Pet-friendly holiday 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, 241 reviews

Historic River House-Riverfront!

JenniferRating, 5 stars1 month ago
Everything was great and we had a wonderful time!
Guest favourite
Home in Downtown Frederick
4.92 out of 5 average rating, 148 reviews

Beautiful 3 BR historic home in downtown Frederick

ErinRating, 5 stars2 weeks ago
We loved the location - easily walkable to everything on Market Street. The home was beautiful and true to the pictures. We would definitely stay here again!
Guest favourite
Home in Inwood
4.88 out of 5 average rating, 635 reviews

Arden House, Inwood WV

SapphireRating, 5 stars1 day ago
Mary was a wonderful host, I loved how private the bnb was.she was very responsive and helpful if we had any questions.
Guest favourite
Home in Hedgesville
4.92 out of 5 average rating, 298 reviews

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

KirkRating, 5 stars3 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 favourite
Home in Castleton
4.95 out of 5 average rating, 115 reviews

Romantic Cottage with Private Hot Tub

AnnRating, 5 stars3 weeks 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 favourite
Home in Martinsburg
4.82 out of 5 average rating, 124 reviews

Sunrise on the Potomac near Shepherdstown, WV

ChristieRating, 5 stars1 week ago
We used to stay in a place not too far from here in PA. It slowly lost its charm, so we ventured out. So glad we did! Excellent hosts! The details they paid attention to did not go unnoticed. A wonderful welcome basket, immaculate home, and plenty of extras. We will be back!
Guest favourite
Home in Harrisonburg
4.94 out of 5 average rating, 380 reviews

The Homeplace - Private House with Backyard

DebraRating, 5 stars1 week ago
Totally enjoyed our stay. The Homeplace was clean, well stocked and exactly as described. Justin was responsive, flexible, and accommodating. The fenced in back yard was a great amenity when traveling with our pups. Great host, beautiful location. Would definitely stay again.
Superhost
Home in Falls Church
4.8 out of 5 average rating, 149 reviews

Cute Cape Cod

MikeRating, 5 stars2 weeks 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
Cabin in Berkeley Springs
4.9 out of 5 average rating, 120 reviews

Pet/Family Friendly, Hot Tub, Large Deck

LaurenRating, 5 stars1 week ago
Connor’s place was nice! We had a small girls trip for 2 nights. There is plenty of room and a nice back porch and covered outdoor seating! Perfect for a get away to Berkeley Springs or surrounding state parks.
Superhost
Home in Town of Rockingham
4.79 out of 5 average rating, 261 reviews

Stone Spring - Heated Salt Pool - on 2.5 Acres

Clinton JohnRating, 5 stars2 weeks ago
Great place for a larger group!
Guest favourite
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 favourite
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
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 favourite
Cabin in Hedgesville
4.94 out of 5 average rating, 140 reviews

Starcatcher Chalet, The Woods Resort

MargaritaRating, 5 stars2 weeks 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, 193 reviews

Stylish Retreat w Fireplace, Games & Pool Access

AlyssaRating, 5 stars1 week ago
A great find! This is a really cute and cozy place that is just as pictured. It was very clean and had all we needed for a perfect get away. The sports complex amenities are very nice and close by. I would definitely recommend and will likely return for another stay!
Superhost
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 favourite
Apartment in Frostburg
4.9 out of 5 average rating, 173 reviews

The GreyLoo

TrentRating, 5 stars2 weeks ago
This a great place. The living room is very cozy, and the bedroom has a lot of space. Located in a nice quiet neighborhood. This was a very good deal, especially for the price!
Guest favourite
Home in Harpers Ferry
4.89 out of 5 average rating, 113 reviews

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

MeganRating, 5 stars2 weeks ago
Lovely area close to the cute town of Harpers Ferry. Loved the Hot Tub.
Top Guest favourite
Guest suite in Edinburg
4.99 out of 5 average rating, 436 reviews

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

ChristineRating, 5 stars4 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
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 favourite
Home in Stanley
4.96 out of 5 average rating, 207 reviews

Pine Grove Retreat

JenniferRating, 5 stars5 months ago
Nice home with all the necessities. My dogs were welcomed and comfortable. Highly recommend.
Superhost
Home in Manassas
4.84 out of 5 average rating, 37 reviews

Cozy Cottage with spacious fenced in yard!

JenniferRating, 5 stars4 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 favourite
Home in McGaheysville
5 out of 5 average rating, 46 reviews

Rocktown Retreat-Massanutten Pet-Friendly 4BR

HareshRating, 5 stars3 weeks 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 favourite
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 holiday rentals that are pet-friendly in Winchester

  • Total rentals

    40 properties

  • Nightly prices starting at

    $31 AUD 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

  • Wi-Fi availability

    30 properties include access to Wi-Fi

Destinations to explore