Vacation rentals with a kayak in Orange County

We had an unforgettable stay at this magical cabin! Izzy and Joe are amazing hosts—warm, responsive, and incredibly thoughtful. Check-in was seamless, and since late checking was requested by them , they kindly offered a late checkout, which we truly appreciated and made our departure more relaxed. The cabin itself is even better than the photos—beautifully decorated, full of natural light, and thoughtfully designed. The bedroom and sunroom with lake views quickly became our favorite cozy spots. The private island with its dreamy daybed swing and breathtaking lake views felt like a hidden paradise, and our dog loved roaming leash-free on the island. Everything in the cabin is intuitively organized, with smart controls for lighting, shades, and TV—managed via an iPad that also contains a well-designed digital guide. We’ve stayed at many cabins over the years, and this one stands out in every way. We’re already planning to return and make this special place an annual tradition

Mom's Place is beautiful! Peaceful, spacious, feels like home. She provides books, indoor/outdoor games, and small comforts. Six of us stayed for my daughter's graduations from West Point. We could not have picked a better place to make the occasion even more special. Coleen is responsive, friendly and accommodating.

We’ve been going to Greenwood Lake for many years but this was our first time with kids and it was the perfect home for two couples and three kids. They loved the slide and hammock and all the space to run around outside as well as the game room upstairs. We took the boat out on the lake during the day and one day a family of swans even came up to the dock. It was so special! Dana had everything we needed plus things we hadn’t even thought to bring (like extra long skewers to roast marshmallows for s’mores in the fire pit!) It was a beautiful backdrop for a lovely weekend and we wished we could have stayed longer. Overall fantastic and above and beyond!

We had amazing stay at the cabin! Location is perfect: views of the lake are gorgeous, cabin is very private, it’s walkable to downtown, and short drive to nearby attractions. Hosts made us feel at home right away. Cabin is pretty big and freshly renovated. I highly recommend to visit drowned lands brewery (10 minutes ride) and stop by at GWL ice cream shack (walkable from the cabin). We enjoyed our vacation and will certainly book again! Thank you

Beautiful well decorated place. So peaceful and relaxing. Jack was also responsive and accommodating.

Staying at Jo's place was an absolute pleasure. The house itself was just as described and sits in a cozy area steps from Greenwood Lake. My fiance and I spent a week there and honestly felt as if it could be our second home. There was plenty to do at the lake where we swam, paddle boarded, and kayaked all around the beautiful water. Jo made sure that life jackets were provided for us and that they were the appropriate size which was incredibly thoughtful. She also gave us lots of recommendations for local places to eat and to see which was also very nice. Communication with her was top notch and was always comfortable. We will absolutely consider coming back to her beautiful home.

What a gorgeous place!! I would stay here forever if I could. Rhona’s home was spotless, beautifully decorated/designed and the views were spectacular. The check in process was extremely easy and smooth and Rhona was proactive and communicative with me throughout. Would absolutely stay here again.

Stefan & Tais’s home was an incredible peaceful getaway. Walking into the main floor was stunning and really took our breathe away with the huge windows and lookout to the lake. The home came with everything we could want from a grill and fire pit to kayaks and paddle boards. I would recommend their home to anyone looking to have a nice getaway with a beautiful sunset view!

House was very well stocked, great location, great communication, recommended!

The house was beautiful and my family loved it. The swingset outside and the toys inside kept my kids occupied and happy the whole time. The house is very kid friendly which was great for us. The house is right by the lake and we were able to go fishing and even use the kayak. We had a very peaceful stay and would definitely come again.

I stayed for a month solo to focus on my projects & it was the most peaceful month. The house is contained in nature with a plethora of birds & animal life that I witnessed.. a crane fishing at the creek beside the house as I worked, a pair of woodpeckers hunting at the lawn, a chipmunk that lives under the house & has a morning ritual of its own. All while the lake boasted breathtaking sunsets. On the practical side, the kitchen was fully equipped with everything one needs to cook everyday, which I did. It was private & safe for a solo girl like me to stay a month. Amazon found its way to it no problem. And there are nice streets to take long walks which I did 1 hour a day. Very friendly neighbors, everyone waves at ya. The covered patio, working from the dinner table, waking up in the bedroom to the lake.. all main areas are flanked by beauty. Really was perfect for a solo getaway. Also wifi was very reliable. Keep in mind lake living = insects. They’re harmless. Highly rec renting!

Beautiful space! Private and tranquil neighborhood with wonderful lake views. The house was extremely clean and cozy with comfortable beds, an extremely stocked kitchen, and toiletries in the shower. Would definitely stay here again!

Absolutely fantastic. Beautiful scenery. Lots to do on the property without even leaving the house. The house is fully stocked. If you accidentally leave anything behind.. this house will have it. Comfortable beds. The pool table and poker table was a lot of fun. The hottub was awesome. WiFi works great. I went in the river a few times but keep in mind the current is strong if you are not a good swimmer. I could have stayed even longer, I did not want to leave! Left feeling very refreshed as if I left the spa. This is a great house for a family or friend’s retreat. I really enjoyed my stay and recommend to anyone thinking about it. There are some shops 15mins away if you need anything. Chinese food, liquor store, convenience store etc

The Nordic Cabin was the perfect setting for my husband and I to celebrate our 22nd wedding anniversary. The cabin is beautiful and the modern design, furnishings, and decor really stand out. Instructions of how to get into the cabin and the pitcures provided made check in and check out a breeze. The kitchen was well stocked. A bottle of white wine and a few treats were left for us. The kitchen offered different spices, oils, milk, and eggs. Kitchen utensils, pots/pans, dishes, cups, glasses, etc are provided, as well as cleaning supplies. The bathroom was stocked with toiletries. We spent a lot of time relaxing in the cozy living room and slept well in the beautiful bedroom. Last, I have to say that the first time we opened the gate at night, after dinner in Warwick, and saw all of the outdoor lights on, really made it feel like we were entering an enchanted garden. Would definitely come back!! Thank you Kamil and Margaret!!

The location exceeded all expectations. This is one of the few Airbnb‘s that’s actually more beautiful than the pictures. Serenity at its finest. We were greeted by baby deer and a beautiful flock of birds that set the tone for an amazing weekend. Wineries and walks over the Hudson River are a short 20 minute drive away. Fantastic dining along the Hudson. Steve is a true professional host. He only took five minutes of our time and we figured everything else out. The fire pit was amazing with ample wood. Lake view and waterfall and ruins are even better in person than the pictures. The house is spotless and well designed with 2 incredible bathrooms. No cons. All pros. One of the few rentals I’d come back to.

Beautiful home on lake with truly amazing views. Had all the amenities for a wonderful weekend getaway. We had a great time kayaking, barbecuing and spending time outdoors.

This place is very special. I almost don’t want the word to get out because it’s so close to the city. The cabin is rustic and fun, the grounds are quiet and beautiful. We came on a rainy spring weekend and used the hot tub and fireplace a lot. In the morning we kayaked in the pond among turtles and newts sunbathing in the water, floating and listening to the birds. Dasha was a very considerate and attentive host. I will come here again.

Our stay at Emily’s lake place was absolutely amazing and exceeded our expectations! We were there for the week leading up to and including our son’s graduation from West Point, which is an hour from “the lake place,” as we affectionately called it. The West Point portion of our week was both wonderful and stress-filled with lots of travel back and forth between the two places, so the fact that the lake place was exactly as advertised was such a relief! The weather was cold and rainy for our entire week there, yet our stay in Emily’s cabin was peaceful, relaxing, and fun-filled. Everything we needed in the kitchen was provided, including the spices for cooking! Our beds were comfortable and there were plenty of blankets. The bathrooms were spotless, as was every room. The views of the lake were truly spectacular!! As we were packing up to leave, my daughter said, “they thought of EVERYTHING!” And she was right. If we ever stay in the area again, we will definitely book Emily’s place!

Anna's place is an amazing getaway from the city. The location is serene, with a beautiful pond right in the backyard. The host was very communicative and kind. We spent the weekend paddling on the peaceful waters and relaxing by the shore. The house was perfectly equipped and spacious, making it easy to enjoy time with our group. Even when it rained, we made great use of the large, covered balcony and the cozy living room and dining area for indoor activities. The surroundings were peaceful and picturesque, with birds chirping and crickets singing in symphony. We’ll definitely be back!

We had a lovely stay at Cynthia’s serene cabin on the lake. The view is beautiful and this home is very well decorated with comfort in mind. We enjoyed the private backyard and dock as a family and we would love to return. She is very communicative and a fantastic host.