Holiday rentals with outdoor seating in Dutchess County

This beautiful property has a special place in our hearts. We stayed in the A frame during COVID and we always wanted to come back. This time we stayed in the main house and it was phenomenal. Wish the weather was better for us to use the pool, but next time! It well worth the price. Only an hr from the city and it feels like a full vacation. Wonderful way to lose time time for a few days. We will be back!

We had a great weekend stay at Katherine’s. The Esopus Bend Nature Preserve is only a ten minute drive and we really appreciated the local recommendations provided in the binder!

This is a lovely house, which is much larger on the inside than it appears from the outside. It would be perfect for a family or a girls weekend or a few couples. Marisa was very responsive when we had any questions.

We had a wonderful stay at this location during my daughter’s graduation from Bard College. The location has beautiful views of the lake and the layout of the property was perfect for the family to gather and celebrate, while also giving everyone the space for their own quiet time or rest. I would definitely recommend this location and hope to have the opportunity to stay again.

We lived in the Hudson Valley before retiring to Maine. For the past 4 years, Sarah and Jonathan’s home has provided the perfect spot for return visits with family and friends and a comfortable place away from home. The house is tastefully decorated and provides all that we require for an extended stay. The kitchen is well appointed with utensils, dishware, pans, and a large assortment of appliances. A special feature in the home is the lower level room with a huge wrap-around couch, large screen tv and toys for the kids. In addition, the grounds are beautiful. The outside deck allows for time to enjoy the gorgeous view and the large yard is fun for romps with our little Havanese. Being close to the town is an added bonus: The Tribute Gardens, Marona’s Market, the little French restaurant (Cafe Les Beaux), Stewart’s for ice cream, The Merritt Bookstore + Toystore, various antique shops are places we frequent. Innisfree Gardens and Dover Stone Church are nearby. We love it here!

Ari’s home was cozy and quiet. We had all we needed for a relaxing writing retreat. Spearate spqces to focus and a table big enough to gather at for meals. The whole space had a peaceful and serene vibe and was a great escape from the city. Would def recommend.

Really lovely home with gorgeous outdoor space. I thought it looked even better than the photos (which look great)! We visited with two 3yos, and the house was very thoughtfully designed for both the kids and the adults (baby gates, a high chair, nothing breakable on low shelves, etc). We loved the house and would absolutely come back again

This house is exactly as described, comfortable, cozy and has everything you need for a great visit. The bedrooms were so comfortable. Our weather wasn’t the best so we were disappointed we could not use the outdoor fire pit. There was no parking in the front because there was always cars there so we did have to park quite far up the road, but that’s not any fault of the owners. I would highly recommend this if you are visiting the area Marist, the CIA or Vassar, it’s a great option instead of an overpriced hotel. Highly recommend!

We had a lovely stay at Carin’s place for a short getaway to Kingston - we appreciated the local food recommendations and went for some great hikes in the area. While we can understand why people might have an issue with the train, we already have a habit of sleeping with earplugs so didn’t find it an issue (Carin also provides complementary earplugs). Thanks and we would stay again!

My husband and I had a great stay at Andrea’s place. It’s well located, quiet, and well decorated. Andrea was very communicative, kind, and thoughtful. Her check-in instructions were also very clear and she made herself available for us to ask for any recommendations, if we desired. Highly recommend!

The apartment was beautiful and exactly as described. It was newly renovated, clean, easy to locate, and in a prime location. We met Graham when we got there. He was outside working on more renovations, and he became a friendly face and helpful resource throughout our stay. The patio was definitely worth it. It was so peaceful and serene to just sit in the hot tub and stare off at the creek and mountains. The less than 10 minute walk to town on the abandoned tracks was so easy, romantic, and fun. This is a great place to stay for couples or families!

We had a great time at The Ridge House! The property was gorgeous, and the creek is even more stunning in person. The apartment was clean, fresh, and felt very cozy. The kitchen was well stocked to make a meal. Instructions were clear and we had no logistical issues. Thanks for great stay!

Constanza and Bill’s place was everything we could hope for. It was extremely clean and had all the amenities we needed. Constanza was also very responsive and helpful when it came to questions. The location was also very convenient for hiking and dining at local restaurants. We felt right at home and will definitely be back if we’re ever looking to stay in Beacon again :)

We had a wonderful stay! The place was spotless and incredibly well-prepared. The host went above and beyond—there was a bottle of wine and a charcuterie board waiting for us when we arrived, which was such a thoughtful touch. She truly thought of everything we might need, from toiletries to kitchen essentials, including a variety of snacks/breakfast items, coffee and teas. It made our stay comfortable, relaxing and stress-free. Highly recommend and would definitely stay again!

Our group went on a hiking trip to Beacon, and this was a nice stay, though about 20+ minutes to town. But we didn't mind the drive! It felt very safe and the second floor of the farmhouse was a peaceful retreat! The hosts were super responsive. The house was clean, beds were very comfortable, and the house was full of books and character! You can tell the hosts put a lot of love in decorating, making each space feel thought through and unique. The 2.5 bathrooms was nice for our group of 4 ladies! Thanks again!

Lloyd was extremely kind and understanding. We had to make a few changes due to a family emergency - all handled with no problems. We highly recommend any of their properties- great hosts.