Cottage vacation rentals in Pioneer Valley

Scott is a wonderful host. The house is just down the hill from his house but a large privacy screen was erected to separate the two and create a smaller nook in this open space. I never felt uncomfortable. Hot tub worked great. Interior had all that you could need. Two things to be aware of for your stay: We arrived later than planned on Friday and did not bring basic food stuffs. When we woke Saturday AM wanting a latte we had trouble finding a very quick to reach store. everything is reachable but we forgot it’s VT not my home town. Note also that cell service is nonexistent on AT&T (can’t speak for the other carriers). The WiFi was down and so I walked up and knocked on Scott’s door (unthinkable today!) for some help at 8:30 PM (the nerve of me!) to get in touch. Scott immediately came down to the house to rectify the situation. We had no problems from there. Fun house, great place. So quiet. Wish we had some More time to explore the trails, art and restaurants. Recommend!

What a beautiful home! We slept like babies, loved the hot tub and fire pit! We got to meet Darcy’s husband when we were coming and going one day- he was such a warm and friendly soul! We really hope to come back and spend more time here!

This is our 2nd stay at Congamond House and it will not be our last - it's my favorite of many, many AirBnB stays. Communication, cleanliness, location - all 5 stars, but what makes it stand out are the little details and comfortable amenities that truly make it feel like home. Comfy beds, oversize ceramic mugs, and plenty of blankets made it a cozy Christmas week stay. And everything is literally at your fingertips - everything is organized and exactly where you would think to look for it. Kudos, Catherine, for creating such a comforting, welcoming space!

Joktan saved us and was the most gracious host! We had to scramble because the original place I booked did NOT match the description - no ac upstairs when we were in the middle of a heat advisory. I booked Joktan's at the last minute, insta-booked and headed over. He responded quickly and scrambled his team and they were just finishing up cleaning as we straggled in 45 minutes later, exhausted, and we plopped on the couch of his perfectly clean, welcoming and most importantly COOL home. The place looks just like the photos, though now that I look at them again, there have been some additions, I imagine in response to feedback because he seems very responsive! Some additions, like an extra cabinet & storage in the kitchen, extended countertop on kitchen counter for additional seating, added some ac units. I didn't realize it was in a mobile home community but it was a small, quiet, well-kept community. Joktan really saved the day and made us feel most welcome.

Very nice place. I think of it as updated rustic. Accurately described. We had a great time.

Katie’s place was a great little spot, just a 15 minute walk from my sister. The attached cottage had everything we needed and the host was responsive when we reached out. I would stay here again.

We loved our stay at the Berkshires Great Escape Cottage. Shay is a wonderful and responsive host, and the house itself is perfect. It’s one of those properties that is clearly designed and maintained as a real home and not just something that photographs well (we all know the type), although it does that too if that’s what you’re looking for. We will definitely return here in the future. We were a couple of families with multiple kids across a variety of ages. The play room with its variety of games, vast outdoor space, with the hot tub, a fire pit, frisbee set up, small soccer field, and grill was everything we could have asked for. Indoors, the house is clean, sensibly laid out giving everybody plenty of space and privacy, well stocked, fun to cook in and the upstairs area has a baby gate for safety. The host really has thought of everything. The property itself is located close to the commercial center of Great Barrington and a short drive away from multiple activities and res

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

A wonderful getaway spot! The view is absolutely gorgeous and the whole house is so very cool and loaded with personal touches. Our grandkids loved the hidden game nook and the star wars room. We all loved the theatre room, but warning- once it gets late, it's so chill and comfy it's easy to fall asleep in there lol. The kitchen had everything we needed to serve a full thanksgiving dinner and the cafe is an excellent gathering space. We used the wood stove most nights and that was yet another fantastic touch to this property. Very happy with the stay and memories made and highly recommend to anyone looking for a quiet getaway with lots of fun and creative touches.

We had a wonderful peaceful stay at Honey Bear, Linda Jane is a fantastic host and her home is beautiful and relaxing. It rained a lot of our stay, but we did get to make the most of our stay when it was nice out with all the wonderful inclusions. The boats and games were a fanatic added bonus. Thank you so much

I love Lake Mattawa, but my visit was on a snowy week in December, and I’d only ever been to the other side of the lake, and in the summer. The little cottage was well appointed, nice and cozy, —quite a beautiful little place to be snowed-in looking out. The kitchen is well equipped, the furniture is comfortable, internet and electricity stayed connected during the snow and wind storms, plenty of towels, etc. Patti was very responsive to my questions and needs.

Best host I’ve ever seen, very communicative and the place is just lovely! If I come back to Connecticut that’s absolutely where I’d stay. Thanks for everything

This was a return visit to Gwendolyn's Airbnb because we so enjoyed our stay earlier in the year. It was fun experiencing it in the winter after a snowstorm. To our great delight, the driveway and stairway to the entrance were shoveled and salted and a light was left on to guide us after telling our host that we'd be arriving after dark. I mean, that's like a MOM-thing to do!! The home was just as cozy and comfortable as we'd remembered. A great place to stay. We highly recommend. Thanks again, Gwendolyn! You are the best.

We loved staying at Suzy’s place for the Thanksgiving holiday weekend. It was a perfect cozy atmosphere with the fireplace and snow outside. We brought our small dog who loved playing fetch in the yard. Suzy gave us recommendations on where to pre-order Thanksgiving dinner and was flexible on check in time! Kitchen and bathrooms were well stocked and spotless. We felt right at home and would recommend to anyone looking for a quiet getaway.

My husband and I booked last minute at the little red school house and we were not disappointed!! They had a welcome sign when we arrived and holiday music playing. You truly felt like you are in New England right when you step in. They have the comfiest daybed downstairs. Comfy sofa, large dining room table and good size bathroom in first floor. The kitchen was fully stocked with everything we needed. We had breakfast at the Harvest Cafe and it was amazing and close by. The scenery is amazing!! If you’re looking for a charming, relaxing, “The Holiday” movie feel…. This is your place! Thank you all so much.

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.

This is the second time that I've stayed at Elle's charming cottage by the babbling stream. It is super-charming and comfortable, and perfectly located for activities in Stockbridge, Lee, and Lenox. The cottage is neat-as-a-pin, with beautiful and stylish appointments, eclectic art, and top-of-the-line appliances. The nearby stream provides the perfect soundtrack to your Berkshires getaway. Highly recommend, and I will be booking again whenever my schedule takes me back to the area.

Had an amazing experience staying at Renee’s beautiful cottage. It’s quiet and tucked away but very accessible from the main roads. I highly recommend staying here if you want a cozy getaway with all the amenities you’d need for a comfortable and enjoyable stay. The fireplace was definitely the highlight of the cottage.

We booked the house for our anniversary get away. The house was exactly as described and was exactly what we were looking for. Great communication

Hard to say enough good things about this cabin. We stayed for four nights and enjoyed every minute. Beautiful, peaceful lake; close to everything in the Berkshires; well-stocked kitchen; comfortable beds; wonderful fire pit which we made good use of. Really the complete Berkshires experience...not to be missed.

Great house! Clean, nice and a 5 minute drive to UMass.

John’s airbnb was absolutely what we were looking for. It was charming yet modern; we felt right at home! We’re so thankful to John, his quick response time made the whole experience that much better. We would absolutely stay again!

LOVED this lil cabin in the woods - hygge vibes all the way. Quiet neighborhood, very clean & well-stocked kitchen (we cooked our first night in), comfy beds, thoughtful decor, strong wifi, plenty of seating for the space, and a lovely outdoor area with Adirondacks under the trees. An easy drive into Wilmington and the surrounding area, and a short walk to the stunning lake nearby. My only complaint is that the description led me to believe it was *on* the water and we would be able to use the kayaks offered, but unless you have a truck or something to load them on, it would be quite a feat to get them down to the lake without dragging them on the road (and that would be inconsiderate). They were not lyin' about needing 4 wheel drive in the winter (our rented convertible struggled to get up the gravel drive in the fall) and after a 7 mile hike, my knees fully appreciated mention of the stairs being the only access point from the parking area. Lovely space, would stay again!

The Boathouse is a jewel! Not only is one visited each morning with beautiful vistas, but the sense of peace is the spirit of the place. We had all we needed. Chris is a generous host who cares about the place and the guests.