Tiny house holiday rentals in Dutchess County

A very cute and rustic cottage stay for a weekend get away. It is perfectly located just minutes away from Tivoli, and feels private enough. Yuko & Ethan were super easy to communicate with and check in + check out was super smooth!

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.

My stay at The GlassHouse was nothing short of magical. The house is absolutely stunning — every little detail is so well thought out, cozy, and beautiful. The views, the comfort, the peace — everything exceeded my expectations. Seth and the team were incredibly kind, responsive, and welcoming throughout my stay. I couldn’t have asked for better hosts. I felt truly cared for, and it made the whole experience unforgettable. I can’t wait to return. Highly recommend to anyone looking for a peaceful escape in a truly special place!🥹❤️✨ Also, for fellow horse lovers like me — there’s a wonderful horse farm (Crotta Farm, home of Applejack Stables) just a short walk away. It felt like a dream being able to spend time near horses in such a peaceful setting.🥰✨✨

We had an amazing stay at the house - it was beautiful and extremely unique. The hosts were responsive and helpful throughout our stay. Highly recommend and we will be sure to return!

Philip and Liza’s place was one of my favorite Airbnb stays ever. If you want a sterile mostly empty space that looks and feels like a display room at Ikea, this is not for you. But if you’re looking for cozy, full of character, beautiful surroundings, and the best cat host ever, you should definitely stay here. (If you’re not a cat person, that’s fine—Claus isn’t actually IN the space, but if you are, it’s definitely a bonus to be able to hang out with him in the adorable garden.) No, there isn’t a kitchen, but there’s delicious food within walking distance and a mini fridge thoughtfully stocked with some snacks and beverages. Bed was very comfortable. Bring your own ground coffee if you’re a coffee drinker (or walk down the street to get some). Easy to find and easy to park. Philip and Liza are super friendly and helpful, and thought of everything.

House was so gorgeous and well appointed with quality, high design things. Was so relaxing and a great view with all the comforts. All of the appliances you could think of- multiple different ways to make coffee, froth milk, blend, toast- had everything!!

We had a great stay at Rupert’s house. As other reviewers have stated, there is a train that passes by the house. Each day, it passed 2-3 times but it wasn’t terribly noisy. We never saw the tenant who also lives on the property. We didn’t realize that the tenant’s home was connected to the house we rented. It didn’t bother us but thought I’d share. Rupert was very responsive when we had questions. His home was a wonderful place for us to spend Thanksgiving. There was more than enough space for my family of 5. We especially loved the dining room with the long table and views of the Esopus Creek, which runs right behind the house. Given the weather, we didn’t spend time down there but it was certainly lovely to look at. We would definitely stay there again in the future.

Magnificent place! Even better hosts!! If ever I need a place to stay when visiting anywhere near, I’m staying here again!! I highly recommend this cottage:))))) They go above and beyond to make your stay as perfect as possible. Thank you, Tommy for being the best!

Awesome and cozy little place to stay. Definitely something fun and new, being a house boat. Had a very fun weekend getaway staying here. Also can't beat being able to bring our dog! Would come back here again for sure! Hosts were very Responsive to any questions we had and made everything a wonderful time!

My boyfriend and I really enjoyed our two day stay here during the holidays. The cottage was cozy and decorated tastefully and with care, perfect for a short and relaxed getaway and on a beautiful plot of land centrally located in the Hudson Valley. My boyfriend and I did actually bring a few of our own cooking supplies as we planned to make a more elaborate meal one of the nights, as we were aware from the listing that the kitchen only supplies the basics in that regard - so I'd recommend planning for that if you wanted to do the same. Wasn't an issue for us ! The woodburning stove was also easy to use. No complaints on our end :)

Very cool and unique setting! A one of a kind experience that will always be remembered. Thank you for letting us stay there.

We greatly enjoyed our stay at Wolf’s Den. It was in pristine condition and had many nice amenities. Its close proximity to Main St made it very easy to enjoy shopping and restaurants, even the Sunday Farmer’s Market! The hosts were responsive to our questions and left a detailed binder of highlights of Beacon. We look forward to returning on our next trip to Beacon.

This place was the cutest! Deirdre, Maureen and Stephen’s daughter, was our main point of contact for our stay. She was incredibly helpful and responsive, and the place was small, cute and cozy - exactly what we were looking for in a quick, one night getaway. She also had an incredible thoughtful basket of snacks and water bottles for our stay, which was a nice surprise.

Just what the doctor ordered. The outdoor hot bathtub on a chilly spring night with glistening stars and the sound of the purling stream was the medicine that we needed!

It’s hard to pick just a few good things to say about this lovely home. The location was perfect for the activities we had planned, however, if we had enough time to just stay at the home, we would have been perfectly happy. Everything exceeded our expectations. The home was very clean, the beds were comfortable. The hot tub and the propane fire pit right next to it, made for a couple of wonderful star filled nights for our small group. There were so many cool things to look at in and around the house, I think we will need to come back to see it all. Can’t wait!

We had a wonderful stay at this charming cabin in Rhinebeck. The space was incredibly warm, cozy, and welcoming, with thoughtful touches throughout that made it feel like a home away from home. The location was perfect—quiet, yet close to everything the area has to offer. The wood stove was a standout feature, providing a cozy ambiance and the perfect warmth for chilly nights. Highly recommend this spot for anyone looking for a relaxing retreat!

Lindsay's cottage is the perfect blend of convenience and seclusion. Just minutes from great shops and restaurants, yet tucked away in a peaceful, natural setting that feels worlds apart. It's beautifully appointed with thoughtful touches throughout, and stocked with every amenity you could possibly need for a comfortable stay. Whether you're looking to explore the local scene or simply unwind in tranquility, this place offers the best of both worlds. Highly recommended!

Our third year in a row and charming as ever. Tammy & Ben are very proactive and quick to respond. Lovely, cozy, comfy and quiet. A true retreat.

This cabin was perfect. we enjoyed cooking out on the grill and sitting at the picnic table for dinner. The amenities made this easy and pleasurable. The bed and linens were very comfortable and everything was uodated and extremely clean.

Our stay with Paul was incredible. we stayed here for our wedding weekend, and found Paul had left us a bottle of bubbly as a gift, very thoughtful. The cabin itself is beautiful and cozy and well kept, he cultivates a great vibe. You're in the woods, bugs and all, and the deck, garden, and waterfall make that so worth it. Since it was spring and had just rained the waterfall had a nice flow (it wouldn't year round). It was idyllic and cozy and private. Now the one downside is the drive up. The "road" is just this side of drivable in good weather. It's narrow, somewhat steep, a little curvy, and has two or three pretty bad potholes. At least it's well paved in most of the steep sections. We made it up in a minivan, a jeep, and a suburban-alike. You could make it in a sedan or hatchback too, but you do need something that doesn't sit too close to the ground. It's workable so long as you drive slowly, and you're greeted by a lovely cabin at the end. Bad weather? Beware! Great stay!