
Holiday houses in Simmons Gap
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Top-rated holiday rentals in Simmons Gap
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Top Guest favourite

Cabin in Stanardsville
5 out of 5 average rating, 59 reviewsThe Crooked Cabin
MakikoRating, 5 stars3 weeks ago
We spent 3 nights there and truly enjoyed what the beautiful property can offer. We definitely lucked out with the weather, which is always a plus. While having cups of coffee in the morning, we used our binocular to watch birds and other wild animals like turkey, geese, deer and bunnies. After coming back from wineries, we took a hike in the trails and meadows in the property (we did not have to drive anywhere). We made a fire in the evening and sat in a hot tub while stargazing. We ended up spending so much time at the house/ property, which is rare for us on vacation. We love to go back and enjoy a different season. Mollie's recommendations were awesome. Fabio NY Pizza was great, but I actually loved their chocolate cake more than pizza. Early Mountain Winery was the best if you like dry wine.
Guest favourite

Home in Crozet
5 out of 5 average rating, 15 reviewsOrso Blu one-of-a-kind VIEWS in Crozet
JamesRating, 5 stars2 weeks ago
The house is in a beautiful setting surrounded by mountains with peaceful views from the front porch that include a field of lavender and a stream. A forested trail network can be accessed at the far end of the lavender field--so bring your hiking shoes. The house is stunning with clean lines, "european" design and decor that includes high-end appliances and fixtures. Francesca is the ultimate host-very friendly and helpful. She provided all the information and details on the house that you would need for an easy check-in, stay, and check-out. From my initial conversations with her when I booked the house to helpful messages just before and during our stay, I felt like I was staying at the house of an old friend. We look forward to staying at Orso Blu on a future trip!
Guest favourite

Cabin in Elkton
5 out of 5 average rating, 10 reviewsShenandoah National Park: Cabin w/ Patio!
TaylorRating, 5 stars1 week ago
This place was absolutely beautiful! Truly was even better in person than the pictures. It’s quiet and peaceful and you are able to walk up the street directly into Shenandoah. The house itself was clean and comfortable and we loved the screened in porch. Definitely recommend to all!
Guest favourite

Cabin in Elkton
5 out of 5 average rating, 12 reviewsCozy cabin for 2 Near Skyline Dr , cool and quiet
IsraelRating, 5 stars3 weeks ago
Kevin’s place is beautiful and peaceful. Pictures in the listing don’t do justice. This is also the more equipped AirB&B I have ever stayed in. It has everything to enjoy the nature and disconnect from the city noise. The location also is perfect to get into Shenandoah, the entrance is just about 10min driving.
Superhost

Home in Dayton
5 out of 5 average rating, 3 reviewsDayton Guesthouse
ChloeRating, 5 stars2 weeks ago
Clean and charming place to stay for my parents who were visiting town for the weekend. Love that it was dog friendly, too.
Guest favourite

Cabin in Madison
4.97 out of 5 average rating, 92 reviewsRelaxing 2BR CABIN, 12 acres, dog friendly, hiking
ShannonRating, 5 stars4 days ago
If you're looking for a worry-free country holiday with your doggos, this is the place. It was so relaxing to be able to let our two run freely in the fenced yard, while still being remote enough to feel you're alone in the woods. We had deer, squirrels, humming birds, fire flies and the neighbour's dog visit. The cabin is really cute yet with all modern comforts and made the experience.

Home in Free Union
4.86 out of 5 average rating, 71 reviewsRiverfront Country Home with Blue Mountain Views
AngelRating, 5 stars1 month ago
Amazing place in Virginia! Would definitely recommend if you want a very peaceful place to spend some time with your loved ones. Everything was great, the hosts are very communicative and very flexible all throughout the stay. Beautiful backyard and land with lots of great things to do around the area. Would definitely stay here again!

Farm stay in Dyke
4.77 out of 5 average rating, 144 reviewsConstellation Farm - Cottage Farm Stay
CameronRating, 5 stars6 days ago
Although the house was a little tricky to find at first we had an amazing time. Clean house, lots of dishes for our group and a great night sky. If I were to visit Virginia again I would choose this place
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- Massanutten Resort
- Luray Caverns
- Ash Lawn-Highland
- Early Mountain Winery
- Bryce Resort
- Chisholm Vineyards at Adventure Farm
- Lake Anna State Park
- Prince Michel Winery
- Spring Creek Golf Club
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- Frontier Culture Museum
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