Cottage holiday rentals in Sperryville

Absolutely perfect stay! The house was cozy, clean, and had everything we needed for a relaxing getaway. The hot tub was the highlight—so peaceful and private, surrounded by nature. We loved unwinding there after a day of exploring. Communication with the host was super easy, and check-in was a breeze. If you’re looking for a quiet escape with a touch of luxury, this is the spot. Already dreaming of our next trip back!

A very nice place in a private setting. Had all the essentials. The pool and hot tub were especially nice. Loved the wine at the winery also🍷 Andrea was helpful and responsive with all questions. Highly recommend staying!

Beautiful setting with large lawn and river. The home is spacious ,clutter free and comfortable. Peaceful setting but just a 10-15 drive to Luray and 20 min to Shenandoah park entrance. It has a remote feeling but it is a convenient base to visit the caverns, hiking Shenandoah, or grabbing a bite in Luray. We had temps in low 70's with no humidity so we also enjoyed sitting on the porch and listening to the river. Follow host instructions about downloading maps offline the GPS was reliable, but once we figured it out it is really quite simple.

We loved Olivia’s Airbnb ! It was secluded and peaceful and it was beautiful inside with lots of space ! We loved the hot tub and outdoor area too !

Thank you so much to Darrel! We absolutely loved our stay here and would 100% come back. Everything was perfect and we enjoyed our time immensely. The river is beautiful and the location is so quiet and private. We were able to see the bald eagle and catch fish, etc. Highly recommend if you want a weekend in nature and just time to relax and unwind!

Another great stay. The house is beautifully decorated, the hot tub is clean and clear, and the location is peaceful. We spent a lot of time at the Winchester Historic Walking Mall, and discovered the Shenandoah Valley Children’s museum where my 20 month old had a blast.

Had an amazing time! Lots of beautiful views. Really enjoyed the screened in porch with hot tub. We had everything we needed. Would definitely book again!!

We had an amazing girls' weekend! The house was cozy, spotless and perfect for our group. Dolly & Brendan were super responsive and gave us terrific recommendations for local restaurants and wineries - everything we tried was a hit. We loved being able to sit outside and unwind by the firepit. Would definitely stay here again!

The cabin was a wonderful, easy space to stay for a quick weekend to the mountains. We very much enjoyed the beautiful views from the windows and the porch.

House was in a quiet neighborhood. Very clean and comfortable. We were there for an overnight trip, we attended a concert in Charlottesville which was only a little over 30 minutes away. We did not spend a lot of time at the house but thought it was lovely. Would recommend to family and friends visiting the area. Thanks for sharing!

Cozy, adorable little cottage close to downtown! It has everything you need for a short or long stay, and plenty of room for a doggo. Amazing shower and cozy bed! Only ‘complaint,’ which is not even one, is that it got chilly inside at night and the heater was a bit difficult to use to raise the heat. Overall a wonderful weekend stay!

Donnie was a wonderful host. He was very flexible and made sure that we had what we needed. The place was a perfect respite!

Everything about the stay was great! Susan was a great host with an impeccable house. You can tell she cares about her guest, their experience and what needs they might want or encounter. The coffee and cream being available was a huge perk! The s’mores kit (wish we could have used it) was a nice touch and the chocolate in the mug. That was just in the kitchen… the bathrooms had other things available if needed. Couldn’t find a spec of dirt, dust or stray hair. Susan’s eye to detail and cleanliness showed! Would recommend this house to anyone and stay here again myself if in the area.

You would be hard pressed to find a better place to stay. The house was very comfortable and relaxing. When we’re back in the area this will be our go to place.

My girlfriend and I absolutely loved this cute romantic cottage. We enjoyed a peaceful and relaxing night, made ourselves breakfast in the full kitchen, and then went for a challenging hike on the AT that wasn't too far away. Would come back for a great getaway. Thanks Reagan!

The cottage on the farm was lovely. Very clean and tidy. The farm itself has such wonderful surroundings and very peaceful outside watching the farm animals around. It was easy to find, although I had a little trouble with the electric lock but that could be my user error and I didn’t bother Nick about that (I just needed a few attempt every time to figure it out, lol), however, the hosts were very responsive with any communication needed which was great. We would definitely love to stay again. It was a perfect quiet getaway yet close to Leesburg for food and drinks, trails, and tons of wineries near by. Thanks Nick!

We loved staying at the Gatekeeper Cottage! The location is so convenient and the view is incredible. Easy to get to the local wineries, Waynesboro and the Blue Ridge Parkway. The house is rustic, but comfortable and updated to include everything you would expect from an AirBnB.

We were in town for a wedding and this place was perfect for 5 of us. Everything was exactly as advertised. Would definitely stay there again!!!

This home was beautifully maintained, with really livable layout, warm and colorful decor, comfie furnishings and bed, warm blanket for porch sitting, sweet little table with mountain view off the bedroom. Lovely kitchen. Meditation/reading/yoga area, wonderful wide selection of books. Windows everywhere, three outside sitting areas, lots of natural light AND bright lights to read by. Coffee provided:). Big bathroom and shower. Really couldn't be better. Incredibly quiet at night. Loved the sweet cows in the pasture. Thank you Jim for being so welcoming!

our stay was perfect in every way. love the home & it's outdoor space . we are big into the great outdoors & so location was great for us . very accommodating. would definitely stay again!

Lovely, comfortable cottage. Very convenient to all things Madison County. Feels like home. We would love to stay again when we return to the area. Thank you!

New construction and very nicely appointed. The screened in porch was a delight. I watched a fawn graze and an indigo bunting perch while sipping my morning coffee. The proximity to Old Rag can’t be beat and it’s a quick drive to Sperryville.

The cottage was a perfect place for my daughter and her new husband’s wedding night and weekend! Christina made their stay so special. She was able to help me with surprising the newlyweds with a basket of goodies, fresh baked goodies, and drinks! They loved the surprise especially after a long day! The host was incredibly kind, helpful amd responsive! The cottage was so cute and very clean! Great location! Close to their wedding venue and local wineries and breweries! Highly recommend!

Great stay. David was super responsive and nice. The place was great and well equipped. The back yard (unfanced) was beautiful and very nice to sit at. Our dog also loved it. We came to hike Old Rag mountain and the drive to there was only 25 minutes to the trail head. The city Culpeper next to it had everything we needed.