Tiny house holiday rentals in Long Island Sound

Nick & I absolutely loved our stay at Dave’s Milk Barn. It was charming, adorable, cozy, and gave us exactly what we needed for a respite from the city. Rio & Toby were incredibly flexible, kind, accommodating and helpful. Beautiful surroundings, adorable quaint rustic accommodation. We couldn’t give this place enough positive marks! Will definitely be coming back.

Gorgeous place in a beautiful town. About a thirty minute walk (or 4 minute drive!) right into downtown with cute shops and restaurants. The cottage is beautiful, clean and so cozy. Highly recommend.

The house is historic and charming. Very walkable to downtown mystic and other activities as described. Wendy and James were amazing hosts and very responsive and helpful. They responded on short notice late in the evening to help me set up an extra bed so that I could be on the main floor with my mother who is handicapped. Would definitely stay here again!

We had a lovely and peaceful 2 night stay at Esopus Studio. Highly recommended - 4 C’s - cute, cozy, comfy, and clean - perfect for two people. Close to Phoenicia Diner and outdoor activities. Alma was very responsive to questions before and during our stay and proactively informed us about her no shoe policy and to bring slippers! Hope to return someday.

We loved our stay at Joe & Barb's place! The cabin is delightful; beautiful surrounds, peaceful and quiet while being just a short drive from the amenities of New Paltz. Joe gave us great tips for nearby hikes, and we enjoyed a tour of the veggie garden (with full credit to Barb the gardener!), and hearing about the sustainability/eco-friendly initiatives of the property. Thanks for having us! : )

Tina’s place is fabulous. The modern decor and architecture is beautiful. The location is peaceful and the fenced in yard was amazing; our dog loved roaming around and exploring. The outdoor space is great for grilling and sitting around the fire pit. We especially loved the kitchen. It is fully appointed and the kitchen island is incredible for prep and serving. The washer dryer combo was an excellent touch and we were able to do a couple of quick washes so that everything was clean and ready to unpack at home. Saving the best for last; the soaker tub in the master bedroom is luxurious and relaxing. Thank you, Tina. We can’t wait to visit again soon.

The cottage was perfect. Rocking chairs by the window for when it was chilly, chairs on the deck, chairs by the pond for when it wasn’t. Terrific recommendations from Tim, particularly the Dog Watch Cafe in Stonington Borough. Our stay was exactly the peaceful respite we needed, we just should have booked three nights!

Linda’s home is absolutely beautiful and unreal! First of all, it was extremely clean with great smelling sheets. Her home had everything you needed from coffee, seasonings, first aid kit, and even marshmallows to roast. My family and I had a bbq as well and Linda had a lot of cookware. We had sooo much space to walk and go on a hike right off the property. There is a little stream of water that connects to the pond which my little 4 year old loved. The horses were a lovely addition and we loved hearing the rooster during the day. We will certainly be returning because a weekend was too short to explore everything. I highly recommend! Thank you again Linda!

Small but mighty! Really cozy place. The house is really well laid out and has very nice renovations. Also really enjoyed lounging in the hammock out back in the sun.

My experience at this Airbnb was great. Everything matched the photos and the place was incredibly clean. My house feels remote but it’s incredibly close to a lot of restaurants and stores. I would absolutely stay here again.

Very cute place to spend the weekend. We found it easy to dine out, spend time in nature. Waking up to the beautiful scenic view from the patio was a great bonus.

Peaceful location, very calm. I loved the area very beautiful scenery, the lake was gorgeous! 🌊 The host was very responsive and gave clear instructions. This is a nice boat house that feels like a cute home away from home!

Thank you for this little gem! It’s really close by the casinos, lots of restaurants, and fun things to do. Due to the weather didn’t get to use the kayaks/canoes but still had an absolute blast. we hope to come back another time. Thank you for everything!

This place is MAGICAL. Mmmm wow, our stay at Mystic Pines was deeply nourishing, peaceful, and restorative. Our intention was to find a secluded space nestled in the woods where we’d see no one, and this fulfilled all of our desires! The cozy warmth is felt and appreciated- this feels more like the hosts made something really special and wanted to share its magic with others, rather than a cookie cutter property made to turn a profit. We spent hours reading the eclectic collection of books by the wood stove whilst listening to the rain pitter patter on the roof. All the best parts of camping balanced out with the creature comforts of home. Endless gratitude to the kind hosts for sharing this absolute gem.

We had an amazing stay at the Darya cabin. The kitchen was nicely stocked up and offered all of the appliances you would need. The cabin feels very private and you are surrounded by nature. I’m looking forward to our next stay here.

I only stayed for one night as I was just passing through the area, but I was incredibly comfortable here. Bed was very cozy and this spot is so peaceful and surrounded by nature! I would definitely stay here again.

A quaint, cozy place that my wife and i enjoyed. A great location as well. Our hosts checked in several times during our stay, however we didnt really need anything. The stay was very smooth and well run. Highly recommend!

The perfect place for a cozy getaway from the city! We really needed an R&R and this place gave us what we needed and would be happy to come back here again ✨

We had a great experience during our stay. The place was clean and very private. We came to the area for a trail race and it was super close to the State Park and would be a great get away for anyone looking to be close to nature and Minnewaska. The hot tub was the perfect addition. I would definitely recommend!

We had a lovely stay at Monica’s place. It was a cozy getaway from the city and we had a wonderful weekend trip to the nearby towns. The space is exactly as listed and even cuter in person. Highly recommend!

We had an amazing stay !! Very private and a great place to get away !!

Johnny was a great host. very responsive and his place was super cute right near the beach. it was a quick getaway for me but would definitely stay there again. Thanks again Johnny

We had a great time here, they were very cool about us bringing my cat and responded to our messages in a timely matter. The place looked just like the photos. I will say the WiFi could have been better but it’s advertised as a place to disconnect so surfing the web wasn’t really the intention.

We absolutely loved our stay! This is such a special, charming cottage and Beverly exceeded expectations. She is so friendly and responsive. The cottage has such character and is in a beautiful surrounding, just a short drive from town. We did not want to leave! We loved the decor, and we loved having Beverly as a host. We hope to come back soon!