The Berkshires Vacation Rentals from $126: Search Short-Term Rentals

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Our top choices for The Berkshires vacation rentals

1. Vacation Village in the Berkshires

Williamstown

Sarah

$122 nightly

Sep 13 - Sep 14

Total with taxes and fees

2. Berkshire Mountain Lodge

Pittsfield

Robert

$113 nightly

Oct 1 - Oct 2

Total with taxes and fees

3. Riverside Retreat in the Berkshires

Great Barrington

Colin E.

$282 nightly

Sep 21 - Sep 22

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

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

Great Barrington

Shelly B.

$148 nightly

Sep 27 - Sep 28

Total with taxes and fees

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

Sherwood Forest

Frank M.

$370 nightly

Sep 15 - Sep 16

Total with taxes and fees

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

Sherwood Forest

Sharon K.

$335 nightly

Sep 14 - Sep 15

Total with taxes and fees

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

Dalton

Allie T.

$357 nightly

Sep 19 - Sep 20

Total with taxes and fees

8. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington

Rebecca K.

$1,189 nightly

Sep 12 - Sep 13

Total with taxes and fees

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

Otis

$306 nightly

Sep 14 - Sep 15

Total with taxes and fees

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

Hancock

Maura D.

$206 nightly

Sep 14 - Sep 15

Total with taxes and fees

11. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stockbridge

Anonymous traveler

$766 nightly

Sep 28 - Sep 29

Total with taxes and fees

12. Home in Great Barrington

Great Barrington

HEATHER G.

$276 nightly

Sep 15 - Sep 16

Total with taxes and fees

Beach nearby, sun loungers, beach towels

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

Great Barrington

Kristin O.

$297 nightly

Oct 12 - Oct 13

Total with taxes and fees

14. Treetop Hideaway in Tyringham

Monterey

"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "

Samantha G.

$546 nightly

Sep 21 - Sep 22

Total with taxes and fees

15. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Hinsdale

Kyle R.

$386 nightly

Sep 13 - Sep 14

Total with taxes and fees

3 bedrooms, iron/ironing board, WiFi, bed sheets

16. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Great Barrington

Mary R.

$495 nightly

Sep 14 - Sep 15

Total with taxes and fees

17. Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic

Peter S.

$285 nightly

Sep 25 - Sep 26

Total with taxes and fees

18. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

$365 nightly

Sep 28 - Sep 29

Total with taxes and fees

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

North Adams

Ruthie K.

$278 nightly

Sep 12 - Sep 13

Total with taxes and fees

20. New Studio In Town, By the Water

Williamstown

Lydia J.

$240 nightly

Sep 13 - Sep 14

Total with taxes and fees

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Top The Berkshires Hotel Reviews

The Whitlock

10/10 Excellent

"My husband and I enjoyed our two-night stay at The Whitlock. This historical inn was well located in town and very walkable. The bed was comfortable, bathroom updated, quiet and when we did encounter staff, Logan and Mary Ann, they were incredibly pleasant and helpful. Thank you for your hospitality."

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good

"The temp was 67 degrees in our unit. I called the front desk and they sent someone immediately however who couldn’t get the heat to turn on. The thermostat was not set to turn on until later in the month. The owner must likely to blame for a lack of heat."

Jiminy Peak Mountain Resort

10/10 Excellent

"My family had a wonderful time at Jiminy Peak Mountain Resort! The staff truly cared about making sure we had a great stay. When we had a last-minute change and needed to upgrade our room, they handled everything so seamlessly and were incredibly accommodating. The space we received was much larger than we expected, with four floors, three bedrooms, two bathrooms, and three pull-out sofas. There was more than enough room for our whole family to stay comfortably, and it was very affordable for the amount of space and amenities we received. They were also very generous with towels and blankets. Although we didn’t end up using everything, it was reassuring to know that plenty was available if we needed more. The view from the backyard was beautiful, and the resort attractions were only minutes away. We especially enjoyed the scenic chairlift ride and mountain coaster. Everyone in our family, from old to young, had a great time. Overall, it was a wonderful and very affordable family getaway. We really appreciated the hospitality, spacious accommodations, beautiful surroundings, and activities for all ages. We would definitely recommend Jiminy Peak Mountain Resort!"

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 $126 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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Check prices for these dates

Our top choices for The Berkshires vacation rentals

1. Vacation Village in the Berkshires

2. Berkshire Mountain Lodge

3. Riverside Retreat in the Berkshires

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

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

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

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

8. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

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

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

11. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

12. Home in Great Barrington

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

14. Treetop Hideaway in Tyringham

15. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

16. Cozy. Clean. Free bagel shop. 3 Fireplaces.

17. Sweet Cozy Victorian in Housatonic. Close to everything.

18. Cheerful 3-bedroom cottage with woodstove

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

20. New Studio In Town, By the Water

Find vacation rentals that suit your style

Top The Berkshires Hotel Reviews

The Whitlock

Find out more about The Berkshires

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