Kid-friendly vacation rentals in Olive

Great stay and service (we were missing coffee filters and they were brought over within minutes of writing!)

We wanted to get away from the city for some peace and quiet and Corina’s place was exactly what we were looking for. It felt very tucked away. The home was stocked with pretty much anything I think one would need. The outdoor space is huge, nice and safe for our dog to frolic. Loved the large firepit - wish we had more time to sit outside. Corina was super friendly, accommodating, and extremely quick to respond to any inquiries, so you should be in good hands if you need any help. I like to try a new airbnb whenever I can, but when we return to Millerton, we’ll be going back to Corina’s!

Well kept clean old house and furnishings. Terrific unobstructed view of the Hudson from two of the bedrooms and living room facing East. I loved sitting by the bay window in the master bedroom with the sun shining in watching barges on the river and with views of the town of Hudson on the far side of the river. The owners stuff was in the closets and refrigerator and freezer full of her food but that did not bother me. I appreciate having condiments, salt, sugar and pepper available. There is a washer/dryer but no dishwasher and only one bathroom. Also no shades on the East facing window in the master bedroom so light streamed in at sunrise.

My family & I spend 5 nights in this beautiful home. We had 4 adults with 3 fur babies. We truly enjoyed our stay. I love to cook & Jane’s kitchen was fabulous and very well equipped. The open fire place was perfect. The outside area was ideal for our dogs to run around safely. Short drive to lots of cute towns. I would highly recommend this home for anyone looking for a great country weekend away.

This home was perfect in many ways. The home itself is bright with sunshine, has a beautifully-updated persona while keeping its mountain cabin charm. The kitchen was well supplied and we were able to cook meals easily. We also enjoyed the selection of books and games during the evening hours. If we still had young children around, they would have loved the fun kid's room upstairs! Plenty of available hiking nearby with a good selection of local restaurants for various libations and meals. Working with Julie was super easy - communications were quick and simple. No problems at all - a very excellent place for a relaxing holiday!

Cooper Creek was above and beyond what we expected for our weekend stay. Eileen was an exceptional host in every way. She has just about every amenity for a family stay you could think of, plenty of space for everyone and a very cozy aura. She even made homemade muffins and bread for us. I have stayed at many airbnb’s and this one is by far top notch and one of my favorites!

Scott is amazing! The airbnb was incredible! Lovely placed filled for immense and loving memories. He allowed me a late Check-Out which was wonderful. Definitely recommend you guys coming more often!

My daughter and I spent a lovely weekend at Chelsey and Dominic’s house. It was the perfect place for reading, laughing and lots of conversation. Easy to get almost anywhere in Hudson Valley. We enjoyed walks around the property and seeing quite a lot of wildlife. The setting is truly magical.

Very comfortable, roomy, spotlessly clean place to stay in Cornwall-on-Hudson. It was a great location...easy walk to a few restaurants, coffee shop, convenience store. Could easily get to many villages, towns, points of interest in the valley.

had a great time here while a group of us did the Breakneck Trail Race! quiet and clean and an very short walk to town for restaurants and coffee.

My family and I loved staying at Tj’s place in Hudson. The apartment was beautiful and exactly as described. Four of us stayed there for a week and we were very comfortable. Tj was very responsive when we had questions or issues (which we didn’t have many of since instructions were super clear). I also enjoyed the multiple yoga classes and spa sessions I participated in at their spa downstairs. The instructors and providers were all super friendly! The town of Hudson is incredible for anyone who loves to shop, look at art, and eat good food. It’s small, but there’s so much to see and eat! Everyone in town was genuinely friendly and welcoming. This was exactly what my family and I were hoping for for our vacation. We’re grateful we found Tj’s place!

My daughter and I had plenty of space to spread out. John’s place is very comfortable, clean, and charming. Thoughtful touches like extra hooks, suitcase stand, and bench at the entry to take off our wet shoes after a rainy Spring day in Hudson. Easy walk to great coffee shop and restaurants. Would definitely return!

We had a great, quick stay at Laurie’s! We were there for one night for a hiking trip. Laurie reached out that morning and check in was quick and easy. There was a coffee shop a quick walk away and the location is central to so many towns. We will be back for more trips!

Conveniently located and accessible to everything the Hudson Valley has to offer. The unit is small, but has what you need.

This was just what I needed for my first trip to Mohegan Lake! Quiet neighborhood. Cozy bed. Great water pressure. I’ll definitely be booking again if I come back to this cute little town.

My partner and I were very familiar with the area as we were traveling to go to a memorial and celebrate Easter with the family. We wanted to pick a place that was private and quiet. This fit the bill in spades. We would stay there again. For those who are traveling for hiking and exploration this is an ideal location as there are many state parks nearby. They have everything mapped out and lots of information at your fingertips.

This condo is absolutely beautiful and comfy! We especially love the bed and pillows.

Pristine clean, cozy, one bedroom condo unit located in Windham with seasonal access to tennis courts and a pool. Walking distance to the beautiful Windham Path. Slept better than at home in the comfy bed. Went for two days of midweek remote work. Agnieszka, the host, was gracious and responsive. The host obviously put some genuine TLC into this place and it shows. Browsed for books at Briars & Brambles, an indie bookstore in Windham adjacent to Windham Pharmacy. Purchased groceries and firewood down the road at Hickory Hill Market . Ate in area at Higher Grounds and Windham Diner. Living room has a fireplace with large screen TV just above. Great for all seasons. Thanks Agnieszka!

Luiza was a wonderful host. She provided detailed check in and out instructions, as well as local recommendations for our stay. Her place was exactly as pictured and cleaned wonderfully for our arrival. We hope to be back for another ski trip!

I highly recommend Suzanne's place for anyone visiting Windham! She was incredibly responsive and helpful throughout the booking process and my stay. As someone who travels constantly for work, my schedule can be quite unpredictable, and Suzanne was unbelievably accommodating and flexible with my changing needs. I truly appreciated her understanding and willingness to work with me. The location is fantastic, right in the heart of Windham, and the view of the ski resort from the back deck was an unexpected bonus! I only wish I could have stayed longer. I'm already looking forward to my next visit, not just for winter skiing, but also to explore the beautiful surroundings throughout the year.

Great people great location I would definitely recommend others and a great price

The basement studio is super clean and well finished with a very comfortable bed. We stayed for a few days while visiting our cadet and the location is great. Nice quiet neighborhood, too.

My boyfriend and I really enjoyed staying at Lubov’s place it was super clean and had lot of amenities. We went around Woodstock for dinner, which is a beautiful neighborhood and not to far, great for a spot to eat or just walk around and spend the afternoon. We also visited the Kaaterskills falls which was super close so that was a wonderful bonus. Didn’t get the chance to this time but we passed many hiking trails and mountains that are in very close distance to the Airbnb! Definitely would recommend staying here to anyone who is looking for a peaceful and tranquil getaway! We had a wonderful time, Lubov couldn’t have been any more amazing! Definitely will be back soon!!

Cozy apartment, walking distance from the water front. Had a great weekend getaway.