Pet-friendly holiday rentals in Hagerstown

Guest suite in Shepherdstown

A spacious sleeping area is centered around a beautifully made bed with a textured gray coverlet. Nightstands on either side feature stylish lamps and small potted plants. Art is displayed on the wall, contributing to a serene atmosphere, with natural light filtering through the window.

4.96 out of 5 average rating, 714 reviews

Historic Scrabble, Shepherdstown

The perfect private guest cottage situated beside a beautiful historic home in the unique community of Scrabble Unincorporated just a half-mile from the Potomac River. Modern, comfortable and tastefully decorated with full amenities and parklike surroundings with an abundance of nature at your doorstep. Close to Shepherdstown / Shepherd Univeristy (12 minutes), Martinsburg (20 minutes), Harpers Ferry (20 minutes) and in the heart of civil war history including the famed Antietam National Park.

4.97 out of 5 average rating, 377 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 w/agreement. 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

4.94 out of 5 average rating, 127 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, 342 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, 276 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.

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, 335 reviews

Harmony Lodge nestled in wooded tranquility!

Tranquil lodge nestled on 3 wooded acres in Myersville, MD. Relax by the heated pool, enjoy the warmth of the fire pit, or receive a massage in the studio. Minutes away from downtown Frederick and Middletown restaurants, shops, and parks. Visit the local wineries and festivals. Tour historic battlefields. Go antiquing. Take in a round of golf, bike the C&O canal, hike the Appalachian trail, boat on the Potomac River, or go skiing. Bring your fur baby with you to enjoy the activities!

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, 265 reviews

Spruce Run Cottage, Farm stay on Catoctin Mountain

The cottage is located on 25 acres of mostly wooded terrain off Highway 17 near Wolfsville, Maryland, less than an hour and a half from D.C. The cottage faces the woods and the private drive down to the creek. There is almost zero light pollution at night so stargazing is incredible from the balcony. The hosts live on the property up the hill in an 1890’s chink log cabin. Although you can see our house, the cottage feels very private and is a quiet comfortable retreat in the hills.

4.98 out of 5 average rating, 282 reviews

The entrance to The Crooked Cottage is framed by wooden planks and surrounded by greenery. Two windows offer glimpses into the inviting interior, while a gravel pathway leads up to the door, playfully adorned with a sign featuring the name of the cottage.

Home in Myersville

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!

An A-frame cabin surrounded by lush greenery features two expansive decks. The front deck includes seating and a decorative railing, inviting relaxation while enjoying the natural setting. Floor-to-ceiling windows allow for ample natural light, enhancing the connection with the surroundings.

4.9 out of 5 average rating, 202 reviews

Unique Gem: Cozy A frame cabin in the woods

Come unwind and enjoy nature in this cozy, quaint, A-frame cabin. Nestled in the woods overlooking a community pond, enjoy the views through floor to ceiling windows or relax outside on one of the two large decks. The home includes a gas grill available for use and fire pit with wood provided. Best suited for two guests, it can accommodate up to 4 with use of the futon in the loft. Located just minutes away from the Potomac River and numerous recreational areas!

4.96 out of 5 average rating, 213 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.

4.96 out of 5 average rating, 142 reviews

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.

5 out of 5 average rating, 148 reviews

A charming two-story cottage features a welcoming front door framed by decorative shutters and flower planters. A covered porch is seen to the left, adding outdoor space for relaxation. The surrounding yard is well-maintained, providing a pleasant view of the greenery.

Cottage in Shepherdstown

The Creekside Cottage: Downtown | Pet-Friendly

Welcome to the Creekside Cottage, a 2 bedroom/1.5 bathroom spacious home, offering a secluded escape by the creek yet just a short stroll through the gardens of Shepherdstown to shopping and dining. Perfect for getaways, family visits, or university stays, this Creekside Cottage offers a roomy interior, cozy living room, modern kitchen, fire pit, and a private patio & porch to be enjoyed along the Town Run.

Popular amenities for Hagerstown pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.99 out of 5 average rating, 121 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, 175 reviews

The historic home features a charming exterior with a green metal roof and rose bushes in front. The house is two stories with classic shutters and a welcoming front door. A wrap-around balcony can be seen above, providing additional outdoor space.

Home in Catoctin Park

The Emerald Roof, Historic Home Downtown Frederick

4.93 out of 5 average rating, 329 reviews

An aerial view captures the cottage nestled among vibrant autumn foliage, surrounded by colorful trees. The serene pond reflects the rich hues of fall, while solar panels are visible on the cottage roof. A winding dirt road leads to the property, enhancing the secluded atmosphere.

Home in Clearville

Grouseland's Pondside Vacation Cottage

4.91 out of 5 average rating, 329 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

4.99 out of 5 average rating, 156 reviews

A spacious home is set on a green lawn, surrounded by tall trees. Mountain and valley views stretch in the background, capturing the serene countryside atmosphere. The home's exterior features a combination of siding and a metal roof, lending a rustic charm.

Home in Fairfield

Liberty Valley View - near ski slopes and golf

4.78 out of 5 average rating, 197 reviews

A view from a covered porch includes two white Adirondack chairs positioned on a wooden deck. The railing offers an unobstructed sightline to the river, framed by trees with early spring foliage along the shore, creating a peaceful atmosphere.

Home in Shepherdstown

Plum Lazy on the Potomac

4.94 out of 5 average rating, 196 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

Spring flowers, spa tub movie room, best beds ever

4.95 out of 5 average rating, 184 reviews

A modern living area features a gray sectional couch with orange accent pillows, positioned on a vibrant blue area rug. A coffee table sits center, surrounded by a spacious layout. A wall-mounted TV and a small dining area are visible in the background.

Home in Bolivar

Contemporary and newly renovated

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.

4.9 out of 5 average rating, 126 reviews

Pet/Family Friendly, Hot Tub, Large Deck

4.94 out of 5 average rating, 142 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

5 out of 5 average rating, 102 reviews

A rustic outdoor seating area features log benches arranged around a circular fire pit. The red chalet with a flag is visible in the background, surrounded by trees shedding their leaves. A gravel pathway connects the seating area and the chalet.

Chalet in Hedgesville

Cherry Run Chalet

4.89 out of 5 average rating, 218 reviews

A spacious backyard is surrounded by a wooden fence, showcasing a patio area with multiple seating options. A hot tub is visible, along with a fire pit and several Adirondack chairs arranged for gathering. Lush green grass and mature trees enhance the outdoor setting.

Home in Harpers Ferry

The Historic Booth House at the Harpers Ferry KOA

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, 261 reviews

The Mountain House

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.

4.87 out of 5 average rating, 143 reviews

Five Oaks Cabin at The Woods Resort

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.

4.95 out of 5 average rating, 167 reviews

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

4.94 out of 5 average rating, 179 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

Private, pet-friendly home rentals

Guest suite in Hagerstown

An elegant Victorian-style house is set against a bright blue sky, flanked by mature trees and manicured shrubs. The grand entrance features a wide staircase leading to a spacious porch, highlighting the architectural details of the building.

4.74 out of 5 average rating, 84 reviews

Stonebraker Retreat: 3-bed suite in historic manor

4.99 out of 5 average rating, 132 reviews

A spacious living area features a modern television mounted on the wall, paired with a wooden console labeled 'TOYS.' A comfortable gray sofa and a wooden coffee table are centered on a decorative rug, with a view of the adjacent kitchen visible through an open doorway.

Townhouse in Frederick

Positive vibes on Market St

4.97 out of 5 average rating, 116 reviews

A cozy cottage is seen from a distance, set amidst a gently sloping lawn. The exterior features a light-colored facade with a red roof and multiple windows. Surrounding grassy areas are dotted with trees and shrubs, enhancing the natural setting.

Cottage in Greencastle

Cozytown Cottage/Whitetail Ski Resort/Hagerstown

4.9 out of 5 average rating, 452 reviews

The cabin exterior features a rustic log design with a metal roof. A star motif is displayed prominently above the front porch, enhanced by flower boxes and decorative accents. The yard includes a garden area and several trees, creating a peaceful outdoor setting.

Cabin in Middletown

Charming vintage cabin in the ❤️ of Middletown.

4.88 out of 5 average rating, 248 reviews

A decorative wreath is displayed on a door, featuring an assortment of flowers and foliage in warm hues. The background consists of a textured glass door, allowing soft light to filter through, and the words 'WELCOME to The LOFT' are prominently featured.

Guest suite in Fairfield

Gettysburg-Ski-Golf-AT Hikes-RoseSniffers LOFT

4.96 out of 5 average rating, 78 reviews

A well-maintained pathway leads to a welcoming front porch, flanked by neat lawns and vibrant flowering bushes. Soft sunlight filters through the trees, casting delicate shadows on the concrete surface, while rolling hills can be seen in the background.

Home in Middletown

Beautiful historical town, 3 bedrooms, countryside

4.77 out of 5 average rating, 47 reviews

A comfortable living area features a light grey sofa adorned with yellow and white decorative pillows. A decorative area rug lies on polished wooden floors. Natural light enters through large windows, highlighting a small dining table and an air conditioning unit in the corner.

Flat in Hagerstown

Hamilton Hideaway (Hagerstown, MD)