calm lake with a wooden boat on the shore.

3. Cozy 3 bedroom condo 2.5 miles to Mount Snow

West Dover

Susan S.

CA $410 total

includes taxes & fees

Sep 8 - Sep 9

A spacious living area with a high ceiling, wooden beams, a fireplace, and a large wooden coffee table.

4. Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Dover

Evan C.

CA $502 total

includes taxes & fees

Aug 31 - Sep 1

A kitchen counter with a bottle of Cabernet Sauvignon, a feedback card, and a basket of fruits.

5. Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)

Dover

Emma C.

CA $817 total

includes taxes & fees

Aug 31 - Sep 1

6. Expansive 2BR | Sleeps 10 | Ski-In

West Dover

CA $813 total

includes taxes & fees

Aug 31 - Sep 1

7. 2BR Loft With Views | Ski-In Access

West Dover

CA $807 total

includes taxes & fees

Aug 31 - Sep 1

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Top The Berkshires Hotel Reviews

Berkshire Mountain Lodge

10/10 Excellent

"Good experience"

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent

"The room was very functional with desk, sitting area & bed. The front desk personnel were helpful & friendly. I was shocked how good the free breakfast was, definitely superior to most complimentary hotel breakfasts I've had elsewhere. I will stay there again when visiting family."

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!"

Find out more about The Berkshires

The Berkshires Condo Rentals information

Number of reviews	12,110
Accommodation	24 Condo Rentals
Lowest Price	CA $133
Highest Price	CA $311

Frequently asked questions

How much do condos in The Berkshires cost?

The price range for condos in The Berkshires is CA $133 to CA $311 per night. No matter your budget, you'll find someplace that suits your needs — as well as your entire squad! These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

How many condos are there in The Berkshires?

Explore our 24 condos in The Berkshires and then select your favorite. Whether you're embarking on a vacation with all the fam or kicking it with friends, your perfect stay is just clicks away.

Why book your condo in The Berkshires with Expedia?

Reserving a condo in The Berkshires is as easy as entering your travel dates and choosing a place that has what you need. On the lookout for something low cost or luxurious, or a stay that also offers a kitchenette? Use Expedia's search filters to narrow your results even further and find the perfect pad.

How can I find cheap condos in The Berkshires?

The quickest way to score cheap condos in The Berkshires is with Expedia's easy-to-use filter tool. Tailor your search results by amenities, budget and star rating to snag awesome prices in just a few clicks.

What is there to do in The Berkshires near my condo?

Whether you enjoy arts, culture, shopping or dining, The Berkshires offers the lot, and then some! The awesome city of Lenox boasts plenty of things to do and see, including Tanglewood Music Center, Shakespeare and Company and The Mount. If you're planning an escape to Williamstown, Chapin Library of Rare Books and Manuscripts, Hopkins Observatory and Williams College Museum of Art are must-do's.

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The Berkshires Vacation Rentals

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for The Berkshires condo rentals

1. 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2. 2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

3. Cozy 3 bedroom condo 2.5 miles to Mount Snow

4. Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities