Vacation rentals in Middletown

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Top-rated vacation rentals in Middletown

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

Cabin in Myersville

4.95 out of 5 average rating, 307 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

Guest favorite

Cabin in Middletown

4.9 out of 5 average rating, 427 reviews

Charming vintage cabin in the ❤️ of Middletown.

Cozy cabin in the ❤️ of Middletown, MD. Within walking distance 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 favorite

Cabin in Myersville

4.97 out of 5 average rating, 147 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 favorite

Apartment in Frederick

4.89 out of 5 average rating, 332 reviews

Downtown Frederick Modern Studio

Modern 1-bedroom studio apartment located on North Market Street (NOMA) in charming downtown Frederick. Walking distance to great restaurants, shops, breweries and nightlife. Studio includes a full kitchen and luxurious bathroom providing everything you need to enjoy your time in downtown Frederick. Conveniently located behind laundromat (Noma Laundry) which is open from 5AM-11PM. 5 minute walk to the heart of Frederick and minutes away from Gravel & Grind coffee cafe and Olde Mother brewery.

Guest favorite

Guesthouse in Middletown

4.94 out of 5 average rating, 292 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 favorite

Condo in Frederick

4.97 out of 5 average rating, 101 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 favorite

Guesthouse in Smithsburg

4.97 out of 5 average rating, 751 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 favorite

Farm stay in Middletown

4.9 out of 5 average rating, 336 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 favorite

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 favorite

Home in Myersville

4.97 out of 5 average rating, 236 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!

Top guest favorite

Guest suite in Downtown Frederick

4.89 out of 5 average rating, 410 reviews

Best location in Historic Frederick-Sleeps 1 to 3!

You will not find a better location in Historic Downtown Frederick. 1.5 blocks from Market St. on a quiet, tree-lined street. Enjoy this second-floor suite in a stately 115 year old home. Easy walk to restaurants, bars, and shops. Space includes two bedrooms, light filled sunroom, spacious bathroom with original tiling/fixtures and antique furniture. Using the separate entrance of a shared home, guests have a spacious private suite completely separated from hosts' residence.

Guest favorite

Guesthouse in Frederick

4.97 out of 5 average rating, 341 reviews

The Shady Bear Cabin

After a complete renovation, we decided the cabin would be perfect for Airbnb. It's completely separate from the main house and offers both of us a great deal of privacy. It is also warm and cozy yet extremely comfortable. Please be aware that we have dogs on the property. If you are not comfortable with dogs, please do not book this cabin. If you are, we hope to see you. DURING THE PANDEMIC WE WILL BE FOLLOWING AIRBNB'S ENHANCED CLEANING PROTOCOL.