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!

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!!!

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.

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!

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.

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!

This cozy cottage on a stream was as peaceful and quiet as it gets. Sophie was a terrific host who responded quickly to our questions. We would definitely stay here again.

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!

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.

Super cute and quaint spot! A short walk to the beach and short bike ride to hot spots on commercial. My boxer boy Maxwell and I will be back😊

Had a wonderful time, very cozy home! The lake location was very peaceful, and enjoyed the paddle boarding.

We had a wonderful peaceful stay at Regina’s cottage. Everything was as described. We had our Labrador Retriever with us and the fenced yard was perfect. There are places that say dogs are allowed and then there’s a special place where they are welcomed. We are from the Berkshires and were out of our home due to construction. This is a beautiful area. For us it was peace and quiet vs. attractions. Loved the fireplace. Very comfortable bed with great linens. Regina sent check in info and it couldn’t have been any easier. GPS brought us right to the cottage which is set back from the street. You’ll be nestle between two mountain ranges. The area is beautiful. Thank you Regina!

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.

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.

This was an ideal space for a weekend away with the dogs. The cottage was welcoming and comfortable, beyond clean and had everything we needed for the weekend. Although dog friendly, there were no signs or smells of dogs in the space, I can’t emphasize the level of clean. I’ve always felt safe in PTown but the extra security measures available in the house were so appreciated. This cottage is in walking distance to everything and super convenient. I would 100% rent again from this host.

The cabin was perfect for a nice weekend peaceful weekend! We got to relax and enjoy the surroundings.

location was nice and walkable to everything in Provincetown. It was a little tough to find and parking on the street wasn't always guaranteed, but we figured it out with the included instructions. It's a little small, but for 2 people there's everything you could possibly need and its reasonably priced for the area. Would rent again for my wife and I.