Family-friendly holiday rentals in Western Massachusetts

This space is so lovely, the hot tub worked perfectly and provided many cozy nights outside. The plants are BEAUTIFULLY tender and bring a loving atmosphere to the space. the linen sheets were so wonderful at the end of the day. we made it up the hill in a Honda insight, but if it were a tiny bit icy I don't think we would have been able to make it. definitely use 4wd if you have it. the hosts were very responsive. if the noise is too much in the bedroom at night (critters, rain,etc.) be sure to use the fan they provide, it helped us a lot :) the kitchen was a delight to use. sharp knives. big, metal surfaces. nice gas stove. big fridge.

We had a wonderful time at Mirav’s place in Woodstock. Made great use of the hot tub and the fireplace. We absolutely plan on returning soon!

We had an amazing stay! The setting was absolutely beautiful, with stunning views and a peaceful atmosphere. The space was impeccably clean, which made our stay even more enjoyable. One of the highlights was the hot tub – it was the perfect way to unwind after a day of exploring. The host was incredibly responsive and saved us with a last-minute booking, which we are so grateful for. We couldn’t have asked for a better experience. Highly recommend!

Enrique's place was conveniently located near Rhinebeck, but alao far enough away that it was peaceful and quiet. Worth having a drink in the tavern at Beekman Arms and breakfast sandwiches at Rhinebeck Bagels. We especially enjoyed the hot tub. Enrique was a wonderful, informative host, and available if we needed (we didn't). Overall, we had a nice, relaxing weekend.

Had a great time at this beautiful home! Felt super peaceful and great for groups. Thanks so much!

Amazing cabin , close to everything, clean ,

My family and I had a wonderful time! Larry is very sweet, gave us a tour, offered to help with docking our boat and even offered my husband the tools to fix the bunk on our trailer. The house is big and beautiful!! Very clean, the beds are comfortable, the kitchen has everything you need!! The hot tub is definitely a bonus as we used it everyday!! The dock was perfect, we had room for our pontoon boat and jet skis. All around the perfect place for some R&R!!! My family and I love Cossayuna Lake as we are semi local and it was our first experience with an Airbnb. Thank you Larry for sharing your home!! Highly recommend this for your next vacation!!

My family loved staying here! There was plenty of snow for activities. We went skiing at Mount Snow and ice fishing on Lake Raponda for a day. The barn is so unique and had everything we needed. There were lots of extra pillows and blankets and a big cozy couch to curl up and relax by the wood stove. Having access to the clubhouse was amazing… the kids loved swimming in the warm pool after a long day outside. Brian was super responsive and easy to talk to! We already want to go back!

I fell in love with this apartment, the living room, kitchen, bathroom and bedroom were excellent, very cozy and endless amenities, the only complaint I have is the ceiling of the room but it is understandable and is not a big deal and they did not tell us where to put the garbage so we had to leave it in front of the door in the garage but other than that a very good experience in this beautiful place, I recommend it!

Lovely place in Saugerties, close to lots of great hiking and restaurants.

Scott is amazing! The airbnb was incredible! Lovely placed filled for immense and loving memories. He allowed me a late Check-Out which was wonderful. Definitely recommend you guys coming more often!

Beautiful location...nice and quiet. 7 or 8 mins to woodstock. Decorated seemingly professionally. All the appointments (convennces) you could ask for.

We really enjoyed our stay at this lovely house!! So many cozy nooks and Miles and Ruth were very responsive and helpful hosts! Would definitely stay again :)

The house was beautiful and Rhonda was great, she was very responsive and helpful. We felt right at home and enjoyed the place more than Lake George :) , the hot tub and pool were great and i would recommend anyone coming to this area to definitely book the place if they get the chance.

We had a wonderful stay at Niall's! It was perfect for our needs. The house was clean and cozy. Niall was friendly and helpful!

Our family of eight were in town for our son’s wedding and spent four nights in this beautiful house. We had plenty of room to spread out, make meals, eat together and yet have privacy with the five bedrooms. The area is beautiful and everyone loved the craftsman style house. If we’re ever in the area again, we will surely stay again.

A fun winter break/birthday getaway! Sarah’s house had plenty of bedrooms for all guests. The game room, pool table, and wood stove/fireplace were great to have on these cold February days. Everyone enjoyed the sunroom and large dining table. The hot tub and outdoor sleds were used as well. The history of the house and beautiful views from the property were an interest to all. I bet this house is a lovely spot in the summer as well!

Six of us stayed over the weekend. We were very comfortable and Brad was very helpful and responsive. House had everything that we needed. Brad is a great host. Would 100% recommend a stay.

My group loved our stay at Alan and Cara’s place for the Sheep & Wool festival. Great space for a large group; we especially loved how comfortable the living room couches were and how there was space for everyone there to gather. The place was immaculately clean. We’d love to come back again!

We had a terrific stay. The house was exactly as advertised.

This wonderful antique home is in a Beautiful spot in the heart of Litchfield CT, and a delight early spring when the fields of daffodils awake! This unique 1793 house has a great view & sunset, fireplace, simple spa/gym making it a gem even when the pool is closed. Nearby the town with lots to offer and local farms for food shopping too. What’s not to love 💛 Bonus is a great host offering a home that is in touch with the realities of rentals, pets and people -not picky, precious or punitive. Happy to recommend and return! Thank you Elizabeth!

The location was great and a nice place to walk. Lots of stuff to see and do that’s not far away. We would come again.

We spent three nights at Rich and Sheila's place and it was an amazing getaway. Our apartment was perfect-clean and comfy. We loved the proximity to the creek and the pool was a huge bonus! Rich and Sheila were both responsive and welcoming. We look forward to a return trip.

The place was excellent. Around the corner from a great coffee shop, though it has a coffee machine and creamer provided for those that don't want to leave in the morning. Close to the main town but quiet. Sculptures that I want for my own house. Comfy beds. Well stocked kitchen. Easy to get in and out. Spacious. Good price. I will absolutely be looking to see if it is available next time I am in Northampton.