Holiday rentals in Wintergreen Resort

Our stay with Steve and Debbie was absolutely amazing! Their home was charming, spacious, and perfect for our girls' trip of four. We had more than enough room to relax and unwind, and there was plenty of parking, which made everything so easy. One of our favorite parts was sitting outside on the lawn chairs, soaking in the beautiful scenery — it was so peaceful and refreshing. Lots of great spots to head to all 30min and under. Pippin Hill was only 10min away! Everything about the stay was wonderful, with no complaints at all. We are already talking about when we can come back. Thank you, Steve and Debbie, for such a memorable and relaxing getaway! --- Would you like one that's a little even more bubbly too, just in case?

We had an absolutely wonderful experience at Ben's rental home. The house was spotless and incredibly well-maintained—every room was clean, comfortable, and exactly as described (if not better!). The photos and description were spot on, and we were pleasantly surprised by how much attention to detail had gone into preparing the space. The owner was outstanding—super responsive and helpful throughout our stay. Any questions we had were answered right away, and it really made us feel welcome and taken care of. Overall, this was one of the best rental experiences we’ve had. Highly recommend to anyone looking for a relaxing, worry-free getaway!

Spectacular view from this lovely condo! Ideal for our weekend to unwind.

I cannot count how many times we’ve stayed at Montfair. Heck, my wife and I got married there in July of 23! This is our home away from home which is a short ride from Richmond, yet worlds away. Thank you again for hosting us. We had an excellent end to Spring break at Loblolly. Until next time.

This was the perfect spot for our trip. A friend of mine and I brought our teenage sons for a quick weekend snowboarding trip, and needed somewhere with three sleeping areas. The loft had 2 beds and a fully bath which was exactly what we needed for the boys. It was super convenient to everything with a shuttle stop right out front. Plenty of parking, great amenities, clean, and easy to find! Also very cozy! We’ll definitely return!

Breanna and her husband were very friendly and easy to get a hold of. The place was out of a fairytale and couldn’t have been cozier. My boys loved the bedroom loft and we enjoyed all of the windows in the bedroom. It felt like sleeping in the woods without sleeping in the woods! Afton is beautiful and full of wineries and breweries that suit both kids and adults.

Absolutely gorgeous house for our getaway!! Truly! We wish we could live here! The views off the deck are stunning. It’s so peaceful up here. The house has lots of space. The kitchen is well-stocked with all the dishes & supplies needed. Coffee maker, tea pot (stovetop & electric), pots/pans, wine glasses, mugs, cutting boards, utensils, spatulas, etc. There are 3 separate deck spaces: one on the lower level, one on ground floor level-off the living room, and one with the hot tub. Rocking chairs on lower level deck with more chairs & a table, outdoor furniture sets and fire pit on main level deck. Everything was spotless & clean! Liquid hand soaps, shampoo, conditioner, & body wash in every bathroom. Tons of towels. We only saw 3 extra blankets, but we didn’t check all the closets, so if u like lots of blankets, ask the host or bring some. Lots of closet space. Master closet has hangers. We didn’t look in the others. Host is very responsive! Super helpful!! Will definitely use again

Very comfortable and clean. Plenty of coffee, comfy bed, nice big yard, private. Didn’t expect stairs to second floor BUT I didn’t read all details carefully. Super convenient to Rt 29. Traffic noise but steady: no truck air brakes or revving engines. Dr Ho had great variety for dinners, not just pizza. Great views of surrounding hills. We’d stay again!

We had a great stay here. Kimberly was kind enough to let us reschedule after some of our party got the flu and we had to cancel the original reservation. Entering the house was easy and there is a book of useful instructions. The hot tub and fire pit were easy to use and nice after a cold day on the mountain. When we checked in we didn’t have paper towels, but the host responded to my message quickly and provided all the paper products we needed the next morning. We had a little trouble with the hot water in 2 of showers, but were able to use the other two. All in all, we had a great stay!