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
The historic home is situated on a spacious lawn, surrounded by a wooden fence. Its two-story façade features light-colored siding, a covered porch with a lattice detail, and several windows allowing natural light into the interior.
Home in Elkton
4.79 out of 5 average rating, 241 reviews

Historic River House-Riverfront!

JenniferRating, 5 stars1 month ago
Everything was great and we had a wonderful time!
Guest favorite
The exterior of a historic townhouse features dark wooden siding contrasted by yellow shutters. A welcoming front door is adorned with a circular wreath and displays the house number prominently. Light-colored window trim complements the overall aesthetic.
Home in Downtown Frederick
4.92 out of 5 average rating, 146 reviews

Beautiful 3 BR historic home in downtown Frederick

MichelleRating, 5 stars1 month ago
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!!
Guest favorite
A well-maintained exterior showcases a brick building with a white double door entrance. Surrounding greenery includes manicured lawns and bushes, enhancing the natural setting. The entrance is easily accessible, providing a welcoming approach to the ground-level unit.
Home in Inwood
4.88 out of 5 average rating, 633 reviews

Arden House, Inwood WV

JuliaRating, 5 stars1 week ago
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!
Guest favorite
A charming roundhouse is nestled amidst a snowy landscape, surrounded by bare trees. A dog stands on a path cleared through the snow, leading toward the entrance. The home features a wooden exterior and large windows, reflecting the serene winter environment.
Home in Hedgesville
4.92 out of 5 average rating, 297 reviews

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

KirkRating, 5 stars2 weeks ago
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!
Top guest favorite
A spacious rural landscape features a well-maintained wooden fence along a grassy field, leading towards trees and a red barn in the background. The scene is bathed in natural light with a clear blue sky and scattered clouds, showcasing the serene surroundings.
Home in Castleton
4.95 out of 5 average rating, 115 reviews

Romantic Cottage with Private Hot Tub

AnnRating, 5 stars1 week ago
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!
Guest favorite
A wooden dock extends into calm waters, surrounded by lush greenery. The shoreline features a blend of trees and rock formations, providing a natural backdrop. Sunlight reflects off the water's surface, enhancing the serene atmosphere of this waterfront setting.
Home in Martinsburg
4.82 out of 5 average rating, 123 reviews

Sunrise on the Potomac near Shepherdstown, WV

NicRating, 5 stars2 months 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
4.94 out of 5 average rating, 378 reviews

The Homeplace - Private House with Backyard

BarakRating, 5 stars1 week ago
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.
Superhost
The image shows a front porch featuring several white rocking chairs lined along the railing, providing a comfortable space to relax. A vibrant welcome mat adds color, while a ceiling fan is mounted above for ventilation. Natural light fills the area, creating an inviting atmosphere.
Home in Falls Church
4.8 out of 5 average rating, 149 reviews

Cute Cape Cod

MikeRating, 5 stars1 week ago
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

Superhost
A modern cabin structure is nestled among trees, featuring a dark wood exterior and a sloped roof. A welcoming front path made of wooden planks leads to the entrance, which is flanked by a light-colored rocky area and mulch for landscaping.
Cabin in Berkeley Springs
4.9 out of 5 average rating, 119 reviews

Pet/Family Friendly, Hot Tub, Large Deck

IsabelRating, 5 stars3 weeks ago
The place was great for our trip and group. Connor and Alex were responsive, friendly hosts.
Superhost
An expansive front yard is featured, showcasing lush green grass and a backdrop of trees lining the perimeter. A brick house stands to one side, with a cloudy sky above, adding to the serene ambiance of the outdoor space.
Home in Town of Rockingham
4.78 out of 5 average rating, 260 reviews

Stone Spring - Heated Salt Pool - on 2.5 Acres

JohnRating, 5 stars2 months ago
Seth was a great host and we loved the place
Guest favorite
Cabin in Hedgesville
4.94 out of 5 average rating, 117 reviews

Dog-friendly, boutique & chic + fireplace

ZondriaRating, 5 stars1 month 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
The image captures the edge of an outdoor pool, with tranquil water reflecting the surrounding greenery and a rustic cabin in the background. Rolling hills and landscaped gardens are visible, enhancing the serene environment of the conservation farm.
Cabin in Delaplane
5 out of 5 average rating, 137 reviews

Herb Cottage-Elegant Cabin plus Optional Farm Tour

WilsonRating, 5 stars5 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
A spacious outdoor area features a blue swimming pool with clear water, surrounded by verdant grass. The backdrop showcases rolling mountains beneath a partly cloudy sky, adding to the serene landscape. The log cabin is visible nearby, enhancing the setting.
Cabin in Rileyville
4.77 out of 5 average rating, 105 reviews

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

SiegfriedRating, 5 stars2 months ago
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.
Guest favorite
Cabin in Hedgesville
4.94 out of 5 average rating, 140 reviews

Starcatcher Chalet, The Woods Resort

MargaritaRating, 5 stars6 days ago
A very welcoming place and has many forms of entertainment for both adults and children.
Superhost
Cabin in Hedgesville
4.85 out of 5 average rating, 192 reviews

Stylish Retreat w Fireplace, Games & Pool Access

TamaraRating, 5 stars6 days ago
The place was very relaxing and peaceful. Tony was very responsive. They have great amenities on the property which we enjoyed.
Superhost
An aerial view of a charming farmhouse surrounded by farmland and rolling hills. The outdoor space includes a fenced-in pool, a hot tub, and a shed, with vibrant autumn foliage in the background and the Blue Ridge Mountains visible in the distance.
Home in Woodstock
4.89 out of 5 average rating, 137 reviews

Sunset Ranch: Hot Tub! Mountain Views! Pool

RickRating, 5 stars1 month ago
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

Guest favorite
A cozy living area features a dark sectional couch complemented by a patterned area rug. A small table is positioned beside the couch, and a television rests on a wooden console, creating a comfortable space for relaxation.
Apartment in Frostburg
4.9 out of 5 average rating, 172 reviews

The GreyLoo

AmandaRating, 5 stars1 week ago
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!!
Guest favorite
Home in Harpers Ferry
4.89 out of 5 average rating, 113 reviews

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

MeganRating, 5 stars1 week ago
Lovely area close to the cute town of Harpers Ferry. Loved the Hot Tub.
Top guest favorite
The welcoming entrance features a white door adorned with a seasonal wreath, framed by greenery. A wooden deck leads to the door, with a decorative bear statue and a blooming potted plant placed nearby, inviting guests into the home.
Guest suite in Edinburg
4.99 out of 5 average rating, 436 reviews

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

ChristineRating, 5 stars3 weeks ago
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.
Superhost
A seating area features a dark gray couch with plush cushions and decorative pillows. A round white coffee table holds magazines and a remote control. A circular wall art piece adds visual interest above the couch, while a light-colored wall complements the space.
Apartment in Frederick
4.86 out of 5 average rating, 286 reviews

Your sanctuary awaits/1-bedroom downtown apartment

VanjaRating, 5 stars5 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
The exterior of the two-story home is seen from a grassy area, showcasing a white façade complemented by greenery. Satellite dishes are positioned on the roof. A driveway leads to a parked vehicle, and surrounding trees provide a natural setting.
Home in Stanley
4.96 out of 5 average rating, 207 reviews

Pine Grove Retreat

JenniferRating, 5 stars4 months ago
Nice home with all the necessities. My dogs were welcomed and comfortable. Highly recommend.
Guest favorite
A charming cottage features a front porch with white railings and four outdoor chairs set on a grassy lawn. A fire pit is positioned nearby for gathering. Trees with autumn leaves surround the property, contributing to a serene outdoor atmosphere.
Home in Manassas
4.84 out of 5 average rating, 37 reviews

Cozy Cottage with spacious fenced in yard!

JenniferRating, 5 stars3 weeks ago
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.
Top guest favorite
Home in McGaheysville
5 out of 5 average rating, 46 reviews

Rocktown Retreat-Massanutten Pet-Friendly 4BR

HareshRating, 5 stars1 week ago
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.
Guest favorite
A spacious outdoor area features a well-maintained lawn surrounded by lush trees. A gravel path leads to the front porch of the house, while a vehicle is parked nearby. The serene environment offers a peaceful retreat in nature.
Home in Warfordsburg
4.95 out of 5 average rating, 91 reviews

Deer Lick Cabin

JonathanRating, 5 stars3 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

    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

Destinations to explore