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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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Cabin in Stanley

4.88 out of 5 average rating, 189 reviews

Ironside Ridge at Skyline Lakes

Modern Nordic style/themed cabin located on 2+ wooded acres with an outdoor fire pit, BBQ grill area, wrap around deck & High Speed Starlink Internet. Fully stocked kitchen, wood burning stove, firewood included, with large bedroom and open floor plan. Incredible hiking from the cabin: SNP, Big Meadows, Appalachian Trail, waterfalls, and more. Nearby fishing pond. Pets and children allowed. Leave the stress of life behind and come relax at Ironside Ridge. Superhost with 750+ Five Star reviews.

Guest favourite

Townhouse in Hagerstown

4.84 out of 5 average rating, 176 reviews

Darling Duplex

*NO cleaning fees in 2025!* Hands down BEST Value in Hagerstown and Surrounding areas Perks include: •Pet friendly (and always free!) •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.

Guest favourite

Home in Mount Crawford

4.99 out of 5 average rating, 218 reviews

Pup-Friendly, Woodsy Getaway, 20 min to ski resort

Welcome to La Casa del Bosque (The House in the Woods)! Situated on 10 wooded acres and surrounded by farms on rolling hills in the heart of the Shenandoah Valley, our recently-updated 5-bedroom, 2.5 bath home is the perfect place for your getaway. We are just 15 minutes from JMU and downtown Harrisonburg, and 25 minutes from Massanutten. Take a walk on the trail, birdwatch, visit a neighboring vineyard, or chase sticks with your pup--- there are so many ways to unwind at La Casa del Bosque!

Cabin in Front Royal

4.85 out of 5 average rating, 195 reviews

♛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.

Guest favourite

Cabin in Luray

4.95 out of 5 average rating, 144 reviews

❤️️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.

Guest favourite

Home in Waynesboro

4.82 out of 5 average rating, 209 reviews

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.

Guest favourite

Cottage in Berkeley Springs

4.95 out of 5 average rating, 430 reviews

Hidden Hill - Cozy Downtown Cottage with Hot Tub!!

Hidden Hill is a renovated 1880’s cottage tucked away just above historic downtown Berkeley Springs. Xfinity high speed internet! Literally steps from spas, restaurants, art, antiques, and nightlife, this cottage also feels hidden just above downtown. Hidden Hill is a great spot to stay while enjoying everything Berkeley Springs has to offer. Explore everything West Virginia has to offer during the day, then retreat to Hidden Hill for the convenience of restaurants and bars at your doorstep.

Guest favourite

Townhouse in Downtown Frederick

4.94 out of 5 average rating, 190 reviews

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).

Guest favourite

Home in Downtown Frederick

4.97 out of 5 average rating, 147 reviews

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

Guest favourite

Home in Luray

4.96 out of 5 average rating, 265 reviews

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!

Guest favourite

Home in Downtown Frederick

4.86 out of 5 average rating, 100 reviews

Renovated tech-house in historic downtown

Come stay in Fredericks Historic District, Just a minutes walk past beautiful row homes will have you in the heart of downtown Frederick, where you can enjoy food, shopping, theater or just enjoying the free local festivities the town has to offer. Our location has been blocked off for a couple months for updates! Enjoy new blinds, fresh paint, black out curtains, updated furniture, indoor baby gate installed, updated entry fence in the yard, updated fixtures in bathroom and more!

Guest favourite

Bungalow in Luray

4.86 out of 5 average rating, 142 reviews

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.**

Holiday rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Flats

Convenient locations with everyday essentials

Houses

A space that's all yours, with room for everyone

Popular amenities for Winchester pet-friendly home rentals

Free parking on premises

Air conditioning

Pet-friendly house rentals

Home in Elkton

4.79 out of 5 average rating, 238 reviews

Historic River House-Riverfront!

Guest favourite

Home in Downtown Frederick

4.92 out of 5 average rating, 140 reviews

Beautiful 3 BR historic home in downtown Frederick

Guest favourite

Home in Washington

4.98 out of 5 average rating, 164 reviews

Across INN Entire Colonial HOUSE 3 Beds+Fast Wi-Fi

Guest favourite

Home in Inwood

4.88 out of 5 average rating, 619 reviews

Arden House, Inwood WV

Guest favourite

Home in Hedgesville

4.92 out of 5 average rating, 290 reviews

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

Guest favourite

Home in Castleton

4.95 out of 5 average rating, 111 reviews

Romantic Cottage with Private Hot Tub

Guest favourite

Home in Downtown Frederick

5 out of 5 average rating, 103 reviews

Sunshine House -Cheerful 2BR/2.5Bath Detached Home

Guest favourite

Home in Martinsburg

4.82 out of 5 average rating, 122 reviews

Sunrise on the Potomac near Shepherdstown, WV

Pet-friendly home rentals with a pool

Cabin in Berkeley Springs

4.91 out of 5 average rating, 113 reviews

Pet/Family Friendly, Hot Tub, Large Deck

Guest favourite

Home in Harpers Ferry

4.97 out of 5 average rating, 186 reviews

Harpers Ferry Farmhouse, Heated Year Round Pool

Home in Rockingham

4.78 out of 5 average rating, 258 reviews

Stone Spring - Heated Salt Pool - on 2.5 Acres

Guest favourite

Cabin in Hedgesville

4.94 out of 5 average rating, 114 reviews

Dog-friendly, boutique & chic + fireplace

Guest favourite

Cabin in Delaplane

5 out of 5 average rating, 137 reviews

Herb Cottage-Elegant Cabin plus Optional Farm Tour

Cabin in Rileyville

4.77 out of 5 average rating, 103 reviews

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

Guest favourite

Cabin in Hedgesville

4.95 out of 5 average rating, 130 reviews

Starcatcher Chalet, The Woods Resort

Cabin in Hedgesville

4.86 out of 5 average rating, 182 reviews

Stylish Retreat w/Fireplace, Games & Pool Access

Private, pet-friendly home rentals

Guest favourite

Flat in Frostburg

4.89 out of 5 average rating, 165 reviews

The GreyLoo

Guest favourite

Home in Harpers Ferry

4.91 out of 5 average rating, 106 reviews

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

Guest favourite

Home in Hagerstown

5 out of 5 average rating, 29 reviews

Welcome Home: Families, pets, remote workers

Guest favourite

Guest suite in Edinburg

4.99 out of 5 average rating, 426 reviews

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

Flat in Frederick

4.86 out of 5 average rating, 286 reviews

Your sanctuary awaits/1-bedroom downtown apartment

Guest favourite

Home in Stanley

4.96 out of 5 average rating, 208 reviews

Pine Grove Retreat

Guest favourite

Cabin in Rileyville

4.96 out of 5 average rating, 135 reviews

Mountain View Retreat

Guest favourite

Cottage in Middleburg

4.93 out of 5 average rating, 122 reviews

English Cottage

Quick stats about holiday rentals that are pet-friendly in Winchester

Total rentals
30 properties
Nightly prices starting at
₹2,598 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