Cottage holiday rentals in Western Massachusetts

We had a GREAT time at Feyza’s cabin. It was clean, quiet and exactly as described. We especially loved the secluded setting, the lake views and the jacuzzi. Feyza was helpful, communicative and very responsive. Her digital guidebook was very insightful as to the local attractions and restaurants. We would definitely stay here again!

We had a great time! Everything was thought of in this space. We especially enjoyed the opportunity to be outdoors and the proximity to the park. I'm not sure if this jumped out in the listing, but the place is walking distance to the Children's Museum which was perfect for us, as I had take the car for a work event and left my husband and 3 year old to explore the museum, and they could easily walk home to the cottage. Thanks for sharing your place with us!

My boyfriend and I had a nice and relaxing one night stay at Martin’s place. It’s a cute house and we enjoyed relaxing in the hot tub! Martin was responsive and communicative. Overall a nice little getaway.

We had a lovely stay at kim’s. The location was great, having a hot tub was really nice even with the weather getting warmer, the space was very clean and kim was very responsive to us throughout the whole stay.

The perfect stay for horse showing at HITS! My only hesitation in writing this review is that I didn't want anyone else to know about this place for future horse shows! ;) An excellent place to stay with above and beyond amenities, easy check in and great for traveling with a dog. Will absolutely be back!

outstanding! we stayed for over a week to be close to Williamstown, which was only a 10 minute drive as promised. Beautiful quiet setting, quick responses to any questions, and a well-appointed cottage with all the necessary amenities. hope to stay here in future.

We stayed at Cora’s property for 1 month and had the best time! Her house felt so cozy and Cora and Paul were very responsive and always helped out when needed. The location is perfect - close to downtown and there are cute cafes and restaurants nearby. We will absolutely be back!

Thank you Ellen for the easeful stay at your cottage with clear instructions. The surroundings are beautiful. We saw an eagle at the lake!

Laurence and Ilze were incredible hosts, incredibly helpful and responsive, going above and beyond to sort out our needs. The house was as advertised and we had a a great time at their place. Should we be back in the area we’d definitely try to stay with them again!

Excellent location for local shopping, lots of food choices, delicious breweries. Most importantly VERY close by for climbing & getting out to nature. The Woodstock & Kaaterskill wilderness areas are within 30 minute drive. Lots of stunning views for a decently low mileage. Rip Van Winkle bridge is 9 minutes away if you want to explore the other side of the Hudson. The place has all the amenities you’d need for a getaway. Very clean, host was very responsive; even on the Memorial Day holiday. Will be back!

Super clean, comfortable and well stocked Air B&B, just what we needed for a quick trip upstate.

Jason’s place was excellent! Exactly what we were looking for in a country getaway-cozy cabin in the woods, full of charm and close to farms, hiking and swimming. we loved listening to the records while cooking. Perfect spot, perfect vacation!

Great spot within walking distance of cute shops, restaurants, bars, and a little public beach & playground on the Hudson. Maria's place is well kept, clean, and safe. The outdoor space was not used as we were out and about exploring other towns during our stay, but would be a great place to wind down and catch some peekaboo water views as the sun sets. Big covered porch was awesome and backed up to the woods on one side, and water views on the other.

5 stars ⭐⭐⭐⭐⭐ We absolutely loved our stay at the Cottage on the Lake in Thompson, Connecticut! The home is charming, beautiful, and immaculately kept—the perfect peaceful getaway. Jan, the host, went above and beyond to make sure we were comfortable from start to finish. She checked in with us multiple times during our stay to ensure we had everything we needed, and her kindness and attentiveness made us feel genuinely cared for. We felt so at home here. The neighborhood was just as welcoming—we even got to know the friendly neighbors and their adorable dog, Gigi, next door! This cottage has quickly become a favorite of ours, and we’re already looking forward to making it one of our regular Airbnb stays for years to come. Thank you, Jan, for such a wonderful experience!

Just like the pictures , very peaceful and serene , the kitchen is well equipped. The beds are comfy. Great place to relax in the Berkshires. With a super responsive host.

This is a beautiful and peaceful cottage with easy access to shops and restaurants in the area. It was perfect for a sisters weekend. Highly recommend.

This was my second stay at Kathleen’s and it was as comfortable and cozy as the first. This spot is private and peaceful, there’s lots of great outdoors to enjoy nearby, and great local spots for exploring. Would absolutely stay again.

This is probably the most well-maintained Airbnb we’ve stayed in. The location was great with lots to do nearby, the cottage itself was super clean, the bed was comfortable, the bathroom was nice, and the second story back deck has a great view. It’s not listed, but there’s a river with a small waterfall across the street that definitely adds to the peaceful vibe of the place. The cottage is very private and quiet, but it’s also only 15 minutes away from both New Paltz and Poughkeepsie so it’s real easy to get around and find something to do. New Paltz is a particularly cool walkable town with lots of great food and coffee. Minnewaska State Park Preserve is also about 25 minutes away and offers a ton of hiking trails. Linda was an excellent host, made communications clear and succinct, made check in/out super easy, and offered up some solid recommendations for places to eat and drink. Again, I really can’t stress enough how clean they keep this place, it was spotless. 10/10!

It was perfect!! Just as described and we loved the whole place - the town is adorable too. Melissa was so helpful with great recommendations and we’ll definitely be back!

We enjoyed our time at Vintage Bolton Lake Cottage. The place is cute, peaceful and quiet. Not having a TV was perfection! Kayaking was fun. Nice bass too! Top notch experience. Jason checked in to make sure we didn’t need anything or have any concerns mid stay, which I appreciate. Phenomenal host. Would love to go back!

I usually stay in village of New Paltz so was a little apprehensive staying a bit outside of village. But I actually now prefer the situation as it's not that far to all the action and the cottage is amazing, which more than makes up for the minor driving inconvenience. Highly recommend!!

This cottage was very lovely, cozy, clean, and just a few minutes from the town of Woodstock, but very secluded and peaceful on a beautiful property. The home was exactly as described and had everything you could need for a short stay. I do recommend having 4-wheel drive and a car with good suspension to get up the gravel road leading to the house. Cayenne is a wonderful host - she was extremely kind and easy to communicate with. I would definitely stay here again!

So thankful to have found this spot for graduation week. Very comfortable in a beautiful neighborhood of stunning rhododendrons and friendly neighbors who welcomed us from the moment we pulled in and walked the block with us during our downtime away from Amherst College. Spectacular coffee, comfortable beds and linens, chirping birds, majestic deer, and caring hosts - we could not have asked for a better home away from home! Thank you Charlene and Luke for sharing your place with us and adding to our book of memories.

R’s place restored our faith in beautiful and affordable air bnbs! We said numerous times during our stay that we would definitely be back. The setting was so beautiful and the outdoor spaces were incredibly enjoyable, especially with our dog. R’s kitchen is the best and super well stocked so we enjoyed many meals in. This place did not disappoint and we cannot wait to go back!