
Vacation rentals in Middletown
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Top-rated vacation 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

Spacious Private cozy apartment near mountains
Unwind in a spacious, private basement apartment in Braddock Heights, ideal for couples, small families, or remote stays. This 910 sq ft retreat features a private entrance, open layout, comfortable living area, bedroom, full bath, and kitchenette. Conveniently located minutes from downtown Frederick and major routes, yet tucked in a quiet area near hiking trails and wineries. Enjoy the large backyard with patio and fire pit. Includes one dedicated parking space. A peaceful and comfortable place

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

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

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.

‘Waterfront’ Farm Escape for Hikers & Wine Lovers
Feel refreshed when you stay in this rustic gem! The Springhouse is nestled in the rolling hills of Northern Virginia’s Wine Country! Originally constructed in the early 1800's, the structure was built over a natural spring that was used for refrigeration. Water from the spring maintains a constant cool temperature throughout the year while also filling a pond. The original stone well, channel and stone flooring are all intact for guests to explore and experience how our ancestors lived.

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.

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.

Cozy West Virginia Treehouse
Thanks for checking out our treehouse! It’s 4 minutes from downtown Shepherdstown and 15 minutes from downtown Harpers Ferry. We are excited to share it with other fun-loving folks! The treehouse has heat and AC, a tiny kitchen with a mini fridge, stove top, toaster oven, gravity-fed sink and kitchenware. There’s a bathhouse built on the back of the host’s home with a conventional toilet and shower. There’s also an outhouse with a light and essentials. We provide wood for the fire pit also.

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.

Amazing view of the Middletown Valley
Comfortable and casual, this interior encourages group interaction and peaceful alone time. The view is one of the best on the "Boulevard", stretching all the way to Harper's Ferry. You can see all the major gaps where the battles took place during the South Mountain campaign in the Civil War. You are ten minutes from the bustling dining and shopping area of downtown Frederick and you can peacefully cook out on the deck while gazing across the valley when you return for the evening.

Harmony Lodge nestled in wooded tranquility!
Tranquil lodge nestled on 3 wooded acres in Myersville, MD. Relax by the heated pool, enjoy the warmth of the fire pit, or receive a massage in the studio. Minutes away from downtown Frederick and Middletown restaurants, shops, and parks. Visit the local wineries and festivals. Tour historic battlefields. Go antiquing. Take in a round of golf, bike the C&O canal, hike the Appalachian trail, boat on the Potomac River, or go skiing. Bring your fur baby with you to enjoy the activities!
Popular amenities for Middletown vacation rentals
Other great vacation rentals in Middletown

Romantic Mirror Cabin • Hot Tub • Fire Pit • Views

Shire Cottage: Come share in an adventure in WV.

Private Woodland Retreat | Near Downtown Frederick

Beautiful historical town, 3 bedrooms, countryside

Mid-Century Farm Cabin w/ Fire Pit & Creeks

Vintage Mobile Home and Storage Workshop

The Milk House at Hereford Grove Farm

Nature Escape Walk to C&O Towpath & Potomac River
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- Georgetown University
- National Mall
- The White House
- Nationals Park
- Walter E Washington Convention Center
- Liberty Mountain Resort
- Johns Hopkins University
- Stone Tower Winery
- Arlington National Cemetery
- National Museum of African American History and Culture
- Washington Monument
- The Anthem
- Capital One Arena
- Georgetown Waterfront Park
- Howard University
- Smithsonian National Zoological Park
- Berkeley Springs State Park
- Jiffy Lube Live
- Merriweather Post Pavilion
- Harpers Ferry National Historical Park
- Museum of the Bible
- Cunningham Falls State Park
- Cowans Gap State Park
- Smithsonian American Art Museum





