Search Vacation Homes in Wintergreen

"There are not enough adjectives in the dictionary to describe this AMAZING home! The views are literally the best in the area! The home was stunning- the layout, convenience, furniture, fixtures, amenities-it was as close to perfection as you can get. Our large Italian family travels a lot and have rented some lavish homes, but we all agreed this was THE BEST OVERALL we have ever stayed in! The owner was also super informative and super quick to respond to messages- and even let us have one...

"Everything was as advertised- family of 6 was well accommodated for a Thanksgiving weekend. Very cold windy and snowy outside but house was warm and comfortable. Very large kitchen was well suited for preparing Thanksgiving dinner. "

"The house was really cozy with lots of space inside and outside to enjoy. We enjoyed playing games, sitting by the fire inside and outside, and visiting the local wineries and breweries. Ashley was an excellent host and quick to respond with any questions. "

"The place was exactly as advertised. We had a great experience. Host was super responsive, would absolutely stay there again. "

"This was a perfect place for our bestie gathering. The location is beautiful...secluded and lovely. The house was truly impeccable. We loved the space. It was so well appointed with the little things that you may need. Simply awesome! Thank you to these great hosts!thoughtfully!"

"We had such a nice relaxing vacation. The views were beautiful. Great resource provided for local activities, trails, restaurants, etc."

"The Cozy Cottage was the perfect home for my husband & I and our friends who joined us for a last minute weekend antique shopping in the area. The location was so close to all the dining & shopping downtown. The home was extremely clean & had everything we needed to feel right at home. We enjoyed our time there and will definitely be back. If we had known this home was so comfortable we would have added an extra day to our trip to simply enjoy a day at home relaxing! "

"Exactly as described. Nice property and a short distance from downtown and hiking. Enjoyed the animals on property as well as interaction w hosts."

"I can’t tell you how accommodating this Cabin was. I traveled with a group of 6 women, between the ages of 45-50 to Celebrate a 50th Birthday! The home was perfect! "

"Amazing! I could spend hours at examining the decorations that each seem to have a story of their own. No detail overlooked! Felt like a step into the past ☺️"

"We recently stayed here in early April 2025. We got to experience amazing spring blooms from native flowers, a beautiful and remote home, quiet atmosphere and surroundings, complete with excellent proximity to a number of outdoor activities.Our hosts were very thoughtful, helpful, and provided plenty of suggestions and tips for the area as well as a clean home with board games, views, amenities, etc.I couldn't recommend this home more and we will assuredly make it a point to return to this home,...

"Four crazy seniors out for a little adventure and sightseeing. The View with a Room is probably one of the best VRBOS we have stayed at to date. Very clean and spacious rooms. Fully stocked kitchen with just about anything you would need to cook or grill! The outdoor spaces were amazing! Lovely front porch and back deck. Our host Peter Was very helpful and quick to respond to any question we might have. We have all talked about booking the house again next year for a longer stay!"