Pet-friendly vacation rentals in Winchester

We stayed here for my Mother in-laws 90th Birthday. She lives ina small place in Frederick. Had people from all over visiting and it was nice to visit at the rental. We really loved the location! Short walk to Starbucks and great shops and restaurants. So fun and gave us a real feel for Frederick life!

Oxana and Jeff were responsive and friendly. The place was easy to find with ample parking. The interior was spotless with plenty of space to lounge. Oxana provided lots of local recommendations. I would stay here again without hesitation!

This was a great spot that we picked at the last minute because it’s dog friendly, not far off rte 81 and also has a no cats policy (my husband is allergic). The space was simple and comfortable. I actually liked it better than the usual schlocky Airbnb decor. Mary was helpful with checkin instructions, and otherwise we had a comfortable and peaceful stay! Recommended!

We absolutely loved our stay! A gorgeous home, a perfect getaway. We did have difficulty getting up the road in our 2wd car. We were just a couple houses away but couldn't get up the hill. It had been rainy/muddy so this may not be an issue in the summer months, but just a warning to anyone else in a 2wd vehicle that you may have some trouble like we did. Once we were inside, everything was perfect!

The Rock Cottage is a perfect romantic getaway! We enjoyed walking all of the hiking trails and exploring the vast property with our 2 dogs (such a treat when they can vacation with us). The wood burning stove and hot tub were wonderful amenities on the cold weekend. It was an easy drive into Culpepper for a fabulous dinner at Piedmont Steakhouse (pricey but worth it). And, our favorite part was the Pool House/Spa, the pictures do not do it justice. The Steam Room/Sauna/Cold Plunge/Sauna regime was rejuvenating and being able to swim in the deep. vast pool with attached hot tub completed a perfect afternoon. On our way home we drove 15 minutes out of our way to visit the Copper Fox Distillery and adjacent shops in Sperryville - a must if you like craft whiskey. We are looking forward to returning during a warmer season to enjoy even more of what the grounds have to offer. Thank you Connie, Paul, and team for being so responsive and helpful!

Our stay at Kaylin & Alex's was fabulous. The house was very clean, beautifully decorated and had all of the little extras. We brought our pups so it was great to have a yard and park close by. We could tell from the photos that it would be helpful to bring a gate to fence off an open part in the yard. Location was very walkable and the driveway was a perk. We love Frederick and would love to stay at Kaylin & Alex's house again.

Excellent stay at Tony's home. The view is fantastic and the home is exactly as pictured. We had a wonderful time with our two kids and another couple. The hot tub was great! We did not explore the area a ton, but we went next door to the equestrian center and they were extremely accommodating to our two very curious 4 year olds. If you are into horses, I recommend giving them a call. I would recommend this home and location to anyone looking to get away.

We enjoyed our weekend getaway! The house was perfect for what we needed.

Great place to gather with our family for hiking and relaxing. Kitchen was well stocked. Propane grill was a nice plus! Connor was a great host!

This was one of the best airbnb rentals I've had. The house is very nice and well maintained, the pool and yard are great, the kitchen was well stocked with cookware and glasses. We all want to go back next year!

Seth and Carla were extremely responsive during our stay! We loved how many beds this house had and we were able to all spend time together while comfortably being seated around tables/living rooms! We wish the fire pit had seating or that fireplaces worked, but we loved this property and its proximity to wineries and ski resorts!

Thank You for making my 54th birthday so pleasant and peaceful. The house is very private but at the same time it has glass window everywhere to let int he natural light. My favorite spot in the house was the back porch. It was private but the furniture was beautifully and comfortable. I spent hours just sitting and mediating out there. The kitchen is well stocked with everything a family would need to make a complete meal. The shower head made me feel like I was in a spa. The towels mad me feel as if I was drying with clouds. ( I have to find out where they bought those towels. I LOVED this house and so did my group of women I brought with me. There was plenty of room for everyone. I will definitely rent this house again.

I planned to propose to my girlfriend over a romantic farm and Shenandoah getaway weekend. Andrea was very excited and helped make the weekend really special. The grounds were amazing and so beautiful with trails to take walks on and many animals to see. We brought our puppy and we had plenty of space to safely let him off leash to run around. He had as much fun as we did (and we got engaged!) Her restaurant recommendations were spot on, so definitely give those a try. We did the farm tour on the last day, and it was so personal, interactive and informative. Do not skip the tour!!! Andrea was so kind and generous with us. We cannot recommend this place highly enough.

As many have reported this is a true gem!! The view is to die for! We spent one day biking to Luray from Rileyville. A stunning country road ride with farms all around, mountains on either side, no cars on the road! Would not recommend biking on overlook drive due to gravel.

Incredibly grateful for this home and for the KOA next to it! We knew we were booking a home with lots of bedrooms a hot tub (the most important things!) but we had no idea it offered so much more. A working fireplace when we got snowed in, a KOA with plenty of activities literally next door, a stunning walking path that we took through the snow when we got snowed in, and an incredibly kind crew who helped us get our cars un-stuck. If I had to be anywhere during a snowstorm, it would be here. And if I had any questions, the KOA was there next door to answer them. Super easy. We were walking distance to tubing, a six minute drive from historic downtown. We just have to come back when the weather is nicer to take advantage of the mini golf!

Such a beautiful chalet! We had a great time celebrating my husband’s birthday with friends. The beds were comfy and loved the cozy family room. The fireplace was a fave! Lisa was helpful and responded quickly to any questions we had. Would definitely stay again!

What a gem of a find. Alicia was over the top exceptionally accommodating and helpful. Her place was exactly as described as well as being extremely convenient. This was a last minute booking and everything went very smooth and was the perfect stay. Thank you again Alicia.

My husband and I had an amazing getaway and this house was perfect! Clean, literally spotless! Close to everything such as restaurants, fun in the snow, and taking a trip down memory lane. We will definitely be booking another stay in the Spring time.

Thank you so much for a wonderful stay. Hosts are always so nice and responsive. Will certainly return when in the area for business.

Ryam is a very responsive host. The apartment was as described and he was very flexible with the check-in which helped us greatly. The apartment was close to the downtown and all of the Frederick amenities. We enjoyed our stay and would recommend it to all.

Nice home with all the necessities. My dogs were welcomed and comfortable. Highly recommend.

This is exactly ad advertised and full of nice touches. The host was super responsive and not fazed when we had a last minute request that she accommodated cheerfully. Heartily recommend

Great location to the ski slopes and water park at Massanutten. The property worked great for our family trip, and everything was clean and cozy.

The Haven was a great place to stay. 5 minutes from the ski lodge and 5 min from the waterpark. The house was clean and comfortable. Spacious enough for a large group of people. The hot tub was a great bonus.