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, 573 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, 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 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
The image features a scenic view of Carroll Creek Promenade with outdoor seating visible along the water. The apartment interior showcases a bright living space with a comfortable bed, a modern kitchen with appliances, and a quaint desk area, all highlighted by natural light from the windows.
Apartment in Downtown Frederick
4.99 out of 5 average rating, 179 reviews

Carroll Creek Private Apt./Luxury King Bed

Within footsteps to Carroll Creek Promenade offering easy access to posh restaurants, fun Breweries, local shops and festivals galore! Modern remodel and furniture including a posh memory foam king bed. Enjoy your own apartment w/ wide open spaces & high ceilings that bring in fantastic light. Historic bldg. (circa 1840) with all the modern appointments to make your stay super comfortable and fun! Owners provide advice on their favorite places and restaurants! Easy self checkin. Free parking.

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 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 bedroom features a king bed with a tufted headboard, complemented by decorative pillows. Warm lighting is provided by bedside lamps on each side. A light-colored sofa with a subtle design sits at the foot of the bed, and natural light enters through the window with white shutters.
Condo in Downtown Frederick
4.93 out of 5 average rating, 291 reviews

Your Hideaway awaits/1-bedroom downtown pad.

There is no place like home when you visit our cozy 1 bed/1 bath abode! This 2nd floor unit is nestled in the rear of a historic home that has been converted into condo living. This space checks all the boxes for a weekend getaway or long-term stay. Enjoy an open living/dinning area, a new memory foam king bed, & a fully furnished bathroom! We offer a keyless entry & 1 parking spot - a rarity for downtown living. Residents live above & below. NO pets, loud music, or parties.

Guest favourite
A modern living area is presented, featuring a sleek, dark leather sofa and contrasting white chairs. A low coffee table with decorative items sits in the center. A colorful wall art piece adds visual interest, while a beverage bar is visible in the background.
Townhouse in Frederick
4.92 out of 5 average rating, 130 reviews

Spacious Townhouse Minutes From Downtown

If you're looking for a wonderful place to stay near downtown with all the amenities, this home is for you. Less than 10 minutes to downtown Frederick in a wonderful neighborhood. Our guests often comment on how close the house is to downtown and all the attractions Frederick has to offer, how comfortable the beds are, and how surprisingly spacious the home is. The home features a comfortable game room, TV room with the most comfortable reclineable chairs, & 2 more living rooms.

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.

Popular amenities for Woodsboro holiday rentals

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