Holiday rentals with outdoor seating in Charlottesville

Alex's place was perfect for us. It was our first experience doing Air B&B and we were amazed by the cleanliness, attention to detail, and the abundance of amenities provided throughout the house. It was perfect for our group of golfers -- close to restaurants and easy drives to some spectacular golf courses. Bobby R.

Lisa was a very good host and responded to my messages in a reasonable amount of time. The house was nicely decorated and spacious for our group (5 people). The beds were comfortable and the bathrooms were clean. The location actually turned out to be better than originally thought for what we wanted to see and do. We were basically 10-15 minutes away from downtown Charlottesville, wineries, and Monticello. We had a great time and plan to come back.

Tyler & Erica, thank you for the use of your beautiful home. We enjoyed the peaceful setting by the river. God bless. Josh & Lori

This home and hosts are both rare gems, from the ease of checking in to the homes beautiful ambiance, its makes a great place to get away and enjoy nature. We would love to come back and explore more of the trails and wineries.

The house was everything we hoped and more! The hosts clearly give a great deal of thought to their guests' comfort, with so many little details covered. It was great to arrive after a long drive and find snacks and breakfast foods in the fridge. Also when I realized I had forgotten a personal care item, I was fairly amazed to see that the hosts provided a variety of those easily forgotten things -- making my stay that much easier. We also truly loved having our morning coffees on the sun porch, and playing games of corn hole in the beautifully maintained back yard. We would absolutely stay here again!

The place was really well set up. the drive up is a bit confusing the first time for sure. The house has everything a couple could need. Little bit of privacy, a nice space and a close proximity to a couple of small towns. The house was clean and had plenty of blankets, towels etc. Only negative (and it's a nitpick cause there was a lot of rain the weeks leading up to our stay) but the back deck furniture was covered in mildew and dead leaves. Would definitely recommend staying here.

We loved our stay at the Glass House! It was a perfect location for brewery, winery and hiking adventures. The neighborhood was beautiful and peaceful. The space itself was homey and comfortable. We appreciated the communication throughout the week and help with accessing the pool! We would definitely recommend!

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.

Great place that is very well located. Quiet and very rustic. Gen is a very proactive and responsive host. Really enjoyed our stay and highly recommend.

Very cozy and cute stay close to Charlottesville! It’s super close to town and easy to ride share. Property is very peaceful and relaxing to be at.

We had a great time at Tara & Mark's. It was as good as advertised and we really enjoyed the comfortable and clean space, and the beautiful surroundings outside.

I had a wonderful stay. Ruthann’s place was beautiful both inside and out. The room was spacious, spotless, and full of light, perfect for a solo traveler. The bed was comfortable, the kitchen well-stocked, great water pressure in the shower. I especially loved the raised nook beside the bed; it was a lovely place to begin the day, reading by the morning light and listening to the birds. The private patio is peaceful, a well-shaded garden with comfortable furnishings; you can spend all day out there. Ruthann is just lovely. Her instructions for parking and accessing the space were clear, and she was very responsive and checked in with me each day. It was great to chat. I felt very welcome. I appreciated all the little touches, from snacks and water to the collection of DVDs. I thoroughly enjoyed my time here and hope to stay again!

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!

Beautifully decorated and extremely clean! Had everything we could have possibly wanted and the location was perfect for visiting wineries and breweries! We would definitely stay here again on our next visit to the area!

Great location close to the arena. Much better than having to drive home 2 hours at midnight. Saw deer and a chipmunk in the yard so that was cool. Nice quiet neighborhood.

Jodi was the sweetest host! She was so quick to respond to any of our questions or needs. The pool was the perfect spot where we spent much of our time. The screened in porch was also so lovely!

We stayed here for my daughter’s college graduation and couldn’t have asked for a better spot. The condo was exactly as described—clean, comfortable, and perfect for our family of four. We didn’t spend much time there (graduation weekends are a blur), but it had everything we needed. It’s about an hour from Lynchburg, Virginia, and the location was ideal for us. Quiet, convenient, and a great fit for our weekend plans. The host was wonderful—responsive, flexible, and easy to communicate with. They helped us adjust our reservation and answered all our questions before and during our stay. I have nothing but praise. Highly recommend if you’re looking for a well-kept, stress-free place to stay.

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!

We really enjoyed our stay at your condo. It was nice to be in a newer unit. It was very clean and comfortable. The location is great being walkable to Fire and Frost, a coffee/wood fired pizza restaurant, and we prefer the upper mountain location also being walkable to golf, tennis and trails. We hope to come back to Wintergreen soon. It is a great place to relax!

Absolutely perfect for a peaceful getaway and being able to bring my dog along was a huge plus! The condo was spotless, very comfortable, and had plenty of nice touches like extra blankets, coffee, cooking essentials, puzzles, etc. The view is gorgeous and makes for a perfect morning coffee spot. Would definitely book again!

Super clean condo with everything we needed. Perfect for a stay in Wintergreen!

Very clean and a great place to sit back and relax after a long day out. The living room features two sliding glass doors with screens, which was perfect for the weather in early-June. That and the covered balcony was where we sat back and relaxed.

You don’t need many word for this place because it is STUNNING. Wonderful one day stay but goodness so worth it!

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.