Family-friendly vacation rentals in Olive

My Family and i really enjoyed the house and there was plenty of space for 8 of us. The kitchen was amazing and had everything we need.

Cute house, open concept first floor was great for a weekend with our girlfriends! Hava was very responsive and kind!

We had a great stay at BorisRungcheewan’s place. Check-in was easy, and the hosts sent us all the necessary information well in advance. The only minor challenge was finding the house—it’s set back from the road and located at the top of a long, steep driveway. I can imagine that arriving for the first time in the dark could be a bit tricky. The house itself was just as advertised: very private and quiet. The interior was comfortably furnished, and we especially appreciated the fireplace and the Bluetooth speaker. The two full bathrooms were also nice . The hot tub was easy to use, although a few of the jets didn’t seem to be working. The kitchen was well-stocked with pots, pans, plates, and glasses. The house is about 15 minutes from the Woodstock area and the nearest grocery store, so we’d recommend stopping to pick up any necessary provisions before checking in. Overall, we would absolutely return to BorisRungcheewan’s place for another stay.

Ami’s place was great! Stayed for my birthday and was surprised with a delicious tres leche cake upon my arrival! The view was incredible, amenities were amazing, overall it was everything I hoped for and more. Thanks Ami!

Great Airbnb, I would highly recommend. I appreciate the flexibility on the check in and check out times. The kitchen was very well stocked as well.

Choosing to stay in Porter's container cabin was the best decision we could have made for our vacation. It was so peaceful and relaxing. We had daily visits from a beautiful deer, and countless butterflies. We chose to use this time to unplug, and really connect with each other, and we could not have chosen a better place to spend our time. We've missed the view from the front door every day since we've left, and we're already planning to come back next year. Thank you so much for having us.

Three friends met at this beautiful carriage house with the feel of a French chalet! We stayed two nights with varied weather conditions. The house, grounds and location was perfect. Hot tub was used and so relaxing. The surroundings were beautiful and peaceful. The host, Diane was very helpful and friendly. What host makes scones each morning and delivers them warm?! Visited the Ashokan Reservoir trail, Opus 40, and Woodstock. Recommend this home highly. You won’t be disappointed!

The house is spacious and elegant. The wooded lot has a pretty creek a little way from the house. We took some walks through the snowy woods and roads beyond the house and could have kept going for a long time - the mountain is peaceful and beautiful. The owners live a few doors down and came by to help set us up before a major snow storm. We had a really nice time.

Right in the heart of Woodstock, walkable to town. And on top of all that, my dogs were as comfortable as they could be away from home. Anne was responsive and kind, the smokeless fire pit was amazing, the bed was ultra comfortable. Air purifiers are abundant, place always felt clean. The balcony on the second floor overlooking the mountain was an added bonus. Wouldn’t have a complaint if I tried.

This is my second time staying at Susan's place. Susan is such a warm and welcoming host. I feel so comfortable when I stay there. She is not only a gracious host to us humans but she is also a fur baby mama too and allows you to bring your fur baby with you. My boy Dunkin enjoyed his second time here again. Susan's place feels like Home. She gives a lot of local recommendations and a variety of things that you could do depending on what you like. You have a parking space and you can walk into town very easily. It's so peaceful where you stay and when you walk later in the evening you can see the deer grazing. It's just such a beautiful sight and I'm grateful for Susan and her place so that way myself and my fur baby have a peaceful and safe place to go to enjoy a nice few days of relaxation. I will continue to come here as I feel it's a home away from home.

Great winter retreat. Prior comments referenced a sulfur smell from the water. We didn’t experience that. Great host and dig friendly!

We had such a lovely weekend staying in this cozy cabin. The views of the river and ridge from the yard were beautiful and calming. We were able to have a late check out with ease! Definitely will be back to stay again!

Our second time staying at Maitopia with our cat, just as wonderful in a different warmer season. Tina was super responsive as usual and even accommodated a late checkout. We enjoyed feasting in the kitchen as well as grilling in the yard, floating around in the pool when it was warm enough out, "hiking" with our cat on a leash around the forest on the property, taking baths, streaming music. We didn't leave the property much, but it was a fun highlight to get a few local produce items at nearby Greig farm and meet the adorable goats. One tip- bring an eyemask if you're sensitive to light in the mornings- there aren't any window shades in the bedroom.

The cabin is beautiful and the perfect place to disconnect any time of year! It truly feels like a home away from home. We did run into a water issue during our stay, but Danielle took quick and thoughtful steps to resolve it and offered a very customer-centered solution. That really showed us how much she cares about her guests and takes her hosting responsibilities seriously. We had a wonderful time and definitely plan to be back soon!

Very comfortable and felt great to be inside this special little cabin. We brought our dogs and they were well accommodated here. The immediate road the house is on isn’t the best for walks but there’s lots of beautiful trails just a short drive a way. Although we were there during a very icy winter, I think the river behind the house would be fun to enjoy other seasons. Also great restaurants super close to the house.

By far the best Airbnb experience I've ever had! Joni was an amazing host, and I also had the pleasure of meeting her husband Rob/seeing their unique, beautiful home. She was responsive and very helpful throughout my stay, and even taught this "non tech savvy" person how to operate the TV! The location is perfect- and in my case even more so, as I attended a family wedding at the Colony just a block away! Its a 5 minute walk to town, and at the same time very peaceful/private- a perfect combination. I fell in love with Woodstock and wish I could have stayed longer. I'll definitely be back, as there is much more to explore in the area- will definitely stay at Logstock when I return!

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!

Billy and Rhobin were so helpful and easy to communicate with. The house was so comfortable and peaceful. The property was lovely! 5 Stars all around! Thank you for a fantastic stay!

We had such a great stay at Eugene’s place! The house was perfect for our group — spacious, comfortable, and full of fun things to do. We especially loved the private theatre, the hot tub, and especially the sauna — such a great touch! The volleyball net was a hit, and there were tons of games in the closet that kept us entertained. The kitchen was well-stocked and roomy enough for us to cook meals for our large group, and there were plenty of different areas to hang out in, everyone could find their own space to relax. The towels were plentiful (huge plus) and having access to the washer and dryer came in handy during our stay. Eugene was a fantastic host — super friendly, very responsive, and just really helpful all around. We also got to enjoy a few deer sightings right in the yard, which felt magical. We visited the nearby alpaca farm and did the Beer Mountain hike, which was a nice outing. All in all, a wonderful stay. Would absolutely come back. Thank you Eugene!

Perfect location — it’s directly in the middle of Minnewaska State Park and downtown New Paltz. Stargazing in the hot tub was a perfect way to relax after a long hike.

We truly enjoyed our stay at Wilderkill Barn. Maria Cristina and William were exceptional hosts—warm, attentive, and genuinely committed to making our visit special. They went above and beyond to make us feel welcome. The home was a haven, with a hot tub, sauna, pool, fire pit, pool table, and immersive sound and movie systems—all of which made our stay delightful despite the cold, dreary May weather. We can't thank them enough. ***That said, we feel it's necessary to address a serious issue with Airbnb itself that arose while booking this property, unrelated to the property itself. An unexpected tax was added after booking, and Airbnb has yet to provide a clear explanation. After years of loyalty, we were disappointed by their evasive and unhelpful customer support. This experience has made us reconsider using the platform in the future. We urge potential users to scrutinize all fees carefully and be aware that Airbnb’s support may be difficult to navigate if problems arise.***

My family stayed here for a weekend trip to Windham. The location to the ski area was very close, only 6 minutes away. There were plenty of nearby restaurants, markets, and coffee. The house is clean and cozy and perfect for a family of 4 or 5.

This comfortable, cozy, magical piece of Catskill paradise was the perfect place to gather to mourn the loss of my father and make some new family memories for a lifetime. Photography is a hobby of mine and the picturesque landscape allowed me to get lost in my passion. We cooked all our meals together in the well-appointed kitchen, challenged each other in the PacMan arcade game and cuddled up together to watch the stars shine and a movie on the comfy couch. We took long walks and met two local farm horses grazing freely in the local fields. The wonderful host was very accommodating and fast to respond. We loved her thorough recommendations for local dining, fun activities and nearby shopping. Book this cabin in the Catskills! You will not be disappointed! We will be back! ". . . there are deeper gorges, greater streams and higher mountains but in no other place is the combination so blended into a harmony so perfect as to form such tempting bits for the camera or the brush.”

Richard and Sheila were wonderful hosts, and we very much enjoyed our stay at their cabin. After receiving a very warm welcome, we enterer a modern but cozy cabin. We especially loved the view of the creek from the bedroom, in addition to the several spots to sit outdoors. The kitchen and outdoor grill were very functional. Richard and Sheila were always responsive and attentive to our needs during our stay, and managed to make our stay unforgettable despite the rainy start and cooler weather. We cannot wait to return!