Holiday houses in Woodsboro

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Top-rated holiday rentals in Woodsboro

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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
The log cabin features a spacious covered porch surrounded by trees. The wooden structure blends into the natural setting, while large windows invite natural light. The front yard is landscaped with shrubs, providing a warm and inviting entrance.
Home in Thurmont
4.87 out of 5 average rating, 574 reviews

Cabin in the Woods - Weekday Specials!

Welcome to our log cabin! This three bedroom, two bath, all-wood home is set on five wooded acres less than a mile from the main highway. There is easy access to historic Frederick and Gettysburg. Surrounded by beautiful National and State Parks and only 20 minutes from Ski Liberty. Enjoy a relaxing time surrounded by trees or take a walk along the neighborhood orchards. Sit on the covered porch, relax by the fire-pit and eat on the back patio – or if it’s cold outside, enjoy the wood stove!

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.
Apartment in Frederick
4.89 out of 5 average rating, 365 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 farmhouse exterior is showcased, featuring a white façade with brown shutters. A wide path leads to the front entrance, framed by landscaped gardens and a spacious lawn. The metal roof and symmetrical design contribute to the country charm against a backdrop of blue sky and fluffy clouds.
Farm stay in Thurmont
4.95 out of 5 average rating, 132 reviews

Private Farmhouse Escape w/ Mountain Views

Welcome to The Farmhouse at Magnolia Meadow Farms! This thoughtfully updated, 5 bedroom, 3.5 bathroom ranch-style home lives on 22 acres of total seclusion. Need a place to stay for a wedding or event, or just need to breathe some fresh air? This stunning home is the perfect, private getaway for you and the whole family while still being conveniently located. You are near: Catoctin Mountain Park Cunningham Falls State Park Downtown Frederick, MD Liberty Mountain Resort Gettysburg, PA & more!

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.
Condo in Frederick
4.96 out of 5 average rating, 123 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
The charming A-frame structure is surrounded by lush greenery, blending seamlessly with the wooded environment. Large windows provide a view into the inviting interior, while a stone pathway leads to the entrance, accentuated by decorative elements and natural landscaping.
Place to stay in Shippensburg
5 out of 5 average rating, 410 reviews

The Frame ~ Charming Nature Escape ~ Hot Tub ~ BBQ

Escape to the charming 2BR 1Bath A-frame on a secluded wooded property just 10 mins away from Shippensburg, PA. Whether you're looking to savor nature‘s tranquility from the luxurious hot tub, share stories around the fire pit, or explore picturesque Cumberland Valley, this will be the ideal starting point for your adventures! *2 Comfortable BRs *Open Design Living *Full Kitchen *Smart TV *Backyard (Hot Tub, Sauna, Fire Pit, BBQ, Outdoor shower) *High-Speed Wi-Fi *Free Parking *EV charger

Top Guest favourite
The exterior of the guesthouse is showcased, featuring a deck with outdoor seating and an umbrella. Tall windows allow for natural light, complementing the green siding. Lush landscaping surrounds the house, creating a natural, inviting setting.
Guesthouse in Smithsburg
4.97 out of 5 average rating, 782 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.

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, 257 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 favourite
The historic stone house features a large front porch with a railing and several steps leading to the entrance. Its facade includes multiple windows framed by red shutters, with a modern addition visible on one side. Lush green grass surrounds the house, adding to the rural setting.
Farm stay in Mount Airy
4.98 out of 5 average rating, 114 reviews

Poole House at Friendship Farm

Welcome to Poole House at Friendship Farm! Escape to the country at this historic stone house built in the 1700s. With accommodations for eight guests it is perfect for a getaway with friends and family, wedding parties and work retreats. The house received a meticulous restoration that includes all mechanical systems and a modern addition with a gourmet kitchen and master bedroom. The property also includes a three car garage as well as a restored smoke house and log cabin.

Top Guest favourite
A modern kitchen is highlighted by a spacious island featuring dark cabinetry and a white countertop. Bright pendant lights hang overhead, illuminating the area. A bouquet of fresh flowers adds a touch of color, while an array of appliances is visible in the open shelving.
Farm stay in Ijamsville
4.96 out of 5 average rating, 301 reviews

Beyond Your Expectations Farm Stay

Escape to our historic farm stay, where charm meets modern comfort. Enjoy the gourmet kitchen, unwind on the magnificent patio with a huge fire pit, and indulge in the infrared sauna. Perfect for families and friends, with an adorable kid's playhouse and games. Interact with friendly animals, immerse yourself in serenity, and experience the ultimate getaway near Whiskey Creek Golf Course in Ijamsville. Contact Fingerboard Farm directly for larger gatherings.

Top Guest favourite
A spacious living area features a modern television mounted on the wall, paired with a wooden console labeled 'TOYS.' A comfortable gray sofa and a wooden coffee table are centered on a decorative rug, with a view of the adjacent kitchen visible through an open doorway.
Townhouse in Frederick
5 out of 5 average rating, 109 reviews

Positive vibes on Market St

This fully renovated historic home in downtown Frederick, provides for a calm, relaxing place to stay, and is a short walk to Frederick restaurant's, breweries, and local shops. The main level provides a beautiful sitting room, living room, and kitchen. Upstairs you will find 3 bedrooms and an updated bathroom. The back yard is fenced, making it perfect for pets. The house is perfect for a quiet getaway or an outing with friends and family.

Popular amenities for Woodsboro holiday rentals

  1. Airbnb
  2. United States
  3. Maryland
  4. Frederick County
  5. Woodsboro