Guest house holiday rentals in Dutchess County

An incredibly charming, rustic, simple and comfortable small cottage, in a gorgeous rural setting. Just as advertised. It was perfect. Right across the road is Tivoli Bays, with beautiful trails for walking and hiking, and a small waterfall too. If you like, it's just a short walk to Broadway, the main strip in the village of Tivoli. You'll find a few restaurant options, a small market, sandwich shop, excellent coffee, and homemade ice cream. I met Yuko who couldn't be nicer and was a pleasure to chat with. A great experience all around - highly recommend booking a stay!

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.

The cottage is very quaint and the surroundings are quite lovely. We had a very pleasant stay. They offered to let us see the baby lambs which are super cute!

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.

My fiancé and I stayed at Lambs hill to celebrate our anniversary. We had the most wonderful time. The views are breathtaking. The wrap around deck with jacuzzi and hammock made our stay calming and serene. I loved seeing the horses and donkeys throughout the day. They made the experience even more special and unique. Charlotte was super responsive and accommodating. We took cabs to Main Street at night for dinner and drinks and it was so close and convenient. I left my heart in lambs hill and can’t wait to return one day.

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!

Great location with lots to do close by! Comfortable and beautiful home that was great for our big group.

Our stay at Kyles guesthouse was wonderful, and we would definitely return. If you’re looking to escape into beautiful serene scenery away from the hustle and bustle this is it! Lots to do in the surrounding areas, but it’s wonderful to return to the peace and quiet of this airbnb. The accommodations were great and just as described. The only thing I’d note is that the guesthouse is attached to the main house, and so noise travels. Nothing that bothered us, but something to note if that’s something you care about. Anyway, I definitely recommend staying here!

Giuseppe was awesome, made us feel right at home. He was very responsive very understandable and very helpful. If we had any questions we need more people like him in this world if we’re in this area 100% we will stay here again. It is beautiful out here beautiful place very comfortable and gave us everything we needed to have fun, board games, and toys for the kids and even a Nintendo switch, the home had everything you need to feel at home!! Would recommend for everyone!!! Thank you so much Giuseppe!!

We loved our stay here! It was incredibly clean and so beautifully designed. We loved the porch and looking at the gardens and chickens. It’s a short walk to a nice little forest walk. Easy check in and Jess is super friendly! Will be back.

I chose The Little Bliss Pond House as my proposal site. The location was absolutely breathtaking and exactly what I imagined. Cara was extremely responsive and helpful during the entire process. I would highly recommend The Little Bliss Pond House to anyone looking for a quaint and peaceful location surrounded by the best nature has to offer. About a 10 minute drive to some great restaurants and shops in Saugerties, The Little Bliss Pond House is the perfect escape for a weekend. 10/10. Thanks Cara!

This is a beautiful Airbnb! Love the lofted ceiling! Felt super private even though it's attached to their home. Connie was super responsive and helpful. We only had it booked for one night but wish we got to stay longer!

Fantastic stay! The view of the river was so magical. The cabin is a quick 5 minute drive from lots of good restaurants and shops. We had everything we needed and more. Would 10/10 recommend!

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!

Debra’s cottage was beautiful and incredibly peaceful. 2 hours from NYC. Debra was a great host, we felt so welcome on arrival and she made our stay so easy and relaxing. Thank you!

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!

Loved our stay here! Small bachelorette weekend and the 4 of us were absolutely at home. Our hosts were wonderful and responsive throughout our whole stay. Though attached to the main house, there is sufficient privacy. Beautiful property , very peaceful. An added bonus was their adorable little dog Ellie! Would definitely stay again. One thing of note, the water in the house I think is like well water so it has a smell, almost like sulfur, not a big deal - just keep that in mind!

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.

This guesthouse was a perfect fit for our weekend visit to the Hudson Valley. It had plenty of space and was very clean. The house had a lot of charm and was a good value for the price. The host was friendly and helpful.