5.0
Outdoorsy memberHost since October 2024
Communication
5.095% response rateTypically responds in less than 6 hours
About Gregory's RV rentals
Hi! Originally from New England, I have lived in 9 states, visited 44 and been to 34 National Parks. As a digital nomad, I live to meet new people and explore new places. In my free time I’m an avid hiker, camper, runner, skier and roadtripper. I am frequently out of the house at local cafes, breweries and shops. We’re here to make your travel ideas a reality.
5.0
Outdoorsy memberHost since October 2024
Communication
5.095% response rateTypically responds in less than 6 hours
1 RV available to rent
loading
loading
loading
Memories made on trips with Gregory Winkelstern's RVs
John B.
5.0April 2026
Gregory’s teardrop was so much fun and easy to use. He has thoughtfully supplied the camper with everything that you could possibly need. Very responsive in his communications and made pickup and drop off super simple and easy. If you have any doubts about renting this delightful teardrop forget them and rent it you will have a blast!!
Gregory’s answer
We're so glad you chose our rig for your exploration of the Outer Banks. Hope to see you again in the future. Safe travels back to Vermont!
4 Photos submitted by John B
G D.
5.0November 2025
Perfect Little Teardrop – Big on Comfort and Charm!
I rented Wink’s Teardrop | Think Small, Live Large for a weekend getaway, and it was absolutely perfect! The trailer is thoughtfully designed, easy to tow, and set up like a dream. Everything we needed was right where it should be — clean, well-stocked, and cozy.
The hosts were fantastic from start to finish — great communication, super friendly, and clearly take pride in keeping the camper in top shape. You can tell they’ve put a lot of care into the details.
I camped in the mountains and loved how this little trailer handled the chilly mornings and misty evenings. It draws a lot of attention — people kept stopping by to admire it!
If you’re looking for a fun, simple, and comfortable way to camp, this is the one. Highly recommend both the trailer and the hosts.
I rented Wink’s Teardrop | Think Small, Live Large for a weekend getaway, and it was absolutely perfect! The trailer is thoughtfully designed, easy to tow, and set up like a dream. Everything we needed was right where it should be — clean, well-stocked, and cozy.
The hosts were fantastic from start to finish — great communication, super friendly, and clearly take pride in keeping the camper in top shape. You can tell they’ve put a lot of care into the details.
I camped in the mountains and loved how this little trailer handled the chilly mornings and misty evenings. It draws a lot of attention — people kept stopping by to admire it!
If you’re looking for a fun, simple, and comfortable way to camp, this is the one. Highly recommend both the trailer and the hosts.
Gregory’s answer
We can't thank you enough, David. Seeing your enjoyment of our camper is why we started doing this. Thanks for letting us be a part of the 44th Tundra Trip, and for all of the photos! We'll see you again next year
19 Photos submitted by G David F
Micah W.
5.0November 2025
Jacqueline J.
5.0October 2025
10/10 experience renting this camper. Greg was incredibly kind, flexible and communicative. You can really tell how much time, love and thought was put into it. The camper has literally everything you need and it is super comfortable and spacious!!! Warning: Don’t rent if you’re antisocial, because everyone will ask you about this thing everywhere you go!!! 🤣
4 Photos submitted by Jacqueline J.
Samuel D.
5.0October 2025
Fantastic camper and great service from the owners. Will definitely be renting again.
Gregory’s answer
Thanks for being so personable and friendly. It was a pleasure to host you!
Ronald G.
5.0July 2025
Communication was awesome and the process of renting this teardrop was seamless. The camper itself is so light you forget you’re pulling it. Comfortable and clean. Will rent again
Gregory’s answer
Glad you were able to squeeze in a quick getaway! We hope to host you for future travels
2 Photos submitted by Ronald G
Sara G.
5.0June 2025
This camper was incredible! It’s very spacious and has everything you need! My husband, Dog (35 lb), and I slept very comfortably for 2 nights. It was equipped with all the kitchen and bedding which made packing very easy. The tow is light weight and easy to tow. Greg was a great host and very quick to reply to questions we had during the trip. We can’t wait to use this camper again! Would strongly recommend to anyone looking for a quick nature get away :)
Gregory’s answer
We love the Shenandoah sticker you added inside the kitchenette!! We look forward to hosting you all again soon
Samson S.
5.0June 2025
Got so many compliments on how cool the camper looked! Was really easy to hook up and tow. Greg messaged me back asap whenever I had any questions or concerns, 10/10 would recommend !!
Gregory’s answer
We're glad you had a great trip, and stayed dry! Thanks for choosing our teardrop
