Pet-friendly vacation rentals in Winchester

Old Town 1920s Gas Station with Hot Tub

1920s Refurbished Gas Station with hot tub repurposed into a beautiful luxury apartment. Private parking/EV charging, 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, laundry and coffee nook in 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 Cottage on Historic Estate & Cattle Farm

Fully restored c.1900 farm house on 190 acre estate, ~1 hr from D.C. Cottage is situated at end of a farm road (past the main house and barns), very private w/ creek and cows right outside. Enjoy walks on the farm, local hikes, breweries & wineries, pick-your-own fruit farms, tubing on the Shenandoah, restaurants, antique shops, and more. 1 queen bdrm and bath on 1st flr, 2nd queen bdrm & loft with twin beds on 2nd flr. wifi, fire pit, small grill. Over 25 only, Max 4 adults. 1 SMALL DOG ONLY.

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.

Sugar Maple Chalet - 67-Acre Farm

✔ Rustic Luxury: Cozy wood interiors, modern comforts, and charming decor. ✔ 67 Acres of Beauty: Private walking trails and historic outbuildings amid pristine nature. ✔ Stunning Views: Panoramic views by day, star-filled skies by night. ✔ Modern Comforts: Well-appointed kitchen, high-speed Wi-Fi, and more. ✔ Outdoor Clawfoot Tub with Shower: Relax under a maple tree when weather permits. ✔ Whole-House Backup Generator: Reliable backup power keeps the chalet running during unexpected outages.

John Pope Cabin Browntown Va. We now have Starlink

Welcome to John Pope Cabin Nestled in foothills of the Appalachian Mountains, John Pope Cabin overlooks an open field where hawks hunt, bears sometimes stroll, and our neighbors’ horses peer over the fence. Feel free to pet them but don’t feed them! Built in 1865 by a Confederate soldier returning from the Civil War birthed and raised 11 children here. The cabin remains rustic, comfortable, and full of character. Ahh…the porch. Relax in the swing, watch the fields change with the light.

The Nest: Modern Cabin Retreat on 5 Wooded Acres

Welcome to The Nest, a light‑filled, chalet‑style cabin tucked into 5 wooded acres. A short drive from Berkeley Springs, Harpers Ferry, and Cacapon State Park, it’s your base for hot springs, hiking, trails, and small‑town restaurants. By day, explore paths, wineries, and historic main streets. By night, come “home” to star‑studded skies, mountain views, and wildlife. With fast Wi‑Fi, a workspace, and a fully stocked kitchen, The Nest is perfect for families, couples, and remote workers.

The Honeymoon Cabin | Private Retreat w/ hot tub

Escape to one of Front Royal's hidden gems, "The Honeymoon Cabin" offers couples & more the opportunity to retreat and sit among the stars overlooking the community's "Lake of Clouds". Whether a romantic getaway, solo adventure, or gathering of friends, you'll find relaxation among the stars over distance towns or the outline of mountains across the Shenandoah Valley. *Romantic decor including fresh flowers, balloons, bubbly, chocolate, and mood lighting is available on request for $299.

Gorgeous cabin on Blue Ridge

Atop the Blue Ridge close to Harper’s Ferry and Virginia wine country this airy retreat overlooks the idyllic Shenandoah. Our two-person soaking tub on a magnificent deck, huge firepit, gorgeous vintage interior, grand piano, and warm pine ceiling and floors, give you the perfect place to get away from city life for a bit. Full kitchen. Two bedrooms plus a big couch that could sleep someone else in a pinch, and a cozy little fireplace top it all off! Just steps to the Appalachian Trail.

Shenandoah Twilight | Hot Tub + Sunset Views

Shenandoah Twilight is a hidden gem just 80 minutes from DC for peaceful mountain getaways, sunset views, and slow evenings in the hot tub. Spend your days hiking, wine tasting, exploring Skyline Drive, or visiting nearby Front Royal, then come back to a comfortable cabin with a fully stocked kitchen, king bedroom, fast WiFi, private hot tub, fire table, and quiet outdoor spaces. It’s an easy place to unwind, reconnect, and enjoy the beauty of the Shenandoah Valley.

Cabin With Wood Burning Hot Tub

Escape to our modern cabin on 12 private acres. Unwind in the wood-burning hot tub, embracing the surroundings and stars at night. With a contemporary design and natural light, this retreat blends with nature. Explore private trails throughout the property, enjoying nature and the fresh air. Inside, find comfort in the fully equipped kitchen and cozy living area. Perfect for a peaceful getaway, our secluded home provides privacy and relaxation.

River Front Retreat *HotTub-FirePit-Kayaks*

Unplug and unwind. *River Front *Steps away from Cacapon River with easy access *Hot tub facing river *Kayaks with Life vests on property *Decks with BBQ and dining Alfresco *Two Fire pits: River Front Wood Fire pit and Propane on the Deck *Yard games/board games *Wi-Fi and Smart TV. *Comfy beds/black out curtains *Pet-Friendly ($25/day for 2 dogs) ***pet policy below Come step into nature and nurture your spirit at our riverfront haven.

Modern Eclectic Treetop Cabin ~ Hottub ~ Romantic

Our cabin in the treetops is the perfect place to rest, work remotely, or use as a basecamp for exploring the surrounding area. 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 and safe for max of 2 adults due to its location on the upper deck. Pellet stove is available Oct-March.