Holiday rentals in Middletown

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Top-rated holiday rentals in Middletown

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Guest favourite

A charming cabin is nestled among lush greenery, featuring a large covered porch that extends along the front. The surrounding area includes well-maintained grass and several trees, creating a serene outdoor environment that invites relaxation.

Cabin in Myersville

4.95 out of 5 average rating, 321 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 favourite

The log cabin features a warm wooden exterior with a blue metal roof, nestled among trees. A screened porch allows for outdoor enjoyment while a fire pit is positioned nearby, surrounded by natural stone. The peaceful setting invites relaxation amidst the greenery.

Cabin in Myersville

4.97 out of 5 average rating, 172 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

A charming cape-style home features a welcoming front porch with rockers and seasonal decorations. The neatly landscaped yard is adorned with colorful plants and pumpkins. A paved driveway leads to the entrance, framed by lush greenery and a white fence in the background.

Cottage in Middletown

4.9 out of 5 average rating, 290 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

Guest favourite

A cozy living area features a gray sectional sofa adorned with two white pillows. Natural light filters through the large windows, highlighting a round orange pouf and two side tables with lamps. Wooden beams are visible on the ceiling, enhancing the cottage’s rustic charm.

Home in Middletown

4.95 out of 5 average rating, 117 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

The studio apartment showcases a compact layout with a modern kitchenette equipped with stainless steel appliances. A cozy sleeping area features a spacious bed adorned with soft linens. A wooden dining table with black stools is positioned nearby, creating a welcoming space for dining.

Flat in Frederick

4.89 out of 5 average rating, 363 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 favourite

The guesthouse exterior presents a gray facade with a welcoming porch. Lush greenery, including manicured bushes and large trees, frames the entrance. A paved walkway leads to the door, surrounded by planters. The house stands under a clear blue sky, providing a serene setting.

Guest house in Middletown

4.94 out of 5 average rating, 309 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

A spacious living area features a pool table centered on a patterned rug. Comfortable seating options surround the space, with light-colored walls complementing the decorative elements. A tall plant adds a touch of greenery, while various artwork adorns the walls, contributing to a welcoming environment.

Apartment in Frederick

4.96 out of 5 average rating, 122 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.

Guest favourite

A charming tiny house is set among greenery, featuring a red tin roof and welcoming porch. A new wooden staircase leads to the entrance, bordered by planters with colorful flowers. Surrounding foliage creates a serene, natural environment.

Tiny home in Jefferson County

4.89 out of 5 average rating, 487 reviews

❤️ Secluded 1940s Romantic Tiny House on the River

Relax and escape to the peace and quiet by the Potomac river, and wake to beautiful romantic views of the river and mountains, in this romantic 200 square foot tiny house situated on 2.5 acres, 450 feet of river front land. Explore and partake of all the activities on the river and surrounding area, just 1 mile from Shepherdstown. Fish, bike, kayak, tube, or just sit by the river and watch the birds and wild life. Read by the river or in the quiet comfort of the house, w/ some wine on us.

Guest favourite

The exterior of a two-story house is surrounded by trees, with warm lights framing the balconies. Large glass windows provide visibility into the interior. A deck with a railing is seen above, and decorative elements are positioned outside the entrance.

Guest suite in Smithsburg

4.98 out of 5 average rating, 306 reviews

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.

Top guest favourite

The entrance to The Crooked Cottage is framed by wooden planks and surrounded by greenery. Two windows offer glimpses into the inviting interior, while a gravel pathway leads up to the door, playfully adorned with a sign featuring the name of the cottage.

Home in Myersville

4.97 out of 5 average rating, 254 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

A serene countryside view showcases a spacious green lawn bordered by trees and hills in the background. Two houses are visible: one with a wraparound porch and the other a smaller structure. An organic garden is seen in the foreground, framed by a simple fence.

Guest house in Keedysville

4.97 out of 5 average rating, 228 reviews

City Dog Farm

Comfortable, light-filled one bedroom apartment on 10 acres in Maryland near Antietam battlefield and Harpers Ferry, WV. We have chickens, an organic garden, hills, woods and a stream. Apartment is 15 minutes from Harpers Ferry, Antietam battlefield, the C&O canal, river rafting on the Potomac or Shenandoah, vineyards, the Appalachian trail and small towns including Boonsboro and Shepherdstown, WV. 30 minutes to Frederick or Hagerstown/1.5 hours to DC or Baltimore. SORRY NO PETS

Guest favourite

The exterior of a two-story carriage home is displayed, featuring a sloped roof and prominent front porch. A manicured lawn surrounds the structure, with evergreen shrubs and small trees in the background. The driveway leads to a spacious path, enhancing accessibility.

Guest suite in Frederick

4.93 out of 5 average rating, 127 reviews

Spacious Carriage Home Suite in Frederick MD

NEAR HISTORIC DOWNTOWN FREDERICK - Super Spacious 2nd Floor Guest Home Suite located on 5 Acres with an amazing view! Freshly painted and newly furnished with fresh appliances. Long Driveway entrance with plenty of parking available. Only 46 miles from Baltimore and 50 miles away from D.C. Downtown Frederick is only a couple of minutes away so you can enjoy shopping, restaurants, and experience everything Frederick has to offer!