Guesthouse vacation rentals in Dutchess County

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.

Deborah was a great host and followed up to any questions or concerns. The cottage was quaint but had just the right amount of amenities. The space was welcoming and the surrounding yard/pond are quite beautiful. Especially during the fall color change. There’s the occasional deer or owl in the yard you can often see over morning coffee.

We really enjoyed our stay at the cottage on Morehouse Farm. It's so cozy and quaint, hearing cows moo in the morning and watching the sheep over a cup of coffee. We always feel totally welcome and at home. The kitchen has everything necessary to make simple meals and you can enjoy relaxing in the living room on a media detox (no TV!).

This bungalow was a magical place to spend an autumn weekend visiting family and the beautiful Hudson valley area. We enjoyed morning walks around the pond with our pup and our coffee. Wish we had time to use the fire pit! Hammocks and bed was comfy, shower and kitchen were clean and lovely! Thanks so much a for a great stay! Would certainly recommend!

This is a beautiful place and exactly what my wife and I needed for a long weekend away! The barn is so cozy and we felt right at home . The hot tub was a nice treat on the cool evenings and the beautiful view. But by far the best part was the animals living below us that we could give snacks to throughout the day and see through the living space windows. Would definitely recommend this to anyone that loves horses and donkeys!

Wonderful stay! The spot lived up to our expectations and Antoinette was exceedingly responsive and helpful in the rare instance that we needed her. Would absolutely return!

I had the pleasure of staying at this house over Christmas with my family. Ida went above and beyond to exceed our expectations. From the Christmas tree to the table settings, everything was perfect to help make our Christmas magical. The kitchen was beautiful and had everything needed for our holiday dinners. The bedrooms were all decorated so nicely and I especially loved the master bathroom. Ida and Matt were great communicators and quickly responded to me with any questions that came up. I would definitely want to stay there again when traveling to upstate NY.

My family and I stayed at Kyle’s the night before we moved into our new home roughly 10 mins from his place. We were moving from out of state, with a baby, and the normal struggles that come with and big move. Kyle was very understanding, kind, friendly, and accommodating. I highly recommend this place.

This was the perfect Airbnb! We had everything we needed and nothing that we didn’t. Perfect for a weekend getaway and great location in between all of the touristy towns.

We had a brief but lovely stay at Connie's studio! The space itself is very welcoming, peaceful, and right by a trail that my partner, my dog and I thoroughly enjoyed. We felt so comfortable and would love to stay there again!

We are repeat customers who love this cabin, the gracious host, the peaceful surroundings, and all the fun and history of the Hudson River Valley. Firstly, the cabin is clean, modern, spacious, and brimming with high end amenities. And if you enjoy seeing the sunrise over a river, watching birds and other wildlife and being free of noise pollution this is the perfect place! We’ve enjoyed amazing food, incredible nature walks, and fun hidden gem shopping based on our host’s suggestions. We are already planning our return visit and know that when we do we’ll again feel utterly cozy, pampered and relaxed. This is a lovely getaway!

The cottage truly is a gem, and Anne is the best! I had a lovely and relaxing weekend. Millerton has a bit of everything. Great restaurant options in town and nearby Lakeville, nature, art, antiques etc. Can’t wait to come back!

Lou's cottage is exactly what I was looking for a weekend getaway and wind-down from the city. It is quiet and peaceful with a lot of nature around. The cottage is decorated with warmth and attention to details. You can easily see how much effort and heart that Lou and his family put in this cottage. It smells like home. Lou is also a very helpful and responsive host - he checks in on me from time to time and makes sure I have everything I need. I am fully charged here and ready to go back to the city to face whatever stress coming at me in real life. Will definitely come back!

Our stay at this adorable cottage was perfect! The space was impeccably clean, comfortable and had a cozy charm that made us feel at home. It offered great privacy while still being conveniently close to town. The host was thoughtful and welcoming, even providing a few local treats that added a special touch to our stay. Everything we needed was readily available. We would absolutely stay here again and highly recommend it to anyone looking for a relaxing retreat!!

Robin's place was warm and comforting with a great kitchen, an easy walk into town, and lovely outdoor areas. Robin was very accommodating, kind, and welcoming. We would be very happy to come back again!

I had a family emergency in the area near Rachel's loft. I made a last-minute booking and kept irregular hours. Rachel and Mark were kind and accommodating of my situation. The loft is exactly what it looks like in the photos and the amenities match the descriptions too. You can keep it very warm during winter with the two heat pumps. Rachel and Mark are thoughtful hosts. I would recommend this loft for people looking to visit Millerton, Sharon, and the surrounding area.

This was the perfect place to stay in Fishkill!

If I could give more stars, I would-- not just for the stay but to also represent Cheryl as a host and human! The stay was absolutely amazing-- the house was gorgeous, the property was exceptional. The location is great given it can satisfy whatever you're looking for: quiet, peaceful, great downtown and food scene, hikes if you'd like, etc. Cheryl quickly gave so many recommendations on local hikes, things to do, and eateries-- she covered all the bases without even being asked. She is also incredibly responsive, kind, and generous. I truly don't have enough great things to say, and I'm hoping to stay here annually with my partner. Our hearts have stayed at Knight Road <3

Shannon’s place was great! It was very clean and all the necessities were provided. Also, the bed was super comfy! And Shannon was super responsive to any questions. Thanks for the wonderful stay.