Cottage holiday rentals in Berkshire County

One of the most clean air bnb I have stayed in. It was spotless and comfortable. The hot tub and kayaks were easy to use and just a few yards walk to the water. I would not change anything about this house. And thank you Darcy for being such a great host!

My girlfriend and I had a great time staying at Joktan’s place. We really enjoyed the home as well as the amenities that came with it. Joktan, provided excellent communication. Would recommend staying here!

Truly a magical spot--in October, the fall colors. Any time, the lake view, and the absolutely lovely sunroom.

We had a wonderful time! The house is beautiful in a spectacular spot on the lake. We were four adults and a large dog and had enough space. We got to use the kayaks/paddle board and fished endless hours from the dock The kitchen is well equipped and we cooked all our meals at the house I highly recommend this place and would come back if the opportunity arises

I cannot thank Joyce enough for opening her lovely home to us. We felt relaxed and refreshed from the minute we arrived. Whether it was sipping coffee and reading by the pond or watching our beagle explore the grounds, I don't think the smile left my face. Joyce was so helpful with recommendations and available to answer any questions we might have had. The proximity to Great Barrington and Stockbridge was fantastic but the local Hillsdale attractions should be missed. We'll absolutely stay here again! Love this house.

Another perfect stay at Laurie's. This is our third stay over Thanksgiving week and we always are sad to leave. My family absolutely loves staying here. There is plenty of room to gather or to have some alone time. Beds are comfortable. Kitchen has everything you could need and is always pristine. Check in is stress free. Area is peaceful and serene. Lee is a lovely New England town. Downtown is less than a 5 minute ride. Many restaurants within a 5-20 minute ride. Outlets are 10 minutes away. Looking forward to our stay next year.

This place was an excellent location for basing our trip to the Berkshires. We liked looking out over the lake, and walking around the community.

Rachel’s carriage house is a charming and beautifully maintained property—just as described and shown in the photos. Even though the weather wasn’t ideal during our stay, we thoroughly enjoyed cozying up and relaxing in the warm, inviting space. One of our favorite features was the natural light streaming through the tall paned windows in the kitchen and dining area, overlooking the garden—a perfect setting for our morning coffee. The carriage house was thoughtfully stocked with everything we needed for a comfortable and restful getaway. It’s clear that Rachel has put a lot of care into creating a welcoming experience for her guests. We truly enjoyed our time in the Berkshires and would happily return!

Lisa’s place was wonderful, and I highly recommend it. She was very responsive to questions, and I appreciated the helpful notes around the house. The space was thoughtfully made dog-friendly, with couch covers that kept things worry-free. The garden was beautiful, and the property offered great outdoor spaces—a back deck, a front grill with seating, and a creekside trail (not fully cleared, but enjoyable). My dog and I loved it. We stayed on the top floor and loved the airy living room with high ceilings and skylights. Lisa’s nature-inspired decor on the desk and fireplace mantle added charm. The bedroom was spacious, and the extra-large bed was incredibly comfortable. The house having three bathrooms was a nice bonus.

Renee was always responsive when we messaged. The Airbnb was super clean and the bed was very comfortable. Check in was so easy! At the end all Renee asked of us is to take the trash out which was super easy. I would definitely recommend this place. It is an especially good location for people who are attending a wedding at Bloom Meadows which is about 2 minutes away.

Enjoy your stay at this beautiful home. Looking for a get away from everyone this is the place to stay. House was perfect when we arrived and everything was smooth and simple from start to finish!

Loved the quick weekend getaway from the city! Wanted somewhere we could stretch out into.. which Ayren’s house fully is.. loved playing the many board games provided and watching movies in the late evenings.. plus a few walks down to the lake and drive to town which is less than 15 min away.. A very communicative host with clear instructions and well laid out amenities and basic kitchen condiments.. Thanks again for a great weekend !

I cannot emphasize enough how responsive, helpful and accommodating Julie was before and during our stay. The property is as shown, interior was clean and beds very comfortable. The walk to the lake is a short, peaceful one. It is a lovely setting with quiet neighbors. Highly recommend for anyone visiting nearby Berkshire attractions or for a quiet getaway near a beautiful lake!

Jane's cabin was just as described. peaceful location with beautiful views.

The cottage is clean and comfortable and the kitchen is well stocked. This is a nice place to serve as home base to explore all that the Berkshires have to offer.

This was our second stay here, and we will hope to be back again next year. Less than three miles from Tanglewood, plus nearby hiking trails & historic sites, the location gave us plenty to do. The home is sparkling clean, has lots of towels, pillows, etc. Screened porch, deck, heat & AC if needed. Barred owls call during the night. Hosts live next door beyond the trees. Excellent communication if needed.

Beautiful, picturesque, and peaceful. All that I was looking for, to spend my New Year’s Eve. I love the vintage decor, took me to another time. I loved every detail! Very cozy and comfortable. I appreciate the distance between the houses. Quiet and safe. I saw a couple of neighbors thru out my stay. Stores are not close by but I didn’t mind driving bc it was nice to see the neighborhood. Everything was great. Host was always responsive and helpful.

Lovely cottage in the heart of the Berkshires. Well-stocked with anything you could need (kitchen utensils, chairs and toys for the lake, etc), comfy beds, and great location (a short walk to the public beach at the Stockbridge Bowl, and a short drive to Lenox, Stockbridge, Tanglewood and more). We loved sitting on the quiet porch in the evening. A great place for kids—loads of toys and games and swimming nearby.

I had a wonderful retreat at this cottage – it’s a true GEM!! The photos don’t do it justice – it actually feels larger and the view is amazing. Having stayed in numerous rentals, I also want to give 2 thumbs-up to the thoughtful layout of the space and attention to detail (hooks where you need them, great lighting, etc.). The bed is comfy as are the couches, and it’s clean. Elizabeth and Al are available if needed, but totally give you space. And it’s deliciously quiet. Walking on the farm was a treat – watching the veggies and tulips grow over the week I visited. I can’t wait to return!

We’ve stayed at the cottage twice, and hope to stay for a visit again. It’s super cozy, clean, and just all around good energy. It’s not far from family which is our main reason for going. The place is a bit off the beaten path, but we’ve enjoyed the property and our excursions around the Berkshires. Mary’s a great host: easygoing, helpful and accommodating. We appreciate her and her place.