Holiday rentals in Boonsboro

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Quick stats about holiday rentals in Boonsboro

  • Nightly prices starting at

    Boonsboro holiday rentals start at £45 per night before taxes and fees

  • Verified guest reviews

    Over 80 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Boonsboro rentals

  • 5 Average rating

    Boonsboro stays are highly rated by guests – averaging 5 out of 5!

Top-rated holiday rentals in Boonsboro

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
The cabin features a striking A-frame design with wooden accents and a stone chimney. Expansive glass windows enhance natural light and provide views of the surrounding forest. A spacious wrap-around porch is supported by sturdy wooden columns, inviting outdoor relaxation.
Chalet in Boonsboro
4.94 out of 5 average rating, 613 reviews

Mountain Myst

A. DESCRIPTION This luxury cabin is nestled in the beautiful Blue Ridge Mountains, an hour from Washington DC. It overlooks the historic town of Boonsboro where you can watch the night lights twinkle from the top of South Mountain. Marvel at the view of Whitetail Ski Resort some forty miles away, or enjoy watching deer and turkey meander along the quiet gravel road. This home boasts log accents, vaulted ceilings and stone fireplaces in the living room and lower level. There are many upscale amenities particularly in the kitchen. The open great room and dining room open up to a modern kitchen with top-of-the-line appliances and a center island for meal prep and casual dining. From the great room step out to an expansive wrap-around porch with beautiful forest views and plenty of blue sky. Enjoy entertaining, grilling, dining outside on the deck, and campfires in the fire circle. There is a luxury master suite on the third level loft. It has a queen bed, wall mounted HDTV, sitting area, and bathroom with a walk-in, double-headed shower. The lower level has two bedrooms. One with a double bed and the other with two twin beds. There is a hall bathroom with a walk-in, double-headed shower, and separate lounging room with stone fireplace and HDTV. B. AMENITIES: • WIFI • HDTV with Full cable (4) • Kitchen stocked for cooking • Quality towels and linen(URL HIDDEN) ACTIVITIES: APPALACIAN TRAIL For a scenic stroll on the most famed of North American hiking trails, pick up the trail at the parking lot of the Washington Monument. RESTAURANTS •Old South Mountain Tavern – There has been an Inn and Tavern on this site for over 200 years •Dan’s Tap House •Vesta’s Pizza •Christies – coffee and pastry, sandwiches WINERIES There are many, but here are some of our favorites. Boonsboro MD: Big Cork Vineyards Mt. Airy MD: Linganore Winery , Black Ankle Vineyard Loudon County VA: Breaux Vineyards, Hillsborough Winery STATE PARKS Washington Monument State Park Greenbriar State Park- swimming lake Gambrill State Park Gapland State Part Cunningham Falls State Park – waterfall, swimming lake, near Camp David HARPERS FERRY WV Museums, rafting, SHEPARDSTOWN, WV Very picturesque, Great window shopping, Cafes, Potomac River FREDERICK, MD: Old Town Market Street Gettysburg Battlefield, MD (allow a full day) •Tours •Interactive museum, films •Educational Center Other Civil War battlefields Antietam, MD, Monocacy, MD, South Mountain Boonsboro SKIING Whitetail, Ski Libert(URL HIDDEN)I

Top guest favourite
A charming cabin is nestled among lush greenery, featuring a large covered porch that extends along the front. The surrounding area includes well-maintained grass and several trees, creating a serene outdoor environment that invites relaxation.
Cabin in Myersville
4.95 out of 5 average rating, 349 reviews

Cabin on Middle Creek - Myersville MD - Middletown

Park the car & walk across the creek on the foot bridge to serenity along Middle Creek. Nestled between South Mountain State Park & Gambrill State Park, lies a beautiful & relaxed 9-acre private cabin retreat. Great place to unwind & de-stress. Let the sound of the creek or rain on the tin porch roof put you to sleep at night. It has all the essentials of home. Enjoy the fire pit on cool evenings or take a dip in the stream on a warm day. The cabin offers a perfect peaceful or romantic setting

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, 208 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 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
4.95 out of 5 average rating, 146 reviews

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.

Top guest favourite
A wooden front porch is showcased, featuring a red swing and a small wooden table. The cable and light fixture create a welcoming presence. The surrounding trees offer a glimpse of the woodlands, enhancing the cozy, rustic setting of the log cabin.
Cabin in Myersville
4.96 out of 5 average rating, 103 reviews

Spruce Run Cabin, a wooded retreat on the mountain

The traditional log cabin is located on 25 acres of mostly wooded terrain in the scenic rural countryside of Wolfsville, Maryland, less than an hour and a half from D.C./Baltimore. The hosts live on the property, but the cabin is situated where it feels very private and you do not see the hosts house from the cabin. The cabin faces the woods and there is a private trail down to the creek. Take a break from everyday life, and escape to this unique and quiet retreat in the Catoctin Mountains.

Top guest favourite
A charming log cabin features a spacious front porch with rocking chairs, surrounded by trees and blooming flowers. The roof shows aged metal, and windows are adorned with shutters, inviting natural light into the home. A landscaped garden area is visible in the foreground.
Home in Sharpsburg
4.97 out of 5 average rating, 158 reviews

Charming Historic Canal House C&O Potomac Antietam

The Canal House at Taylors Landing. We are in the countryside, bordering the Chesapeake & Ohio Canal Historic National Park, 2 miles from the Civil War's Antietam Battlefield. Our home is an original 1790 log cabin with 1857 additions, also features modern amenities, including a chef's kitchen. Multiple outdoor venues, extensive grounds and amazing views of a 4-seasons garden, the C&O Canal National Park, and the Potomac river. Enjoy a creative retreat, nature, history, adventure, romance.

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
4.97 out of 5 average rating, 383 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, 223 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.

Guest favourite
A wooden deck extends from the cabin, surrounded by lush green trees. A striped awning provides shade over a picnic table, creating a space for outdoor dining or relaxation. The natural ambiance enhances the secluded feel of the property.
Cabin in Keedysville
4.82 out of 5 average rating, 127 reviews

Quiet Antietam Cabin

This quiet cabin is located between Boonsboro and Sharpsburg in Keedysville, MD. It is surrounded by tall oaks and pines. A wide path leads to Antietam Creek, popular for fishing, kayaking, and tubing. 45-min drive to Whitetail Ski Resort (30 miles); 1-hr to Gettysburg, PA; Close to Antietam Battlefield, Shepherdstown, Harpers Ferry, Hagerstown, Frederick, Washington, D.C., C&O canal bike trail and Appalachian Trail. Minimum age to rent is 25 yrs. Families with children are welcome.

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, 310 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, 530 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 charming tiny home is nestled among tall trees, featuring a modern exterior with a combination of white siding and natural wood accents. A small deck is visible, adorned with potted plants, inviting relaxation in a serene natural setting.
Tiny home in Mercersburg
4.98 out of 5 average rating, 199 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 Boonsboro holiday rentals

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  2. United States
  3. Maryland
  4. Washington County
  5. Boonsboro