
Holiday houses in Middletown
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Top-rated holiday rentals in Middletown
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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

Charming "Cream of the Crop" Cape ~โค๏ธof Middletown
Cozy cape in the โค๏ธ 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

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 itโs 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.

The Grand Delphey: Downtown Modern Penthouse
Enjoy this stylish condo located in the heart of downtown's Historic District. The condo resides within a beautiful mansion known as the The Grand Delphey with lounge rooms on the first level perfect for photo sessions or gathering. The unit has the ability to rent with 3 other units to SLEEP UP TO 16 PEOPLE! Please let us know if you would like to book the entire mansion for wedding parties or other events. Just steps away from wedding venues, Baker Park, the creek, downtown nightlife & shops!

Seven East Patrick
"7 East" Welcome to beautiful & historic Downtown Frederick, Maryland. Find yourself nestled among the tree tops above our lovely town...at "Square Corner", the intersection of Patrick and Market Streets. The commercial and financial heart of Frederick for over 250 years. Here, the National Road meets several important north-south roads leading to PA, Virginia, and Washington, D.C., all in under an hour drive! Entertainment and nightlife, historic sites & tours, enough for the whole family.

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.

Carroll Creek Private Apt./Luxury King Bed
Within footsteps to Carroll Creek Promenade offering easy access to posh restaurants, fun Breweries, local shops and festivals galore! Modern remodel and furniture including a memory foam king bed. Enjoy your own apartment w/ wide open spaces & high ceilings that bring in fantastic light. Historic bldg. (circa 1840) with all the modern appointments to make your stay super comfortable & fun! Owners provide advice on their favorite places & restaurants! Easy self checkin. Free parking on site.

In Town Charmer
Experience Frederick! Just steps from Market Street you can walk to restaurants, bars, shops and activities. Our home located in Frederick's historic district is completely renovated on the inside. Two bedrooms each with their own full bath, central air, open concept kitchen and family room, private off street parking, comfy beds, smart TV, internet & furnished with guests in mind. Perfect for a Frederick getaway, our cozy home is not suitable for small children and no pets are allowed.

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 1890โs chink log cabin. Although you can see our house, the cottage feels very private and is a quiet comfortable retreat in the hills.

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 itโs warm. Welcome to The Crooked Cottage!

Spacious Private Basement Apartment
You and your loved ones will be comfortable in this spacious and unique private basement apartment. 910 sq/ft. Beautifully decorated. Braddock heights area, less than half a mile to I 70, 3 miles to I 270 and two miles to route 340. Restaurants and shopping plazas, less than 6 miles to Downtown Frederick. There are many attractions around such as local breweries, parks, museums and more. Private entrance with 1 parking spot on the premisses. Huge backyard and patio.

Downtown Frederick Getaway
Great location in historic downtown Frederick, with parking for one car on the premises! Private first floor apartment, large living room with large TV, bedroom with very comfortable king size bed, new television, and plenty of closet space. House has historic charm, located on the edge of Frederick's historic downtown and very close to Frederick Memorial Hospital. Photos don't do it justice, space is larger than it appears, new paint in kitchen.
Popular amenities for Middletown holiday rentals
Other great holiday rentals in Middletown

Room #2 with shared bathroom

Basemnt apt, kitchen, no shared space woods w/deer

Peaceful Farmette, Blue Bedroom

Nordic Haus | Mural, Coffee, & more! Steps from DT

Designer Penthouse w/ Fire Pit + Private Balcony

Cozy Cove

Sampler Room

Private Room in Townhouse, Pet Friendly
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- Walter E Washington Convention Center
- Georgetown University
- National Mall
- Nationals Park
- The White House
- District Wharf
- Capital One Arena
- Liberty Mountain Resort
- National Museum of Natural History
- Whitetail Resort
- Hampden
- National Museum of African American History and Culture
- Stone Tower Winery
- Arlington National Cemetery
- Washington Monument
- Georgetown Waterfront Park
- Cunningham Falls State Park
- Smithsonian American Art Museum
- Great Falls Park
- Codorus State Park
- The Pentagon
- Lincoln Park
- Cowans Gap State Park
- Caledonia State Park




