Holiday Rentals in Berkshire County

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Top Cities in Berkshire County

Lee featuring a sunset
Holiday RentalsHoliday Rentals

Lee

Lee
North Adams featuring autumn colours
Holiday RentalsHoliday Rentals

North Adams

North Adams

Featured Holiday Rentals in Berkshire County

7 bedrooms, iron/ironing board, cots/infant beds, travel cot
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
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
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
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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
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!
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
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!
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 €940
per night
26 May - 27 May
Find your Sanctuary at The Rectory at Stockbridge
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 €4,322
per night
13 Jun - 14 Jun
The Winthrop Estate - 12K SF 32 Acres
Exterior
Enjoy comfortable elegance in this secluded grand home located in town
10.0 out of 10, Exceptional, (57)
"Charming and spacious historic home in the Berkshires"
Enjoy comfortable elegance in this secluded grand home located in town
Interior
Hancock Village Inn at Jiminy Peak
10.0 out of 10, Exceptional, (2)
"The hosts were excellent communicators and kept in touch throughout the stay and were super helpful. Property was as described and so close to jimny peak. If we return to the mountain we would book this house agai ."
The price is €937
per night
18 Jun - 19 Jun
Hancock Village Inn at Jiminy Peak
Property grounds
Beautiful N. Adams-Williamstown Lake House-With Sat.-Sat. Stays in July & Aug
10.0 out of 10, Exceptional, (84)
"This was the best time away from home we ever had. The cottage and the lake are so peaceful and beautiful. The hosts were kind and helpful thru the hole planning stage. We hope to visit again next year....and one special thing we will never forget is the wonderful quiet..."
Beautiful N. Adams-Williamstown Lake House-With Sat.-Sat. Stays in July & Aug
Outdoor pool
Private and Cheerful Berkshire Oasis in Dalton with in-ground pool
10.0 out of 10, Exceptional, (2)
"Wish we'd known about 2nd floor bedroom. (Might have made an error on my part) Dishwasher was broken & no washer or dryer. Comfortable beds. Senior Center right across the street. Perfect facility for two Senior couples. Would stay here again, after we get an education on Fire Sticks for the TV. No live TV. For Thursday Night football we had to go out to a sports bar and leave at the start of the 4th quarter. Would've preferred seeing it in my jams."
Private and Cheerful Berkshire Oasis in Dalton with in-ground pool
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
Private kitchen
Amore Estate - sleeps 12 in beds
9.6 out of 10, Exceptional, (8)
"Great space for a group of friends! House has a lot of character. Beautiful property and great location! Easy access to downtown Lenox and surrounding area. We really enjoyed our stay!"
Amore Estate - sleeps 12 in beds
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
Interior
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
9.4 out of 10, Exceptional, (29)
"Perfectly location for Lenox, Stockbridge, and other local towns. House was just as described and comfortable for a family of 5. Property contact was proactive, reaching out to make sure we were settled in. Pacman and air hockey games were a big hit! We would book again."
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Property grounds
Simple and Elegant 19th Century Williamstown Home
9.4 out of 10, Exceptional, (8)
"We did not stay at this property, we were moved to another location, I think due to scheduling. The coordinator was very responsive and the other location was beautiful. We had a wonderful stay and would work with these folks again in the future."
The price is €480
per night
23 May - 24 May
Simple and Elegant 19th Century Williamstown Home
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!
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
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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.

Holiday Homes in Berkshire County

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Recent reviews in Berkshire County
Expedia verified reviews

The Lenox Collection

The Lenox Collection

5/5 Excellent
"😊"
A verified traveller stayed at The Lenox Collection
Posted 1 day ago
The Lenox Collection