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Pet-friendly vacation 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

4.89 out of 5 average rating, 178 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.

Townhouse

4.82 out of 5 average rating, 158 reviews

Darling Duplex

*NO cleaning fees in 2024!* 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.

Home

4.99 out of 5 average rating, 210 reviews

Charming, Pup-Friendly Woodland Getaway!

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

4.95 out of 5 average rating, 140 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.

Cabin

4.85 out of 5 average rating, 185 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.

Home

4.82 out of 5 average rating, 203 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.

Cottage

4.95 out of 5 average rating, 416 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.

Townhouse

4.94 out of 5 average rating, 183 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).

Tiny home

4.9 out of 5 average rating, 117 reviews

Quiet tiny home. Dog-friendly. Private fenced yard

Bright and clean cottage in a quiet, secluded neighborhood bordering national parkland. Close to everything Harpers Ferry has to offer. Dog-friendly with fully-fenced private yard and kitchenette. Relax on the spacious deck with forest view, or the cozy living room with smart TV. The bedroom features a plush queen-size bed. Just 1.2 miles from historic Lower Town and one mile from the National Park Visitor Center, you'll also be walking distance to restaurants, shops, and even nightlife.

Cabin

4.96 out of 5 average rating, 263 reviews

Acorn Hill, relaxing getaway, WiFi / pet friendly

Acorn Hill is an inviting escape and the perfect opportunity to unplug and enjoy the unparalleled beauty of the Shenandoah Valley and the nearby Shenandoah River. Acorn Hill is located in a quiet neighborhood and is walking distance to the Shenandoah River Outfitters, where you can enjoy canoeing, tubing, and fishing. Whether having fun on the river, cruising along Skyline Drive, exploring local wineries, golfing, antiquing, or just relaxing - all are conveniently located near Acorn Hill.

Home

4.97 out of 5 average rating, 141 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

Bungalow

4.86 out of 5 average rating, 138 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.**

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Winchester pet-friendly home rentals

Free parking on premises

Air conditioning

Pet-friendly house rentals

Home

4.92 out of 5 average rating, 132 reviews

Beautiful 3 BR historic home in downtown Frederick

Home

4.98 out of 5 average rating, 103 reviews

Historically Modern Rowhouse in Downtown

Home

4.98 out of 5 average rating, 161 reviews

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

Home

4.88 out of 5 average rating, 604 reviews

Arden House, Inwood WV

Home

4.92 out of 5 average rating, 282 reviews

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

Home

4.94 out of 5 average rating, 104 reviews

Romantic Cottage with Private Hot Tub

Home

5 out of 5 average rating, 103 reviews

Sunshine House -Cheerful 2BR/2.5Bath Detached Home

Home

4.81 out of 5 average rating, 117 reviews

Sunrise on the Potomac near Shepherdstown, WV

Pet-friendly home rentals with a pool

Cabin

4.91 out of 5 average rating, 109 reviews

Pet/Family Friendly, Hot Tub, Large Deck

Home

4.97 out of 5 average rating, 180 reviews

Harpers Ferry Farmhouse, Heated Year Round Pool

Home

4.78 out of 5 average rating, 256 reviews

Stone Spring - Heated Salt Pool - on 2.5 Acres

Cabin

4.94 out of 5 average rating, 110 reviews

NEW! Boutique-Chic w/fireplace @ The Woods

Cabin

4.99 out of 5 average rating, 210 reviews

Cedarfield Cabin

Cabin

5 out of 5 average rating, 135 reviews

Herb Cottage-Elegant Cabin plus Optional Farm Tour

Cabin

4.77 out of 5 average rating, 103 reviews

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

Cabin

4.95 out of 5 average rating, 116 reviews

Starcatcher Chalet, The Woods Resort

Private, pet-friendly home rentals

Rental unit

4.89 out of 5 average rating, 154 reviews

The GreyLoo

Guest suite

4.99 out of 5 average rating, 421 reviews

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

Rental unit

4.87 out of 5 average rating, 281 reviews

Your sanctuary awaits/1-bedroom downtown apartment

Guesthouse

4.79 out of 5 average rating, 33 reviews

Mint Chip !

Home

4.98 out of 5 average rating, 202 reviews

Pine Grove Retreat

Cabin

4.96 out of 5 average rating, 119 reviews

Mountain View Retreat

Cottage

4.93 out of 5 average rating, 119 reviews

English Cottage

Home

4.91 out of 5 average rating, 229 reviews

Renovated Cozy Cottage

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

Total rentals
30 properties
Nightly prices starting at
€ 29 before taxes and fees
Total number of reviews
2.1K 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