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

Historic River House-Riverfront!
The Riverhouse was so nice and cozy! Loved how close it was to the river - view out of the front was all river and the view out of the back still had the mountains, it was lovely. Scot was super responsive to any questions and so personable! If you want a cozy little getaway with friends/family, this is definitely a good pick for you!

Beautiful 3 BR historic home in downtown Frederick
This home is in the hotbed of Frederick. It's extremely walkable, with a plethora of great eateries. I personally recommend Maxwell's and Bean & Bagel. The home itself is a little quirky due to it being built in 1890, but Steve has added amenities which will not leave you feeling as though you're living in the past. We felt right at home the moment we walked in. If you choose to stay here, I will caution you to read the signs carefully. Every night is a game of musical chairs with parking spaces, and I wasn't in on it (I got a parking citation). But if anything, this only encourages you to walk and see beautiful Frederick. Just stick to the main roads at night.

Arden House, Inwood WV
Mary was very kind when one of my parents mistook the fire alarm for a thermostat and set the alarm off. I called her immediately to figure out how to turn it off and she gave me the code. Then after she called the fire dept she called back and graciously apologized for not marking it more clearly to avoid this mistake. Like I said, so kind.

Round Mountn Top House! Prof. Cleaned w EV-chrger
Absolutely LOVED this place. Cabin was homey and comfortable, felt like we were staying at a friend’s place. The views were amazing, we stared at the mountains on the deck for hours. What an awesome bonus that there’s a trail right outside that has miles and miles of hiking in both directions. We loved how in tune to nature we felt, especially being unplugged and cozying up to the fire at night. Beds were comfortable, we cooked all our meals, and the hosts were super communicative. Would recommend this place to everyone looking for a peaceful mountain getaway, and hope to be back soon!

Romantic Cottage with Private Hot Tub
Beautiful, peaceful place for a getaway! We loved walking around the property to take in the views and see the animals, relaxing in the hot tub, and the bed was the comfiest bed ever. Highly recommend and am definitely planning to come back!

Sunshine House -Cheerful 2BR/2.5Bath Detached Home
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.

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
i rented this airbnb for a work crew that stayed for a week. The location was a bit far out from Harrisonburg but that is the charm of this small home. It was a nice quiet peaceful gateway where one could rest and recover from a busy day of work. The views are amazing and being able to see farm animals out in the surrounding fields was an odd treat. The home itself was very clean and comfortable. If you're traveling with kids or for work, this is a perfect spot.
Pet-friendly home rentals with a pool

Pet/Family Friendly, Hot Tub, Large Deck
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!

Stone Spring - Heated Salt Pool - on 2.5 Acres
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!

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
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.

Starcatcher Chalet, The Woods Resort
This place made me and my family feel right at home. They had everything we needed. They even provided a few snacks, coffee, and toys to accommodate the younger kids. I’ve never stayed anywhere that felt this at home. I didn’t reach out much during my trip, but when I did, they responded right away. I look forward to coming back in the future.

Stylish Retreat w/Fireplace, Games & Pool Access
Beautiful home in a great location. Home was well kept with great amenities. You can tell the owners go above and beyond to take care of this property. Great location if you have dogs!

Sunset Ranch: Hot Tub! Mountain Views! Pool
the house & the property was beautiful !! Definitely will be back in the summer ! Our time was so relaxing and peaceful
Private, pet-friendly home rentals

The GreyLoo
Another fantastic stay at Alicia's! We love it here. It's comfortable, spacious, and has everything we need. We feel rested and relaxed when we stay here, and Alicia is such a gracious host. Definitely would recommend!

Hot Tub, Wi-fi, Rural Setting, Smrtv, Convenient
Very peaceful stay!

Garage Apartment, King Bed, Easy access to I-81
Thank you so much for a wonderful stay. Hosts are always so nice and responsive. Will certainly return when in the area for business.

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!
Virginia’s cozy cottage was exactly what we needed for the weekend. My wife, daughter, and I felt right at home and had lots to do for our time there. Just a short train ride from DC and we did not have to fight traffic getting in our out. Lovely place that we will definitely visit again soon.

April-Rent 2 Nights, Get 1 Free @Pet-Friendly 4BR
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.

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
$20 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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- Whitetail Resort
- Bryce Resort
- Luray Caverns
- Cacapon Resort State Park
- Stone Tower Winery
- South Mountain State Park
- Car and Carriage Caravan Museum
- Shenandoah Valley Golf Club
- Creighton Farms
- Dinosaur Land
- Robert Trent Jones Golf Club
- Sly Fox Golf Club
- Bowling Green Country Club
- River Creek Club
- The Golf Club at Lansdowne
- Twin Lakes Golf Course
- Reston National Golf Course
- Hidden Creek Country Club
- Herndon Centennial Golf Course
- JayDee's Family Fun Center
- Berkeley Springs State Park
- Notaviva Vineyards
- Gambrill State Park
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