Holiday houses in Hagerstown

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Top-rated holiday rentals in Hagerstown

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Top Guest favourite
The log cabin features a warm wooden exterior with a blue metal roof, nestled among trees. A screened porch allows for outdoor enjoyment while a fire pit is positioned nearby, surrounded by natural stone. The peaceful setting invites relaxation amidst the greenery.
Cabin in Myersville
4.96 out of 5 average rating, 191 reviews

Sleepy Hollow Log Cabin

Sleepy Hollow Log Cabin at Beechnut Springs is nestled in the majestic Blue Ridge Mountains. A short distance from Rt 70 as you travel down scenic route 17 following a bustling trout stream to Beechnut Springs entrance. After you arrive & settle into your secluded cabin, you will find many unique activities & quiet places in this serene setting amid the wonders of quiet waterfalls, easy walking paths, a wildlife haven, natural running streams & "The Bog Shack". Welcome to Sleepy Hollow Log Cabin

Top Guest favourite
A covered patio area is presented with a picnic table and a decorative rug. Lush flower beds filled with vibrant blooms line the space, adding color and charm. A small wooden chair enhances the inviting outdoor setting.
Apartment in Hagerstown
4.99 out of 5 average rating, 157 reviews

Private, relaxing, scenic 2 bdrm unit, Sleeps 1-5

My mother said over and over again, “The most beautiful place in Washington County “. Start your day with a brisk walk on a nearly 1 mile path that surrounds the perimeter of this beautiful farmland property. Enjoy your morning coffee as you listen to the birds. Relax in a rocking chair on the gazebo as you watch the sun go down behind the mountains. Less than 10 min from I 70 and I 81 and 20 min from Whitetail Ski. Don't expect everything brand new, but expect everything to be neat and clean.

Top Guest favourite
Apartment in Falling Waters
4.95 out of 5 average rating, 224 reviews

Near I-81, but private! Laundry! No fees!

Welcome to your peaceful retreat! This spacious and clean apartment features a fully equipped kitchen, dual shower heads, a cozy living area, and a washer/dryer for your convenience. Ideal for travelers seeking a quiet getaway or a stopover along I-81, our home is close to Antietam Battlefield, Hagerstown Shopping Outlets, C&O Canal, Tomahawk MotoX, Greenbrier State Park, Shepherdstown, and Harper's Ferry. Enjoy a comfortable stay with thoughtful amenities designed to make you feel at home!

Top Guest favourite
A spacious bed is dressed in a textured white quilt, accented with dark brown pillows. A lamp softly illuminates the space next to the bed, and a piece of art featuring hands is displayed on the wall, adding a touch of elegance.
Guest suite in Hagerstown
4.95 out of 5 average rating, 102 reviews

Clover Cove

Simple, peaceful, private, & central location. Relax on the back porch, snooze on the hammock, or venture out - just minutes to I81 & I70, C&O Canal, Antietam Battlefield NP, Appalachian Trail, Hiking, Wineries, Biking, Festivals, Potomac Rivr, & Meritus Hospital. We reside in a separate area of home. We offer privacy & safety for our guests. Private entrance, bedroom, bathroom, den, kitchenette, driveway parking. Expect to cross paths with our family & dog on the shared back porch/yard.

Top Guest favourite
The exterior of the historic colonial house is depicted, showcasing a light stone facade complemented by a slanted metal roof. A spacious front porch with a wooden railing is visible, surrounded by a well-maintained garden featuring various plants. Two doors lead into the home.
Cottage in Hagerstown
4.96 out of 5 average rating, 451 reviews

Unique historic home - Springhouse 1803

If you are looking for a unique place to stay, come visit us at Springhouse 1803. Yes, there really is a spring under the house. After sitting empty for 20+ years, the house has been restored to be lived in again and it has maintained much of its colonial charm. The house has all the amenities you need for a comfortable stay. NOT A PARTY HOUSE, OWNER IS ON SITE in separate house. If you're looking for a day that is blocked, you can inquiry if it's available, see below for more details.

Top Guest favourite
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.
Guest suite in Smithsburg
4.98 out of 5 average rating, 359 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.

Top Guest favourite
An expansive open-concept living area is highlighted by large windows, providing ample natural light and panoramic views of the surroundings. Comfortable seating areas are arranged around a central coffee table, while a cozy stone fireplace serves as a focal point against a feature wall.
Home in Smithsburg
4.96 out of 5 average rating, 207 reviews

The Great Escape Lodge ~ Exquisite Mountain Views

The Great Escape Lodge is a soaring A-frame offering luxury accommodations. Owner designed and custom built in 2022, this luxury getaway is nestled in the stunning Catoctin Mountains with views parallel to those seen on Paramount's hit series Yellowstone. This exquisite residence offers outstanding interior and exterior custom touches and amenities. From the open concept great room to the massive deck with rockers and hot tub, there are endless opportunities to enjoy the scenic views.

Top Guest favourite
The exterior showcases a modern cottage with a stone facade and dark siding, framed by wood pillars. Two inviting entry doors provide access, with large windows above. Flanking the doors, two comfortable chairs are positioned, each accompanied by planters, adding a welcoming charm to the entrance.
Cottage in Shepherdstown
4.97 out of 5 average rating, 204 reviews

NEW * The Getaway Cottage at Rocky Marsh Farm

Welcome to The Getaway Cottage, a charming two-bedroom, two-bath home nestled in a peaceful country setting, located just 3.5 miles from Shepherdstown. Our location offers easy access to all the exciting activities and attractions the eastern panhandle has to offer, enjoy a short country side drive to dining, shopping, hiking trails, white water rafting and kayaking adventures. The historic town of Harpers Ferry is a short 25-minute drive away, and 15 minutes to Antietam Battlefield.

Top Guest favourite
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
4.98 out of 5 average rating, 296 reviews

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!

Top Guest favourite
The entrance features a welcoming porch area surrounded by colorful potted plants and flowers. A wooden rocking chair sits on the deck, complemented by a textured area rug. Double doors with grid-patterned glass provide access to the suite, framed by lush greenery.
Guest suite in Hagerstown
5 out of 5 average rating, 521 reviews

Oak Hill Private Suite Historic North End

A recently renovated private suite only 1.5 miles from town center. Welcoming ‘walking’ neighborhood of architecturally diverse homes inspired by the Garden City Movement of early 20th C. Near both Interstate 81 and 70, Museum of Fine Arts, Whitetail Ski Resort, New Baseball Stadium, Antietam, Gettysburg, Frederick, C&O bike trail, wineries, outlets. Guests enjoy stays for tourism, conferences, trainings, the MD Int’l Film Festival, JFK 50, family visits and artist retreats.

Top Guest favourite
A tree-lined driveway leads to a charming home, partially obscured by lush greenery. Sunlight filters through the leaves, casting gentle shadows on the well-maintained lawn. The sky is bright with fluffy clouds, contributing to a serene, inviting atmosphere.
Home in Hagerstown
4.76 out of 5 average rating, 152 reviews

Private Country Club Home

I am an experienced super host with eight years of hosting. I have a charming mother-in-law suite with your own entrance in an upscale country club development. Features a beautiful two acre backyard, a fire pit, outdoor deck and grill, private living room, kitchen, bath, and bedroom. We are just 20 minutes from White Tail Ski Resort and less than an hour to Gettysburg, Antietam Battlefield, the Appalachian trail, and C&O Canal. Come join us for a relaxing stay.

Guest favourite
Tiny home in Mercersburg
4.98 out of 5 average rating, 189 reviews

Boxed Inn ~ Hot Tub ~ Fire Pit

This charming, tiny home offers the perfect blend of cozy comfort and the great outdoors, all while nestled close to the Whitetail Resort. Inside is an open space bathed in natural light, where modern style meets mountain tranquility. The interior, with its thoughtfully designed features, comes with a comfortable loveseat, a smart TV, and bar seating: perfect for those intimate conversations or just catching up after a busy day on the trails.

Popular amenities for Hagerstown holiday rentals

When is the best time to visit Hagerstown?

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Frequently Asked Questions

  • What are the best places to stay in Hagerstown?

    Hagerstown has welcoming options in the downtown area, around North End, and near City Park for those interested in historic neighborhoods, arts, or green spaces. Many stays embrace the region’s classic architecture, with easy access to local shops and cafes.

  • What are the best things to do in Hagerstown with kids?

    Families often explore the Hagerstown City Park, known for its playgrounds and lake, or visit the Discovery Station for hands-on science and history exhibits. The Hagerstown Roundhouse Museum sparks interest in trains and local history.

  • What are some of the best things to do in Hagerstown?

    Explore the Washington County Museum of Fine Arts, stroll through Hagerstown City Park, or stop by the Maryland Theatre for performances. The Jonathan Hager House Museum shares the city's early history and architecture.

  • How is the weather in Hagerstown?

    Hagerstown has cold winters around 25–43°F (-4–6°C), with moderate snowfall, and warm summers reaching 67–88°F (19–31°C), often humid with regular rainfall. Spring and fall are milder, inviting layers for variable weather.

  • When is the best time to visit Hagerstown?

    Late spring and early fall are frequently suggested for comfortable temperatures and outdoor activities, while summer brings popular festivals and lush park scenery. Winters are quieter, appealing for those seeking a slower pace and local museums.

  • What are the best places to visit in Hagerstown?

    Hagerstown City Park, the Washington County Museum of Fine Arts, and the Maryland Theatre are often recommended for arts, nature, and performance. The Jonathan Hager House Museum highlights the city’s heritage.

  • What are some hiking trails in Hagerstown?

    Hagerstown has walking trails around City Park and Pangborn Park, suitable for relaxed strolls under shade trees. Those interested in longer hikes often explore scenic routes at South Mountain State Park or nearby nature preserves.

  • What are some family activities we can do in Hagerstown?

    Families frequently tour Discovery Station for interactive exhibits, relax by the lake at Hagerstown City Park, or watch a game at the local stadium. Outdoor areas and museums invite hands-on learning and play.

  • What are some of the best day trip ideas from Hagerstown?

    Explore Antietam National Battlefield’s extensive history, wander the charming streets and shops of Shepherdstown, or hike in South Mountain State Park. Several state parks and heritage sites are found in the surrounding region.

  • Are there any pet friendly accommodations available in Hagerstown?

    Many accommodations in Hagerstown welcome pets, especially in neighborhoods near parks like City Park and Pangborn Park. Local green spaces make it easy to enjoy strolls with your dog.

  • What are some local tips for visiting Hagerstown?

    Hagerstown’s farmer’s markets showcase local produce, and downtown murals highlight the area’s creative community. Visiting the arts district or attending a live performance at the Maryland Theatre adds a local touch to your stay.

  • What is Hagerstown known for?

    Hagerstown is known for its railroad heritage, vibrant arts scene, and preserved Civil War and early American history. Its creative community gathers at museums, historic sites, and frequent cultural events.

  • What are the best hidden gems to explore in Hagerstown?

    Many visitors discover the Miller House Museum for local stories, and the Hagerstown Cultural Trail, which connects art installations with city history. Downtown shops and cafes often provide unique finds beyond the main streets.

  • What are the best foods to try in Hagerstown?

    Hagerstown has traditional favorites like country ham, scrapple, and apple dumplings, often found at local diners or markets. Seasonal produce and baked goods reflect the region’s farming roots.

  • What should I bring for a trip to Hagerstown?

    Bring layers for changing weather, comfortable shoes for exploring parks and museums, and a rain jacket during spring and summer. If you plan outdoor activities, sun protection and a refillable water bottle are helpful.

  • What is the nightlife in Hagerstown like?

    Hagerstown’s nightlife centers around downtown with local pubs, live music venues, and casual bars. The Maryland Theatre frequently features performances, and some spots have open mic nights or themed events.

  • What are the most popular events or festivals in Hagerstown?

    Hagerstown frequently hosts an annual Blues Fest and holiday parades, with cultural festivals in late spring and summer. Outdoor concerts and art events at City Park and the arts district are also community highlights.

  • Are there family friendly vacation rentals in Hagerstown?

    Many vacation rentals in Hagerstown suit families, with several located near parks, museums, and kid-friendly activities. Stays around the North End or City Park neighborhoods often offer extra space and green areas.

Quick stats about holiday rentals in Hagerstown

  • Total holiday rentals

    Explore 90 holiday rentals in Hagerstown

  • Nightly prices starting at

    Hagerstown holiday rentals start at $55 AUD per night before taxes and fees

  • Verified guest reviews

    Over 3,610 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    80 of Hagerstown holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Hagerstown rentals

  • 4.6 Average rating

    Hagerstown stays receive an average rating of 4.6 out of 5 from guests

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