Guesthouse 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!

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!).

If you're looking for a private retreat in a gorgeous setting, this is your place. The property is stunning, super walkable grounds, and a gorgeous back patio. S.A. is a super host, and when we ran into an issue, he was quick to respond and help. We recommend this place, and intend to stay again in the future.

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!

My family and I had a work related trip and staying at Ida’s felt as if we were right at home. The home itself was fully equipped with everything we needed and more. It really was as if staying in someone’s home and not your typical Airbnb rental. Enjoyed the peacefulness of the area and the retreat feel of being in the woods. Looks like during the warmer months it must look great. Cold Spring is only a few minutes away driving and it is a nice quaint town that looks to be more active during the summer/fall times.

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 loved our stay at the cottage! Connie was a responsive and helpful host. We felt right at home. The space is beautiful, walkable to hiking trails, and very peaceful. It’s also close to downtown Beacon and all the restaurants, shops, and breweries. Absolutely recommend for anyone wanting a quiet getaway!

We had an incredibly comfortable and peaceful stay at Arthur's Cabin with our 2 year old. Michael and Anne are gracious hosts - communicative and thoughtful. Their cabin has gorgeous water and mountain views, was easy to find, and was incredibly clean and cozy. They even set out the pack and play for us and had a box of coloring pencils for our toddler. We also asked about the firepit and they set out a pack of firewood for us. We saw many beautiful birds and the sweetest little bunny during the weekend. It was the perfect getaway from the city!!

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!

Second time staying here. Rachel and Mark are really responsive hosts.

Olivia’s place was a very quiet and peaceful place to stay. It was as described, and Olivia was very responsive when contacted. We had 2 adults and 1 child and felt very comfortable in the space.

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.