Pet-friendly holiday rentals in Winchester

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Winchester

Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite

Home

4.88 out of 5 average rating, 604 reviews

Arden House, Inwood WV

Ground level two room unit. No steps. Separate entrance from main house. Private entrance and parking. There is an entrance room with a double bed, twin bed, sofa and full refrig.. In a separate living area, there is a queen bed, TV, bathroom, desk, table, microwave, convection oven, air fryer, gas fireplace. No oven. Outside there is a large area to use outdoor gas grill, picnic table and fire pit. Dogs allowed and must be kept on a leash when outside. Please NO CATS. The owner is allergic.

Guest favourite

Guest suite

4.96 out of 5 average rating, 636 reviews

Historic Scrabble, Shepherdstown

The perfect private guest cottage situated beside a beautiful historic home in the unique community of Scrabble Unincorporated just a half-mile from the Potomac River. Modern, comfortable and tastefully decorated with full amenities and parklike surroundings with an abundance of nature at your doorstep. Close to Shepherdstown / Shepherd Univeristy (12 minutes), Martinsburg (20 minutes), Harpers Ferry (20 minutes) and in the heart of civil war history including the famed Antietam National Park.

Guest favourite

Bungalow

4.9 out of 5 average rating, 512 reviews

Rooster Wrest in the Trees

Sweet 2 bedroom bungalow. Cozy, ideal for lovers, or a quiet beautiful somewhat rustic retreat environment. Rooster has 1 full bath. Living room with satellite TV, Netflix; wood burning stove fireplace, wood provided, fully equipped kitchen, dining table, linens and starter paper goods furnished. Large deck and screen porch looking out on Cacapon Mountain. Hot tub off master bedroom deck in trees, feels like a tree house. Many mornings mist rises up from river, half mile away as crow flies.

Guest favourite

Cabin

4.89 out of 5 average rating, 211 reviews

Modern Eclectic Cabin with Views - Hot Tub - Creek

Our cabin in the treetops is the perfect place to rest, work remotely, or use as a basecamp for exploring the surrounding area. Our aesthetic is modern eclectic. We do our best to use only chemical/cruelty free products that are ethically and sustainably sourced. The cabin has many modern conveniences including an eco-friendly hot tub with epic views, high speed internet and chromecast for streaming your connected devices. Hot tub is available year round. Pellet stove is available Oct-March.

Guest favourite

Rental unit

4.92 out of 5 average rating, 308 reviews

Downtown 1920's Gas Station with Hot Tub

Luxury 1920’s Refurbished Gas Station and hot tub repurposed into a beautiful apartment. Private parking/EV charging station, private hot tub, full kitchen, custom rain shower, high speed wifi, and smart TV. There is plenty of light with frosted garaged doors, all modern appliances, coffee nook, and an open living design. Be a part of Old Town Winchester in this unique getaway, walking distance to shops, downtown eateries and our neighborhood Pizzoco Pizza Parlor one block away. Pets welcome!

Guest favourite

Cabin

4.97 out of 5 average rating, 104 reviews

Mary's Cabin

Nestled on 2 acres in the woods of West Virginia, kick back and relax in this quiet, chic cabin. Soak in the oversized copper tub, read on the porch swing, or cuddle by the electric fireplace. All the amenities of home, but away from the hustle and bustle of daily life. Only 25 minutes to quaint Old Town Winchester, where there are unique shops, breweries, restaurants and history! The cabin is located 20 minutes from a variety of scenic hiking trails that provide opportunities for adventure.

Guest favourite

Cottage

4.91 out of 5 average rating, 132 reviews

Lockley Cottage at Historic Perry Farm

Peace and tranquility await you at a quaint cottage on historic Perry Farm, where the original 19th century farmhouse still stands today. Stroll several acres of land and enjoy pastoral views while you unwind at this peaceful historic property in the hills of northern Shenandoah Valley. This rural retreat is easily accessed from I-81 and located a short 10-minute drive from historic downtown Winchester. Enjoy local wineries, breweries, farm markets, and the renowned Apple Blossom Festival.

Guest favourite

Guest suite

4.99 out of 5 average rating, 204 reviews

Creekside Retreat at the Jewel Vinsota

Relax in a quiet, curated, dog-friendly art exhibit. Live with paintings & sculptures that are for sale. This garden apartment is tucked into a hillside above a creek, along the Jewel Vinsota Sculpture Trail. Your host/gallery curators live upstairs. The “Artist’s Guesthouse” is next door. The private entrance is down a stone-stepped path. Perfect for 2 w/ the queen bed but room for 4 w/ the living room futon. Fully equipped kitchen. Private charcoal grill and fire pit next to the creek.

Guest favourite

Rental unit

4.88 out of 5 average rating, 100 reviews

Last Minute Deals! Luxe 2 BD Apt in OT Winchester

The Loudoun Luxe-Winchester’s Newest AirBnB just steps to the Old Town walking mall. One of the best addresses in Winchester! Don’t miss the chance to stay at this 100+ year old historic home newly renovated and customized with gorgeous hardwood flooring, quartz marbled countertops, professionally designed tile, Frigidaire/GE stainless steel appliance package (fridge, electric range, microwave, dishwasher, W/D), LED lighting, well-appointed and perfectly stocked for a fabulous holiday!

Superhost

Barn

4.79 out of 5 average rating, 107 reviews

Modern House Barn on 66 acre Horse Farm

Enjoy your stay at this completely renovated and unique barn home on a 66-acre horse farm with sweeping meadow and mountain views nestled between wine country and the Blue Ridge Mountains. This stay will allow you the peace and tranquility of farm life, while only being 5-10 minutes from restaurants, grocery stores, hiking trails, overlooks, coffee shops, breweries, and some of wine countries best wineries! Horse boarding & stall available upon request for an additional charge!

Guest favourite

Home

4.94 out of 5 average rating, 167 reviews

Indigo Blue modern open vibe on tree lined street

Come stay in this lovely spacious downtown home located on a beautiful tree lined street. Enjoy its open mid century modern style and relaxing outdoor areas! This 3BR 2BA home w/ sunroom w/ gas fireplace & rear fully fenced courtyard is the perfect place get away to & explore downtown Winchester. Walking distance to everything. Park & walk & enjoy nearby John Handley HS /walking mall /shopping/live music /art galleries/ walk to the iconic Handley Library, You will LOVE it!

Guest favourite

Cabin

4.96 out of 5 average rating, 149 reviews

Rustic and stylish mountain getaway

The Little Black Cabin is everything you've been dreaming about for your cozy mountain getaway! Take in sweeping views, curl up by the fireplace, or make s'mores at the fire pit. Whip up a gourmet meal in the small but well-appointed kitchen. Three dining areas offer options for dinner -- or a remote office, thanks to wifi. Sample nearby hiking, yoga, and farmers' market. We're a little rustic (no TV, AC, microwave, laundry or dishwasher) and a lot stylish!