
Holiday rentals with outdoor seating in Wintergreen Resort
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Top-rated Holiday Houses with Outdoor Seating in Wintergreen Resort
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.
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Popular amenities for Wintergreen Resort outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Wren Time
Great views, great location, nice house, close to wineries and breweries, and responsive host. Overall great stay. Might make this an annual trip!

Hot Tub! Wintergreen Resort!
Camille's place at Wintergreen was perfectly situated for our weekend at Devil's Backbone. The house was clean and tidy, it was easy to find, and her directions and instructions for getting there and getting in the house were spot on. it's an adorable little place and has plenty of room with the three bedrooms. We would love to come back and rent again. Our dog loved it too!!

Luxury|Hot Tub|Sauna|Cold Plunge|Game Room|Views
We enjoyed the house. It was a great place for eleven people and two dogs - spacious and comfortable. Kids (and adults) enjoyed the game room and large tv downstairs. The host was very friendly and communicated and responded to our questions very quickly. Peaceful location.

Llama Loft | Low Fees | Darts | Fire Pit | Off 151
The house is wonderful, plenty of storage, but would be helpful if kitchen supplies were labeled. Not sure if customary, but dishes were still in washer.

Perfect house
I really enjoyed our stay. The wintergreen resort area was beautiful. Great views of the mountains! The home was in a very private area on a very quiet street with very quiet neighbors. Quiet all the way around! It was a short drive to the Devils knob brewery which was a great dinner, and the little market down the street had anything you needed in a pinch.

Bear's Mountain Escape
Great stay! Perfect location and space was great. A tad smaller than what it looked like in the photos, but overall, great! The kitchen did not have any pantry space, but we made do with a shelf above the microwave and bins on top of the fridge. A day prior to check-in, I received an email stating the pool in the complex was closed for repairs. A bit disappointed at first, but it ended up working out really well. We had access to the SPA indoor and outdoor pools and the outdoors ended up being too cold to swim in. The indoor pool was no problem at all and they were very accommodating with lettings us have access throughout our stay. We would stay here again for sure!

Wooded Haven | Family Friendly | Fire Pit | Trail
We can’t say enough about our stay at The Wooder House. The home was perfect for our group of six, giving us all our own space to retreat while also offering large spaces to enjoy meals and movies together. Our kids loved the collections of board games, vinyl records and Calvin & Hobbes books. Everything we needed was readily available and thoughtfully organized, and Amy was such an attentive and kind host for our entire stay. Our visit revolved around hiking in Shenandoah, so the home was a great base camp for our adventures. It’s about a 30 minute drive to the south entrance of the park, and 20 minutes to a variety of breweries, coffee shops and vineyards. We truly can’t wait to visit again.

Mountain Bauhaus | Sleeps 8 | Large Deck
Great house! We really enjoyed our stay for a weekend golf trip! Dinner at The Edge was close by and tasty, and the house was exactly as described!
Apartment rentals with outdoor seating

Lovingston Get-Away Lovingston, VA
Ed and Camille were amazing, they have a sweet apartment with a great Jacuzzi and pool. We were in town for a wedding and were blessed that Ed’s spot was open as it was only 15 minutes from the wedding venue. The apt was clean and everything was working, the kitchen was spotless as well. Ed and Camille were great, very communicative and nice people.

Luxury Condo: Stunning Slope Views, Sauna, Dogs-Ok
Spectacular views. The condo was well stocked with anything you may need for a family getaway.

Mountain View Nest
Becky was a friendly and gracious host and the place had all the extra touches. Communication and notes were clear to help support our comfort in the condo and exploration around the area. The place was well stocked and had little extras like extra towels under the sink, plenty of spices/kitchenware, even firewood ready as needed. Very clean!! The view from the balcony is spectacular and the perfect place to start and end a day of hiking and breweries/wineries.

Endless Mountain Top Views from All The Way Up!
Loved our stay here. Loved it. The view was incredible! The home was clean and cozy. It will be one of my favorite stays that Ive had. And Frost and Fire across the street had the most amazing pizza and pastries, as an added bonus.

Blue Ridge Bliss - For family & friends to enjoy!
We loved our stay at this condo in Wintergreen. The condo was beautifully furnished. Very clean. And the views from the balcony are unbelievable. Since it was spring, it was very quiet which we enjoyed. The mountains were so lush and green. The host responded to any questions within minutes. Check out was a breeze. We will be booking again!

The Barn at Haden near Wineries and C'ville
We had a wonderful stay at The Barn and would come back again in a heartbeat! Dawn and Damond were friendly, approachable, and provided all kinds of local recommendations during our visit. Their apartment was spotless, light, and equipped with just about everything one could need. We'd highly recommend to anyone looking for a peaceful getaway, especially small families with children. Thank you so much!

Loft on the Knoll -Private pool now open
We've stayed at this property before and because of the beautiful apartment, the kindness and responsiveness of the hosts we returned. This time we had a special request to accomodate a horse we are traveling with, yes, a horse. We were able to work out this special request because of their kindness. It made this stay very very enjoyable beyond words that can describe! Since we last stayed they've added a pool that was so refreshing on the hot Virginia days! We will definitely return!!!

3 Ridges 3 min walk to slopes,besides inn,King bed
Great stay! The place was super clean and easy to get into. A perfect spot for a week in mountain getaway. The host was super responsive and friendly. I highly recommend this stay!
Condo rentals with outdoor seating

Cozy 1-bedroom Condo with Fireplace Near Ski Slope
Laleh is a great and perfect host. I have stayed with her numerous times and I have enjoyed her space, her continued communication and her quickness to address any number of questions. Enjoy your stay with her.

Five Minute Walk to Everything!
This place was great! Conveniently located with tons of things to do, many walkable from the condo. The photos and descriptions were super accurate and our dogs even felt welcomed! We appreciated the convenience of The Market, The Edge, Upper Crust, and really enjoyed all of the Memorial Day activities that Dave ad Paige let us know were happening. It was the perfect place to unwind after a day of adventuring. Dave and Paige were super hosts all the way around. We'd love to come back here again!

Mtn/Firework Views from Private Deck ~ King Suite
Susie’s place was PERFECT for my weekend of solitude and peace. I was able to relax and just take it easy in a comfortable home with a beautiful view. The home was clean and felt so comfortable. There were lots of personal touches that really show Susie put a lot of thought into the space. For example, the motion sensor nightlights in the bathrooms. And the dimmable lights in the bedroom. Check in and check out instructions were very clear and easy to follow, she even included a map of where to park! I can’t say enough great things about this experience.

Panoramic Peak: Wintergreen Condo with Views
We felt right at home the moment we walked in! The views are breathtaking, and the space itself is so charming. The resource guide provided truly gives you everything and more in terms of instructions and things to do. Response times are also fantastic if you reach out with any questions. If my husband & I ever find ourselves in the area, we are absolutely coming back to this location!

Tips Up: Cozy Slopeside Retreat w/ Fireplace
Nice home, in an ideal location. Great communication and quick to respond as needed. Recommend the home and location!

Wander Lodge: Golf, Spa, Wine, or just a getaway
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!

Cozy, clean, quiet mountain condo- King bed
John and Ritta were amazing to work with and so helpful. We found their cozy condo after a trip fell through. We were so glad to have found this amazing place in close proximity to hiking spots, good food, wineries and breweries. We will definitely be back.

Cozy Comfort with a View - Wintergreen Resort
We had a wonderful time while staying at this condo. There kitchen had plenty of pots and pans, the deck was relaxing, the bed we slept in downstairs was extremely comfortable. When Emile found out we were going to get in late, he had someone turn on the outside light. So nice because it would have been harder to get into the lockbox. So happy we stayed here for our getaway from the city.
Quick stats about holiday rentals with outdoor seating in Wintergreen Resort
Total rentals
360 properties
Nightly prices starting at
$116 NZD before taxes and fees
Total number of reviews
19K reviews
Family-friendly rentals
320 properties are a good fit for families
Pet-friendly rentals
140 properties allow pets
Rentals with a pool
200 properties have a pool
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