The Berkshires Vacation Rentals

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Vacation Rentals in The Berkshires

Property entrance
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (857)
"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"
The price is CA $203
CA $222 total
includes taxes & fees
May 17 - May 18
Jiminy Peak Mountain Resort
7 bedrooms, iron/ironing board, cribs/infant beds, travel crib
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
Interior
Peace and quiet on the lake
9.6 out of 10, Exceptional, (183)
"We rented the house to celebrate mom’s 70th birthday. We wanted a quiet, simple place where we could spend time together, visit, and spend time outdoors. That’s exactly what we got. We all fished and kayaked and enjoyed the peaceful scenery. Thank you."
Peace and quiet on the lake
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Interior
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
Fridge, microwave, oven, stovetop
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
TV, fireplace, DVD player, books
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!
Fridge, microwave, oven, stovetop
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
Pool
Mountainside Condo Ski In Ski Out
8.8 out of 10, Excellent, (8)
"Great location and nice unit. Had a blast!"
The price is CA $203
CA $254 total
includes taxes & fees
May 20 - May 21
Mountainside Condo Ski In Ski Out
Interior
Rockspring by AvantStay | Huge Berkshires Estate
8.8 out of 10, Excellent, (10)
"We stayed with friends and family and had plenty of room. The separate game room is great! The house was as pictured and described. It is close to a few ski mountains and Great Barrington. We would happily stay at RockSpring or a different AvantStay again!"
Rockspring by AvantStay | Huge Berkshires Estate
Outdoor dining
Moose Lodge by AvantStay | Luxe Berkshires Escape
10.0 out of 10, Exceptional, (11)
"We had a wonderful time at the Moose Lodge. It was perfect for our family. Very clean, everything we needed and the property managers were extremely communicative. Thank you!"
Moose Lodge by AvantStay | Luxe Berkshires Escape
Lake
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
Fridge, microwave, oven, stovetop
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (11)
"We have a lovely stay, house is super clean and has all you need to relax and enjoy the space. I loved the fact we could take our small dog with us to make it a lovely family’s vacation. The house is central to everything and all towns in the Berkshires which we appreciated so much. We will return and would recommend to other highly also."
Stockbridge Home, Come Experience The Berkshires!
TV, DVD player
Peaceful, Post and Beam Loft, Sleeps 9
10.0 out of 10, Exceptional, (8)
"beautifully stay for couples."
Peaceful, Post and Beam Loft, Sleeps 9
Golf
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
10.0 out of 10, Exceptional, (90)
"Very clean property. Close to trails. Host thought of everything we might have needed. Quiet neighborhood. Fenced in yard made things much easier with our dog. She even provided dog bowls, towels, rug and a treat!"
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Property grounds
Chic Pittsfield Home With A View!
9.0 out of 10, Wonderful, (4)
"Nicely decorated and clean. It had everything we needed, including kitchen supplies and detergent for the washer/dryer. Great rental for our family getaway."
Chic Pittsfield Home With A View!
Exterior
The Winthrop Estate - 12K SF 32 Acres
10.0 out of 10, Exceptional, (2)
"Absolutely stunning property - truly incredible stay. Recommend to anyone looking for a large group getaway. Fast WiFi, commercial grade kitchen and plentiful supplies make it easy for large groups. beautiful property and room for activities on a huge lawn. Highly recommend."
The price is CA $4,075
CA $6,303 total
includes taxes & fees
Jun 13 - Jun 14
The Winthrop Estate - 12K SF 32 Acres
Exterior
The Kemble- Built by a US Secretary of State in Lenox
10.0 out of 10, Exceptional, (15)
"We were a big group..16 adults and 7 children. The families with children were well situated with nearby or adjacent rooms. Everyone had comfortable rooms which afforded privacy and quiet times. Each room had its own beautiful newly renovated bathrooms ( with great water pressure). The living and dining rooms were large and comfortable. The dining table was a loooong table with benches all around which easily sat our crowd. The backyard was gorgeous with beautiful views of the distant mountains....
The Kemble- Built by a US Secretary of State in Lenox
Property grounds
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 $204
CA $367 total
includes taxes & fees
May 20 - May 21
Perfect Vacation Get Away - Historical New Marlborough
Outdoor dining
Find your Sanctuary at The Rectory at Stockbridge
10.0 out of 10, Exceptional, (2)
"I stayed here with seven girlfriends, all aged 25-30, for a weekend, and we found it incredibly homey and nice. As a Catholic, it was lovely staying at the rectory, visiting the beautiful altar in the backyard, and knowing that any proceeds from our stay were going to a good cause. All the rooms have saint names, and there is a lot of thoughtful charm throughout. Samantha was very helpful and great at communicating through the entire process. Highly recommend this stay in the heart of...
The price is CA $802
CA $1,354 total
includes taxes & fees
May 17 - May 18
Find your Sanctuary at The Rectory at Stockbridge
Fridge, microwave, oven, stovetop
Great Barrington Get Away
9.6 out of 10, Exceptional, (16)
"The house was exactly as advertised, comfortable, and with great location. We enjoyed a great weekend of skiing at both Catamount and Butternut, and the kids enjoyed their first ski lessons. We even got a few inches of snow to go with it. Howard was an excellent host, very easy to communicate and always reachable. We will be back for sure!"
The price is CA $374
CA $694 total
includes taxes & fees
May 20 - May 21
Great Barrington Get Away
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See all available properties in The Berkshires
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.

The Berkshires Vacation Rental Travel Info

Vacation rentals
34
Popular accommodation
The Berkshires private vacation homes
International airports
Hartford, CT (BDL-Bradley Intl.) and Albany, NY (ALB-Albany Intl.)

Other types of properties in The Berkshires you may be interested in

Lobby
Life House Berkshires
3.5 star property
9.0 out of 10, Wonderful, (240)
"Great stuff"
The price is CA $135
CA $150 total
includes taxes & fees
May 20 - May 21
Life House Berkshires
Outdoor pool, sun loungers
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (882)
"."
The price is CA $170
CA $221 total
includes taxes & fees
May 28 - May 29
The Red Lion Inn
Hypo-allergenic bedding, laptop workspace, blackout drapes
Hotel Downstreet
3.0 star property
8.6 out of 10, Excellent, (922)
"Property is beautiful but 1 elevator out service and saunas out service need take care better the Property "
The price is CA $203
CA $226 total
includes taxes & fees
May 20 - May 21
Hotel Downstreet
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 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, 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 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 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 The Berkshires 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 The Berkshires vacation rentals we have selected for you start as low as CA $203 per night. Entering your travel dates in the search wizard 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. 

Recent reviews of The Berkshires properties
Expedia verified reviews

Monument Mountain Motel

Monument Mountain Motel

5/5 Excellent
"Very convenient and affordable price!!"
A verified traveller from Freeport stayed at Monument Mountain Motel
Posted 1 day ago
Monument Mountain Motel