100% (720)
Top-rated campgrounds near Winslow
100% (720)
Top-rated campgrounds near Winslow
Recent reviews from the Hipcamp community
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Valerie
2 weeks ago
With kids
My husband, our 3 boys, and I stayed in the camping cabin for last minute, quick, weekend getaway. Kerry”s directions were clear, so we had no difficulty finding it. When we arrived, he met us near the front and showed us where we were staying. He showed us around and told the boys about the net, the pigs, and the rope swing. They couldn’t wait to start exploring, and even though it was cold outside, they had a blast playing and didn’t want to come inside. The cabin was clean and cozy. The bed was comfortable and the heater worked really well. Everything was just as described, and my only regret is that we only got to stay for one night. None of us were ready to leave. Kerry was friendly, very accommodating, and responded super quickly to messages. I definitely plan to make another trip here when we are able to stay longer.
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Krista
November 2025
Group trip
Beautiful place and perfect for what we needed. Carrie was so helpful and friendly. We felt very welcomed.
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Liv
November 2025
With pets
We stayed in one of the tiny glamping cabins and absolutely loved it. It is a simple little wooden box with a full-size bed you crawl into, and it ended up being the perfect cozy nest for the night. There was enough room to sit up, stash our gear, and our dog fit comfortably with us. It was a cold night, but our sleeping bags plus the structure kept us warm, and the sound of rain on the tin roof was unreal.
Check-in was easy and the cabin was simple to find. It was clean in that ideal glamping way: not spotless, just naturally rustic and comfortable.
The location is incredibly quiet and peaceful. We heard the occasional bit of road noise from a distant back country road, but nothing distracting. The sites are spaced far apart, so everything feels private.
The host was wonderful. They gave us plenty of space but were also happy to chat with my husband about permaculture and building ponds.
My favorite part of the stay was climbing into the web at night to look at the stars. It felt magical. The outhouse was also surprisingly nice, which was a great little bonus.
Would absolutely come back. This place just has something special! ✨
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ED
November 2025
Weekend Trip to Happy Hollow Homestead
I was for years trying to sleep in a cottage like that and it finally happened. It was a pretty unique cottage, but the experience was good. Very happy with the place all around. Would recommend to others who like something different!. Great host, helpful and respectful.
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Riley
October 2025
Weekend Trip to Happy Hollow Homestead
We had an amazing experience staying at the cozy camping cottage at Happy Hollow Homestead! My favorite part was the tree web - there's something magical and therapeutic about being midair and surrounded by trees. We also enjoyed everything else at the homestead, from the friendly animals, the outdoor shower, to the natural surroundings. Kerry has been a fantastic host and responsive throughout booking and our stay. 10/10 would recommend!
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Samantha
October 2025
1 night at Happy Hollow Homestead
The cozy cottage was perfect for a chilly evening. Kerry was a fantastic host and has some epic land. We will definitely be back to explore and see what else he has built on the land. If the maple syrup is available you should definitely indulge! Big plus that all the dogs on the property were so sweet.
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Kevin
October 2025
With kids
Stayed at the cabin with our 1 year old. Kerry was so nice to us, and we shared great conversations with him. He has an ever present smile and is so welcoming. The cabin was perfect for us and the property had everything we needed. His neighbor even let our little guy play with the pigs and chickens.
The cabin was furnished and the water is delicious spring water right under the cabin.
We visited Louisville for a day trip and Marengo cave on our way out back to STL.
This property is a beautiful representation of the forested hills of southern Indiana and the mindset of a working homestead. Kerry is a do-it-yourself-er, and it’s awe inspiring to see what he and his neighbor have done to this piece of land.
Thanks for having us, Kerry! Well come back once baby #2 is with us!
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Raeann
October 2025
Group trip
Very kind and beautiful property. So relaxing! Would be happy to come back!
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Jamie
October 2025
Weekend Trip to Happy Hollow Homestead
Kerry was very kind and has the most beautiful land! Friendly pups joined us for breakfast and even found us along the trails, guiding us along them. The sky net at night is so relaxing and I hope to see it expanded! We had a wonderful trip and cannot wait to come back with our littles next year! Thank you Kerry!
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Chris
October 2025
With kids
The cabin was awesome, comfy and quiet. Highly recommendable!
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Crystal
September 2025
1 night at Happy Hollow Homestead
Amazing property, we stayed overnight as a quick stop. The host was very welcoming, the directions were easy to follow. The outhouse had a sink with running and automatic lighting. Loved the hot shower in the morning. We wish we had more time to stay! We were even able to use the host's wifi, which was very nice as service can be spotty.
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Rachel
September 2025
Weekend Trip to Happy Hollow Homestead
Once again, we had a fantastic stay on Kerry's beautiful property! Tried out the cabin this time and it was wonderful to immediately start relaxing when we arrived! The cabin was so cozy and inviting.
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Megan
September 2025
With kids
Beautiful spot, kind and friendly host, clean and comfy camping with my 12 year old son.
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Madison
August 2025
1 night at Happy Hollow Homestead
This was my second visit to Happy Hollow Homestead.
Last year we stayed in the tree house, this year the cozy cottage.
Kerry is a fantastic host, will be returning!
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Alanah
July 2025
Weekend Trip to Happy Hollow Homestead
My boyfriend and I had the best weekend, camping on Kerry’s land! He is very hospitable! Knowing my birthday was approaching, he gave me some fresh maple syrup, as a gift, to take home! 🥰 Very private location. We ABSOLUTELY plan on returning! Already made plans. 😉 Kerry and his land come very highly recommended! If you’re looking for the perfect getaway. From people, from all the demands of everyday life, Happy Hollow Homestead is the place to go! ❤️
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Adam
July 2025
Weekend Trip to Happy Hollow Homestead
Very friendly. We were led directly to our campsite with a bundle of wood waiting for us
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Chintothechin
July 2025
Group trip
Me and my friends booked this place and it was amazing! It was our first time camping outdoor and didn’t know what to expect but this was everything we needed. Kerry was very accommodating! He provided us with fishing and canoeing places nearby. We went to one of the place which was only 11 minutes away. The canoeing was so much fun. I would totally recommend this place if you’re someone looking for a fun getaway with friends or family.
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Trisha
June 2025
1 night at Happy Hollow Homestead
Kerry's homestead is fabulous. I'm an entomologist and he let me use some electricity to set up a collecting light at night. I spent most if not all of my time wandering around in the woods and watching my fire. No mosquitoes and an amazing number of fireflies.
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Scott
June 2025
Weekend Trip to Happy Hollow Homestead
The owner, Kerry, met us and showed us to our site. It was awesome. He gave us a quick tour of the property so we would be able to find our way around. Kerry pointed out some key features toilet/shower, walking trails, property lines, etc. It was a good stay and I didn’t have any problems or issues. The owners dog wandered over to say hi which was awesome. I will stay here again.
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Kelley
June 2025
3 nights at Happy Hollow Homestead
Me and my partner thoroughly enjoyed our time at the Happy Hollow! The woodland is beautiful, the campsite was incredibly relaxing, and Kerry was an incredible, attentive host who helped guide us to our lot even at around 11PM. The site was deep enough in the forest to be wonderfully quiet, while also being not too bad from groceries/general stores in the nearby town. I will say, my partner was scared half to death during early morning when he heard an animal walking around - it turned out to be a very sweet dog named Jersey, who was so very excited to both give and receive snuggles. Definitely would recommend this spot!
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