Pet-friendly holiday rentals in Winchester

♛Royal A-Frame♛HOT TUB★PetsOK★WoodStove★FASTwifi

As featured in The Washingtonian! Forest bathing in cozy retreat nestled in treetops of Shenandoah Valley. Stunning indoor/outdoor views. Features hot tub, wood-burning stove, wrap-around deck, grill, fire pit, and Xfinity Wi-Fi. For kids: outdoor playground, pack n' play, and highchair. Sleeps six comfortably with queen, double, and trundle bed (single/single). Shenandoah hiking, biking, canoeing/tubing, breweries/wineries, museum and golf nearby. Happy dog fee $150. AWD required in winter.

❤️️Wildflower Cabin❤️️ A Luxury Riverfront Retreat

*Come in and relax in this tranquil, peaceful hideaway. *Newly renovated cabins on Shenandoah River. *100 feet riverfront on a 2 acre property *AC/heat, satellite Wifi, fresh linens, towels, DVDs, board games. *Full kitchen w/ utensils, microwave, toaster, K-cups. *Secluded, close tohiking, caverns, wineries, and river adventures.*Dog friendly (extra fee of $40/dog/stay and will be asked for after booking, not included in booking fees) ! *King-size bed in bedroom, queen sofa bed in living room.

Adventure with the Family - Pets Welcome

The cozy house for the whole family, furry friends included. Quietly located in the town of Waynesboro, a short walk to downtown and excellent Sushi - Sapporo. Eat in or explore Waynesboro's charm. 1.5 hours from Baltimore or Washington DC. 23 miles from Historic Gettysburg. 13 miles from Ski Liberty and 23 miles from Whitetail Ski resorts. Covered carport parking. Perfect for the family vacation or ski trip. Stocked with toys and games. Full line of baby amenities available upon request.

Charming Historic Frederick Home

Charming 1910 brick home with fenced yard located in the heart of Downtown Frederick, just steps to Frederick's best breweries, beautiful Carroll Creek, and the quaint shops at Everedy Square. The house is the perfect blend of old and new, combining exposed brick/stone, natural light and hardwood floors with modern amenities such as a remodeled kitchen, WiFi, central air, luxury mattresses and cozy furnishings. Family, work, and dog friendly ($50/stay fee; no dogs on furniture; max 2 dogs).

The Cottage on Dill (Pet Friendly)

Cozy and historic home located in the heart of downtown Frederick. The house is just a block and a half from New Market Street, minutes to Hood College, and all of downtown Frederick within a 10-15 minute walk. This charming, 1901 historic home is both comfortable and upgraded with a remodeled, fully stocked kitchen, and stunning brand new bathroom. Modern amenities, include: high speed Wifi, smart TV, coffee station, luxury mattresses, air conditioning, and washer/dryer. Pet friendly

Charming pet friendly home, 15 mins to caverns

Acorn Hill is your perfect escape to unwind and reconnect with nature in the heart of the Shenandoah Valley. Nestled in a peaceful neighborhood, this charming retreat is just a short walk from the Shenandoah River Outfitters, where you can enjoy canoeing, tubing, and fishing. Whether you're exploring Skyline Drive, visiting local wineries, hiking, or simply relaxing in the serene surroundings, Acorn Hill is the ideal home base for you to experience the beauty of the Shenandoah Valley!

Darling Duplex

*NO cleaning fees in 2025!* Hands down BEST Value in Hagerstown and Surrounding areas Perks include: •Pet friendly •Entire private home •Central HVAC (dual units) •Walk-in shower •Fenced-in backyard •Full size washer and dryer (with essentials!) •Dishwasher/Garbage disposal •Piano •Multiple bathrooms and beds • and so much more! Comfy 100 year old duplex minutes away from downtown. Remodeled kitchen and posh upstairs bath. A short walk to the beautiful Hagerstown city park.

Dream View | Hot tub | Kids’ Activities | Trails

The best of Shenandoah Family Home | 2 hs from DC | Crystal Clear Hot Tub | No cleaning Fee or dogs Fee | 13 activities | 3 Beds, 3 Queen-Size Beds | 1 Bath | 3 Decks | Child-Dog-Friendly | WiFi | Three 55” HDTVs with Netflix, Prime Video | Outdoor Movie Theater | 2 Hammocks | 2 Fire-Tables | Mini Golf (putt-putt) | Grill | Max. 2 dogs | GW National Forest ( 10 min), Shenandoah NP ( 45 min), Luray Caverns ( 30 min) | No Cats. | NO Parties. No kids Hot tub !

Journey's End in Luray

Enjoy the mountains and the river in beautiful Luray, Virginia in a cozy bungalow with mountain views. Sit in the glass enclosed sun room to eat breakfast, sip coffee and leisurely read. Enjoy the indoor and outdoor fireplaces. Grill outdoors. Nearby access to Shenandoah River for canoeing, kayaking, and tubing. The home abuts the George Washington National Forest. We are approximately 15 minutes from downtown Luray. **PETS are welcome. There is a $35 dollar pet fee.**