Holiday houses in Boonsboro

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Top-rated holiday rentals in Boonsboro

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Guest favourite

Cabin in Myersville

4.97 out of 5 average rating, 254 reviews

Cabin on Middle Creek - Myersville MD - Middletown

Park the car & walk across 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. Amazing place to unwind, de-stress & get away. 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.

11 – 18 Feb

$1,380 AUD total

Guest favourite

Guest suite in Shepherdstown

4.95 out of 5 average rating, 569 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.

12 – 19 Sept

$1,014 AUD total

Guest favourite

Guesthouse in Middletown

4.95 out of 5 average rating, 247 reviews

Indulge, Fresh Flowers, Frederick County Haven

2 bedroom, full kitchen and laundry, 1 level guesthouse beside detached garage (separate from main house). The front has a rose garden, birdbath and your own patio. An apple tree is beside the guesthouse. A farm is to the back. Asian cafe, Subway, Dempsey's Grill, Amvets, Main Cup bar and restaurant, Tapia's and 3 ice cream parlors are all a short walk away. More restaurants and grocery store are less than a mile. Farmer's market in season on Thursdays. Fresh flowers and coffee are provided.

21 – 28 Sept

$1,218 AUD total

Guest favourite

Guest suite in Sharpsburg

4.99 out of 5 average rating, 167 reviews

The River Bend Retreat ~ C&O Canal ~ Antietam

Welcome to The River Bend Retreat at Taylor's Landing: a relaxing get-away along the C&O Canal Towpath and the Potomac River. Whether you're in the area to enjoy the river and the towpath, soak up some history at Antietam National Battlefield, or explore the quaint nearby towns and attractions, we look forward to hosting your stay! The RBR's 2 bedrooms and 1 bathroom can accommodate up to 4 guests. Visit us online for even more details, information, and local recommendations. See you soon!

6 – 13 Aug

$1,519 AUD total

Guest favourite

Guest suite in Smithsburg

4.99 out of 5 average rating, 156 reviews

Creekside Retreat at the Jewel Vinsota

Relax in a quiet, curated, dog-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 4 w/ the living room futon. Fully equipped kitchen. Private charcoal grill and fire pit next to the creek.

19 – 26 Feb

$1,031 AUD total

Guest favourite

Home in Myersville

4.97 out of 5 average rating, 150 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!

3 – 10 Oct

$2,033 AUD total

Guest favourite

Guesthouse in Myersville

4.93 out of 5 average rating, 192 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.

13 – 20 July

$1,114 AUD total

Guest favourite

Guest suite in Hagerstown

5.0 out of 5 average rating, 400 reviews

Oak Hill Private Suite Historic North End

A recently renovated private suite in historic home 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, Antietam, Gettysburg, Frederick, C&O bike trail, wineries and outlets. Guests have enjoyed stays for tourism, conferences, trainings, the MD Int’l Film Festival, JFK 50, family visits and artist retreats.

5 – 12 Sept

$966 AUD total

Guest favourite

Farm stay in Knoxville

4.97 out of 5 average rating, 262 reviews

Paradise Farm—Near Harpers Ferry

If you love animals and the country this is the place for you! Come visit our "paradise." Horses, cows, goats, donkey and a range of feathered exotics are right out your front door. Short drive to the Potomac river, C&O Canal, Harpers Ferry National Historic Park, Antietam Battlefield, Appalachian Trail, Shepherdstown, WV. Outfitters nearby offer rafting, kayaking/canoeing, tubing, ziplines. Vineyards all around. Hosts live in attached house and are nearby if needed.

27 Aug – 3 Sept

$1,391 AUD total

Guest favourite

Guest suite in Sharpsburg

4.93 out of 5 average rating, 179 reviews

Guest Apartment by C & O Canal and Battlefield

Affordable Luxury! 1200 square feet Bright & modern newly remodeled basement apartment with private entrance. Fully equipped kitchen, 2 BR, 1 BA. It’s on the ground floor of a newly renovated home. Hostess and boyfriend, Charles, live on top, main floor. Shepherdstown, WV 7 mi. C & O canal 1/3 mi. Antietam Battlefield 1/2 mi. Sharpsburg 2mi. Harpers Ferry 25 min. Hagerstown 10 min.Many cool breweries & wineries within 15 min. 7 mi to Rockland Estates venue.

5 – 12 Aug

$1,229 AUD total

Guest favourite

Apartment in Burkittsville

4.98 out of 5 average rating, 100 reviews

Charming Burkittsville 1747 Home

Studio apartment located in the rural historic town of Burkittsville MD (Est. 1824) at the base of South Mountain, surrounded by beautiful farmland. About 25 minutes to Antietam battlefield, Harpers Ferry WV, Shepherdstown WV, Middletown MD, Frederick MD. Close to many activities including wineries, breweries, award winning restaurants, theater, hiking, biking, river activities, Appalachian trail, C&O canal, national and state parks.

26 Sept – 3 Oct

$862 AUD total

Guest favourite

Home in Blue Ridge Summit

4.99 out of 5 average rating, 452 reviews

Colonial Era Spring House

A unique and private mountain top colonial era spring house, with two springs flowing thru the basement. Originally the site of a tannery in the 1700s. Here you can relax, recharge, and rejuvenate. We celebrate all four seasons where you can enjoy Mother Nature's ever changing scenery at 1300' above sea level with fresh mountain air. Our area offers many things to do, or you may choose to stay in and do nothing at all.

18 – 25 Sept

$1,705 AUD total