Pet-friendly holiday rentals in Hagerstown

4.95 out of 5 average rating, 179 reviews

A gravel area features several rustic wooden chairs arranged around a stone fire pit, with a gentle fire burning. Soft string lights illuminate the space, enhancing the cozy atmosphere. The exterior of the cabin is visible in the background, surrounded by trees.

Cabin in Hedgesville

Modern Cabin: Hot Tub, Arcade, FirePit, Pets+Pool

Experience the epitome of luxury in our breathtaking A-frame cabin, nestled amidst the serene woods. This modern retreat offers lavish amenities and a stunning open living space with floor-to-ceiling windows, immersing you in nature's beauty. Indulge in the private hot tub, relax by the fire pit, and unleash your culinary skills in our fully equipped kitchen. The large screened porch provides a tranquil oasis, while nearby hiking trails, golf courses, and a spa offer an unforgettable getaway!

4.95 out of 5 average rating, 140 reviews

A cozy living area features a gray sectional sofa adorned with two white pillows. Natural light filters through the large windows, highlighting a round orange pouf and two side tables with lamps. Wooden beams are visible on the ceiling, enhancing the cottage’s rustic charm.

Home in Middletown

Mountain Church Cottage

Mountain Church Cottage offers a great stay in the hills of Middletown, Maryland. Activities nearby include access to the Appalachian Trail. The roads are a perfect challenge for the serious cyclist and runner, but it’s just a 15 minute drive to the flat terrain of the C&O Canal bike path. For kayakers, Potomac River access is in Harpers Ferry, West Virginia. It's just a short drive to Antietam National Battlefield. And for those who enjoy a glass, there are a number of wineries in the region.

5 out of 5 average rating, 262 reviews

The treehouse is elevated among the trees, featuring large windows that offer views of the surrounding forest. The exterior is constructed with dark wood shingles and is supported by sturdy stilts, blending seamlessly with the natural environment.

Treehouse in Waterford

Hummingbirds Hideaway Treehouse

Do not book on airbnb and ask for early arrival. experience the magic of being among the treetops at our newly built treehouse. Whether you are seeking a romantic getaway, peaceful retreat, or family fun this slice of heaven will offer you an unforgettable stay. Features large windows for stunning views of the surrounding woods and very detailed woodwork. 2 bedrooms with king beds, open living space with full kitchen and bathroom will be sure to impress. Please message us prior to booking

4.97 out of 5 average rating, 401 reviews

Home in Greencastle

Country 2-Bed/2-Bath Barndominium w/Beautiful View

Rural agricultural setting but convenient to towns, golfing, Whitetail Ski Resort and civil war historical sites. Two bedrooms with queen beds w/linens, two full baths, full kitchen living room area, desk and outdoor firepit and chairs (firewood for additional fee). Queen pull-out sofa bed. Wi-Fi and HDTV. Paved drive/parking area. Pets welcome-Dogs Only. Short drive to I-81 and I-70 20 mins to Hagerstown 15 mins to Chambersburg 20 mins to Whitetail Ski Resort 1.5 hrs to Baltimore/Washington

4.95 out of 5 average rating, 131 reviews

Two classic wooden Adirondack chairs are positioned near the bank of a gently flowing stream. Lush greenery surrounds the area, with trees casting dappled sunlight on the water. A clear blue sky adds a serene backdrop, enhancing the peaceful atmosphere of the outdoor space.

Cottage in Waynesboro

Antietam Toll House~an historic waterfront cabin

The Antietam Toll House (@antietamtollhouse) is a renovated historic property circa 1800. Sitting on the bank-head of the Antietam stream, this cabin has it's own private fishing hole. Secluded, yet close to amenities and attractions, this property is the perfect place for an artist retreat, respite from the city or a base from which to explore local gems of the area. Wineries, Appalachian Trail, Antietam, Gettysburg battlefields, Ski Liberty, Catoctin , Cunningham Falls and more nearby.

Guest suite in Smithsburg

The exterior of a two-story house is surrounded by trees, with warm lights framing the balconies. Large glass windows provide visibility into the interior. A deck with a railing is seen above, and decorative elements are positioned outside the entrance.

4.98 out of 5 average rating, 365 reviews

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.

4.86 out of 5 average rating, 277 reviews

A well-arranged living area features a comfortable dark sofa with decorative pillows. A wooden coffee table holds various items, including hand soap and informational cards. A television is mounted above a tasteful electric fireplace, while dining space is visible through an adjacent doorway.

Townhouse in Hagerstown

Darling Duplex

*NO cleaning fees in 2025!* 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.

4.96 out of 5 average rating, 104 reviews

A well-lit deck hosts a modern soaking tub, surrounded by forest views. Steps lead down from the deck, which is adorned with warm lighting that highlights the natural wood. The evening sky offers soft hues as the sun sets beyond the trees.

Home in Harpers Ferry

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.

4.91 out of 5 average rating, 158 reviews

A polycarbonate dome is nestled among trees, illuminated in soft green light. The spacious deck includes a seating area and a small table. A colorful sunset is visible in the background, casting a warm glow over the Appalachian landscape.

Dome in Shippensburg

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.

4.96 out of 5 average rating, 277 reviews

A modern cabin is set amongst lush greenery, featuring a dark exterior and a welcoming front porch. Surrounding landscaping includes a variety of shrubs and trees, creating a peaceful atmosphere. The driveway leads to the entrance, providing easy access to the secluded retreat.

Cabin in Star Tannery

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.

4.96 out of 5 average rating, 228 reviews

Home in Sharpsburg

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.

4.97 out of 5 average rating, 146 reviews

Cabin in Hedgesville

Waterfront Cabin on the Potomac River w/ Hot tub

Our Cabin is located right on the Potomac River. Walk right down and sit right in it. Sleeps 5 people. It has2 bedrooms & 2 balconies facing the water & brings such peace and serenity. Read a book? Take a nap? Go Fishing? At this location, it's the perfect depth to swim, float, kayak, wade fish & more. Also facing the River is a private Hot tub Outdoor Pavillion w/ Gas Grill, Fridge, Sink, Seating, Fire pit, & more.

Popular amenities for Hagerstown pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.94 out of 5 average rating, 145 reviews

A spacious mountain home is set against a backdrop of trees, with a gently sloping field leading to a small pond in the foreground. A wooden fence encircles the property, highlighting the serene outdoor environment that encompasses the house.

Home in Sabillasville

Stoney Spring Overlook

4.99 out of 5 average rating, 125 reviews

A serene exterior view of Everlong showcases the inviting front deck surrounded by lush greenery. The wooden railing and steps lead to a comfortably designed patio space, framed by trees that highlight the home's natural setting.

Home in Berkeley Springs

Everlong ~ Pet-friendly Retreat on 2 Wooded Acres

4.98 out of 5 average rating, 367 reviews

A scenic view of rolling hills under a pastel sky at sunset, with a fence line in the foreground. A hot tub is situated on a spacious deck, surrounded by scenic greenery. A cozy living area features a neutral color palette, a comfortable seating arrangement, and soft lighting. The exterior showcases a charming house on expansive grounds.

Home in Berkeley Springs

Abby's Lookout - Raised Retreat w/Hot Tub & WiFi

Home in Downtown Frederick

The remodeled bathroom features dual sinks with modern faucets, positioned below two matching mirrors. Natural light filters in through a window, illuminating the sleek green tile shower enclosure with a glass door. Stylish light fixtures add a contemporary touch to the clean design.

4.97 out of 5 average rating, 213 reviews

Cottage:Walkable 2 Everything-Super Clean-Downtown

4.96 out of 5 average rating, 146 reviews

Home in Berkeley Springs

Sleepy Creek -hot tub, pets, grill, fire pit, wifi

4.91 out of 5 average rating, 338 reviews

A panoramic view of lush green mountains stretches out below, with a soft sunrise illuminating the horizon. The scene captures varying shades of green from the trees, contrasting with the delicate pastel colors of the sky.

Home in Hedgesville

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

4.94 out of 5 average rating, 203 reviews

The spa-inspired master bath features a freestanding tub with a sleek design, set against a backdrop of rich wooden tile. A wooden stool complements the space, while a glass shower enclosure and minimalist fixtures contribute to a modern aesthetic.

Home in Bolivar

Spa tub, movie room, best beds ever, Luxury design

4.82 out of 5 average rating, 247 reviews

A dining area with a wooden table is surrounded by eight matching chairs, featuring a centerpiece of fresh flowers. Soft lighting is provided by a pendant lamp. A staircase with a black railing is visible, leading to a cozy living area with a dark sofa and art on the walls.

Home in Waynesboro

Waynesboro Adventure with the Family

Pet-friendly home rentals with a pool

Cabin in Berkeley Springs

A spacious living area features a dark sectional sofa, complemented by a wooden coffee table and patterned area rug. Large glass doors provide views of the wooded outdoors, while a dining area with a wooden table is visible in the background. Wooden paneling adds warmth to the space.

4.91 out of 5 average rating, 128 reviews

Pet/Family Friendly, Hot Tub, Large Deck

Guest suite in Myersville

A heated pool is surrounded by a stone wall and lush greenery, offering a serene atmosphere. The lodge features large windows and a balcony overlooking the pool area, seamlessly connecting indoor and outdoor spaces.

4.91 out of 5 average rating, 337 reviews

Harmony Lodge nestled in wooded tranquility!

Chalet in Berkeley Springs

A spacious interior features vaulted wooden ceilings and large windows, allowing natural light to fill the room. A wooden dining table is surrounded by several chairs. A comfortable seating area includes an armchair and a rocking chair, offering views of the outdoors.

4.87 out of 5 average rating, 265 reviews

The Mountain House

4.96 out of 5 average rating, 213 reviews

The exterior of the farmhouse is showcased at dusk, highlighting the blend of historic and modern architecture. A stone path leads to the welcoming entry, framed by glowing flower pots. The wraparound porch features multiple illuminated windows, reflecting a cozy and inviting ambiance.

Home in Harpers Ferry

Historic Farmhouse | Heated Plunge Pool, Billiards

Farm stay in Purcellville

A horse stands peacefully in a lush green pasture, surrounded by a black wooden fence. In the background, a well-maintained barn with a cupola is visible, complemented by a clear blue sky and scattered clouds.

4.98 out of 5 average rating, 222 reviews

The Hunt Box @ Tally Yo Farm

4.86 out of 5 average rating, 151 reviews

A charming cabin is nestled among lush trees, featuring a spacious deck that overlooks the surrounding greenery. The structure highlights a gabled roof and large windows, inviting natural light into the house. The forested setting enhances the feeling of seclusion and tranquility.

Cabin in Hedgesville

Five Oaks Cabin at The Woods Resort

4.94 out of 5 average rating, 184 reviews

A spacious great room features a large sectional sofa in rich orange, inviting relaxation. Tall windows allow natural light to fill the space, offering views of the surrounding forest. A decorative area rug anchors the seating area, complemented by a coffee table and thoughtfully arranged decor.

Chalet in Hedgesville

Starcatcher Chalet, The Woods Resort

Cabin in Berkeley Springs

The modern cabin is nestled among lush green trees, featuring a dark exterior with large windows. Two decks are visible, providing outdoor space. Stairs lead up from the gravel path to the main entrance, surrounded by nature.

4.98 out of 5 average rating, 122 reviews

Private hot tub, wooded, EV charger, 1-gig fiber i

Private, pet-friendly home rentals

5 out of 5 average rating, 50 reviews

An open living area combines a cozy seating arrangement with a large couch, a round table, and a rectangular dining table. A fireplace adds a focal point, while a large TV is mounted on the wall. Natural light enters through multiple windows, enhancing the space.

Home in Hagerstown

Welcome Home: Families, pets, remote workers

4.97 out of 5 average rating, 61 reviews

Guest house in Frederick

Private Woodland Retreat | Near Downtown Frederick

5 out of 5 average rating, 93 reviews

The exterior of the historic building features a large bay window, framed in teal, complemented by a black door. A lush array of vibrant red flowers and green foliage enhances the welcoming entrance, leading to stone steps that invite guests into the Inn.

Flat in Hagerstown

Inn on Potomac-South

Guest house in Myersville

A two-story cottage is set amidst lush greenery, featuring a large upper deck that offers views of the surrounding woods. Colorful azaleas and shrubs enhance the entrance, while a gravel drive leads to the property, surrounded by trees exhibiting signs of spring.

4.94 out of 5 average rating, 280 reviews

Spruce Run Cottage, Farm stay on Catoctin Mountain

4.78 out of 5 average rating, 93 reviews

The exterior of a duplex features a beige brick facade complemented by light grey siding. The entrance is marked by a white door, adorned with a circular wreath, and flanked by two large windows showcasing evenly placed shutters. A small table is positioned near the door, enhancing the welcoming ambiance.

Home in Greencastle

The Quick Escape

4.83 out of 5 average rating, 127 reviews

The cabin features an A-frame structure with a gray exterior and a vibrant red door. Surrounding trees shed their leaves, and a serene river can be seen in the background. The entrance is framed by steps leading up to the porch, adding charm to the setting.

Cabin in Falling Waters

Mike’s Cabin on the Potomac!

4.97 out of 5 average rating, 29 reviews

The exterior of the stone cottage is visible, featuring a welcoming entrance with steps leading to the front door. A flag displaying the Maryland state colors hangs from the porch. Tall trees and neighboring architecture are seen along the sidewalk.

Home in Hagerstown

Hub City Cottage