Berkshire County Vacation Rentals

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Top Cities in Berkshire County

Top Vacation Rentals in in Berkshire County

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (860)
"This is a sweet property. I visited in the summer. The dining options were great. The country store is awesome. I love how the rooms are suites. They feel like small apartments. I like that they have kitchens. The bed was comfortable. The ac is loud but at least it works well and it drowns out other noises. I needed a late check out and they were very cool about it. They let me hang out at the pool and then shower at the spa because I was like of stuck there several hours after check out time....
The price is CA $218
CA $239 total
includes taxes & fees
Jun 20 - Jun 21
Jiminy Peak Mountain Resort
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (29)
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
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Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (8)
"I really loved my stay at this beautiful property surrounded by nature and peacefulness in the Berkshire mountains. The owners were great too with communication and making things easy for check in and check out. Highly recommend this place!"
Pristine Home In Becket Woods
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (195)
"We’ve stayed at the cabin with our dog four times and always enjoy our peaceful stay. It’s cozy, clean and private. Also, the Sherwood Shoppe - just down the road - is a wonderful place for breakfast, homemade chili and much more."
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Peace and quiet on the lake
9.6 out of 10, Exceptional, (186)
"The house was clean and cozy. The kitchen was well stocked, especially important as we like to cook at home. Justin was responsive when I contacted him with questions. Love that the house was dog friendly with a fenced in back yard. The house has been updated inside but the deck needs some TLC, which I am sure are in the plans. A perfect get away!"
Peace and quiet on the lake
Serene Acreage - Pond - Hiking Trails Nearby
10.0 out of 10, Exceptional, (5)
"Wonderful accommodation."
Serene Acreage - Pond - Hiking Trails Nearby
Private Estate, Heated YEARROUND Outdoor Pool
10.0 out of 10, Exceptional, (8)
"The pictures simply do not do this place justice, it’s an incredible home. Our friend group was cozy all weekend! We loved the hot tub/pool, the really interesting artwork, the driving range mat and basketball hoop. Plenty of towels and kitchen supplies. The in law apartment (which we didn’t use as sadly part of our group was unable to join us) is attached to the main home and is so cute. We had a small issue upon arrival and the hosts were immediately responsive with us troubleshooting and...
Private Estate, Heated YEARROUND Outdoor Pool
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
6.0 out of 10, (2)
"Be aware they will not proactively provide you with a local host name or contact info. It was very difficult to get Vacasa support to help me get this info to resolve wifi issue - like hours long to get them to just give me the property managers info and even then, they wouldn't give it to me, just had them contact me. Otherwise, amazing pool and great location. Outdated indoors but clean to the extent that it could be. Utensils were dirty and tons of flies in the house upon arrival - like 50...
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, (39)
"This house was the perfect get away house for out family! The place was clean and the kitchen well stocked! We had wonderful large family dinners and enjoyed heading into town for meals and fun too. We had the best hikes with are wonderful dog that we got to include, it was a very special week. Great location and the most peaceful and amazing views from the deck and the dock. Would stay here again for sure! Thank you for sharing your home."
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Berkshires Cabin 2 Mi to Appalachian Trail!
9.8 out of 10, Exceptional, (6)
"My wife and I were looking for a nice little getaway within reasonable driving distance and came across this great property. As soon as we saw the big windows in the living room we were sold. Definitely getting added to our short list of places to go back to."
Berkshires Cabin 2 Mi to Appalachian Trail!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (206)
"Had an absolutely amazing time! great location, quiet, close to everything! Plenty of things to do nearby, and host left plenty of brochures to find food or activities. Only minor downer was that the oven seemed touchy"
Berkshire Village Carriage House - Super Private!!
Perfect Vacation Get Away - Historical New Marlborough
9.6 out of 10, Exceptional, (49)
"This was our first stop on a long journey from VA to ME, traveling with 2 dogs. It was perfect, the dogs were safe with lots of freedom to roam. What a beautiful, peaceful village and sweet little cottage."
The price is CA $206
CA $371 total
includes taxes & fees
Jun 24 - Jun 25
Perfect Vacation Get Away - Historical New Marlborough
Berkshire Lake access
10.0 out of 10, Exceptional, (41)
"Living space is bigger than the pictures, plenty of room for everyone, well stocked kitchen, everything we needed!"
Berkshire Lake access
The Meadows House @ Otis Ridge w/ 7-person hot tub
9.8 out of 10, Exceptional, (21)
"The rental property was just as described online. We had a very relaxing time. We also enjoyed playing all the games provided. This is a beautiful location and very quiet area. We loved sitting out in the hot tub at night looking up at the stars. Really special experience."
The Meadows House @ Otis Ridge w/ 7-person hot tub
Private Island - Largest Fresh Water Reservoir in Mass....
10.0 out of 10, Exceptional, (3)
"So grateful to Bill for such a wonderful stay! The cottage was so lovely and had everything you could need for a weekend on the lake. Will definitely be returning in the future 😊"
Private Island - Largest Fresh Water Reservoir in Mass....
Private Lake House in the Berkshires
9.8 out of 10, Exceptional, (15)
"This was our first VRBO experience, and we are hooked. We had a wedding in Pittsfield with events over three days, so we decided to try this lakeside retreat, and it was a treat! The Berkshires in the fall are absolutely beautiful and Hinsdale is a pretty little town. Ozzie's is definitely worth the trip for breakfast. The lake is lovely and we were looking forward to kayaking and fishing. Unfortunately the weather was not on our side, but we still got one fish! Mary is a wonderful host who is...
Private Lake House in the Berkshires
Waterview Home in the Berkshires: Near Hiking
9.2 out of 10, Wonderful, (14)
"Lovely house and kind owner. We had a great time. The view is amazing."
Waterview Home in the Berkshires: Near Hiking
Fox Hollow Luxury Ranch Laurel Lake
9.4 out of 10, Exceptional, (12)
"Generous facility, nicely located, accommodating host."
Fox Hollow Luxury Ranch Laurel Lake
Moose Lodge by AvantStay | Luxe Berkshires Escape
10.0 out of 10, Exceptional, (12)
"Our family had a wonderful time at this lovely home. The area is quiet yet you are still close to restaurants and shopping. I would definitely stay there again"
Moose Lodge by AvantStay | Luxe Berkshires Escape
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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.

Everything you need to know about Berkshire County 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 Berkshire County vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... 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 Berkshire County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Berkshire County vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Berkshire County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Berkshire County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Berkshire County vacation rentals we have selected for you start as low as CA $206 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Berkshire County rentals

At Expedia, we put the best Berkshire County 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 Berkshire County 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 Berkshire County 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 Berkshire County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Berkshire County Vacation Rental Travel Info

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