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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

Hot Tub · 4BR Creek Cabin ·Sleepy Creek ·90 Min DC

90 min from DC/Baltimore, this secluded 4BR mountain cabin on Sleepy Creek is your private escape with a new 6 person hot tub, STAR LINK INTERNET, creek access for fishing, kayaking, and a wood burning fireplace. Without the resort price tag. ★ NEW BIGGER HOT TUB 2025 ★ ★ VERY DOG FRIENDLY ★ ★ STAR LINK High-Speed Wi-Fi 2026★ ✔ Creek Access ✔ Hot Tub ✔ Fishing/Kayaking ✔ Pet friendly ✔ 4 BRs (3 Main Cabin + Private Loft) ✔ Full Kitchen ✔ Deck, Patio, Dining, BBQ, Fire Pit ✔ Smart TVs ✔ Parking

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.

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.

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.

Darling Duplex

*NO cleaning fees in 2026!* 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.

Gorgeous cabin on Blue Ridge

Atop the Blue Ridge close to Harper’s Ferry and Virginia wine country this airy retreat overlooks the idyllic Shenandoah. Our two-person soaking tub on a magnificent deck, huge firepit, gorgeous vintage interior, grand piano, and warm pine ceiling and floors, give you the perfect place to get away from city life for a bit. Full kitchen. Two bedrooms plus a big couch that could sleep someone else in a pinch, and a cozy little fireplace top it all off! Just steps to the Appalachian Trail.

The Forge on Sunnyside Farm

Sunnyside Farm offers a luxurious stay in a beautifully restored historic forge. You’ll be greeted by the farm’s delightful hosts, Jimmy and Dean, two friendly Potbelly pigs. Beautiful cows forage right outside your door. The Forge features exposed wooden beams, brick walls, and cozy furnishings. The interior is designed with plush bedding, a fully equipped kitchen, and spacious living reminiscent of yesteryear. Breweries, wineries and famous antique stores nearby offer entertainment.

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!

Spectacular views, intimate dome

Come experience a truly one of a kind polycarbonate dome tucked away in the Appalachian mountains! Situated on the mountainside overlooking the scenic Cumberland valley. Complete privacy, stunning sunsets, and amazing amenities! The dome is climate controlled. The spacious deck is equipped with a meticulously maintained hot tub, and a blackstone griddle. This offers the unique opportunity to be immersed in nature, yet enjoy numerous amenities and comfort.

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.

Mimi's Cottage - Fenced Yard & No Extra Fees!

At little bougie, gaudy, and a lot of fun! Mimi’s cottage is an eclectic blend of luxury and coziness that you just don’t get from a hotel. Single family home on a quiet street in the South End of Hagerstown, Maryland. Perfect for families, couples, or if you just want to treat yourself! This sleekly decorated house has everything you need, just like you are at your own home. Why stay in a hotel when you can come to Mimi's?