The Berkshires Vacation Rentals from $118: Search Short-Term Rentals

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Our top choices for The Berkshires vacation rentals

1. Berkshire Mountain Lodge

Pittsfield

Robert

$125 nightly

Aug 31 - Sep 1

Total with taxes and fees

2. Vacation Village in the Berkshires

Williamstown

Alex

$106 nightly

Sep 7 - Sep 8

Total with taxes and fees

3. Huttopia Berkshires

Williamstown

GEORGINA

$108 nightly

Sep 8 - Sep 9

Total with taxes and fees

4. Cozy 1-bedroom studio in serene Great Barrington with AC

Great Barrington

bob i.

$148 nightly

Sep 7 - Sep 8

Total with taxes and fees

5. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Dalton

Megan A.

$293 nightly

Aug 31 - Sep 1

Total with taxes and fees

6. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Hancock

Maura D.

$230 nightly

Sep 1 - Sep 2

Total with taxes and fees

7. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Sherwood Forest

Sharon K.

$340 nightly

Sep 9 - Sep 10

Total with taxes and fees

8. 2-Bdr Apt In Town, By the Water

Williamstown

Thomas

$263 nightly

Sep 14 - Sep 15

Total with taxes and fees

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Top The Berkshires Hotel Reviews

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."

Berkshire Mountain Lodge

8/10 Good

"the good….full kitchen, living room, king bedroom, clean bathroom, VERY reasonable nightly rate, especially for central berkshire county in the summer. there is no daily room cleaning, but extra towels, etc are always available from the front desk… the less than good…we’ve stayed here now u time in the past 18 months, but the last couple of stays the rooms have been a little musty and damp, despite (or because of?) the a/c being on constantly. ya gotta hold the handle down on the toilet to get a complete flush. no food service, but the is a stop&shop literally across the street… i would still recommend BML for the room rate and location alone…"

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

Everything you need to know about The Berkshires vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the The Berkshires vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect The Berkshires vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

The Berkshires vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in The Berkshires. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit The Berkshires in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $118 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on The Berkshires rentals

At Expedia, we put the best The Berkshires vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top The Berkshires rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream The Berkshires vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around The Berkshires. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Our top choices for The Berkshires vacation rentals

1. Berkshire Mountain Lodge

2. Vacation Village in the Berkshires

3. Huttopia Berkshires

4. Cozy 1-bedroom studio in serene Great Barrington with AC

5. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

6. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

7. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

8. 2-Bdr Apt In Town, By the Water

9. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

10. Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

11. Home in Great Barrington

12. Real Estate: Therapy - Lake, Laundry, Love it

13. WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

14. Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature

15. stylish Berkshires Retreat

16. Cozy Riverside Berkshires Retreat

17. Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

18. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

19. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

20. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

Find vacation rentals that suit your style

Top The Berkshires Hotel Reviews

Berkshires Untold

The Yankee Inn

Vacation Village in the Berkshires

Quality Inn Great Barrington

Berkshire Mountain Lodge

Holiday Inn Club Vacations Oak 'n Spruce Resort

Hotel On North

The Red Lion Inn

The Cornell Inn, Lenox & The Berkshires

Find out more about The Berkshires

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Expedia's Latest Trends