
Vacation rentals in Boonsboro
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Boonsboro vacation rentals start at G$12,554 GYD per night before taxes and fees

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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 vacation rentals in Boonsboro
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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
LocationFamilyBackyard
4.94 out of 5 average rating, 619 reviews
Guest Apartment by C & O Canal and Battlefield
Private entrance.Luxurious, modern comfort with KING & QUEEN sized super comfy beds.Newly remodeled. 3min to center of Sharpsburg in quiet country setting, w/1200 square ft. of space that’s all one level inside. Bright & modern basement apartment with private entrance. Firepit and beautiful outdoor seating. Lots of large windows and natural light. Fully equipped kitchen, 2 BR, 1 BA. It’s on the ground floor and Host lives on top, main floor. Shepherdstown 7 mi. C & O canal 1/3 mi. Antietam 1mi
FamilyLocationSleep quality
4.93 out of 5 average rating, 306 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 Snowball Stand" Welcome to paradise!
FamilyLocationSleep quality
4.96 out of 5 average rating, 220 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
ValueLocationBackyard
4.95 out of 5 average rating, 358 reviews
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
FamilyLocationParks
4.91 out of 5 average rating, 331 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.
LocationFamilyHiking
4.96 out of 5 average rating, 156 reviews
Private Woodland Retreat | Near Downtown Frederick
Escape to a beautiful one-bedroom retreat. The guesthouse has a queen bed, kitchenette, luxurious bathroom with two shower heads, including a rain head, and a queen pull-out sofa bed. Nestled in the woods with a covered porch for morning coffee, yet a short drive to downtown Frederick, Civil War sites, Frederick Watershed with hiking and cycling trails, Mount St. Mary’s University, Cunningham Falls, and Catoctin. Free WiFi, and Smart Roku TV’s. Parking for 2 cars is included. Dogs are welcome.
ValueLocationComfort
4.96 out of 5 average rating, 109 reviews
[New] Stargazing Retreat. 15 Mile Views on 5 Acres
<b>Hilltop Modern by Stay Hideaway</b> • Complimentary Early Check-in & Late Check-out, based on availability • 20% discounts on select dates A secluded stargazing retreat on 5 private acres with breathtaking 15-mile valley views. Thoughtfully designed with timeless mid-century style, a chef's kitchen, fire pit, and private walking paths. Just 10 minutes to the Appalachian Trail and a short drive to Frederick, golf, and skiing. Unplug, reconnect, and experience a truly one-of-a-kind escape.
LocationFamilyAccuracy
5.0 out of 5 average rating, 23 reviews
Hillside Hideaway
Relax with the whole family at this peaceful place to stay. Ideally located!--1 mile to Appalachian Trail Parking (off Rt.40) and Greenbrier State Park. We are just a short drive to other State Parks, Cunningham Falls WaterFalls, Antietam and Gettysburg Battlefields. We are halfway between Hagerstown and Frederick, both with downtown dining, shops, wineries, breweries and distilleries. Convenient to Interstate 1-70 and Highways leading to Baltimore and Washington, DC and/or Metro Stations.
FamilyValueNearby
4.95 out of 5 average rating, 37 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.
FamilyLocationOutdoor spaces
4.97 out of 5 average rating, 159 reviews
The Overlook~ Exquisite Views
Our home sits atop the highest peak, allowing for exquisite views! Enjoy your scenic stay in our spacious eat in kitchen. Relax with a glass of wine around the fire table on our deck and watch the gorgeous sunset. We are conveniently located less than 10 minutes from Big Cork Vineyards as well as downtown Boonsboro! Our location makes a trip to historic Harpers Ferry or the Antietam Battlefield a breeze. Adventure lovers can experience numerous outdoor activities just 15 minutes away.
ValueFamilyAmenities
4.92 out of 5 average rating, 53 reviews
Beautiful historical town, 3 bedrooms, countryside
Beautiful home is on the 3.5 acres around peaceful farm area, with a barn and stunning views of the valley and mountains. You are able to see and hear the neighbor’s animals, see the rhythm of farm life, and enjoy being in nature. We hope you will find the house is supper comfy, welcoming. Great location not too far from Main St in Middletown with its restaurants & shopping. Minutes from the highway, yet still in the country. A little over 20 minutes drive to the Whitetail Ski Resort.
FamilyValueGrill
4.97 out of 5 average rating, 91 reviewsPopular amenities for Boonsboro vacation rentals
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