Vacation rentals in Middletown

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Top-rated vacation rentals in Middletown

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Guest favourite

Cabin in Myersville

4.95 out of 5 average rating, 308 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

Top guest favourite

Cabin in Myersville

4.97 out of 5 average rating, 150 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". Welcome to Sleepy Hollow Log Cabin

Guest favourite

Cottage in Middletown

4.9 out of 5 average rating, 284 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

Top guest favourite

Condo in Downtown Frederick

4.97 out of 5 average rating, 98 reviews

The Grand Delphey: Downtown Artist Retreat

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 shared 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!

Top guest favourite

Home in Middletown

4.97 out of 5 average rating, 101 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.

Guest favourite

Guesthouse in Middletown

4.94 out of 5 average rating, 295 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.

Top guest favourite

Condo in Frederick

4.96 out of 5 average rating, 104 reviews

2 Queen & 1 Twin Bed / Mountain & Museum Fun

Perched well above the city and in between Gambrill State Park and Cunningham Falls State Park, enjoy your stay in this extra large living space. Fifteen minutes from the city limits of Frederick, come and enjoy the peaceful surroundings with all the amenities of modern life. Bring your bikes and hiking boots to experience the myriad of trails and wildlife throughout the region. Close to the quaint City of Frederick. Dozens of wineries, craft breweries, and antique stores located nearby.

Top guest favourite

Guesthouse in Smithsburg

4.97 out of 5 average rating, 757 reviews

Jewel Vinsota Artist's Guesthouse

Less than a mile from the Appalachian Trail, the dog-friendly Jewel Vinsota Artist's Guesthouse is the perfect get-away to explore nature or your artistic leanings. The house is full of original artwork, hand-crafted details, and books on art and architecture. Wander the grounds and find sculpture, ponds, and trails through the woods. Want to hike the entire 40-mile length of Maryland on the Appalachian Trail? Start and end at the Jewel Vinsota and we can drop you off and pick you up.

Guest favourite

Farm stay in Middletown

4.91 out of 5 average rating, 339 reviews

Fox Haven Organic Farm's Spring House

Peaceful countryside surrounds you with woods, streams, and pasture. The restored farmhouse has loads of room and porches where you can soak in a sunrise and a sunset. Birders paradise! Harper's Ferry, Frederick, Shepherdstown offer loads of fun and history. Two other houses, and a re-purposed Dairy Parlor are available for retreats too. Your stay supports farm programs that we offer children and adults from low income communities, people suffering with PTSD, and other life challenges.

Guest favourite

Home in Frederick

4.91 out of 5 average rating, 106 reviews

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.

Top guest favourite

Home in Myersville

4.97 out of 5 average rating, 239 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!

Guest favourite

Home in Frederick

4.99 out of 5 average rating, 150 reviews

The Emerald Roof, Historic Home Downtown Frederick

Built in 1860, The Emerald Roof is a historic home that provides a comfortable getaway near downtown Frederick. The house is decorated to reflect the city's rich history but comes equipped with modern amenities. The walk to downtown is about 10-15 minutes, and less than a 5 minute drive. The driveway can park 4 vehicles and there is ample street parking right in front of the house. The house is also centrally located to other historic sites and retail stores.