Save with direct booking!
Come find your next adventure!
Reviews
Meghan
June 2025 · Airbnb
We loved staying at Justin’s place! The location was incredible, right off the Deschutes river trail, which was wonderful for walking the dog in the morning. The kitchen was well stocked with everything needed to cook with, the apartment was as very clean, instructions were easy and Justin was very responsive. Would definitely stay again!!
Richard
May 2025 · Airbnb
We really enjoyed our stay at Tips Up. We’ve living in VA for 20 years and this was the first time to Wintergreen! Kicking ourselves. It’s a very cozy apartment on the ground floor, a comfy bedroom with a soft comfortable King-sized bed with clean white linen. Small kitchen/living room with fireplace was comfortable and would have been very cozy with a fire (it was too warm our weekend). Neighbors were quiet. And the trail right outside the door was wonderful. Can’t speak to activities as we were there off season and felt like we had the place to ourselves. We’ll be back. Thanks Justin
Rebecca
April 2025 · Airbnb
We loved our stay at Justin’s place. The view from the back deck was my favorite thing. You can switch the wildlife while you sip your morning coffee, the trees are so beautiful. The hosts were warm and very quick to respond. I highly recommend booking here.
Megan
March 2025 · Airbnb
It was a great stay here! It’s in the Wintergreen Resort which was great for hikes with the pups, restaurants within walking distance at the resort, and not too far of a drive to wineries & breweries. Would definitely stay again!
Rena
March 2025 · Airbnb
A perfect home base for skiing at Mt Bachelor! It’s really nice to be just a little closer to the mountain than downtown Bend. Plenty of amenities around the property. Will definitely stay here again for our next trip to Mt Bachelor!
Crystal
March 2025 · Airbnb
Our stay was lovely and so thankful we could bring our fur kid too! We loved the location and place was very clean. Perfect for our family! We plan to stay again.
Roy
March 2025 · Airbnb
Great little spot to enjoy Wintergreen. it's a few steps from the mountain. The condo had all the amenities we needed to enjoy our stay. We loved having the fireplace and there are piles of wood outside all the condos so we didn't have to bring anything. We didn't get to ski this late in the season like we planned but there were some beautiful waterfalls to hike to only minutes away. The convenience of being in the resort was nice. We also didn't realize there was a convenient store down the street in case you forget something when you get up there. There are plenty of wineries and hard cider places to visit also. The owners were very responsive to our questions. Thank you for our awesome stay at Tips Up!!
Yogi
March 2025 · Airbnb
Great place for a just me and my son for a couple of days skiing. Location is great. You can see the slope and the top of the Blue Ridge lift from the apartment. Just a short 5 min (with ski boots on) walk down 2 sets of easy to navigate stairs bring you to the top of the mountain, which is nice and flat so perfect if you are with some beginners.
It's not a big apartment but comfy for a small family. The heating units is bit noisy throughout the place but not bad, we just turned it off at night.
The Keurig machine and a stand filled with K-cups and the firewood outside the door, were a nice touch!
All in all, a great place, quick responsive host in excellent location (you can even walk down to pick up your excellent pizza from the Upper Crust restaurant). Would definitely stay here again.
Yogi
Maria
February 2025 · Airbnb
We had a great stay at Justin's place. The condo was perfect for our family's needs. We really enjoyed the amenities and close proximity to Mount Bachelor. We would love to stay again.
Joanne
February 2025 · Airbnb
Perfect location for walking to all the bars/restaurants at the top and easy access to skiing without having to drive. Great train access for hikes with our dog too!
