Pet-friendly vacation rentals in Winchester

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Winchester pet-friendly home rentals

Pet-friendly house rentals

Superhost
Home in Elkton
4.79 out of 5 average rating, 239 reviews

Historic River House-Riverfront!

JessieRating, 5 stars1 month ago
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!
Guest favorite
Home in Downtown Frederick
4.92 out of 5 average rating, 143 reviews

Beautiful 3 BR historic home in downtown Frederick

MaxRating, 5 stars1 week ago
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.
Guest favorite
Home in Inwood
4.88 out of 5 average rating, 625 reviews

Arden House, Inwood WV

IngeRating, 5 stars3 weeks ago
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.
Guest favorite
Home in Hedgesville
4.92 out of 5 average rating, 292 reviews

Round Mountn Top House! Prof. Cleaned w EV-chrger

DianaRating, 5 stars3 weeks ago
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!
Guest favorite
Home in Castleton
4.95 out of 5 average rating, 113 reviews

Romantic Cottage with Private Hot Tub

FrancescaRating, 5 stars4 days ago
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!
Top guest favorite
Home in Downtown Frederick
5 out of 5 average rating, 103 reviews

Sunshine House -Cheerful 2BR/2.5Bath Detached Home

KristinRating, 5 stars5 months ago
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.
Guest favorite
Home in Martinsburg
4.82 out of 5 average rating, 122 reviews

Sunrise on the Potomac near Shepherdstown, WV

NicRating, 5 stars1 month ago
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.
Guest favorite
Home in Harrisonburg
4.95 out of 5 average rating, 368 reviews

The Homeplace - Private House with Backyard

ManuelRating, 5 stars1 week ago
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

Superhost
Cabin in Berkeley Springs
4.91 out of 5 average rating, 116 reviews

Pet/Family Friendly, Hot Tub, Large Deck

GretaRating, 5 stars3 weeks ago
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!
Superhost
Home in Town of Rockingham
4.78 out of 5 average rating, 259 reviews

Stone Spring - Heated Salt Pool - on 2.5 Acres

KarenRating, 5 stars2 months ago
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!
Guest favorite
Cabin in Hedgesville
4.94 out of 5 average rating, 116 reviews

Dog-friendly, boutique & chic + fireplace

ZondriaRating, 5 stars2 weeks ago
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.
Top guest favorite
Cabin in Delaplane
5 out of 5 average rating, 137 reviews

Herb Cottage-Elegant Cabin plus Optional Farm Tour

WilsonRating, 5 stars4 months ago
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.
Superhost
Cabin in Rileyville
4.77 out of 5 average rating, 104 reviews

Log Cabin, *Pool, Hot Tub* Views, Views, Log Fires

JamieRating, 5 stars4 months ago
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.
Guest favorite
Cabin in Hedgesville
4.95 out of 5 average rating, 134 reviews

Starcatcher Chalet, The Woods Resort

TakeishaRating, 5 stars1 week ago
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.
Superhost
Cabin in Hedgesville
4.85 out of 5 average rating, 187 reviews

Stylish Retreat w/Fireplace, Games & Pool Access

CourtneyRating, 5 stars1 week ago
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!
Superhost
Home in Woodstock
4.89 out of 5 average rating, 135 reviews

Sunset Ranch: Hot Tub! Mountain Views! Pool

HalieyRating, 5 stars2 months ago
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

Guest favorite
Apartment in Frostburg
4.89 out of 5 average rating, 166 reviews

The GreyLoo

RachelRating, 5 stars1 month ago
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!
Guest favorite
Home in Harpers Ferry
4.91 out of 5 average rating, 110 reviews

Hot Tub, Wi-fi, Rural Setting, Smrtv, Convenient

KristenRating, 5 stars1 week ago
Very peaceful stay!
Top guest favorite
Guest suite in Edinburg
4.99 out of 5 average rating, 429 reviews

Garage Apartment, King Bed, Easy access to I-81

AmyRating, 5 stars4 weeks ago
Thank you so much for a wonderful stay. Hosts are always so nice and responsive. Will certainly return when in the area for business.
Superhost
Apartment in Frederick
4.86 out of 5 average rating, 286 reviews

Your sanctuary awaits/1-bedroom downtown apartment

VanjaRating, 5 stars4 months ago
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.
Guest favorite
Home in Stanley
4.96 out of 5 average rating, 207 reviews

Pine Grove Retreat

JenniferRating, 5 stars3 months ago
Nice home with all the necessities. My dogs were welcomed and comfortable. Highly recommend.
Guest favorite
Home in Manassas
4.84 out of 5 average rating, 32 reviews

Cozy Cottage with spacious fenced in yard!

KennethRating, 5 stars4 days ago
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.
Top guest favorite
Home in McGaheysville
5 out of 5 average rating, 44 reviews

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

AshleyRating, 5 stars2 months ago
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.
Guest favorite
Home in Warfordsburg
4.96 out of 5 average rating, 90 reviews

Deer Lick Cabin

JonathanRating, 5 stars2 months ago
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

Destinations to explore