Tiny house holiday rentals in Massachusetts

Beautiful quaint spot on the cape for a weekend getaway. Maureen's place was quiet, relaxing and cozy.

Dean's place was amazing! I felt at peace and felt like I was really in the middle of nature. Quiet and very cozy place! I will be back again! Dean is very friendly and communication is quick and easy!

Cozy little place in the perfect location if you want to be basically on the beach! Great for one or two people and the beach was beautiful. Lauren gave good detailed instructions to find the place and parking too which was helpful!

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!

We loved staying at Carolyn’s place. It was just how the listing and photos described: clean, private, had plenty of amenities, etc. Carolyn was quick to respond to questions, and graciously let us return after checkout to retrieve something we had left behind. Would highly recommend this place if you are looking to stay in the berkshires!

This was such a a delightful place to stay. The surroundings were so beautiful and calm. We were greeted by turkeys, and a mother and newborn deer crossed our path as we left. The hosts, Susan and Mark, were friendly, attentive and accommodating. I would certainly come back in a heartbeat.

Cesar's place is amazing! it's a good combination with being close to everything within a few minutes drive or ride or tens of minutes walks and being pretty quiet and close to nature with the ponds and plenty of birds. it's also close to the cycle path making it a great options for cyclists going to Woods Hole or just wanting to ride around for fun. the cottage is cute and very practical. everything is well thought and Cesar is very caring, friendly, and helpful. excellent kitchen and functional bathroom. the deck is stellar. The space is very well thought. I strongly recommend this listing and I'd be delighted to stay there again.

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.

I highly recommend staying at Chad’s tiny home! The space was beautiful, user friendly and a great escape! Chad was a proactive host and you can tell he very much cares for the space and his guests!

Gorgeous cottage in a beautiful neighborhood. Perfect for celebrating our anniversary. Highly recommend the intimate setting.

We had a wonderful stay at this cozy guest house! Kat & Lucy send us different messages regarding check-in, things to do, best restaurants etc. which made our process easy and our time in Gloucester much more enjoyable. We will definitely be back!

My friend and I enjoyed our stay in Dennis, it was the perfect location for our girls getaway! We were within walking distance of the beach and it was a good proximity to other towns, which we explored on cooler/rainy days! It was the perfect island cottage! The host was very responsive and sent multiple local recommendations!

Such a perfect spot directly on the beach. Loved my stay & Daniela was extremely responsive for any questions!

Linlin was a wonderful host and we loved this adorable cottage. It was incredibly clean, while still being warm and welcoming for us (and our pup). It's a little farther from the water than we had anticipated, but it's a relatively short and private walk to a dock with kayaks and beautiful views. Highly recommend!

Great spot to stay and explore the cape from. Micaran was incredibly helpful with his communication and the place was perfect.

This was my second time staying at Maureen’s beautiful lakeside home and it surely won’t be my last. It’s the coziest, peaceful and inspiring place. Looking forward to future visits!

Songbird Studio was the perfect b&b for me and my partner during our 3 days on the Cape. Private and peaceful, yet centrally located made getting anywhere of interest within 45 minutes extremely easy. The space was both clean and comfortable while also being very affordable compared to other listings. Ann was also such a gracious and hospitable host. The coffee shop right across the street was an added bonus in the mornings! Overall could not recommend this location enough and would 1000% stay here again.

Such a great place. Everything was thought about at the Goat Shanty. You can’t go wrong here. We will absolutely be back.

Tomi and Jim warmly greeted us when we arrived, showed us the place and offered recommendations for restaurants etc. Beds comfortable, towels soft…..just a beautiful cottage as listed!!!

A beautiful cottage. Our dogs loved the beach and we loved hearing the ocean at night. Best of all, we saw North Atlantic Right Whales at Long Point. In a world where it can be difficult to sleep well - I slept like a baby!

What can my wife and I say about Jo Leal and John and their sweet carriage house. Every detail in the house showed such care, such attention, and such beauty. Nothing could have prepared us for the experience of spending time in this charming house , and more notably, nothing could have prepared us for the wonderful experience we shared with Jo Leal and John. We so look forward to our next visit and the continuation of this experience.

I had a wonderful stay at Great Harbor Getaway. The apartment was beautiful - well decorated, excellent outdoor space, and a lovely living room and kitchen. The location of the apartment was excellent: walking distance to Town and the Morning Glory Farm. Jennifer was an excellent host: super responsive and helpful. I highly recommend Great Harbor Getaway; really looking forward to my next visit.

We had a wonderful time in Westport it was a beautiful setting and Laurie was the perfect host. We learned lots of interesting things about what living on a goat farm entails. Plenty of hard work which speaks to the care taken in being a great host. The location in Westport is perfect - an easy drive to have coffee, the best ice cream around at Woods and Twelve Cousins for pizza. We accidentally left a toy stuffie and Laurie was so responsive taking the initiative to let us know. A great spot!

My husband and I stayed at the huddle hut for three days. The place worked better than we expected from the description. We wanted a stay connected to nature and yet comfortable. The hut is set up with charm and lovely taste. Everything you might need is there. It is just thoroughly enjoyable. Susan is a generous, responsive, and responsible host and she runs the place impeccably. One couldn’t ask for a better host and a better place. We felt very well taken care of from start to finish.