Cottage vacation rentals in Shenandoah Valley

Holly Tree Retreat was just as described, so peaceful with beautiful views. We stayed for a two day getaway to celebrate our 22nd anniversary. We went to a local restaurant, Chop House Bistro based on Jennifer’s recommendation and it was amazing! We wouldn’t hesitate to stay here again!

A wonderful weekend getaway! The cottage was so cozy and we loved the hot tub in the snowy weather! Andrea was very responsive and proactive. We will be back!

thanks Olivia, our overnight stay was ideal!

Our stay was immaculate. The cabin and view are both way more beautiful in person. Very clean, home like feel and everything that you need is inside. There are a lot of fun activities that you can get into on the property as well. I loved renting from Darrel, he seems like such a kind person. We have definitely discussed renting out the cabin again in the upcoming spring. I think this will be a reoccurring rental for us. Top 3 rental that I’ve had on to is app.

Booked this lovely little spot for a romantic getaway with my boyfriend for his birthday! The view and vibes of the place were amazing and everything inside was clean and comfy. We very much enjoyed our stay and will most definitely visit again in the future!! Thanks Gillian :)

We had a great time at Sandy’s! The house was very comfy cozy and gave us a chance to get off our screens and just hang out! I will say, if you are traveling with a friend(s) who are under 21 or if you are under 21, this may not be the place for you. There isn’t much to do area wise expect winery’s!! Which was nice for me lol. We stopped by a small ice cream shop and went to a petting zoo about 12 miles away! All in all a much needed relaxing trip! We will definitely be looking into coming back for the summer !

My mom and I stayed here to prep for my wedding. It was well heated for the winter, we actually got very warm. Great layout. Our suggestion would be a new mattress cover though, the one on there has firm lumps in places that render the bed not as comfy unfortunately. We had a one night stay.

We had a great stay! We even got engaged on this trip, so some extra love!! The house is super cozy/cute and is of course on the small side since it’s situated on a mountain side. The shower is awesome, spacious, has a seat and handle bar. Hot tub is fabulous. We preferred the mattress in the room on the right (so dibs that one if you’re staying with others, haha). The house is on a mountain, so make sure you have a vehicle and driver that can handle it. But just wow, getting to hot tub with the views of the mountains behind is amazing! The host is very easy to communicate with, and even had a delightful card and drink on the counter when we came in, perfect for our Christmas adventure! We recommend Luray Caverns, Skyline Caverns, getting a pass at the Shenandoah National Park, and going to Culler Overlook, just wow!

We truly enjoyed our stay at Willie’s Place! Patti was a great host, she stayed in touch and made sure we knew she was close by if we needed anything. The location was perfect, very quiet and within close driving of all of our points of interest. Orange itself is a wonderful town, plenty to see and do. The house was great for a week stay, perhaps the most comfortable Airbnb bed we’ve ever used. Patti provided very easy instructions for accessing the house and everything was clean and ready for our stay. We highly recommended staying here and will definitely stay again if we come back to the area.

We had a great time at Lisa’s place! Everything was exactly like the pictures, and her host guidebook was such a nice touch to have! Easy to get an uber and surrounded by local breweries and wineries, and hiking trails. The place was very clean and such a cute location. We would stay here again.

Great easy to find place with large back yard for the dog. Would stay here again

Only stayed one night as we were passing through. Yard was great for our dogs! Hosts were friendly and responsive. Exactly as listed. I would stay here again and recommend to others!

This house, which I have stayed at 5 different times, is my-go-to for when I am planning to do hikes at Lost River State Park as it is a 10m drive to the park and only about 5 minute drives to places where I can get food. The home is nice and clean and has a nice deck where I can sit out and drink my noon coffee. And the host is great- accommodated my requests and responded to my questions in a very speedy fashion.

The place is cute with the perfect mix of being out in the country yet not too far from everything. The hosts are super responsive and kind.

I booked Pink Cottage for a week-long solo writing retreat, accompanied by Zane, my beloved golden doodle. From the minute I walked inside this charming old cottage I felt I’d found a tiny corner of Nirvana. The inviting seating options, colourful décor and whimsical art on display are exactly as represented in the listing, only more vibrant and comfortable in person. Owing to the Jan 2025 Big Freeze I spent the majority of my time indoors, appreciative of the great central heating system as the temps barely made it into the 20’s, and the functional work spaces available for writing. The kitchen is fully functional, equipped for most cooking and dining needs, including basic small appliances. The bedroom is spacious and comfortable - and came with a plush warm bathrobe which I put to good use. The bathroom is on the cozy side but serves its purpose. Eli is a terrific host. She has created a warm, welcoming and whimsical get away in Pink Cottage. Especially for us dog lovers!!

Awesome stay! Billy's place is a gem. The pictures are good, but when you arrive you get a cheerful warmth that is not conveyed in the pics. The kitchen stuff was good quality and well maintained. Beds comfortable, details were well thought out. esp the guest book with the SNP hike maps and the coffee. Location is perfect for hikers and people who want to explore the valley. All the correspondence was warm, friendly and informative. We had a great time and hope to stay again in the future!

Beautiful cozy cottage on an even more beautiful vineyard. Perfect size for two people. Comfortable bed, great hvac, wood stove was so cozy, and being greeted by Sammie to play fetch was a huge bonus! We highly recommend!

Spent the weekend hiking in Shenandoah. The house provided easy access to the park and a great place to rest up. Wish we had more time to enjoy sitting outside but the inside was just as welcoming. Kitchen was well stocked for cooking as well.

It was a lovely, peaceful stay at Wineberry Cottage. My favorite parts of the cottage were the loft where the bed was, along with the nook downstairs in the living area. It is located in a very pretty woods outside the surrounding cities. Perfect for quiet time and relaxation. The host left us pumpkin bread, cider, granola and other treats from the local shops/market. I recommend this property, there is lots of activities to do in the surrounding towns and it’s nice to come back to after a long day. The property was perfect for what we were envisioning out of this trip! Our host was wonderful and responsive!

This was an excellent stay. It was well located on the edge of town, about 10 minutes from everything we were interested in doing. It was very easy and convenient to come and go. The house is just adorable. It is like the pages of a Pottery Barn magazine, which I appreciate. The kitchen is immaculate and well-equipped. It's not that we cooked much, but it would be possible and enjoyable to do so here. It was perfect for storing leftovers and having light breakfast and coffee in the mornings. It has a cute covered patios in the back and front. The fire pit is also charming. This place is everything a couple needs for a few days away or a little wine-country adventure. The hosts were excellent and responsive. They were also proactive when there was pending inclement weather (snow/ice) forecasted during our stay.

Incredible location within 10 mins to Shenandoah National Park which is absolutely worth passing though at the least. This place was super clean and easy to get in and out of, key code given ahead of time and all questions answered made this place definitely worth the value. Would stay again if ever in the area. 5/5

Cute & cozy cottage with everything needed for a comfy stay - at a great price! Easy unloading right at the door. We loved the privacy, but we didn't walk the property as we had many hiking plans. Michael's communication was A+, and we appreciated the early c/i and late c/o. We were pleasantly surprised by the sofa bed. which was just briefly mentioned. It appears to be simply a sofa with chaise. However, if you pull out and up you have a double bed. And if you pull up on the chaise section, you'll find a memory foam mattress. It was amazingly comfortable! The water pressure in the shower was fantastic, and we couldn't believe how new and fancy the fridge is! The only negative was the lack of area rugs, considering how unbelievably SLIPPERY the wood floors are. Actually, there are two area rugs - without non-skid backing. That on the slick floors was even more dangerous, and we put them away for our stay. We bought some area rugs and non-slip socks at the Dollar Store!

We had a great relaxing stay. The place was extremely clean, very simplistic, and charming. Walked to the brewery from the cottage and had some great tasting beers. Would recommend staying here

My husband and I had a great overnight stay! The home was just as described. Very clean and comfortable bed. The muffins were a sweet touch. We would absolutely return!