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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
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, 324 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

ValueFamilyCondition

Top guest favorite
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, 353 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

LocationValueGrill

Top guest favorite
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
4.96 out of 5 average rating, 212 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

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Top guest favorite
Guest suite in Middletown
4.97 out of 5 average rating, 38 reviews

Cozy Farmhouse Guest Suite w/ Private Deck

Imagine soaking some sunshine from the private deck of a lovingly renovated 1800s farmhouse. On warm days dip into one of the two creeks bordering the 25-acre farm; in cooler seasons, enjoy peaceful walks under open skies. This private guest suite with bedroom, bath, kitchenette, and living area blends comfort, history, and charm. Just 20 minutes to Frederick & Harpers Ferry, it’s ideal for solo travelers, couples, or small families visiting this beautiful area. Blazing WiFi keeps you connected.

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Top guest favorite
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, 151 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.

LocationValueHeating

Guest favorite
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.
Guesthouse in Middletown
4.93 out of 5 average rating, 334 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.

ValueLocationAir conditioning

Top guest favorite
The treehouse is elevated among the trees, featuring large windows that offer views of the surrounding forest. The exterior is constructed with dark wood shingles and is supported by sturdy stilts, blending seamlessly with the natural environment.
Treehouse in Waterford
5.0 out of 5 average rating, 280 reviews

Hummingbirds Hideaway Treehouse

Do not book on airbnb and ask for early arrival. experience the magic of being among the treetops at our newly built treehouse. Whether you are seeking a romantic getaway, peaceful retreat, or family fun this slice of heaven will offer you an unforgettable stay. Features large windows for stunning views of the surrounding woods and very detailed woodwork. 2 bedrooms with king beds, open living space with full kitchen and bathroom will be sure to impress. Please message us prior to booking

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Top guest favorite
Guesthouse in Frederick
4.96 out of 5 average rating, 90 reviews

Private Woodland Retreat | Near Downtown Frederick

Escape to a beautiful one-bedroom retreat. The guesthouse has a queen bed, kitchenette, luxurious bathroom with two shower heads, including a rain head, and a queen pull-out sofa bed. Nestled in the woods with a covered porch for morning coffee, yet a short drive to downtown Frederick, Civil War sites, Frederick Watershed with hiking and cycling trails, Mount St. Mary’s University, Cunningham Falls, and Catoctin. Free WiFi, and Smart Roku TV’s. Parking for 2 cars is included. Dogs are welcome.

ValueLocationNearby

Top guest favorite
The treehouse is perched among tall trees, featuring a wooden deck that wraps around its structure. A gentle staircase leads to the entrance. In the foreground, purple flowers bloom beside a rock outcropping, enhancing the natural landscape under a bright blue sky.
Treehouse in Shepherdstown
4.98 out of 5 average rating, 441 reviews

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.

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Top guest favorite
Farm stay in Middletown
4.95 out of 5 average rating, 76 reviews

The Milk House at Hereford Grove Farm

The Milk House at Hereford Grove Farm is a completely renovated efficiency space located on a beautiful, 128 acre, historic farm. All facilities are brand new and modern. Come experience the magic of this unique and tranquil getaway for two. The pastoral setting includes breathtaking views and sunsets, beautiful barns, a spring-fed pond, and nearby grazing cattle. The farm is a great setting for pets. Due to the size of the Milk House, only one pet is allowed and no cats are permitted.

LocationFamilyAccess

Top guest favorite
A two-story house is shown with a white exterior and black accents. A spacious deck is visible, supported by wooden posts. A set of stairs leads to the entrance. The surrounding landscape features a grassy area with boulders, complemented by bare trees in the background.
Home in Boonsboro
4.92 out of 5 average rating, 51 reviews

The Overlook~ Exquisite Views

Our home sits atop the highest peak, allowing for exquisite views! Enjoy your scenic stay in our spacious eat in kitchen. Relax with a glass of wine around the fire table on our deck and watch the gorgeous sunset. We are conveniently located less than 10 minutes from Big Cork Vineyards as well as downtown Boonsboro! Our location makes a trip to historic Harpers Ferry or the Antietam Battlefield a breeze. Adventure lovers can experience numerous outdoor activities just 15 minutes away.

ValueLocationCleanliness

Top guest favorite
A well-maintained pathway leads to a welcoming front porch, flanked by neat lawns and vibrant flowering bushes. Soft sunlight filters through the trees, casting delicate shadows on the concrete surface, while rolling hills can be seen in the background.
Home in Middletown
4.97 out of 5 average rating, 91 reviews

Beautiful historical town, 3 bedrooms, countryside

Beautiful home is on the 3.5 acres around peaceful farm area, with a barn and stunning views of the valley and mountains. You are able to see and hear the neighbor’s animals, see the rhythm of farm life, and enjoy being in nature. We hope you will find the house is supper comfy, welcoming. Great location not too far from Main St in Middletown with its restaurants & shopping. Minutes from the highway, yet still in the country. A little over 20 minutes drive to the Whitetail Ski Resort.

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Popular amenities for Middletown vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation rentals in Middletown

Guest favorite
The exterior of a renovated mobile home showcases a colorful façade with horizontal stripes of orange, yellow, and white. Lush greenery surrounds the home, with a well-maintained lawn and coniferous trees providing a natural backdrop. A shed is visible alongside the mobile home.
Place to stay in Middletown
4.87 out of 5 average rating, 68 reviews

Vintage Mobile Home and Storage Workshop

ValueFamilyAccuracy

Top guest favorite
A rustic cabin exterior is shown, featuring a sloped roof and wooden siding. Comfortable seating is arranged on a stone patio alongside a fire pit. A stacked firewood pile is visible, with green plants enhancing the natural surroundings.
Farm stay in Myersville
5.0 out of 5 average rating, 46 reviews

Mid-Century Farm Cabin w/ Fire Pit & Creeks

LocationValueBackyard

Top guest favorite
Lush greenery dominates the foreground, leading to a panoramic view of the distant landscape. A small structure with a white roof sits among the trees, while expansive blue skies are scattered with white clouds, enhancing the natural setting.
Guesthouse in Frederick
4.96 out of 5 average rating, 47 reviews

Boutique space at Marble Ridge

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Guest favorite
Home in Myersville
5.0 out of 5 average rating, 22 reviews

[New] Stargazing Retreat. 15 Mile Views on 5 Acres

LocationFamilySleep quality

Superhost
Farm stay in Woodsboro
5.0 out of 5 average rating, 4 reviews

Farm Retreat- Sauna, Hot Tub, Cold Plunge, Trails

LocationFamilyKitchen

Guest favorite
A modern villa is set against a backdrop of tall trees, with its mirrored exterior reflecting the surrounding forest. A stone pathway leads to the entrance, illuminated by a nearby light fixture. The soft glow of dusk highlights the natural beauty of the area.
Tiny home in Mercersburg
4.97 out of 5 average rating, 30 reviews

Romantic Mirror Cabin • Hot Tub • Fire Pit • Views

ValueLocationCheckout

Superhost
A spacious deck area is featured, lined with wooden planks and surrounded by lush greenery. Two Adirondack chairs provide a cozy spot for relaxation, while a small platform extends into the yard, enhancing the outdoor space for enjoyment.
Apartment in Middletown
4.66 out of 5 average rating, 62 reviews

Woodsy Lair in Historic Middletown Valley!

ValueFamilyComfort

Top guest favorite
Treehouse in Smithsburg
5.0 out of 5 average rating, 25 reviews

Bin There Treehouse, a grain bin treehouse!

LocationFamilyComfort

Frequently Asked Questions

  • What are the best places to stay in Middletown?

    Many guests choose stays near Main Street to enjoy walkable access to shops, cafes, and local events. The surrounding countryside also has accommodations with views of farmland and nearby hills.

  • What are the best things to do in Middletown with kids?

    Kids often enjoy playgrounds and open spaces in neighborhood parks, visits to hands-on farms, or participating in seasonal community events featuring crafts, games, or storytelling. Many families find nature walks and local fairs engaging.

  • What are some of the best things to do in Middletown?

    Explore historic architecture on Main Street, hike local trails like those in South Mountain State Park, or attend markets in the town square. Middletown’s seasonal events and small-town festivals highlight its calendar.

  • How is the weather in Middletown?

    Middletown has cold winters around 25–43°F (-4–6°C) and warm, humid summers near 67–88°F (19–31°C). Spring and fall are milder, with increased rainfall in late spring.

  • When is the best time to visit Middletown?

    Late spring and early fall are frequently suggested for milder temperatures, blooming landscapes, and outdoor events around Middletown. Summer is also popular with families enjoying parks and seasonal festivities.

  • What are the best places to visit in Middletown?

    Middletown has scenic parks, historic sites, and local shops that are often recommended by travelers. Explore Catoctin Creek Park or take in the architecture and stories around Main Street.

  • What are some hiking trails in Middletown?

    Explore Catoctin Creek Park’s nature trails or wander through South Mountain State Park’s wooded paths near Middletown. These areas bring opportunities for forest walks and gentle climbs with scenic views.

  • What are some family activities we can do in Middletown?

    Families frequently have picnics and enjoy playgrounds at local parks or visit farms to explore seasonal activities such as fruit picking and hayrides. Community festivals and town fairs often feature interactive exhibits, food, and games.

  • What are some of the best day trip ideas from Middletown?

    Consider exploring historic Frederick for museums and galleries, hiking in Catoctin Mountain Park, or visiting local wineries and orchards around the Middletown Valley. The area has several nature preserves and outdoor recreation spots.

  • Are there any pet friendly accommodations available in Middletown?

    Many Middletown accommodations welcome pets, especially those in the countryside or near parks. Outdoor spaces and nearby nature trails make it convenient to explore the area with your companion animal.

  • What are some local tips for visiting Middletown?

    Locals suggest exploring early in the day for quieter walks, trying small eateries for regional flavors, and checking community boards for pop-up events. Late spring and fall are popular for outdoor activities and markets.

  • What is Middletown known for?

    Middletown is known for its historic Main Street, Civil War heritage, and its role as a gateway to Maryland’s scenic valleys. The town has welcoming parks and a strong sense of local history.

  • What are the best hidden gems to explore in Middletown?

    Explore locally owned farm stands and nearby preserves, which highlight Middletown's agricultural roots and quiet scenery. Artisan shops around the town have handcrafted goods and unique finds reflecting community traditions.

  • What are the best foods to try in Middletown?

    Regional comfort food is often suggested—sample homemade pies, locally roasted coffee, and traditional Maryland crab dishes at local diners or farm-to-table restaurants. During fall, apple-based treats from nearby orchards are a favorite.

  • What should I bring for a trip to Middletown?

    Bring layers, as Middletown's weather ranges from cold winters to warm, humid summers. Comfortable shoes, a rain jacket, and items for outdoor activities help you make the most of the natural surroundings and town events.

  • What is the nightlife in Middletown like?

    Nightlife in Middletown tends to be casual, centered around local pubs, family restaurants, and occasional live music events. Some evenings feature local community gatherings or outdoor performances.

  • What are the most popular events or festivals in Middletown?

    The Middletown Heritage Festival in late summer is often recommended, celebrating local history and community traditions. Throughout the year, the town has seasonal farmers markets and holiday parades.

  • Are there family friendly vacation rentals in Middletown?

    Middletown has family friendly rentals, particularly near parks or in the quieter residential neighborhoods. Many have space for kids to play and easy access to outdoor activities.

Destinations to explore