Cottage vacation rentals in Berkshire County

Darcy is a top host. We loved the in-wall USB chargers and the bluetooth speaker, the welcoming wine, the beautiful layout and decor, the cozy feeling with lots of space for us to sprawl out and the high quality of the renovation. I felt secure and cozy and everything from the hot tub to the sheets were super clean and fresh. We will be back in the summer for kayaking on the lake. Thank you Darcy!

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

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!

This place was absolutely beautiful and perfect for our weekend away. The house was spotless, had everything we needed, and was the most cozy little cabin right on the water. We really enjoyed our stay, and would love to go back in the near future!!

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.

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.

House was absolutely adorable. Cozy and warm. Felt like we were in the middle of nowhere, but we were close to everything - would certainly stay again.

Just the right amount of space. We were attending an event at Jiminy Peak resort which is not pet friendly. Renee's cabin was cozy and quiet. We loved listening to the Brook in the backyard.

Gillian was a super host. The place was clean and ready for us when we arrived including a decorated Christmas tree, doggie dishes, and a full wood pile. She got back to us in a timely manner for all questions. And all expectations and facts about our stay were communicated in a clear way. Thank you Gillian!

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 !

Suzy's cottage was impeccably clean and beautiful! Perfect for a cozy weekend in the Berkshires, and not far from Great Barrington and other towns. We ended up being there over a snowstorm, and Suzy proactively reached out to let us know people would come and plow the driveway, so we didn't need to worry about it. And she offered us late check out! Would definitely stay here again.

A great place, exactly as described. Pub at end of drive is convenient and delicious. Absolutely anything we could have possibly needed was thought of and made available. The retro feel made me think of family cabin stays when I was a kid . We played Apple to Apples and put together three puzzles in the evenings, all were provided. Although a quirky older cabin (in a great way), we loved loved loved the character, and it was super clean! Way up in the hills, so natural areas are close and spectacular. Plenty of things to do within a drive, which is a visual treat in itself. Saw black bears twice as we were out and about. Nothing fancy, but for us it was just what we wanted/needed. Thanks so much, Linda for being a 5 star host!

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.

We had such a nice time at Cathy’s place! It was perfect for our family of four. It was comfortable, clean, and we loved looking at all the different types of art on the walls. Thank you Cathy!

Easy to find & easy to get into the place. Great self check in process. The porch, yard, and fire pit are very cute. Comfy beds.

We had an absolutely wonderful 4-day stay at 13 Damond Road in New Lebanon, NY, during Thanksgiving. The house was cozy, well-equipped, and perfect for a relaxing holiday getaway. The serene location provided a peaceful retreat, and the surrounding views were stunning, especially in the crisp fall weather. We were traveling with our two teenage children, and the home provided the perfect setting for us to spend quality time together. From preparing our Thanksgiving meal in the well-stocked kitchen to enjoying family conversations in the inviting living spaces, every moment felt special and memorable. The hosts, Paul and Kaveri, were incredibly thoughtful and responsive, ensuring that we had everything we needed for a comfortable stay. We truly enjoyed our time here and wouldn’t hesitate to recommend it to anyone looking for a tranquil and family-friendly place to stay.

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.

The setting on the lake was just gorgeous, and the accommodations were immaculate. It is definitely off the beaten path but within driving distance to Berkshires attractions like Tanglewood, museums etc. If it’s R&R you’re seeking, then this is the place for you!