
Pet-friendly vacation rentals in Winchester
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Top-rated pet-friendly home rentals in Winchester
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Pet-friendly house rentals

Historic River House-Riverfront!
Everything was great and we had a wonderful time!

Beautiful 3 BR historic home in downtown Frederick
So charming and exactly what we were looking for. The house had everything we needed and was so cozy. It is within walking distance to so much. I would LOVE to book again!! Thank you!!

Arden House, Inwood WV
Mary is an absolute wonderful host! Her space is full of everything you could want/need for an overnight stay! Mary communicated wonderfully and clear. The space was easy to find, with the clear directions and was in a peaceful area. For our little family of 3, traveling through on our spring vacation, Mary's space was perfect for us and the price point was a big part of that too! If you are debating on booking, you absolutely should!

Round Mountn Top House! Prof. Cleaned w EV-chrger
This was a great stay for my wife, dog, and I. Jacqueline was an excellent communicator and answered the couple questions we had instantly. The place is very cozy and welcoming. The views didn’t prevent the unfortunately rainy weather from ruining a perfect weekend! Would definitely come back!

Romantic Cottage with Private Hot Tub
Connie's Rock Cottage was amazing! much thought was put into this cottage. Firewood and fire starter for the wood stove on chilly nights, robes we used for getting to and from the private hot tub just steps outside the back door,map of entire 550 acres of land including the wonderful paved walkway which meanders through the property. This was the mosr exceptionally prepared kitchen we have seen in out travels. Tons of utensils, a full set of potsand pans, dish towels, trivets, cutting boards and cooking sheets! We love to cook together when we travel and this kitchen was big enough for 2! We got some amazing pictures all over the farm. The lack of light pollution allowed us to enjoy the stars and Pink Full Moon in all their glory! We will be back to enjoy this cottage again!

Sunrise on the Potomac near Shepherdstown, WV
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.

The Homeplace - Private House with Backyard
We had a great time at Justin's house. It was immaculate, had all the amenities we needed, and is a great location for exploring Shenandoah National Park and the Shenandoah Valley. Justin provided very detailed instructions, which made checking in a breeze. We would definitely stay there again.

Cute Cape Cod
Shang’s place was a home away from home. Nice subdivision with friendly neighbors. He was very responsive & it was in a perfect location for us to visit family with the location being close to everything.
Pet-friendly home rentals with a pool

Pet/Family Friendly, Hot Tub, Large Deck
The place was great for our trip and group. Connor and Alex were responsive, friendly hosts.

Stone Spring - Heated Salt Pool - on 2.5 Acres
Seth was a great host and we loved the place

Dog-friendly, boutique & chic + fireplace
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.

Herb Cottage-Elegant Cabin plus Optional Farm Tour
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.

Log Cabin, *Pool, Hot Tub* Views, Views, Log Fires
Very private location. The house was a nice cabin with spectacular views and comfortable furnishings. Very spotty Verizon cell service, but wifi worked very well for calling and internet. Would recommend for a private get-away.

Starcatcher Chalet, The Woods Resort
A very welcoming place and has many forms of entertainment for both adults and children.

Stylish Retreat w Fireplace, Games & Pool Access
The place was very relaxing and peaceful. Tony was very responsive. They have great amenities on the property which we enjoyed.

Sunset Ranch: Hot Tub! Mountain Views! Pool
Our stay was peaceful. Our first time for my wife and I along with our 15 year old daughter in Woodstock. The home is located around 3 other homes on open cow pasture land, but far enough to be very private. The kitchen was just remodeled and looks very nice along with new appliances. Inside was very clean and beds comfortable with memory foam mattresses. Internet was good enough to stream over TV in home. It was quiet at night, road you're on is private and very limited noise from vehicles on it day or night, although I did not see a speed limit sign so vehicles go any speed along that route. We didn't use the hot tub, pool(off season), grill or firepit(burning ban). We did use the ping pong table in garage and watched the TV in the area attached to it, very nice addition! It turned out very windy during our stay and with that it carried the highway traffic noise downwind which was worse at certain times outside, not inside. Other than that out stay was relaxing, visiting the area.
Private, pet-friendly home rentals

The GreyLoo
This was my 2nd stay stay at Alicia’s. She is an amazing host & her home is spotless and well accommodated. Thank you so much for all of your help, getting us checked in on such late notice. I’d give you 100 stars if I could!!

Hot Tub, Wi-fi, Rural Setting, Smrtv, Convenient
Lovely area close to the cute town of Harpers Ferry. Loved the Hot Tub.

Garage Apartment, King Bed, Easy access to I-81
What a great place to stay! Easy to find, private and we really enjoyed the suggestions of things to do and places to eat. Bed was comfy and the whole place felt like home.

Your sanctuary awaits/1-bedroom downtown apartment
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.

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

Cozy Cottage with spacious fenced in yard!
The house was great. The fenced yard was nice for my dog and granddaughter. It was quiet and peaceful. We loved the hot tub. I hope we can stay again.

Rocktown Retreat-Massanutten Pet-Friendly 4BR
Fantastic place to stay and spend time. Sadly we only had 2 nights here due to our short stay, but definitely would love to be back again.

Deer Lick Cabin
A little slice of heaven. Beautiful area. Had a wonderful weekend getaway.
Quick stats about vacation rentals that are pet-friendly in Winchester
Total rentals
40 properties
Nightly prices starting at
ﺩ.ﺇ73 before taxes and fees
Total number of reviews
2.2K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
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- Bryce Resort
- Whitetail Resort
- Luray Caverns
- Cacapon Resort State Park
- Stone Tower Winery
- Gambrill State Park
- Cunningham Falls State Park
- South Mountain State Park
- Twin Lakes Golf Course
- Robert Trent Jones Golf Club
- Shenandoah Valley Golf Club
- Notaviva Vineyards
- Whiskey Creek Golf Club
- Bowling Green Country Club
- Sly Fox Golf Club
- River Creek Club
- Reston National Golf Course
- Berkeley Springs State Park
- JayDee's Family Fun Center
- Car and Carriage Caravan Museum
- Dinosaur Land
- The Golf Club at Lansdowne
- Herndon Centennial Golf Course
- Hidden Creek Country Club