Tiny house holiday rentals in Western Massachusetts

We had a wonderful stay at Ali and Carson’s cabin! They were incredibly helpful and welcoming hosts. The Mountain View from the cabin is absolutely stunning, even with the rainy weather, it was breathtaking. We also enjoyed exploring the charming nearby towns, and our two dogs had a great time as well. Despite the rain, we loved our stay and are already looking forward to coming back when the weather is better. Highly recommend!

This is a unique and special stay. From the very first interaction, Rich was very responsive and kind in his communications. The property is well cared for and very welcoming. The school room on the main floor is accessible and open to children playing - lots of books and toys. The living space upstairs was large, yet cozy. Stocked with all the things someone might need during their stay. It was so quiet at night, and filled with birdsong in the morning. My young nephews visited in the mornings (Rich was totally okay when I asked him) and they loved "my house." The farm adjacent to their property has alpacas and mini-horses that loved to crunch up the carrots we fed them (provided by Rich). The hosts have honored the history of the one-room school house, while making a fun and very enjoyable place to stay. Highly recommend!

Andrea’s place was stunning. Even though we had to head home early due to circumstances beyond our control with a Nor’easter that took place, Andrea was very understanding and accommodating. The accommodation was stunning. Modern, clean, and the views were immaculate. I can’t thank Andrea enough for being so easy to work with and being flexible with our check in and communicating! Thanks again, would highly recommend anyone looking!

so beautiful and cozy! private and in just the right location.

Cynsie was a great host! Very communicative up front and during my stay. The cabin was cozy and property was incredibly beautiful and peaceful. Plenty of fans for the warmer days! The bed in the loft was super comfy, the linens were fresh, and the bathroom was clean. Cynsie had a lot of great local recommendations for things to do, places to see and tourist destinations. Couldn't recommend this cabin enough.

Our second time staying at Maitopia with our cat, just as wonderful in a different warmer season. Tina was super responsive as usual and even accommodated a late checkout. We enjoyed feasting in the kitchen as well as grilling in the yard, floating around in the pool when it was warm enough out, "hiking" with our cat on a leash around the forest on the property, taking baths, streaming music. We didn't leave the property much, but it was a fun highlight to get a few local produce items at nearby Greig farm and meet the adorable goats. One tip- bring an eyemask if you're sensitive to light in the mornings- there aren't any window shades in the bedroom.

Porter & Sara run an amazing cabin. Their container cabins are well equipped for a fun, romantic stay. The layout of the cabin lends itself to a warm welcome and the positioning of the couch, bed, and table make perfect use of the landscape - all facing the beautiful pristine meadow that hosts a ton of wonderful sights including deer, flowers and interesting insects! One thing that stood out was the lack of mosquitoes. Given the clearing and the amount of other wildlife, we were pleasantly surprised how comfortable it was to stay outside and not worry about being eaten alive. There are plenty of lounging accommodations, from nicely kept hammocks, to comfortable lounging chairs to a lovely hot tub . The low lights outside make the hot tub and patio a fun place to hang all night. When getting into bed, you’re greeted by the beautiful stary night. It was amazing to lay down and feel like we were all alone in the woods. We will absolutely be coming back for another romantic adventure.

My girlfriend and I stayed at Mike & Anna's cabin for a long weekend with the intention of spending the weekend inside, enjoying a fire, and disconnecting from work and technology. It was incredible, such a comfortable, beautiful, tranquil, and cozy home. We're already planning a chance to go back. Genuinely exactly what we wanted for a cozy cabin with a fire.

We had an outstanding time here Heidi was an amazing host we had asked her for fishing spots and we ended up catching fish we had an amazing time here and the food in the area is just walking distance so it’s super convenient and such a cute little town it was definitely the break we needed from all the hustle and noise from the city it was so private and cozy we felt so comfortable everything was perfect!!!

Mark’s & Lori’s tiny house was perfect base to show my parents around the Catskills. I was very impressed by the attention to detail in the house - I noticed great little touches like a torch, headlamps, and insect repellant. They even had a little stationary draw in the kitchen. I personally loved the fresh coffee beans available for use by guests. The house is located a short 10 min drive from Woodstock village if you want to grab groceries or eat out. It’s worth nothing that while the bedrooms aren’t full height, my 70 and 75 year old parents were able to navigate the stairs and low ceiling just fine. I can’t wait to go back to Mark & Lori’s tiny but perfect house! ❤️

Excellent and beautiful location. Very scenic and tranquil. The location allows you to relax while still being in reach of everything. The unit was very well maintained and clean. All the Amenities of home without the chaos.

The owners and all of their friends and family who helped them build this amazing place deserve a fantastic review, although admittedly, I wish I could keep it secret! The place is phenomenal. My daughter and I came to horse show at HITS and just had the most amazing stay. We cannot wait to come back.

We really enjoyed our stay and the town of Brattleboro as a whole. We loved the local restaurants and cafes. Kiplings and The Porch are a must visit. We found the recommendations in the welcome binder. While there we explored the trails surrounding the property. We did the full loop (yellow trail). It was about a mile and a half and a moderate hike, coming from a beginner. The interactions we had with Sean and others on the property were all pleasant. The cats roaming around the outdoor areas were adorable and fun to watch. We also really enjoyed the hot tub! The view is spectacular. Overall the stay was fantastic, just be aware this is an off grid kind of experience. This cabin is also down at the bottom of a fairly steep hill, making it more secluded but quite far from the wash house and hot tub. The cabin is a bit dusty and gets quite warm during the day. The bed and sofa are a bit uncomfortable but did the trick for a two night stay.

We really enjoyed our stay at Cabin Noir. The cabin was much bigger than expected but perfect for 2. The location was peaceful and the privacy was great. The rooftop seating was a cute addition to enjoy your morning coffee and nature. The host was very responsive, offering many suggestions about the area from hiking trails, shops, and eateries. We used their recommendations as a guide that afforded us the opportunity to see so much in short amount of time. We would stay here again.

Honestly, I was very nervous when we started the short but steep hike to the treehouse. I thought, I’ve made a mistake. By the time we got there and I got my wits about me, I had the most magical stay. The pictures don’t do justice to how amazing the treehouse, loft and artist’s space are. We stayed out pretty late by the firepit enjoying the glow of the house from outside. With tons of cds to choose from we listened to music until we fell asleep. Early morning coffee with a morning fire was a treat too. The outhouse is clean and even pleasant (not your great grandma’s outhouse!). Like others, I would have been more than happy to have more time there. The treehouse is an architectural wonder, a bucket list “must see” and, all around, the thing that kids’ crazy dreams are made of. If you can make the hike — and it is a hike — I recommend this gem. I’ll never forget it.

Great little getaway. Nice fire stove outside to sit by with a beautiful forest. Floor to ceiling window in the cabin to admire the nature. Would recommend!

A great place to stay and explore the local area. It was small but had everything that we might need, including a kettle which was very handy. The decor was tasteful and the bed was really comfortable. Nick and Kelly communicated well, and check in was very easy. The only thing that we had an issue with was the shower as the hot water took a very long time to run through. The second morning we ran it for longer as advised but it still wasn't really hot enough for me. A small niggle - overall we really enjoyed our stay.

Wonderful cottage with gorgeous, home made furniture. Clean, comfortable, uncluttered. A perfect space! Exactly as described. Thanks Marc!

Erin’s place was absolutely lovely! We really enjoyed the location - so peaceful and conveniently close to Art Omi. The cabin was beautifully maintained, and we especially loved the interior design, which felt both stylish and cozy. We stayed for two nights but honestly wish we could have stayed longer. Highly recommend!

What a fantastic stay and experience! Vidar was awesome with recommendations and quick reponse time! Tiny house and property were perfect and as described! And our dogs absolutely loved it! We will be back!

I enjoyed my initial stay at Mahalo Temple Retreat so much that I rebooked it for tomorrow. That's when I'll return to the friendly community and pristine area for a matter of extreme importance.

We had a lovely stay! The place was clean, cozy, and just as described. . The view was absolutely amazing—such a treat to wake up to. The location was perfect for our needs, and the hosts were responsive and welcoming.

Perfect location to relax and unwind but not too far from places to eat and shop! We especially loved having the lake right in the backyard for fishing and kayaking. Christopher was an excellent host and we would definitely stay again!

Amazing little tiny house, had one issue when we first got there with the A/C and Ben came over in 5 mins took care of it. Highly recommend checking out the waterfalls in the area. Very quiet and peaceful location. We look forward to renting from Ben in the future.