The Berkshires Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for The Berkshires vacation rentals

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,406 reviews)
"Property is great and stay was great"
United States
Isha
$129 nightly
The price is $144
Jun 25 - Jun 26
Total with taxes and fees
Vacation Village in the Berkshires

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
9.4 out of 10, Exceptional, (10 reviews)
"Healthy food too!"
United States
GEORGINA
$128 nightly
The price is $143
Jun 24 - Jun 25
Total with taxes and fees
Huttopia Berkshires

2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.0 out of 10, Wonderful, (13 reviews)
"Location was very good-close to campus. Host was responsive. Accommodations were just right"
United States
Dan R.
$252 nightly
The price is $283
Jun 24 - Jun 25
Total with taxes and fees
2-Bdr Apt In Town, By the Water

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

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
United States
Maura D.
$223 nightly
The price is $249
Jun 23 - Jun 24
Total with taxes and fees
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

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

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
North Adams
$167 nightly
The price is $187
Jun 23 - Jun 24
Total with taxes and fees
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
10.0 out of 10, Exceptional, (8 reviews)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
$249 nightly
The price is $280
Jun 29 - Jun 30
Total with taxes and fees
Downtown | Waterfront | Walk to Shops

New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (13 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
$235 nightly
The price is $264
Jun 29 - Jun 30
Total with taxes and fees
New Studio In Town, By the Water

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

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Hancock
9.6 out of 10, Exceptional, (17 reviews)
"Host very responsive. I gave feedback that could make stay better like more hangars and some coat hooks. Massage chair in unit was a hit with the whole family.Unit is literally the last unit in last builing of Coubtry Inn away from ski school and Express lift. Still walkable, just not in ski boots.Parking in front of unit super easy.No elevator nearby. Upstairs with luggage. "
United States
Joe C.
$223 nightly
The price is $249
Jun 23 - Jun 24
Total with taxes and fees
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock
10.0 out of 10, Exceptional, (12 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
$223 nightly
The price is $249
Jun 23 - Jun 24
Total with taxes and fees
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

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

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$333 nightly
The price is $372
Jun 23 - Jun 24
Total with taxes and fees
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

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

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Hancock
9.0 out of 10, Wonderful, (17 reviews)
"Great stay! Perfect location by the pool and nicely renovated as advertised!"
United States
Matthew B.
$230 nightly
The price is $256
Jun 23 - Jun 24
Total with taxes and fees
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

Charming Apt in 18th c Berkshire Farmhouse

Charming Apt in 18th c Berkshire Farmhouse
Lanesborough
9.4 out of 10, Exceptional, (40 reviews)
"Clean, friendly, but isolated. On premises coffee shop was a bonus."
United States
Karl K.
$188 nightly
The price is $206
Jul 16 - Jul 17
Total with taxes and fees
Charming Apt in 18th c Berkshire Farmhouse

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (3 reviews)
"Stayed one night at one of my favorite ski spots. Will be back again!"
United States
Neil J.
$223 nightly
The price is $249
Jun 23 - Jun 24
Total with taxes and fees
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

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

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (38 reviews)
"Gorgeous place.Great stay.Will diff be backG"
United States
Gerard C.
$393 nightly
The price is $439
Jun 24 - Jun 25
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (33 reviews)
"Perfect space for an overnight stay. Very clean and well appointed. Communication from host was great and check in was a breeze. 2 minute drive from downtown Great Barrington."
United States
Anonymous traveler
$329 nightly
The price is $367
Jun 23 - Jun 24
Total with taxes and fees
Home in Great Barrington

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.6 out of 10, Exceptional, (4 reviews)
"Excellent communication with our host and property exactly as described. Easy check in/check out."
United States
Jillian G.
$310 nightly
The price is $347
Jun 23 - Jun 24
Total with taxes and fees
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Hancock
9.6 out of 10, Exceptional, (33 reviews)
"The suite was a great. Comfortable, clean and decorated very nicely. Bed was very comfortable with nice linens and pillows. "
United States
Eileen O.
$230 nightly
The price is $256
Jun 23 - Jun 24
Total with taxes and fees
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Hancock
9.4 out of 10, Exceptional, (6 reviews)
"Convenience to slopes and restaurants really great….,had a nice stay"
United States
Thomas S.
$222 nightly
The price is $248
Jun 23 - Jun 24
Total with taxes and fees
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Hancock
9.6 out of 10, Exceptional, (34 reviews)
"Great and clean property! Very easy to access and good parking too."
United States
Todd A.
$297 nightly
The price is $332
Jun 23 - Jun 24
Total with taxes and fees
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Hancock
7.6 out of 10, Good, (13 reviews)
"Great location, right on the mountain's property "
United States
J S.
$350 nightly
The price is $391
Jun 23 - Jun 24
Total with taxes and fees
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top The Berkshires Hotel Reviews

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 $143 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.

Explore a world of travel with Expedia