Pet-friendly vacation rentals in Hagerstown

Charming "Cream of the Crop" Cape ~❤️of Middletown

Cozy cape in the ❤️ of Middletown, MD. Walking distance (1/2 mile)to quaint Middletown restaurants, shops, & parks. Set your sights on adventure within a short drive. Enjoy downtown Frederick restaurants, shops, parks, & nightlife.Visit the local wineries, breweries & festivals. Hike the Appalachian trail. Float the Potomac River. Bike the C&O Canal. Ski the slopes @ area ski resorts. Golf 18 holes @ the championship golf course. Visit wedding venues. Go antiquing. Tour quaint nearby towns. Etc

Hot Tub · 4BR Creek Cabin ·Sleepy Creek ·90 Min DC

90 min from DC/Baltimore, this secluded 4BR mountain cabin on Sleepy Creek is your private escape with a new 6 person hot tub, STAR LINK INTERNET, creek access for fishing, kayaking, and a wood burning fireplace. Without the resort price tag. ★ NEW BIGGER HOT TUB 2025 ★ ★ VERY DOG FRIENDLY ★ ★ STAR LINK High-Speed Wi-Fi 2026★ ✔ Creek Access ✔ Hot Tub ✔ Fishing/Kayaking ✔ Pet friendly ✔ 4 BRs (3 Main Cabin + Private Loft) ✔ Full Kitchen ✔ Deck, Patio, Dining, BBQ, Fire Pit ✔ Smart TVs ✔ Parking

One-bedroom apartment with separate entrance.

Adorable one-bedroom apartment with separate entrance. Located 10 minutes from downtown Chambersburg. Whether its historical sight-seeing, culturally diverse restaurants, or local craft beer, there is plenty to see and do in this area. Built in 2021, this apartment is on the lower level of our custom built home. It also has a fully equipped gym. We live upstairs with our two children and two dogs. We maintain quiet hours between 10pm and 7am. Pet friendly, No smoking, No parties.

Creekside Retreat at the Jewel Vinsota

Relax in a quiet, curated, pet-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 3 w/ the living room futon. Fully equipped kitchen. Private charcoal grill and fire pit next to the creek.

Darling Duplex

*NO cleaning fees in 2026!* Hands down BEST Value in Hagerstown and Surrounding areas Perks include: •Pet friendly •Baby 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 •2 bathrooms and 6 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.

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.

The Crooked Cottage: a Cozy, Curated Escape

You will instantly relax in this stylish, pet-friendly home only 8 mins from I-70, exit 42. Under a canopy of trees find a beautifully landscaped yard with decks and two fire pit areas. Enjoy the well-apportioned kitchen with organic, fair trade coffee. Relax with 2 Roku TVs, games and puzzles, bathe with soaking salts and Turkish towels. For outdoor enthusiasts, pitch your tents. Sit by the wood-stove in the winter, or lay in a hammock when it’s warm. Welcome to The Crooked Cottage!

The Cottage at Forest Hills Farm

Beautiful one bedroom, one bath cottage on a picturesque 14 acre farm just outside of downtown Leesburg. Nestled in close to local vineyards, this charming, free-standing cottage is yours and perfect for a weekend getaway or alternative to a hotel. Enjoy the fresh air, beautiful views, and peace and quiet on our little farm. Wander the property and say hello to our donkey, mule, Long Horn cows, goats, chickens, and 3 barn cats (and 3 kiddos!). Just 3 miles to downtown Leesburg.

Spectacular views, intimate dome

Come experience a truly one of a kind polycarbonate dome tucked away in the Appalachian mountains! Situated on the mountainside overlooking the scenic Cumberland valley. Complete privacy, stunning sunsets, and amazing amenities! The dome is climate controlled. The spacious deck is equipped with a meticulously maintained hot tub, and a blackstone griddle. This offers the unique opportunity to be immersed in nature, yet enjoy numerous amenities and comfort.

Inn on Potomac-South

The "Inn On Potomac" offers quaint, upscale accommodations in a pre-civil war historic home when visiting Hagerstown, Maryland. The Inn is only 2 blocks from the City Center, the Maryland Theatre, restaurants, and the downtown entertainment district. We are close to museums, wineries, breweries, and civil war battlefields. We offer 2 suites, the "Potomac South" and the "Potomac North", across the hallway from each other-- each listed separately on Airbnb.

Steps to Winery and Battlefield – 1 Acre Retreat

Unwind at this breathtaking 1-acre hilltop retreat overlooking Antietam Battlefield and lush vineyards. Perfect for a romantic escape or family getaway, our newly remodeled home offers stunning views from the deck, cozy interiors, and easy access to Antietam Creek Vineyards—just a short walk away. Explore nearby trails, relax by the outdoor fire pit under the stars, and enjoy the peaceful setting while experiencing all the comforts of home.

Mimi's Cottage - Fenced Yard & No Extra Fees!

At little bougie, gaudy, and a lot of fun! Mimi’s cottage is an eclectic blend of luxury and coziness that you just don’t get from a hotel. Single family home on a quiet street in the South End of Hagerstown, Maryland. Perfect for families, couples, or if you just want to treat yourself! This sleekly decorated house has everything you need, just like you are at your own home. Why stay in a hotel when you can come to Mimi's?